##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Journal  #
# of Applied Crystallography. It has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary may be obtained from        #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_Compound_1_Below
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 O2 S'
_chemical_formula_sum     'C14 H14 O2 S'
_chemical_formula_weight     246.31
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     4.736(3)
_cell_length_b     10.819(5)
_cell_length_c     12.206(6)
_cell_angle_alpha     89.727(15)
_cell_angle_beta     78.904(14)
_cell_angle_gamma     89.977(18)
_cell_volume     613.6(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     317
_cell_measurement_theta_min     3.77
_cell_measurement_theta_max     21.83
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.333
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     260
_exptl_absorpt_coefficient_mu     0.250
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.4707
_exptl_absorpt_correction_T_max     0.8852
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4509
_diffrn_reflns_av_R_equivalents     0.2004
_diffrn_reflns_av_sigmaI/netI     0.2861
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     22.80
_diffrn_reflns_theta_full     22.80
_diffrn_measured_fraction_theta_max     0.963
_diffrn_measured_fraction_theta_full     0.963
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1596
_reflns_number_gt     628
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2348
_refine_ls_R_factor_gt     0.0988
_refine_ls_wR_factor_gt     0.2460
_refine_ls_wR_factor_ref     0.3207
_refine_ls_goodness_of_fit_ref     0.980
_refine_ls_restrained_S_all     0.980
_refine_ls_number_reflns     1596
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1406P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.032
_refine_ls_shift/su_mean     0.004
_refine_diff_density_max     0.424
_refine_diff_density_min     -0.422
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.3529(6) 0.2502(3) 0.5002(3) 0.0371(11) Uani d . 1 . .
    O O1 0.2212(15) 0.3500(8) 0.4474(7) 0.052(3) Uani d . 1 . .
    O O2 0.1687(15) 0.1538(8) 0.5500(8) 0.055(3) Uani d . 1 . .
    C C1 0.275(3) 0.0704(16) 0.1172(14) 0.063(4) Uani d . 1 . .
    H H1 0.1958 0.0463 0.0565 0.076 Uiso calc R 1 . .
    C C2 0.224(3) 0.0055(16) 0.2125(16) 0.072(5) Uani d . 1 . .
    H H2 0.1094 -0.0650 0.2178 0.087 Uiso calc R 1 . .
    C C3 0.338(3) 0.0417(12) 0.3031(13) 0.053(4) Uani d . 1 . .
    H H3 0.2988 -0.0038 0.3692 0.064 Uiso calc R 1 . .
    C C4 0.511(2) 0.1444(11) 0.2961(12) 0.039(3) Uani d . 1 . .
    C C5 0.633(2) 0.1823(11) 0.3966(10) 0.038(3) Uani d . 1 . .
    H H5A 0.7873 0.2417 0.3741 0.046 Uiso calc R 1 . .
    H H5B 0.7125 0.1106 0.4280 0.046 Uiso calc R 1 . .
    C C6 0.529(2) 0.3159(11) 0.6027(10) 0.044(3) Uani d . 1 . .
    H H6A 0.6584 0.2557 0.6254 0.052 Uiso calc R 1 . .
    H H6B 0.6415 0.3870 0.5715 0.052 Uiso calc R 1 . .
    C C7 0.309(2) 0.3546(11) 0.7020(11) 0.036(3) Uani d . 1 . .
    C C8 0.262(2) 0.2880(13) 0.7984(12) 0.053(4) Uani d . 1 . .
    H H8 0.3674 0.2162 0.8027 0.063 Uiso calc R 1 . .
    C C9 0.058(3) 0.3257(15) 0.8921(12) 0.066(4) Uani d . 1 . .
    H H9 0.0337 0.2821 0.9591 0.079 Uiso calc R 1 . .
    C C10 -0.106(3) 0.4286(16) 0.8818(15) 0.067(4) Uani d . 1 . .
    H H10 -0.2474 0.4533 0.9414 0.081 Uiso calc R 1 . .
    C C11 0.448(3) 0.1747(16) 0.1108(13) 0.070(5) Uani d . 1 . .
    H H11 0.4868 0.2196 0.0445 0.085 Uiso calc R 1 . .
    C C12 0.564(2) 0.2136(13) 0.1999(11) 0.051(4) Uani d . 1 . .
    H H12 0.6760 0.2848 0.1950 0.062 Uiso calc R 1 . .
    C C13 0.146(2) 0.4600(11) 0.6943(13) 0.054(4) Uani d . 1 . .
    H H13 0.1754 0.5071 0.6292 0.065 Uiso calc R 1 . .
    C C14 -0.061(3) 0.4936(14) 0.7865(14) 0.061(4) Uani d . 1 . .
    H H14 -0.1726 0.5635 0.7815 0.073 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.418(9) ?
    S1 O1 . 1.455(8) ?
    S1 C6 . 1.782(12) ?
    S1 C5 . 1.807(12) ?
    C1 C2 . 1.34(2) ?
    C1 C11 . 1.389(19) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.38(2) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.371(16) ?
    C3 H3 . 0.9300 ?
    C4 C12 . 1.371(17) ?
    C4 C5 . 1.514(17) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.499(16) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.357(16) ?
    C7 C13 . 1.389(16) ?
    C8 C9 . 1.412(17) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.37(2) ?
    C9 H9 . 0.9300 ?
    C10 C14 . 1.34(2) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.377(18) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.393(18) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 116.9(5) ?
    O2 S1 C6 . . 109.0(5) ?
    O1 S1 C6 . . 108.2(5) ?
    O2 S1 C5 . . 107.9(5) ?
    O1 S1 C5 . . 108.2(5) ?
    C6 S1 C5 . . 106.0(5) ?
    C2 C1 C11 . . 118.6(13) ?
    C2 C1 H1 . . 120.7 ?
    C11 C1 H1 . . 120.7 ?
    C1 C2 C3 . . 120.9(15) ?
    C1 C2 H2 . . 119.6 ?
    C3 C2 H2 . . 119.6 ?
    C4 C3 C2 . . 120.2(14) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C12 . . 120.2(13) ?
    C3 C4 C5 . . 119.3(12) ?
    C12 C4 C5 . . 120.5(11) ?
    C4 C5 S1 . . 109.6(7) ?
    C4 C5 H5A . . 109.8 ?
    S1 C5 H5A . . 109.8 ?
    C4 C5 H5B . . 109.8 ?
    S1 C5 H5B . . 109.8 ?
    H5A C5 H5B . . 108.2 ?
    C7 C6 S1 . . 109.6(7) ?
    C7 C6 H6A . . 109.8 ?
    S1 C6 H6A . . 109.8 ?
    C7 C6 H6B . . 109.8 ?
    S1 C6 H6B . . 109.8 ?
    H6A C6 H6B . . 108.2 ?
    C8 C7 C13 . . 119.4(13) ?
    C8 C7 C6 . . 121.6(11) ?
    C13 C7 C6 . . 119.0(12) ?
    C7 C8 C9 . . 121.4(12) ?
    C7 C8 H8 . . 119.3 ?
    C9 C8 H8 . . 119.3 ?
    C10 C9 C8 . . 118.2(14) ?
    C10 C9 H9 . . 120.9 ?
    C8 C9 H9 . . 120.9 ?
    C14 C10 C9 . . 120.3(14) ?
    C14 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C12 C11 C1 . . 121.9(14) ?
    C12 C11 H11 . . 119.0 ?
    C1 C11 H11 . . 119.0 ?
    C4 C12 C11 . . 118.2(13) ?
    C4 C12 H12 . . 120.9 ?
    C11 C12 H12 . . 120.9 ?
    C7 C13 C14 . . 118.5(14) ?
    C7 C13 H13 . . 120.8 ?
    C14 C13 H13 . . 120.8 ?
    C10 C14 C13 . . 122.2(13) ?
    C10 C14 H14 . . 118.9 ?
    C13 C14 H14 . . 118.9 ?
data_Compound_1_Centre
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 O2 S'
_chemical_formula_sum     'C14 H14 O2 S'
_chemical_formula_weight     246.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     C12/c1
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     24.003(3)
_cell_length_b     4.7435(6)
_cell_length_c     10.8255(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.185(4)
_cell_angle_gamma     90.00
_cell_volume     1232.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2014
_cell_measurement_theta_min     3.39
_cell_measurement_theta_max     24.99
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.249
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7685
_exptl_absorpt_correction_T_max     0.8857
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3757
_diffrn_reflns_av_R_equivalents     0.0305
_diffrn_reflns_av_sigmaI/netI     0.0299
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1094
_reflns_number_gt     894
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0537
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.1045
_refine_ls_wR_factor_ref     0.1321
_refine_ls_goodness_of_fit_ref     1.162
_refine_ls_restrained_S_all     1.162
_refine_ls_number_reflns     1094
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0805P)²+0.0091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.240
_refine_diff_density_min     -0.334
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.5000 0.14712(15) 0.2500 0.0388(3) Uani d S 1 . .
    O O1 0.47410(6) 0.3057(3) 0.15153(14) 0.0516(5) Uani d . 1 . .
    C C1 0.69124(12) 0.4134(6) 0.0722(3) 0.0700(9) Uani d . 1 . .
    H H1 0.7216 0.5214 0.0479 0.084 Uiso calc R 1 . .
    C C2 0.69521(11) 0.2466(7) 0.1749(3) 0.0708(8) Uani d . 1 . .
    H H2 0.7282 0.2405 0.2200 0.085 Uiso calc R 1 . .
    C C3 0.64978(10) 0.0866(5) 0.2114(2) 0.0559(7) Uani d . 1 . .
    H H3 0.6522 -0.0243 0.2820 0.067 Uiso calc R 1 . .
    C C4 0.60086(9) 0.0907(4) 0.1436(2) 0.0407(6) Uani d . 1 . .
    C C5 0.55117(9) -0.0820(4) 0.1842(2) 0.0440(6) Uani d . 1 . .
    H H5A 0.5628 -0.2209 0.2448 0.053 Uiso calc R 1 . .
    H H5B 0.5354 -0.1807 0.1138 0.053 Uiso calc R 1 . .
    C C6 0.59791(10) 0.2614(5) 0.0397(2) 0.0513(6) Uani d . 1 . .
    H H6 0.5652 0.2664 -0.0067 0.062 Uiso calc R 1 . .
    C C7 0.64250(12) 0.4227(6) 0.0043(3) 0.0645(8) Uani d . 1 . .
    H H7 0.6399 0.5377 -0.0651 0.077 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.4437(15) ?
    S1 O1 2_655 1.4437(15) ?
    S1 C5 . 1.790(2) ?
    S1 C5 2_655 1.790(2) ?
    C1 C2 . 1.368(4) ?
    C1 C7 . 1.380(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.387(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.383(3) ?
    C3 H3 . 0.9300 ?
    C4 C6 . 1.388(3) ?
    C4 C5 . 1.513(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.371(3) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O1 . 2_655 117.21(14) ?
    O1 S1 C5 . . 108.47(10) ?
    O1 S1 C5 2_655 . 108.41(10) ?
    O1 S1 C5 . 2_655 108.41(10) ?
    O1 S1 C5 2_655 2_655 108.48(10) ?
    C5 S1 C5 . 2_655 105.22(14) ?
    C2 C1 C7 . . 120.5(3) ?
    C2 C1 H1 . . 119.7 ?
    C7 C1 H1 . . 119.7 ?
    C1 C2 C3 . . 119.7(3) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 120.5(2) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C6 . . 118.6(2) ?
    C3 C4 C5 . . 120.5(2) ?
    C6 C4 C5 . . 120.9(2) ?
    C4 C5 S1 . . 109.24(14) ?
    C4 C5 H5A . . 109.8 ?
    S1 C5 H5A . . 109.8 ?
    C4 C5 H5B . . 109.8 ?
    S1 C5 H5B . . 109.8 ?
    H5A C5 H5B . . 108.3 ?
    C7 C6 C4 . . 121.0(2) ?
    C7 C6 H6 . . 119.5 ?
    C4 C6 H6 . . 119.5 ?
    C6 C7 C1 . . 119.6(3) ?
    C6 C7 H7 . . 120.2 ?
    C1 C7 H7 . . 120.2 ?
data_Compound_1_Side
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 O2 S'
_chemical_formula_sum     'C14 H14 O2 S'
_chemical_formula_weight     246.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     C12/c1
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     24.012(3)
_cell_length_b     4.7429(5)
_cell_length_c     10.8321(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.197(4)
_cell_angle_gamma     90.00
_cell_volume     1233.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2014
_cell_measurement_theta_min     3.39
_cell_measurement_theta_max     24.99
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.326
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.249
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7831
_exptl_absorpt_correction_T_max     0.8858
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3662
_diffrn_reflns_av_R_equivalents     0.0240
_diffrn_reflns_av_sigmaI/netI     0.0199
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1097
_reflns_number_gt     960
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0439
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.1154
_refine_ls_wR_factor_ref     0.1217
_refine_ls_goodness_of_fit_ref     1.204
_refine_ls_restrained_S_all     1.204
_refine_ls_number_reflns     1097
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0759P)²+0.2443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.237
_refine_diff_density_min     -0.326
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.5000 0.14726(12) 0.2500 0.0365(3) Uani d S 1 . .
    O O1 0.47421(6) 0.3056(3) 0.15149(13) 0.0499(4) Uani d . 1 . .
    C C1 0.69130(10) 0.4145(6) 0.0721(3) 0.0678(7) Uani d . 1 . .
    H H1 0.7217 0.5222 0.0479 0.081 Uiso calc R 1 . .
    C C2 0.64257(11) 0.4232(5) 0.0043(2) 0.0625(7) Uani d . 1 . .
    H H2 0.6400 0.5378 -0.0651 0.075 Uiso calc R 1 . .
    C C3 0.59767(9) 0.2611(5) 0.03988(19) 0.0501(6) Uani d . 1 . .
    H H3 0.5649 0.2660 -0.0062 0.060 Uiso calc R 1 . .
    C C4 0.60095(7) 0.0913(4) 0.14369(18) 0.0384(5) Uani d . 1 . .
    C C5 0.55121(7) -0.0823(4) 0.18398(19) 0.0422(5) Uani d . 1 . .
    H H5A 0.5628 -0.2216 0.2444 0.051 Uiso calc R 1 . .
    H H5B 0.5355 -0.1806 0.1135 0.051 Uiso calc R 1 . .
    C C6 0.69499(9) 0.2478(6) 0.1750(3) 0.0691(7) Uani d . 1 . .
    H H6 0.7279 0.2425 0.2203 0.083 Uiso calc R 1 . .
    C C7 0.64984(8) 0.0870(5) 0.2119(2) 0.0535(6) Uani d . 1 . .
    H H7 0.6524 -0.0238 0.2825 0.064 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 2_655 1.4429(14) ?
    S1 O1 . 1.4429(14) ?
    S1 C5 2_655 1.7930(18) ?
    S1 C5 . 1.7930(18) ?
    C1 C6 . 1.369(4) ?
    C1 C2 . 1.380(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.380(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9300 ?
    C4 C7 . 1.385(3) ?
    C4 C5 . 1.516(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.386(3) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O1 2_655 . 117.25(12) ?
    O1 S1 C5 2_655 2_655 108.32(9) ?
    O1 S1 C5 . 2_655 108.54(8) ?
    O1 S1 C5 2_655 . 108.54(8) ?
    O1 S1 C5 . . 108.32(9) ?
    C5 S1 C5 2_655 . 105.22(12) ?
    C6 C1 C2 . . 120.2(2) ?
    C6 C1 H1 . . 119.9 ?
    C2 C1 H1 . . 119.9 ?
    C3 C2 C1 . . 119.8(2) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 120.6(2) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C3 C4 C7 . . 119.17(19) ?
    C3 C4 C5 . . 120.46(18) ?
    C7 C4 C5 . . 120.36(18) ?
    C4 C5 S1 . . 109.09(13) ?
    C4 C5 H5A . . 109.9 ?
    S1 C5 H5A . . 109.9 ?
    C4 C5 H5B . . 109.9 ?
    S1 C5 H5B . . 109.9 ?
    H5A C5 H5B . . 108.3 ?
    C1 C6 C7 . . 120.3(2) ?
    C1 C6 H6 . . 119.9 ?
    C7 C6 H6 . . 119.9 ?
    C4 C7 C6 . . 120.0(2) ?
    C4 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
data_Compound_2_APEX
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     258.31
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.100(2)
_cell_length_b     11.365(2)
_cell_length_c     11.300(2)
_cell_angle_alpha     90
_cell_angle_beta     97.464(5)
_cell_angle_gamma     90
_cell_volume     1286.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2568
_cell_measurement_theta_min     2.5526
_cell_measurement_theta_max     22.4523
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     'Plate '
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.246
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.83
_exptl_absorpt_correction_T_max     0.95
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     13491
_diffrn_reflns_av_R_equivalents     0.0390
_diffrn_reflns_av_sigmaI/netI     0.0244
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     24.67
_diffrn_reflns_theta_full     24.67
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2180
_reflns_number_gt     1698
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0484
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_gt     0.0761
_refine_ls_wR_factor_ref     0.0847
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     2180
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0358P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.137
_refine_diff_density_min     -0.268
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2008, 7, 0, 0'
_computing_cell_refinement     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.34284(5) 0.47322(4) 0.12743(4) 0.05047(17) Uani d . 1 . .
    F F18 0.12948(13) 0.63513(11) 0.16614(12) 0.0783(4) Uani d . 1 . .
    N N2 0.40076(18) 0.36620(15) 0.05260(15) 0.0669(5) Uani d . 1 . .
    N N4 0.36314(19) 0.37798(18) -0.16644(17) 0.0754(5) Uani d . 1 . .
    C C15 -0.0887(3) 0.3848(3) 0.1554(2) 0.0872(8) Uani d . 1 . .
    H H15 -0.1777 0.367 0.1603 0.105 Uiso calc R 1 . .
    C C14 -0.0465(2) 0.5001(2) 0.16551(18) 0.0736(7) Uani d . 1 . .
    H H14 -0.1054 0.5605 0.1776 0.088 Uiso calc R 1 . .
    C C13 0.0851(2) 0.52274(19) 0.15715(16) 0.0551(5) Uani d . 1 . .
    C C12 0.17434(18) 0.43502(17) 0.14101(15) 0.0488(5) Uani d . 1 . .
    C C5 0.42218(19) 0.43316(18) 0.27464(16) 0.0569(5) Uani d . 1 . .
    H H5A 0.4127 0.3492 0.2862 0.068 Uiso calc R 1 . .
    H H5B 0.5168 0.451 0.2812 0.068 Uiso calc R 1 . .
    C C6 0.36170(18) 0.49808(17) 0.36994(16) 0.0505(5) Uani d . 1 . .
    C C11 0.3991(2) 0.61265(19) 0.39841(18) 0.0607(5) Uani d . 1 . .
    H H11 0.4621 0.6499 0.3583 0.073 Uiso calc R 1 . .
    C C10 0.3432(2) 0.6717(2) 0.4860(2) 0.0713(6) Uani d . 1 . .
    H H10 0.3684 0.7489 0.5045 0.086 Uiso calc R 1 . .
    C C9 0.2509(3) 0.6177(2) 0.5457(2) 0.0757(7) Uani d . 1 . .
    H H9 0.2137 0.658 0.6049 0.091 Uiso calc R 1 . .
    C C16 -0.0016(3) 0.2960(2) 0.1382(2) 0.0843(7) Uani d . 1 . .
    H H16 -0.0321 0.2188 0.1311 0.101 Uiso calc R 1 . .
    C C17 0.1307(2) 0.31998(19) 0.13135(18) 0.0671(6) Uani d . 1 . .
    H H17 0.1899 0.2595 0.1204 0.081 Uiso calc R 1 . .
    C C3 0.37844(18) 0.37816(17) -0.0639(2) 0.0552(5) Uani d . 1 . .
    C C7 0.2681(2) 0.44387(18) 0.43051(18) 0.0611(5) Uani d . 1 . .
    H H7 0.2421 0.3669 0.412 0.073 Uiso calc R 1 . .
    C C8 0.2133(2) 0.5038(2) 0.5185(2) 0.0754(7) Uani d . 1 . .
    H H8 0.1506 0.4671 0.5594 0.09 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N2 . 1.6325(16) ?
    S1 C12 . 1.7822(19) ?
    S1 C5 . 1.8084(19) ?
    F18 C13 . 1.353(2) ?
    N2 C3 . 1.313(3) ?
    N4 C3 . 1.149(3) ?
    C15 C16 . 1.369(4) ?
    C15 C14 . 1.378(4) ?
    C15 H15 . 0.93 ?
    C14 C13 . 1.369(3) ?
    C14 H14 . 0.93 ?
    C13 C12 . 1.372(3) ?
    C12 C17 . 1.380(3) ?
    C5 C6 . 1.499(3) ?
    C5 H5A . 0.97 ?
    C5 H5B . 0.97 ?
    C6 C7 . 1.382(3) ?
    C6 C11 . 1.382(3) ?
    C11 C10 . 1.376(3) ?
    C11 H11 . 0.93 ?
    C10 C9 . 1.365(3) ?
    C10 H10 . 0.93 ?
    C9 C8 . 1.372(3) ?
    C9 H9 . 0.93 ?
    C16 C17 . 1.375(3) ?
    C16 H16 . 0.93 ?
    C17 H17 . 0.93 ?
    C7 C8 . 1.380(3) ?
    C7 H7 . 0.93 ?
    C8 H8 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 S1 C12 . . 105.87(9) ?
    N2 S1 C5 . . 98.23(9) ?
    C12 S1 C5 . . 99.99(9) ?
    C3 N2 S1 . . 114.56(14) ?
    C16 C15 C14 . . 121.0(2) ?
    C16 C15 H15 . . 119.5 ?
    C14 C15 H15 . . 119.5 ?
    C13 C14 C15 . . 117.8(2) ?
    C13 C14 H14 . . 121.1 ?
    C15 C14 H14 . . 121.1 ?
    F18 C13 C14 . . 119.2(2) ?
    F18 C13 C12 . . 118.60(18) ?
    C14 C13 C12 . . 122.2(2) ?
    C13 C12 C17 . . 119.37(19) ?
    C13 C12 S1 . . 119.06(15) ?
    C17 C12 S1 . . 121.53(16) ?
    C6 C5 S1 . . 111.33(13) ?
    C6 C5 H5A . . 109.4 ?
    S1 C5 H5A . . 109.4 ?
    C6 C5 H5B . . 109.4 ?
    S1 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C7 C6 C11 . . 119.25(19) ?
    C7 C6 C5 . . 120.33(18) ?
    C11 C6 C5 . . 120.42(18) ?
    C10 C11 C6 . . 120.1(2) ?
    C10 C11 H11 . . 119.9 ?
    C6 C11 H11 . . 119.9 ?
    C9 C10 C11 . . 120.4(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C10 C9 C8 . . 120.0(2) ?
    C10 C9 H9 . . 120.0 ?
    C8 C9 H9 . . 120.0 ?
    C15 C16 C17 . . 120.6(2) ?
    C15 C16 H16 . . 119.7 ?
    C17 C16 H16 . . 119.7 ?
    C16 C17 C12 . . 119.1(2) ?
    C16 C17 H17 . . 120.5 ?
    C12 C17 H17 . . 120.5 ?
    N4 C3 N2 . . 173.6(2) ?
    C8 C7 C6 . . 120.1(2) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C9 C8 C7 . . 120.1(2) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
data_Compound_2_CCDC
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     258.31
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.100(2)
_cell_length_b     11.365(2)
_cell_length_c     11.300(2)
_cell_angle_alpha     90
_cell_angle_beta     97.464(5)
_cell_angle_gamma     90
_cell_volume     1286.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2568
_cell_measurement_theta_min     2.5526
_cell_measurement_theta_max     22.4523
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     'Plate '
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.246
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.83
_exptl_absorpt_correction_T_max     0.95
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     13491
_diffrn_reflns_av_R_equivalents     0.0390
_diffrn_reflns_av_sigmaI/netI     0.0244
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     24.67
_diffrn_reflns_theta_full     24.67
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2180
_reflns_number_gt     1698
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0484
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_gt     0.0761
_refine_ls_wR_factor_ref     0.0847
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     2180
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0358P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.137
_refine_diff_density_min     -0.268
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2008, 7, 0, 0'
_computing_cell_refinement     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.34284(5) 0.47322(4) 0.12743(4) 0.05047(17) Uani d . 1 . .
    F F18 0.12948(13) 0.63513(11) 0.16614(12) 0.0783(4) Uani d . 1 . .
    N N2 0.40076(18) 0.36620(15) 0.05260(15) 0.0669(5) Uani d . 1 . .
    N N4 0.36314(19) 0.37798(18) -0.16644(17) 0.0754(5) Uani d . 1 . .
    C C15 -0.0887(3) 0.3848(3) 0.1554(2) 0.0872(8) Uani d . 1 . .
    H H15 -0.1777 0.367 0.1603 0.105 Uiso calc R 1 . .
    C C14 -0.0465(2) 0.5001(2) 0.16551(18) 0.0736(7) Uani d . 1 . .
    H H14 -0.1054 0.5605 0.1776 0.088 Uiso calc R 1 . .
    C C13 0.0851(2) 0.52274(19) 0.15715(16) 0.0551(5) Uani d . 1 . .
    C C12 0.17434(18) 0.43502(17) 0.14101(15) 0.0488(5) Uani d . 1 . .
    C C5 0.42218(19) 0.43316(18) 0.27464(16) 0.0569(5) Uani d . 1 . .
    H H5A 0.4127 0.3492 0.2862 0.068 Uiso calc R 1 . .
    H H5B 0.5168 0.451 0.2812 0.068 Uiso calc R 1 . .
    C C6 0.36170(18) 0.49808(17) 0.36994(16) 0.0505(5) Uani d . 1 . .
    C C11 0.3991(2) 0.61265(19) 0.39841(18) 0.0607(5) Uani d . 1 . .
    H H11 0.4621 0.6499 0.3583 0.073 Uiso calc R 1 . .
    C C10 0.3432(2) 0.6717(2) 0.4860(2) 0.0713(6) Uani d . 1 . .
    H H10 0.3684 0.7489 0.5045 0.086 Uiso calc R 1 . .
    C C9 0.2509(3) 0.6177(2) 0.5457(2) 0.0757(7) Uani d . 1 . .
    H H9 0.2137 0.658 0.6049 0.091 Uiso calc R 1 . .
    C C16 -0.0016(3) 0.2960(2) 0.1382(2) 0.0843(7) Uani d . 1 . .
    H H16 -0.0321 0.2188 0.1311 0.101 Uiso calc R 1 . .
    C C17 0.1307(2) 0.31998(19) 0.13135(18) 0.0671(6) Uani d . 1 . .
    H H17 0.1899 0.2595 0.1204 0.081 Uiso calc R 1 . .
    C C3 0.37844(18) 0.37816(17) -0.0639(2) 0.0552(5) Uani d . 1 . .
    C C7 0.2681(2) 0.44387(18) 0.43051(18) 0.0611(5) Uani d . 1 . .
    H H7 0.2421 0.3669 0.412 0.073 Uiso calc R 1 . .
    C C8 0.2133(2) 0.5038(2) 0.5185(2) 0.0754(7) Uani d . 1 . .
    H H8 0.1506 0.4671 0.5594 0.09 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N2 . 1.6325(16) ?
    S1 C12 . 1.7822(19) ?
    S1 C5 . 1.8084(19) ?
    F18 C13 . 1.353(2) ?
    N2 C3 . 1.313(3) ?
    N4 C3 . 1.149(3) ?
    C15 C16 . 1.369(4) ?
    C15 C14 . 1.378(4) ?
    C15 H15 . 0.93 ?
    C14 C13 . 1.369(3) ?
    C14 H14 . 0.93 ?
    C13 C12 . 1.372(3) ?
    C12 C17 . 1.380(3) ?
    C5 C6 . 1.499(3) ?
    C5 H5A . 0.97 ?
    C5 H5B . 0.97 ?
    C6 C7 . 1.382(3) ?
    C6 C11 . 1.382(3) ?
    C11 C10 . 1.376(3) ?
    C11 H11 . 0.93 ?
    C10 C9 . 1.365(3) ?
    C10 H10 . 0.93 ?
    C9 C8 . 1.372(3) ?
    C9 H9 . 0.93 ?
    C16 C17 . 1.375(3) ?
    C16 H16 . 0.93 ?
    C17 H17 . 0.93 ?
    C7 C8 . 1.380(3) ?
    C7 H7 . 0.93 ?
    C8 H8 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 S1 C12 . . 105.87(9) ?
    N2 S1 C5 . . 98.23(9) ?
    C12 S1 C5 . . 99.99(9) ?
    C3 N2 S1 . . 114.56(14) ?
    C16 C15 C14 . . 121.0(2) ?
    C16 C15 H15 . . 119.5 ?
    C14 C15 H15 . . 119.5 ?
    C13 C14 C15 . . 117.8(2) ?
    C13 C14 H14 . . 121.1 ?
    C15 C14 H14 . . 121.1 ?
    F18 C13 C14 . . 119.2(2) ?
    F18 C13 C12 . . 118.60(18) ?
    C14 C13 C12 . . 122.2(2) ?
    C13 C12 C17 . . 119.37(19) ?
    C13 C12 S1 . . 119.06(15) ?
    C17 C12 S1 . . 121.53(16) ?
    C6 C5 S1 . . 111.33(13) ?
    C6 C5 H5A . . 109.4 ?
    S1 C5 H5A . . 109.4 ?
    C6 C5 H5B . . 109.4 ?
    S1 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C7 C6 C11 . . 119.25(19) ?
    C7 C6 C5 . . 120.33(18) ?
    C11 C6 C5 . . 120.42(18) ?
    C10 C11 C6 . . 120.1(2) ?
    C10 C11 H11 . . 119.9 ?
    C6 C11 H11 . . 119.9 ?
    C9 C10 C11 . . 120.4(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C10 C9 C8 . . 120.0(2) ?
    C10 C9 H9 . . 120.0 ?
    C8 C9 H9 . . 120.0 ?
    C15 C16 C17 . . 120.6(2) ?
    C15 C16 H16 . . 119.7 ?
    C17 C16 H16 . . 119.7 ?
    C16 C17 C12 . . 119.1(2) ?
    C16 C17 H17 . . 120.5 ?
    C12 C17 H17 . . 120.5 ?
    N4 C3 N2 . . 173.6(2) ?
    C8 C7 C6 . . 120.1(2) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C9 C8 C7 . . 120.1(2) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
data_Compound_2_Run_1
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_weight     258.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.1414(9)
_cell_length_b     11.3865(9)
_cell_length_c     11.3289(9)
_cell_angle_alpha     90.00
_cell_angle_beta     97.400(3)
_cell_angle_gamma     90.00
_cell_volume     1297.31(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2425
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     22.39
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.244
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8878
_exptl_absorpt_correction_T_max     0.9305
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8247
_diffrn_reflns_av_R_equivalents     0.0289
_diffrn_reflns_av_sigmaI/netI     0.0276
_diffrn_reflns_theta_min     2.02
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2277
_reflns_number_gt     1729
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0578
_refine_ls_R_factor_gt     0.0384
_refine_ls_wR_factor_gt     0.1161
_refine_ls_wR_factor_ref     0.1469
_refine_ls_goodness_of_fit_ref     1.080
_refine_ls_restrained_S_all     1.080
_refine_ls_number_reflns     2277
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0954P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.012
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.274
_refine_diff_density_min     -0.347
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.84242(6) 0.47328(5) 0.12753(5) 0.0501(3) Uani d . 1 . .
    F F1 0.62909(17) 0.63504(13) 0.16615(16) 0.0791(5) Uani d . 1 . .
    N N1 0.9003(2) 0.36623(18) 0.05259(19) 0.0672(6) Uani d . 1 . .
    N N2 0.8633(2) 0.3788(2) -0.1664(2) 0.0768(7) Uani d . 1 . .
    C C1 0.4123(3) 0.3846(4) 0.1554(3) 0.0890(11) Uani d . 1 . .
    H H1 0.3236 0.3667 0.1603 0.107 Uiso calc R 1 . .
    C C2 0.4537(3) 0.5002(3) 0.1658(3) 0.0734(8) Uani d . 1 . .
    H H2 0.3948 0.5602 0.1780 0.088 Uiso calc R 1 . .
    C C3 0.5851(2) 0.5228(2) 0.1575(2) 0.0552(6) Uani d . 1 . .
    C C4 0.6739(2) 0.4351(2) 0.14091(19) 0.0472(6) Uani d . 1 . .
    C C5 0.9219(2) 0.4334(2) 0.2749(2) 0.0574(6) Uani d . 1 . .
    H H5A 0.9126 0.3496 0.2865 0.069 Uiso calc R 1 . .
    H H5B 1.0160 0.4513 0.2812 0.069 Uiso calc R 1 . .
    C C6 0.8616(2) 0.4984(2) 0.3702(2) 0.0503(6) Uani d . 1 . .
    C C7 0.7683(3) 0.4444(2) 0.4306(2) 0.0612(7) Uani d . 1 . .
    H H7 0.7426 0.3674 0.4122 0.073 Uiso calc R 1 . .
    C C8 0.7129(3) 0.5044(3) 0.5183(3) 0.0761(8) Uani d . 1 . .
    H H8 0.6500 0.4680 0.5588 0.091 Uiso calc R 1 . .
    C C9 0.7513(3) 0.6181(3) 0.5455(3) 0.0756(9) Uani d . 1 . .
    H H9 0.7144 0.6584 0.6047 0.091 Uiso calc R 1 . .
    C C10 0.4990(3) 0.2956(3) 0.1381(3) 0.0848(9) Uani d . 1 . .
    H H10 0.4687 0.2185 0.1308 0.102 Uiso calc R 1 . .
    C C11 0.6298(3) 0.3199(2) 0.1317(2) 0.0654(7) Uani d . 1 . .
    H H11 0.6889 0.2595 0.1211 0.078 Uiso calc R 1 . .
    C C12 0.8778(2) 0.3785(2) -0.0636(3) 0.0554(6) Uani d . 1 . .
    C C13 0.8433(3) 0.6722(3) 0.4860(3) 0.0721(8) Uani d . 1 . .
    H H13 0.8683 0.7492 0.5047 0.086 Uiso calc R 1 . .
    C C14 0.8993(3) 0.6133(2) 0.3986(2) 0.0602(7) Uani d . 1 . .
    H H14 0.9621 0.6504 0.3586 0.072 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.637(2) ?
    S1 C4 . 1.788(2) ?
    S1 C5 . 1.816(2) ?
    F1 C3 . 1.353(3) ?
    N1 C12 . 1.315(4) ?
    N2 C12 . 1.155(3) ?
    C1 C10 . 1.373(5) ?
    C1 C2 . 1.381(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.373(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.374(3) ?
    C4 C11 . 1.386(3) ?
    C5 C6 . 1.502(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.381(3) ?
    C6 C14 . 1.389(3) ?
    C7 C8 . 1.383(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.375(4) ?
    C8 H8 . 0.9300 ?
    C9 C13 . 1.366(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.366(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C13 C14 . 1.377(4) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C4 . . 105.87(12) ?
    N1 S1 C5 . . 98.30(11) ?
    C4 S1 C5 . . 100.20(11) ?
    C12 N1 S1 . . 114.37(17) ?
    C10 C1 C2 . . 121.4(3) ?
    C10 C1 H1 . . 119.3 ?
    C2 C1 H1 . . 119.3 ?
    C3 C2 C1 . . 117.4(3) ?
    C3 C2 H2 . . 121.3 ?
    C1 C2 H2 . . 121.3 ?
    F1 C3 C2 . . 119.1(2) ?
    F1 C3 C4 . . 118.7(2) ?
    C2 C3 C4 . . 122.1(3) ?
    C3 C4 C11 . . 119.2(2) ?
    C3 C4 S1 . . 119.03(18) ?
    C11 C4 S1 . . 121.76(19) ?
    C6 C5 S1 . . 111.38(16) ?
    C6 C5 H5A . . 109.4 ?
    S1 C5 H5A . . 109.4 ?
    C6 C5 H5B . . 109.4 ?
    S1 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C7 C6 C14 . . 119.3(2) ?
    C7 C6 C5 . . 120.3(2) ?
    C14 C6 C5 . . 120.3(2) ?
    C6 C7 C8 . . 120.2(3) ?
    C6 C7 H7 . . 119.9 ?
    C8 C7 H7 . . 119.9 ?
    C9 C8 C7 . . 119.8(3) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C13 C9 C8 . . 120.4(3) ?
    C13 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C11 C10 C1 . . 120.2(3) ?
    C11 C10 H10 . . 119.9 ?
    C1 C10 H10 . . 119.9 ?
    C10 C11 C4 . . 119.6(3) ?
    C10 C11 H11 . . 120.2 ?
    C4 C11 H11 . . 120.2 ?
    N2 C12 N1 . . 173.4(3) ?
    C9 C13 C14 . . 120.4(3) ?
    C9 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C13 C14 C6 . . 119.9(3) ?
    C13 C14 H14 . . 120.0 ?
    C6 C14 H14 . . 120.0 ?
data_Compound_2_Run_2
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_weight     258.32
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.1385(11)
_cell_length_b     11.3898(11)
_cell_length_c     11.3325(12)
_cell_angle_alpha     90.00
_cell_angle_beta     97.467(4)
_cell_angle_gamma     90.00
_cell_volume     1297.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4016
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     24.73
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.244
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9109
_exptl_absorpt_correction_T_max     0.9667
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12421
_diffrn_reflns_av_R_equivalents     0.0409
_diffrn_reflns_av_sigmaI/netI     0.0274
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.06
_diffrn_reflns_theta_full     25.06
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2291
_reflns_number_gt     1818
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0497
_refine_ls_R_factor_gt     0.0346
_refine_ls_wR_factor_gt     0.0926
_refine_ls_wR_factor_ref     0.1149
_refine_ls_goodness_of_fit_ref     1.089
_refine_ls_restrained_S_all     1.089
_refine_ls_number_reflns     2291
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0589P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.015
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.258
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.84219(5) 0.52676(5) 0.12735(5) 0.0491(2) Uani d . 1 . .
    F F1 0.62902(15) 0.36501(12) 0.16636(14) 0.0786(4) Uani d . 1 . .
    N N1 0.8998(2) 0.63377(17) 0.05248(17) 0.0666(6) Uani d . 1 . .
    N N2 0.8630(2) 0.6212(2) -0.1664(2) 0.0765(6) Uani d . 1 . .
    C C1 0.7513(3) 0.3823(3) 0.5455(2) 0.0763(8) Uani d . 1 . .
    H H1 0.7143 0.3420 0.6046 0.092 Uiso calc R 1 . .
    C C2 0.7133(3) 0.4959(3) 0.5183(2) 0.0755(8) Uani d . 1 . .
    H H2 0.6508 0.5325 0.5590 0.091 Uiso calc R 1 . .
    C C3 0.7682(2) 0.5557(2) 0.4305(2) 0.0621(6) Uani d . 1 . .
    H H3 0.7423 0.6326 0.4120 0.075 Uiso calc R 1 . .
    C C4 0.8617(2) 0.50161(19) 0.36974(18) 0.0507(5) Uani d . 1 . .
    C C5 0.9215(2) 0.5668(2) 0.27466(19) 0.0562(6) Uani d . 1 . .
    H H5A 1.0158 0.5493 0.2810 0.067 Uiso calc R 1 . .
    H H5B 0.9117 0.6506 0.2863 0.067 Uiso calc R 1 . .
    C C6 0.6735(2) 0.56475(19) 0.14085(17) 0.0473(5) Uani d . 1 . .
    C C7 0.6298(3) 0.6799(2) 0.1313(2) 0.0662(6) Uani d . 1 . .
    H H7 0.6889 0.7401 0.1204 0.079 Uiso calc R 1 . .
    C C8 0.4987(3) 0.7043(3) 0.1381(2) 0.0848(9) Uani d . 1 . .
    H H8 0.4685 0.7814 0.1311 0.102 Uiso calc R 1 . .
    C C9 0.4118(3) 0.6152(4) 0.1554(2) 0.0883(10) Uani d . 1 . .
    H H9 0.3231 0.6329 0.1602 0.106 Uiso calc R 1 . .
    C C10 0.8438(3) 0.3280(2) 0.4859(2) 0.0715(7) Uani d . 1 . .
    H H10 0.8691 0.2511 0.5047 0.086 Uiso calc R 1 . .
    C C11 0.8995(2) 0.3871(2) 0.3980(2) 0.0595(6) Uani d . 1 . .
    H H11 0.9622 0.3500 0.3578 0.071 Uiso calc R 1 . .
    C C12 0.5850(2) 0.4772(2) 0.15752(19) 0.0553(6) Uani d . 1 . .
    C C13 0.4537(3) 0.5002(3) 0.1656(2) 0.0736(8) Uani d . 1 . .
    H H13 0.3948 0.4400 0.1776 0.088 Uiso calc R 1 . .
    C C14 0.8776(2) 0.62124(19) -0.0639(2) 0.0548(6) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.6356(19) ?
    S1 C6 . 1.789(2) ?
    S1 C5 . 1.815(2) ?
    F1 C12 . 1.353(3) ?
    N1 C14 . 1.316(3) ?
    N2 C14 . 1.152(3) ?
    C1 C10 . 1.372(4) ?
    C1 C2 . 1.374(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.381(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.387(3) ?
    C3 H3 . 0.9300 ?
    C4 C11 . 1.385(3) ?
    C4 C5 . 1.500(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C12 . 1.372(3) ?
    C6 C7 . 1.384(3) ?
    C7 C8 . 1.370(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.375(4) ?
    C8 H8 . 0.9300 ?
    C9 C13 . 1.378(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.382(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.371(4) ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C6 . . 105.89(11) ?
    N1 S1 C5 . . 98.31(10) ?
    C6 S1 C5 . . 100.06(10) ?
    C14 N1 S1 . . 114.38(16) ?
    C10 C1 C2 . . 120.2(2) ?
    C10 C1 H1 . . 119.9 ?
    C2 C1 H1 . . 119.9 ?
    C1 C2 C3 . . 119.9(3) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C11 C4 C3 . . 119.4(2) ?
    C11 C4 C5 . . 120.4(2) ?
    C3 C4 C5 . . 120.2(2) ?
    C4 C5 S1 . . 111.37(15) ?
    C4 C5 H5A . . 109.4 ?
    S1 C5 H5A . . 109.4 ?
    C4 C5 H5B . . 109.4 ?
    S1 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C12 C6 C7 . . 119.4(2) ?
    C12 C6 S1 . . 119.06(17) ?
    C7 C6 S1 . . 121.50(18) ?
    C8 C7 C6 . . 119.4(3) ?
    C8 C7 H7 . . 120.3 ?
    C6 C7 H7 . . 120.3 ?
    C7 C8 C9 . . 120.2(3) ?
    C7 C8 H8 . . 119.9 ?
    C9 C8 H8 . . 119.9 ?
    C8 C9 C13 . . 121.2(3) ?
    C8 C9 H9 . . 119.4 ?
    C13 C9 H9 . . 119.4 ?
    C1 C10 C11 . . 120.3(2) ?
    C1 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C10 C11 C4 . . 119.9(2) ?
    C10 C11 H11 . . 120.1 ?
    C4 C11 H11 . . 120.0 ?
    F1 C12 C13 . . 119.3(2) ?
    F1 C12 C6 . . 118.8(2) ?
    C13 C12 C6 . . 121.9(2) ?
    C12 C13 C9 . . 117.9(3) ?
    C12 C13 H13 . . 121.1 ?
    C9 C13 H13 . . 121.1 ?
    N2 C14 N1 . . 173.3(3) ?
data_Compound_2_Run_3
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_weight     258.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.1375(11)
_cell_length_b     11.3871(14)
_cell_length_c     11.3412(14)
_cell_angle_alpha     90.00
_cell_angle_beta     97.482(4)
_cell_angle_gamma     90.00
_cell_volume     1298.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2278
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     22.71
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.322
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.244
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8879
_exptl_absorpt_correction_T_max     0.9879
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8248
_diffrn_reflns_av_R_equivalents     0.0431
_diffrn_reflns_av_sigmaI/netI     0.0391
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2275
_reflns_number_gt     1692
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0582
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.0980
_refine_ls_wR_factor_ref     0.1222
_refine_ls_goodness_of_fit_ref     1.087
_refine_ls_restrained_S_all     1.087
_refine_ls_number_reflns     2275
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0637P)²+0.1168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.233
_refine_diff_density_min     -0.229
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.34243(6) 0.02671(5) 0.12747(5) 0.0493(2) Uani d . 1 . .
    F F1 0.12900(15) -0.13483(13) 0.16612(15) 0.0781(5) Uani d . 1 . .
    N N1 0.4002(2) 0.13378(19) 0.05241(19) 0.0665(6) Uani d . 1 . .
    N N2 0.3629(2) 0.1214(2) -0.1664(2) 0.0760(7) Uani d . 1 . .
    C C1 0.2510(3) -0.1177(3) 0.5455(2) 0.0748(8) Uani d . 1 . .
    H H1 0.2138 -0.1579 0.6044 0.090 Uiso calc R 1 . .
    C C2 0.3433(3) -0.1720(3) 0.4858(3) 0.0711(8) Uani d . 1 . .
    H H2 0.3685 -0.2491 0.5044 0.085 Uiso calc R 1 . .
    C C3 0.3991(2) -0.1129(2) 0.3983(2) 0.0606(7) Uani d . 1 . .
    H H3 0.4618 -0.1501 0.3584 0.073 Uiso calc R 1 . .
    C C4 0.3618(2) 0.0016(2) 0.3699(2) 0.0501(6) Uani d . 1 . .
    C C5 0.4216(2) 0.0667(2) 0.2746(2) 0.0557(6) Uani d . 1 . .
    H H5A 0.5159 0.0491 0.2810 0.067 Uiso calc R 1 . .
    H H5B 0.4120 0.1505 0.2861 0.067 Uiso calc R 1 . .
    C C6 0.1739(2) 0.0651(2) 0.14121(19) 0.0466(5) Uani d . 1 . .
    C C7 0.1303(3) 0.1801(2) 0.1314(2) 0.0657(7) Uani d . 1 . .
    H H7 0.1893 0.2404 0.1201 0.079 Uiso calc R 1 . .
    C C8 -0.0010(3) 0.2043(3) 0.1384(3) 0.0836(9) Uani d . 1 . .
    H H8 -0.0313 0.2814 0.1316 0.100 Uiso calc R 1 . .
    C C9 -0.0877(3) 0.1156(4) 0.1554(3) 0.0874(11) Uani d . 1 . .
    H H9 -0.1764 0.1336 0.1602 0.105 Uiso calc R 1 . .
    C C10 0.2683(3) 0.0559(2) 0.4306(2) 0.0613(7) Uani d . 1 . .
    H H10 0.2424 0.1328 0.4121 0.074 Uiso calc R 1 . .
    C C11 0.2135(3) -0.0039(3) 0.5182(3) 0.0746(8) Uani d . 1 . .
    H H11 0.1510 0.0329 0.5588 0.089 Uiso calc R 1 . .
    C C12 0.0848(2) -0.0227(2) 0.1578(2) 0.0537(6) Uani d . 1 . .
    C C13 -0.0462(3) -0.0002(3) 0.1656(2) 0.0737(8) Uani d . 1 . .
    H H13 -0.1052 -0.0603 0.1773 0.088 Uiso calc R 1 . .
    C C14 0.3779(2) 0.1213(2) -0.0639(3) 0.0545(6) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.638(2) ?
    S1 C6 . 1.790(2) ?
    S1 C5 . 1.813(2) ?
    F1 C12 . 1.353(3) ?
    N1 C14 . 1.317(3) ?
    N2 C14 . 1.152(3) ?
    C1 C2 . 1.371(4) ?
    C1 C11 . 1.375(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(3) ?
    C3 H3 . 0.9300 ?
    C4 C10 . 1.387(3) ?
    C4 C5 . 1.502(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C12 . 1.376(3) ?
    C6 C7 . 1.382(3) ?
    C7 C8 . 1.371(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.369(5) ?
    C8 H8 . 0.9300 ?
    C9 C13 . 1.384(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.379(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.367(4) ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C6 . . 105.85(12) ?
    N1 S1 C5 . . 98.39(11) ?
    C6 S1 C5 . . 99.90(11) ?
    C14 N1 S1 . . 114.45(17) ?
    C2 C1 C11 . . 120.0(3) ?
    C2 C1 H1 . . 120.0 ?
    C11 C1 H1 . . 120.0 ?
    C1 C2 C3 . . 120.3(3) ?
    C1 C2 H2 . . 119.9 ?
    C3 C2 H2 . . 119.9 ?
    C2 C3 C4 . . 120.2(3) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C10 . . 119.2(2) ?
    C3 C4 C5 . . 120.6(2) ?
    C10 C4 C5 . . 120.2(2) ?
    C4 C5 S1 . . 111.51(16) ?
    C4 C5 H5A . . 109.3 ?
    S1 C5 H5A . . 109.3 ?
    C4 C5 H5B . . 109.3 ?
    S1 C5 H5B . . 109.3 ?
    H5A C5 H5B . . 108.0 ?
    C12 C6 C7 . . 119.4(2) ?
    C12 C6 S1 . . 119.00(18) ?
    C7 C6 S1 . . 121.57(19) ?
    C8 C7 C6 . . 119.2(3) ?
    C8 C7 H7 . . 120.4 ?
    C6 C7 H7 . . 120.4 ?
    C9 C8 C7 . . 120.4(3) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8 C9 C13 . . 121.4(3) ?
    C8 C9 H9 . . 119.3 ?
    C13 C9 H9 . . 119.3 ?
    C11 C10 C4 . . 120.2(3) ?
    C11 C10 H10 . . 119.9 ?
    C4 C10 H10 . . 119.9 ?
    C1 C11 C10 . . 120.1(3) ?
    C1 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    F1 C12 C13 . . 119.2(2) ?
    F1 C12 C6 . . 118.6(2) ?
    C13 C12 C6 . . 122.2(3) ?
    C12 C13 C9 . . 117.4(3) ?
    C12 C13 H13 . . 121.3 ?
    C9 C13 H13 . . 121.3 ?
    N2 C14 N1 . . 173.3(3) ?
data_Compound_2_Run_4
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 S'
_chemical_formula_sum     'C14 H11 F N2 S'
_chemical_formula_weight     258.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.137(3)
_cell_length_b     11.413(4)
_cell_length_c     11.345(3)
_cell_angle_alpha     90.00
_cell_angle_beta     97.465(11)
_cell_angle_gamma     90.00
_cell_volume     1301.5(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2021
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     22.36
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.318
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.243
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7932
_exptl_absorpt_correction_T_max     0.8882
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8133
_diffrn_reflns_av_R_equivalents     0.0433
_diffrn_reflns_av_sigmaI/netI     0.0424
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2277
_reflns_number_gt     1626
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0680
_refine_ls_R_factor_gt     0.0397
_refine_ls_wR_factor_gt     0.0967
_refine_ls_wR_factor_ref     0.1252
_refine_ls_goodness_of_fit_ref     1.093
_refine_ls_restrained_S_all     1.093
_refine_ls_number_reflns     2277
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0586P)²+0.1803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.016
_refine_ls_shift/su_mean     0.003
_refine_diff_density_max     0.215
_refine_diff_density_min     -0.181
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.84217(6) 0.47329(6) 0.12755(6) 0.0501(2) Uani d . 1 . .
    F F1 0.62881(17) 0.63496(16) 0.16605(16) 0.0786(5) Uani d . 1 . .
    N N1 0.8999(2) 0.3662(2) 0.0527(2) 0.0667(7) Uani d . 1 . .
    N N2 0.8629(3) 0.3789(3) -0.1664(2) 0.0767(8) Uani d . 1 . .
    C C1 0.4122(4) 0.3848(5) 0.1552(3) 0.0890(12) Uani d . 1 . .
    H H1 0.3233 0.3673 0.1596 0.107 Uiso calc R 1 . .
    C C2 0.4545(3) 0.5003(3) 0.1657(3) 0.0741(9) Uani d . 1 . .
    H H2 0.3958 0.5604 0.1779 0.089 Uiso calc R 1 . .
    C C3 0.5852(3) 0.5227(3) 0.1576(2) 0.0548(7) Uani d . 1 . .
    C C4 0.6739(2) 0.4349(2) 0.1410(2) 0.0471(6) Uani d . 1 . .
    C C5 0.9213(3) 0.4330(3) 0.2747(2) 0.0570(7) Uani d . 1 . .
    H H5A 0.9113 0.3494 0.2863 0.068 Uiso calc R 1 . .
    H H5B 1.0157 0.4503 0.2811 0.068 Uiso calc R 1 . .
    C C6 0.8615(2) 0.4983(2) 0.3700(2) 0.0506(7) Uani d . 1 . .
    C C7 0.7679(3) 0.4444(3) 0.4306(2) 0.0612(8) Uani d . 1 . .
    H H7 0.7418 0.3677 0.4121 0.073 Uiso calc R 1 . .
    C C8 0.7131(3) 0.5043(3) 0.5184(3) 0.0757(9) Uani d . 1 . .
    H H8 0.6508 0.4677 0.5593 0.091 Uiso calc R 1 . .
    C C9 0.7508(3) 0.6176(3) 0.5452(3) 0.0739(9) Uani d . 1 . .
    H H9 0.7133 0.6578 0.6040 0.089 Uiso calc R 1 . .
    C C10 0.4986(4) 0.2960(4) 0.1385(3) 0.0851(11) Uani d . 1 . .
    H H10 0.4681 0.2192 0.1317 0.102 Uiso calc R 1 . .
    C C11 0.6294(3) 0.3198(3) 0.1316(2) 0.0671(8) Uani d . 1 . .
    H H11 0.6882 0.2593 0.1208 0.081 Uiso calc R 1 . .
    C C12 0.8775(2) 0.3789(2) -0.0639(3) 0.0546(7) Uani d . 1 . .
    C C13 0.8433(3) 0.6721(3) 0.4860(3) 0.0717(9) Uani d . 1 . .
    H H13 0.8686 0.7488 0.5048 0.086 Uiso calc R 1 . .
    C C14 0.8988(3) 0.6127(3) 0.3982(2) 0.0614(8) Uani d . 1 . .
    H H14 0.9614 0.6498 0.3581 0.074 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.639(2) ?
    S1 C4 . 1.787(3) ?
    S1 C5 . 1.815(3) ?
    F1 C3 . 1.355(3) ?
    N1 C12 . 1.320(4) ?
    N2 C12 . 1.153(3) ?
    C1 C10 . 1.369(5) ?
    C1 C2 . 1.387(5) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.364(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.376(4) ?
    C4 C11 . 1.389(4) ?
    C5 C6 . 1.504(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C14 . 1.385(4) ?
    C6 C7 . 1.386(4) ?
    C7 C8 . 1.383(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.372(5) ?
    C8 H8 . 0.9300 ?
    C9 C13 . 1.371(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.365(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C13 C14 . 1.383(4) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C4 . . 105.67(13) ?
    N1 S1 C5 . . 98.21(13) ?
    C4 S1 C5 . . 99.92(12) ?
    C12 N1 S1 . . 114.27(19) ?
    C10 C1 C2 . . 121.3(3) ?
    C10 C1 H1 . . 119.4 ?
    C2 C1 H1 . . 119.4 ?
    C3 C2 C1 . . 117.7(3) ?
    C3 C2 H2 . . 121.2 ?
    C1 C2 H2 . . 121.2 ?
    F1 C3 C2 . . 118.9(3) ?
    F1 C3 C4 . . 119.1(2) ?
    C2 C3 C4 . . 122.0(3) ?
    C3 C4 C11 . . 119.2(3) ?
    C3 C4 S1 . . 118.7(2) ?
    C11 C4 S1 . . 122.0(2) ?
    C6 C5 S1 . . 111.34(18) ?
    C6 C5 H5A . . 109.4 ?
    S1 C5 H5A . . 109.4 ?
    C6 C5 H5B . . 109.4 ?
    S1 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C14 C6 C7 . . 119.2(3) ?
    C14 C6 C5 . . 120.7(2) ?
    C7 C6 C5 . . 120.1(3) ?
    C8 C7 C6 . . 120.2(3) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
    C9 C8 C7 . . 120.0(3) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C13 C9 C8 . . 120.5(3) ?
    C13 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C11 C10 C1 . . 120.3(3) ?
    C11 C10 H10 . . 119.8 ?
    C1 C10 H10 . . 119.8 ?
    C10 C11 C4 . . 119.5(3) ?
    C10 C11 H11 . . 120.3 ?
    C4 C11 H11 . . 120.3 ?
    N2 C12 N1 . . 173.3(3) ?
    C9 C13 C14 . . 119.9(3) ?
    C9 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C13 C14 C6 . . 120.2(3) ?
    C13 C14 H14 . . 119.9 ?
    C6 C14 H14 . . 119.9 ?
data_Compound_3_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H20 Cl2 N2 Pd'
_chemical_formula_sum     'C17 H20 Cl2 N2 Pd'
_chemical_formula_weight     429.65
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.356(2)
_cell_length_b     9.9295(19)
_cell_length_c     19.357(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.470(7)
_cell_angle_gamma     90.00
_cell_volume     1798.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8388
_cell_measurement_theta_min     2.94
_cell_measurement_theta_max     25.15
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.587
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     1.326
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6539
_exptl_absorpt_correction_T_max     0.6996
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16537
_diffrn_reflns_av_R_equivalents     0.0660
_diffrn_reflns_av_sigmaI/netI     0.0457
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.23
_diffrn_reflns_theta_full     25.23
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3229
_reflns_number_gt     2821
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0462
_refine_ls_R_factor_gt     0.0388
_refine_ls_wR_factor_gt     0.1083
_refine_ls_wR_factor_ref     0.1210
_refine_ls_goodness_of_fit_ref     1.185
_refine_ls_restrained_S_all     1.185
_refine_ls_number_reflns     3229
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0717P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.755
_refine_diff_density_min     -1.666
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Pd' 'Pd' -0.9988 1.0072
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Pd Pd1 0.34165(3) 0.36794(3) 0.474015(13) 0.03696(15) Uani d . 1 . .
    Cl Cl2 0.33207(12) 0.48746(11) 0.37305(5) 0.0569(3) Uani d . 1 . .
    Cl Cl3 0.39048(14) 0.17596(12) 0.41288(6) 0.0700(3) Uani d . 1 . .
    N N17 0.2901(3) 0.5254(3) 0.53575(14) 0.0362(6) Uani d . 1 . .
    N N4 0.3513(3) 0.2777(3) 0.56776(16) 0.0421(7) Uani d . 1 . .
    C C18 0.2724(4) 0.6643(4) 0.5106(2) 0.0445(8) Uani d . 1 . .
    H H18A 0.3438 0.6818 0.4757 0.053 Uiso calc R 1 . .
    H H18B 0.2899 0.7259 0.5487 0.053 Uiso calc R 1 . .
    C C19 0.1262(4) 0.6928(4) 0.4804(2) 0.0547(10) Uani d . 1 . .
    H H19A 0.0552 0.6929 0.5166 0.066 Uiso calc R 1 . .
    H H19B 0.1006 0.6238 0.4470 0.066 Uiso calc R 1 . .
    C C20 0.1306(5) 0.8321(5) 0.4448(3) 0.0648(12) Uani d . 1 . .
    H H20A 0.1659 0.8983 0.4776 0.078 Uiso calc R 1 . .
    H H20B 0.1973 0.8284 0.4067 0.078 Uiso calc R 1 . .
    C C21 -0.0122(6) 0.8767(5) 0.4179(3) 0.0791(16) Uani d . 1 . .
    H H21A -0.0780 0.8855 0.4561 0.095 Uiso calc R 1 . .
    H H21B -0.0499 0.8090 0.3865 0.095 Uiso calc R 1 . .
    C C22 -0.0016(8) 1.0109(6) 0.3802(4) 0.108(2) Uani d . 1 . .
    H H22A 0.0232 1.0805 0.4125 0.162 Uiso calc R 1 . .
    H H22B -0.0919 1.0316 0.3588 0.162 Uiso calc R 1 . .
    H H22C 0.0707 1.0051 0.3454 0.162 Uiso calc R 1 . .
    C C10 0.2750(3) 0.4970(3) 0.59983(18) 0.0370(7) Uani d . 1 . .
    C C11 0.2242(4) 0.5924(4) 0.65287(18) 0.0410(8) Uani d . 1 . .
    C C12 0.0778(5) 0.6088(4) 0.6635(2) 0.0566(10) Uani d . 1 . .
    H H12 0.0124 0.5602 0.6370 0.068 Uiso calc R 1 . .
    C C13 0.0306(6) 0.6968(5) 0.7130(3) 0.0755(14) Uani d . 1 . .
    H H13 -0.0670 0.7070 0.7199 0.091 Uiso calc R 1 . .
    C C14 0.1242(6) 0.7695(5) 0.7521(3) 0.0753(14) Uani d . 1 . .
    H H14 0.0903 0.8286 0.7854 0.090 Uiso calc R 1 . .
    C C15 0.2709(6) 0.7557(5) 0.7423(2) 0.0743(14) Uani d . 1 . .
    H H15 0.3350 0.8053 0.7690 0.089 Uiso calc R 1 . .
    C C16 0.3202(5) 0.6677(5) 0.6927(2) 0.0594(11) Uani d . 1 . .
    H H16 0.4180 0.6586 0.6858 0.071 Uiso calc R 1 . .
    C C9 0.3110(4) 0.3580(3) 0.6206(2) 0.0383(8) Uani d . 1 . .
    C C5 0.3924(5) 0.1505(4) 0.5816(3) 0.0610(12) Uani d . 1 . .
    H H5 0.4218 0.0951 0.5457 0.073 Uiso calc R 1 . .
    C C6 0.3918(5) 0.1009(5) 0.6483(3) 0.0715(14) Uani d . 1 . .
    H H6 0.4198 0.0125 0.6567 0.086 Uiso calc R 1 . .
    C C7 0.3506(5) 0.1803(5) 0.7016(2) 0.0628(12) Uani d . 1 . .
    H H7 0.3498 0.1470 0.7465 0.075 Uiso calc R 1 . .
    C C8 0.3093(4) 0.3130(5) 0.6877(2) 0.0502(9) Uani d . 1 . .
    H H8 0.2811 0.3698 0.7233 0.060 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Pd1 N4 . 2.025(3) ?
    Pd1 N17 . 2.028(3) ?
    Pd1 Cl2 . 2.2875(10) ?
    Pd1 Cl3 . 2.2917(11) ?
    N17 C10 . 1.281(5) ?
    N17 C18 . 1.471(5) ?
    N4 C5 . 1.347(5) ?
    N4 C9 . 1.353(5) ?
    C18 C19 . 1.511(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 C20 . 1.546(6) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 C21 . 1.498(7) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 C22 . 1.523(8) ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    C10 C9 . 1.476(5) ?
    C10 C11 . 1.478(5) ?
    C11 C12 . 1.396(5) ?
    C11 C16 . 1.397(6) ?
    C12 C13 . 1.372(6) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.360(8) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.393(7) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.380(6) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C9 C8 . 1.373(5) ?
    C5 C6 . 1.381(7) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.357(7) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.399(6) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N4 Pd1 N17 . . 79.75(11) ?
    N4 Pd1 Cl2 . . 175.01(9) ?
    N17 Pd1 Cl2 . . 95.49(8) ?
    N4 Pd1 Cl3 . . 94.99(9) ?
    N17 Pd1 Cl3 . . 174.12(8) ?
    Cl2 Pd1 Cl3 . . 89.83(4) ?
    C10 N17 C18 . . 120.9(3) ?
    C10 N17 Pd1 . . 115.4(2) ?
    C18 N17 Pd1 . . 123.7(2) ?
    C5 N4 C9 . . 118.9(3) ?
    C5 N4 Pd1 . . 127.1(3) ?
    C9 N4 Pd1 . . 114.0(2) ?
    N17 C18 C19 . . 113.8(3) ?
    N17 C18 H18A . . 108.8 ?
    C19 C18 H18A . . 108.8 ?
    N17 C18 H18B . . 108.8 ?
    C19 C18 H18B . . 108.8 ?
    H18A C18 H18B . . 107.7 ?
    C18 C19 C20 . . 108.2(3) ?
    C18 C19 H19A . . 110.1 ?
    C20 C19 H19A . . 110.1 ?
    C18 C19 H19B . . 110.1 ?
    C20 C19 H19B . . 110.1 ?
    H19A C19 H19B . . 108.4 ?
    C21 C20 C19 . . 113.1(4) ?
    C21 C20 H20A . . 109.0 ?
    C19 C20 H20A . . 109.0 ?
    C21 C20 H20B . . 109.0 ?
    C19 C20 H20B . . 109.0 ?
    H20A C20 H20B . . 107.8 ?
    C20 C21 C22 . . 111.4(5) ?
    C20 C21 H21A . . 109.4 ?
    C22 C21 H21A . . 109.4 ?
    C20 C21 H21B . . 109.4 ?
    C22 C21 H21B . . 109.4 ?
    H21A C21 H21B . . 108.0 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    N17 C10 C9 . . 116.3(3) ?
    N17 C10 C11 . . 124.8(3) ?
    C9 C10 C11 . . 118.9(3) ?
    C12 C11 C16 . . 118.9(4) ?
    C12 C11 C10 . . 119.9(3) ?
    C16 C11 C10 . . 121.2(3) ?
    C13 C12 C11 . . 119.9(4) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C14 C13 C12 . . 121.2(5) ?
    C14 C13 H13 . . 119.4 ?
    C12 C13 H13 . . 119.4 ?
    C13 C14 C15 . . 120.1(4) ?
    C13 C14 H14 . . 119.9 ?
    C15 C14 H14 . . 119.9 ?
    C16 C15 C14 . . 119.5(4) ?
    C16 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    C15 C16 C11 . . 120.4(4) ?
    C15 C16 H16 . . 119.8 ?
    C11 C16 H16 . . 119.8 ?
    N4 C9 C8 . . 121.9(3) ?
    N4 C9 C10 . . 114.1(3) ?
    C8 C9 C10 . . 123.9(3) ?
    N4 C5 C6 . . 121.1(4) ?
    N4 C5 H5 . . 119.4 ?
    C6 C5 H5 . . 119.4 ?
    C7 C6 C5 . . 120.5(4) ?
    C7 C6 H6 . . 119.8 ?
    C5 C6 H6 . . 119.8 ?
    C6 C7 C8 . . 118.7(4) ?
    C6 C7 H7 . . 120.6 ?
    C8 C7 H7 . . 120.6 ?
    C9 C8 C7 . . 118.9(4) ?
    C9 C8 H8 . . 120.6 ?
    C7 C8 H8 . . 120.6 ?
data_Compound_3_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H20 Cl2 N2 Pd'
_chemical_formula_sum     'C17 H20 Cl2 N2 Pd'
_chemical_formula_weight     429.65
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.356(2)
_cell_length_b     9.9295(19)
_cell_length_c     19.357(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.470(7)
_cell_angle_gamma     90.00
_cell_volume     1798.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8388
_cell_measurement_theta_min     2.94
_cell_measurement_theta_max     25.15
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.587
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     1.326
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.2196
_exptl_absorpt_correction_T_max     0.6996
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16537
_diffrn_reflns_av_R_equivalents     0.0660
_diffrn_reflns_av_sigmaI/netI     0.0457
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.23
_diffrn_reflns_theta_full     25.23
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3229
_reflns_number_gt     2821
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0460
_refine_ls_R_factor_gt     0.0387
_refine_ls_wR_factor_gt     0.1073
_refine_ls_wR_factor_ref     0.1204
_refine_ls_goodness_of_fit_ref     1.151
_refine_ls_restrained_S_all     1.151
_refine_ls_number_reflns     3229
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0723P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.011
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.755
_refine_diff_density_min     -1.658
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Pd' 'Pd' -0.9988 1.0072
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Pd Pd1 0.34165(3) 0.36794(3) 0.474015(13) 0.03692(15) Uani d . 1 . .
    Cl Cl1 0.33208(12) 0.48747(11) 0.37305(5) 0.0569(3) Uani d . 1 . .
    Cl Cl2 0.39048(14) 0.17595(12) 0.41289(7) 0.0699(3) Uani d . 1 . .
    N N1 0.3512(3) 0.2777(3) 0.56775(16) 0.0421(7) Uani d . 1 . .
    N N2 0.2902(3) 0.5254(3) 0.53575(14) 0.0362(6) Uani d . 1 . .
    C C1 0.3923(5) 0.1504(4) 0.5816(3) 0.0610(12) Uani d . 1 . .
    H H1 0.4214 0.0950 0.5456 0.073 Uiso calc R 1 . .
    C C2 0.3918(6) 0.1009(5) 0.6483(3) 0.0713(14) Uani d . 1 . .
    H H2 0.4200 0.0126 0.6567 0.086 Uiso calc R 1 . .
    C C3 0.3506(5) 0.1803(5) 0.7016(2) 0.0627(12) Uani d . 1 . .
    H H3 0.3499 0.1471 0.7465 0.075 Uiso calc R 1 . .
    C C4 0.3092(4) 0.3129(5) 0.6877(2) 0.0502(9) Uani d . 1 . .
    H H4 0.2809 0.3697 0.7233 0.060 Uiso calc R 1 . .
    C C5 0.3110(4) 0.3580(3) 0.6206(2) 0.0384(8) Uani d . 1 . .
    C C6 0.2750(3) 0.4970(3) 0.59986(18) 0.0371(7) Uani d . 1 . .
    C C7 0.2723(4) 0.6643(4) 0.5106(2) 0.0444(8) Uani d . 1 . .
    H H7A 0.3437 0.6819 0.4757 0.053 Uiso calc R 1 . .
    H H7B 0.2897 0.7259 0.5487 0.053 Uiso calc R 1 . .
    C C8 0.1262(4) 0.6928(4) 0.4804(2) 0.0546(10) Uani d . 1 . .
    H H8A 0.0552 0.6929 0.5166 0.066 Uiso calc R 1 . .
    H H8B 0.1007 0.6238 0.4470 0.066 Uiso calc R 1 . .
    C C9 0.1307(5) 0.8321(5) 0.4448(3) 0.0647(12) Uani d . 1 . .
    H H9A 0.1660 0.8983 0.4775 0.078 Uiso calc R 1 . .
    H H9B 0.1973 0.8284 0.4067 0.078 Uiso calc R 1 . .
    C C10 -0.0122(7) 0.8767(5) 0.4179(4) 0.0789(16) Uani d . 1 . .
    H H10A -0.0779 0.8855 0.4561 0.095 Uiso calc R 1 . .
    H H10B -0.0500 0.8090 0.3866 0.095 Uiso calc R 1 . .
    C C11 -0.0016(8) 1.0109(6) 0.3802(4) 0.108(2) Uani d . 1 . .
    H H11A 0.0236 1.0804 0.4125 0.162 Uiso calc R 1 . .
    H H11B -0.0921 1.0318 0.3590 0.162 Uiso calc R 1 . .
    H H11C 0.0703 1.0050 0.3452 0.162 Uiso calc R 1 . .
    C C12 0.2242(4) 0.5925(4) 0.65285(18) 0.0410(8) Uani d . 1 . .
    C C13 0.0778(5) 0.6087(4) 0.6635(3) 0.0566(11) Uani d . 1 . .
    H H13 0.0124 0.5600 0.6371 0.068 Uiso calc R 1 . .
    C C14 0.0307(6) 0.6968(6) 0.7130(3) 0.0757(15) Uani d . 1 . .
    H H14 -0.0670 0.7071 0.7199 0.091 Uiso calc R 1 . .
    C C15 0.1245(6) 0.7695(5) 0.7522(3) 0.0753(15) Uani d . 1 . .
    H H15 0.0906 0.8284 0.7856 0.090 Uiso calc R 1 . .
    C C16 0.2708(6) 0.7556(5) 0.7423(3) 0.0741(14) Uani d . 1 . .
    H H16 0.3349 0.8053 0.7690 0.089 Uiso calc R 1 . .
    C C17 0.3202(5) 0.6678(5) 0.6928(2) 0.0594(11) Uani d . 1 . .
    H H17 0.4180 0.6586 0.6859 0.071 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Pd1 N1 . 2.025(3) ?
    Pd1 N2 . 2.028(3) ?
    Pd1 Cl1 . 2.2876(11) ?
    Pd1 Cl2 . 2.2917(12) ?
    N1 C1 . 1.347(5) ?
    N1 C5 . 1.353(5) ?
    N2 C6 . 1.282(5) ?
    N2 C7 . 1.472(5) ?
    C1 C2 . 1.382(7) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.358(8) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.398(7) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.374(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.475(5) ?
    C6 C12 . 1.479(5) ?
    C7 C8 . 1.510(5) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.546(6) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.497(7) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.523(8) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.395(6) ?
    C12 C17 . 1.397(6) ?
    C13 C14 . 1.373(7) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.362(8) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.390(7) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.380(6) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 Pd1 N2 . . 79.76(12) ?
    N1 Pd1 Cl1 . . 175.01(9) ?
    N2 Pd1 Cl1 . . 95.49(8) ?
    N1 Pd1 Cl2 . . 94.99(9) ?
    N2 Pd1 Cl2 . . 174.12(9) ?
    Cl1 Pd1 Cl2 . . 89.83(4) ?
    C1 N1 C5 . . 118.9(4) ?
    C1 N1 Pd1 . . 127.1(3) ?
    C5 N1 Pd1 . . 114.0(2) ?
    C6 N2 C7 . . 120.9(3) ?
    C6 N2 Pd1 . . 115.4(2) ?
    C7 N2 Pd1 . . 123.7(2) ?
    N1 C1 C2 . . 121.1(4) ?
    N1 C1 H1 . . 119.4 ?
    C2 C1 H1 . . 119.4 ?
    C3 C2 C1 . . 120.5(4) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 118.7(4) ?
    C2 C3 H3 . . 120.6 ?
    C4 C3 H3 . . 120.6 ?
    C5 C4 C3 . . 118.9(4) ?
    C5 C4 H4 . . 120.6 ?
    C3 C4 H4 . . 120.6 ?
    N1 C5 C4 . . 121.9(3) ?
    N1 C5 C6 . . 114.2(3) ?
    C4 C5 C6 . . 123.9(4) ?
    N2 C6 C5 . . 116.3(3) ?
    N2 C6 C12 . . 124.7(3) ?
    C5 C6 C12 . . 119.0(3) ?
    N2 C7 C8 . . 113.8(3) ?
    N2 C7 H7A . . 108.8 ?
    C8 C7 H7A . . 108.8 ?
    N2 C7 H7B . . 108.8 ?
    C8 C7 H7B . . 108.8 ?
    H7A C7 H7B . . 107.7 ?
    C7 C8 C9 . . 108.2(4) ?
    C7 C8 H8A . . 110.1 ?
    C9 C8 H8A . . 110.1 ?
    C7 C8 H8B . . 110.1 ?
    C9 C8 H8B . . 110.1 ?
    H8A C8 H8B . . 108.4 ?
    C10 C9 C8 . . 113.1(4) ?
    C10 C9 H9A . . 109.0 ?
    C8 C9 H9A . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    C8 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    C9 C10 C11 . . 111.3(5) ?
    C9 C10 H10A . . 109.4 ?
    C11 C10 H10A . . 109.4 ?
    C9 C10 H10B . . 109.4 ?
    C11 C10 H10B . . 109.4 ?
    H10A C10 H10B . . 108.0 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C13 C12 C17 . . 119.0(4) ?
    C13 C12 C6 . . 119.9(3) ?
    C17 C12 C6 . . 121.2(3) ?
    C14 C13 C12 . . 119.8(4) ?
    C14 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
    C15 C14 C13 . . 121.1(5) ?
    C15 C14 H14 . . 119.4 ?
    C13 C14 H14 . . 119.5 ?
    C14 C15 C16 . . 120.1(4) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C17 C16 C15 . . 119.6(5) ?
    C17 C16 H16 . . 120.2 ?
    C15 C16 H16 . . 120.2 ?
    C16 C17 C12 . . 120.3(4) ?
    C16 C17 H17 . . 119.8 ?
    C12 C17 H17 . . 119.8 ?
data_Compound_4_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H18 Cl2 N2 Pd'
_chemical_formula_sum     'C16 H18 Cl2 N2 Pd'
_chemical_formula_weight     415.62
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.5305(11)
_cell_length_b     9.6211(14)
_cell_length_c     10.9880(16)
_cell_angle_alpha     72.593(4)
_cell_angle_beta     78.780(5)
_cell_angle_gamma     83.039(4)
_cell_volume     842.2(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4927
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     25.20
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.51
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.639
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     416
_exptl_absorpt_coefficient_mu     1.413
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.5326
_exptl_absorpt_correction_T_max     0.7751
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8425
_diffrn_reflns_av_R_equivalents     0.0248
_diffrn_reflns_av_sigmaI/netI     0.0250
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     25.26
_diffrn_reflns_theta_full     25.26
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3017
_reflns_number_gt     2740
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0307
_refine_ls_R_factor_gt     0.0235
_refine_ls_wR_factor_gt     0.0699
_refine_ls_wR_factor_ref     0.0986
_refine_ls_goodness_of_fit_ref     1.449
_refine_ls_restrained_S_all     1.449
_refine_ls_number_reflns     3017
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.750
_refine_diff_density_min     -0.777
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Pd' 'Pd' -0.9988 1.0072
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Pd Pd1 0.24607(3) 1.03943(2) 0.48489(2) 0.03525(13) Uani d . 1 . .
    Cl Cl3 0.16891(13) 1.21022(11) 0.30576(11) 0.0561(3) Uani d . 1 . .
    Cl Cl2 0.32131(13) 1.22359(10) 0.54955(10) 0.0539(3) Uani d . 1 . .
    N N17 0.3073(3) 0.8747(3) 0.6379(3) 0.0321(6) Uani d . 1 . .
    N N4 0.1933(3) 0.8650(3) 0.4348(3) 0.0360(6) Uani d . 1 . .
    C C18 0.3699(4) 0.9003(4) 0.7444(3) 0.0376(8) Uani d . 1 . .
    H H18A 0.4520 0.9697 0.7083 0.045 Uiso calc R 1 . .
    H H18B 0.4199 0.8094 0.7918 0.045 Uiso calc R 1 . .
    C C19 0.2416(4) 0.9583(4) 0.8387(3) 0.0387(8) Uani d . 1 . .
    H H19 0.1847 1.0454 0.7898 0.046 Uiso calc R 1 . .
    C C20 0.1206(4) 0.8458(4) 0.9148(4) 0.0498(9) Uani d . 1 . .
    H H20A 0.0613 0.8261 0.8567 0.075 Uiso calc R 1 . .
    H H20B 0.0483 0.8833 0.9780 0.075 Uiso calc R 1 . .
    H H20C 0.1762 0.7572 0.9577 0.075 Uiso calc R 1 . .
    C C21 0.3272(5) 1.0017(5) 0.9319(5) 0.0676(13) Uani d . 1 . .
    H H21A 0.2492 1.0393 0.9919 0.101 Uiso calc R 1 . .
    H H21B 0.3999 1.0752 0.8834 0.101 Uiso calc R 1 . .
    H H21C 0.3857 0.9175 0.9786 0.101 Uiso calc R 1 . .
    C C10 0.2878(4) 0.7450(4) 0.6329(3) 0.0342(7) Uani d . 1 . .
    C C11 0.3177(4) 0.6086(4) 0.7384(3) 0.0355(7) Uani d . 1 . .
    C C12 0.1848(4) 0.5353(4) 0.8153(4) 0.0454(9) Uani d . 1 . .
    H H12 0.0822 0.5666 0.7970 0.054 Uiso calc R 1 . .
    C C13 0.2090(5) 0.4146(4) 0.9198(4) 0.0574(11) Uani d . 1 . .
    H H13 0.1213 0.3666 0.9728 0.069 Uiso calc R 1 . .
    C C14 0.3621(6) 0.3649(4) 0.9459(4) 0.0586(11) Uani d . 1 . .
    H H14 0.3769 0.2849 1.0164 0.070 Uiso calc R 1 . .
    C C15 0.4912(5) 0.4346(4) 0.8671(4) 0.0562(10) Uani d . 1 . .
    H H15 0.5938 0.3997 0.8833 0.067 Uiso calc R 1 . .
    C C16 0.4719(4) 0.5557(4) 0.7640(4) 0.0449(9) Uani d . 1 . .
    H H16 0.5610 0.6021 0.7117 0.054 Uiso calc R 1 . .
    C C9 0.2284(4) 0.7344(4) 0.5188(3) 0.0362(8) Uani d . 1 . .
    C C5 0.1371(5) 0.8662(4) 0.3301(4) 0.0483(9) Uani d . 1 . .
    H H5 0.1125 0.9553 0.2723 0.058 Uiso calc R 1 . .
    C C6 0.1145(5) 0.7388(5) 0.3050(4) 0.0563(11) Uani d . 1 . .
    H H6 0.0724 0.7432 0.2319 0.068 Uiso calc R 1 . .
    C C7 0.1532(5) 0.6060(5) 0.3863(4) 0.0520(10) Uani d . 1 . .
    H H7 0.1414 0.5196 0.3685 0.062 Uiso calc R 1 . .
    C C8 0.2104(4) 0.6050(4) 0.4956(4) 0.0436(9) Uani d . 1 . .
    H H8 0.2369 0.5167 0.5537 0.052 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Pd1 N4 . 2.037(3) ?
    Pd1 N17 . 2.039(3) ?
    Pd1 Cl2 . 2.2940(11) ?
    Pd1 Cl3 . 2.3052(10) ?
    N17 C10 . 1.297(4) ?
    N17 C18 . 1.471(4) ?
    N4 C5 . 1.326(5) ?
    N4 C9 . 1.358(5) ?
    C18 C19 . 1.529(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 C20 . 1.527(5) ?
    C19 C21 . 1.542(5) ?
    C19 H19 . 0.9800 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C10 C9 . 1.475(5) ?
    C10 C11 . 1.502(5) ?
    C11 C16 . 1.402(5) ?
    C11 C12 . 1.401(5) ?
    C12 C13 . 1.396(6) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.389(6) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.369(6) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.380(5) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C9 C8 . 1.374(5) ?
    C5 C6 . 1.377(6) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.367(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.379(5) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N4 Pd1 N17 . . 80.38(11) ?
    N4 Pd1 Cl2 . . 175.33(8) ?
    N17 Pd1 Cl2 . . 95.56(8) ?
    N4 Pd1 Cl3 . . 94.57(9) ?
    N17 Pd1 Cl3 . . 174.93(8) ?
    Cl2 Pd1 Cl3 . . 89.50(4) ?
    C10 N17 C18 . . 122.7(3) ?
    C10 N17 Pd1 . . 114.3(2) ?
    C18 N17 Pd1 . . 123.0(2) ?
    C5 N4 C9 . . 118.6(3) ?
    C5 N4 Pd1 . . 127.7(3) ?
    C9 N4 Pd1 . . 113.6(2) ?
    N17 C18 C19 . . 113.6(3) ?
    N17 C18 H18A . . 108.9 ?
    C19 C18 H18A . . 108.9 ?
    N17 C18 H18B . . 108.9 ?
    C19 C18 H18B . . 108.9 ?
    H18A C18 H18B . . 107.7 ?
    C20 C19 C18 . . 112.2(3) ?
    C20 C19 C21 . . 110.1(3) ?
    C18 C19 C21 . . 107.8(3) ?
    C20 C19 H19 . . 108.9 ?
    C18 C19 H19 . . 108.9 ?
    C21 C19 H19 . . 108.9 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C19 C21 H21A . . 109.5 ?
    C19 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C19 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    N17 C10 C9 . . 117.2(3) ?
    N17 C10 C11 . . 123.2(3) ?
    C9 C10 C11 . . 119.5(3) ?
    C16 C11 C12 . . 119.7(3) ?
    C16 C11 C10 . . 122.4(3) ?
    C12 C11 C10 . . 117.9(3) ?
    C13 C12 C11 . . 118.8(4) ?
    C13 C12 H12 . . 120.6 ?
    C11 C12 H12 . . 120.6 ?
    C14 C13 C12 . . 121.0(4) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    C15 C14 C13 . . 119.4(4) ?
    C15 C14 H14 . . 120.3 ?
    C13 C14 H14 . . 120.3 ?
    C14 C15 C16 . . 121.3(4) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    C15 C16 C11 . . 119.7(4) ?
    C15 C16 H16 . . 120.1 ?
    C11 C16 H16 . . 120.1 ?
    N4 C9 C8 . . 121.4(3) ?
    N4 C9 C10 . . 114.4(3) ?
    C8 C9 C10 . . 124.2(3) ?
    N4 C5 C6 . . 121.6(4) ?
    N4 C5 H5 . . 119.2 ?
    C6 C5 H5 . . 119.2 ?
    C7 C6 C5 . . 120.7(4) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C7 C8 . . 117.5(4) ?
    C6 C7 H7 . . 121.2 ?
    C8 C7 H7 . . 121.2 ?
    C9 C8 C7 . . 120.0(4) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
data_Compound_4_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H18 Cl2 N2 Pd'
_chemical_formula_sum     'C16 H18 Cl2 N2 Pd'
_chemical_formula_weight     415.62
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.5305(11)
_cell_length_b     9.6211(14)
_cell_length_c     10.9880(16)
_cell_angle_alpha     72.593(4)
_cell_angle_beta     78.780(5)
_cell_angle_gamma     83.039(4)
_cell_volume     842.2(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4927
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     25.20
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.51
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.639
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     416
_exptl_absorpt_coefficient_mu     1.413
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.5326
_exptl_absorpt_correction_T_max     0.7751
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8425
_diffrn_reflns_av_R_equivalents     0.0248
_diffrn_reflns_av_sigmaI/netI     0.0250
_diffrn_reflns_theta_min     1.97
_diffrn_reflns_theta_max     25.26
_diffrn_reflns_theta_full     25.26
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3017
_reflns_number_gt     2740
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0290
_refine_ls_R_factor_gt     0.0218
_refine_ls_wR_factor_gt     0.0637
_refine_ls_wR_factor_ref     0.0913
_refine_ls_goodness_of_fit_ref     1.227
_refine_ls_restrained_S_all     1.227
_refine_ls_number_reflns     3017
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0530P)²+0.1355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.011
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.660
_refine_diff_density_min     -0.777
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Pd' 'Pd' -0.9988 1.0072
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Pd Pd1 0.24612(3) 1.03943(2) 0.48490(2) 0.03536(12) Uani d . 1 . .
    Cl Cl1 0.32147(13) 1.22355(9) 0.54961(10) 0.0541(3) Uani d . 1 . .
    Cl Cl2 0.16898(12) 1.21023(10) 0.30576(10) 0.0561(3) Uani d . 1 . .
    N N1 0.3076(3) 0.8746(3) 0.6379(3) 0.0322(6) Uani d . 1 . .
    N N2 0.1938(3) 0.8650(3) 0.4349(3) 0.0363(6) Uani d . 1 . .
    C C1 0.3700(4) 0.9005(3) 0.7440(3) 0.0375(7) Uani d . 1 . .
    H H1A 0.4518 0.9702 0.7077 0.045 Uiso calc R 1 . .
    H H1B 0.4203 0.8098 0.7913 0.045 Uiso calc R 1 . .
    C C2 0.2419(4) 0.9582(4) 0.8385(3) 0.0388(7) Uani d . 1 . .
    H H2 0.1848 1.0452 0.7895 0.047 Uiso calc R 1 . .
    C C3 0.3271(5) 1.0024(5) 0.9309(5) 0.0674(12) Uani d . 1 . .
    H H3A 0.2490 1.0389 0.9915 0.101 Uiso calc R 1 . .
    H H3B 0.3984 1.0770 0.8821 0.101 Uiso calc R 1 . .
    H H3C 0.3872 0.9188 0.9768 0.101 Uiso calc R 1 . .
    C C4 0.1210(4) 0.8459(4) 0.9145(4) 0.0495(9) Uani d . 1 . .
    H H4A 0.0625 0.8255 0.8562 0.074 Uiso calc R 1 . .
    H H4B 0.0480 0.8838 0.9771 0.074 Uiso calc R 1 . .
    H H4C 0.1765 0.7577 0.9581 0.074 Uiso calc R 1 . .
    C C5 0.2885(4) 0.7449(3) 0.6331(3) 0.0339(7) Uani d . 1 . .
    C C6 0.2293(4) 0.7342(4) 0.5192(3) 0.0365(7) Uani d . 1 . .
    C C7 0.1374(4) 0.8661(4) 0.3301(3) 0.0491(9) Uani d . 1 . .
    H H7 0.1128 0.9552 0.2723 0.059 Uiso calc R 1 . .
    C C8 0.1145(5) 0.7389(5) 0.3047(4) 0.0570(10) Uani d . 1 . .
    H H8 0.0720 0.7431 0.2318 0.068 Uiso calc R 1 . .
    C C9 0.1541(5) 0.6058(4) 0.3866(4) 0.0522(9) Uani d . 1 . .
    H H9 0.1425 0.5193 0.3689 0.063 Uiso calc R 1 . .
    C C10 0.2115(4) 0.6045(4) 0.4961(3) 0.0435(8) Uani d . 1 . .
    H H10 0.2382 0.5162 0.5541 0.052 Uiso calc R 1 . .
    C C11 0.3179(4) 0.6085(3) 0.7383(3) 0.0354(7) Uani d . 1 . .
    C C12 0.1856(4) 0.5352(4) 0.8152(4) 0.0456(8) Uani d . 1 . .
    H H12 0.0830 0.5666 0.7970 0.055 Uiso calc R 1 . .
    C C13 0.2091(5) 0.4148(4) 0.9195(4) 0.0573(10) Uani d . 1 . .
    H H13 0.1212 0.3671 0.9723 0.069 Uiso calc R 1 . .
    C C14 0.3615(5) 0.3650(4) 0.9456(4) 0.0581(10) Uani d . 1 . .
    H H14 0.3761 0.2850 1.0160 0.070 Uiso calc R 1 . .
    C C15 0.4907(5) 0.4347(4) 0.8668(4) 0.0562(10) Uani d . 1 . .
    H H15 0.5933 0.3998 0.8830 0.067 Uiso calc R 1 . .
    C C16 0.4713(4) 0.5558(4) 0.7635(3) 0.0451(8) Uani d . 1 . .
    H H16 0.5603 0.6020 0.7110 0.054 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Pd1 N2 . 2.036(3) ?
    Pd1 N1 . 2.040(3) ?
    Pd1 Cl1 . 2.2944(10) ?
    Pd1 Cl2 . 2.3054(10) ?
    N1 C5 . 1.296(4) ?
    N1 C1 . 1.466(4) ?
    N2 C7 . 1.328(4) ?
    N2 C6 . 1.361(4) ?
    C1 C2 . 1.529(4) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C4 . 1.524(5) ?
    C2 C3 . 1.536(5) ?
    C2 H2 . 0.9800 ?
    C3 H3A . 0.9600 ?
    C3 H3B . 0.9600 ?
    C3 H3C . 0.9600 ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 C6 . 1.472(5) ?
    C5 C11 . 1.499(4) ?
    C6 C10 . 1.377(5) ?
    C7 C8 . 1.378(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.374(6) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.381(5) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.397(4) ?
    C11 C16 . 1.394(5) ?
    C12 C13 . 1.391(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.384(6) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.369(6) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.381(5) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 Pd1 N1 . . 80.34(11) ?
    N2 Pd1 Cl1 . . 175.21(8) ?
    N1 Pd1 Cl1 . . 95.52(8) ?
    N2 Pd1 Cl2 . . 94.63(8) ?
    N1 Pd1 Cl2 . . 174.96(7) ?
    Cl1 Pd1 Cl2 . . 89.52(4) ?
    C5 N1 C1 . . 122.7(3) ?
    C5 N1 Pd1 . . 114.5(2) ?
    C1 N1 Pd1 . . 122.9(2) ?
    C7 N2 C6 . . 118.8(3) ?
    C7 N2 Pd1 . . 127.7(2) ?
    C6 N2 Pd1 . . 113.4(2) ?
    N1 C1 C2 . . 113.7(3) ?
    N1 C1 H1A . . 108.8 ?
    C2 C1 H1A . . 108.8 ?
    N1 C1 H1B . . 108.8 ?
    C2 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    C4 C2 C1 . . 112.3(3) ?
    C4 C2 C3 . . 110.4(3) ?
    C1 C2 C3 . . 107.9(3) ?
    C4 C2 H2 . . 108.7 ?
    C1 C2 H2 . . 108.7 ?
    C3 C2 H2 . . 108.7 ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    C2 C4 H4A . . 109.5 ?
    C2 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C2 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N1 C5 C6 . . 117.1(3) ?
    N1 C5 C11 . . 123.5(3) ?
    C6 C5 C11 . . 119.3(3) ?
    N2 C6 C10 . . 121.3(3) ?
    N2 C6 C5 . . 114.5(3) ?
    C10 C6 C5 . . 124.2(3) ?
    N2 C7 C8 . . 121.8(3) ?
    N2 C7 H7 . . 119.1 ?
    C8 C7 H7 . . 119.1 ?
    C9 C8 C7 . . 120.3(4) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C8 C9 C10 . . 117.9(4) ?
    C8 C9 H9 . . 121.0 ?
    C10 C9 H9 . . 121.0 ?
    C6 C10 C9 . . 119.9(3) ?
    C6 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C12 C11 C16 . . 119.5(3) ?
    C12 C11 C5 . . 118.2(3) ?
    C16 C11 C5 . . 122.3(3) ?
    C13 C12 C11 . . 119.2(3) ?
    C13 C12 H12 . . 120.4 ?
    C11 C12 H12 . . 120.4 ?
    C14 C13 C12 . . 120.9(3) ?
    C14 C13 H13 . . 119.6 ?
    C12 C13 H13 . . 119.6 ?
    C15 C14 C13 . . 119.4(3) ?
    C15 C14 H14 . . 120.3 ?
    C13 C14 H14 . . 120.3 ?
    C14 C15 C16 . . 121.2(4) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    C15 C16 C11 . . 119.8(3) ?
    C15 C16 H16 . . 120.1 ?
    C11 C16 H16 . . 120.1 ?
data_Compound_5_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 O S'
_chemical_formula_sum     'C13 H10 O S'
_chemical_formula_weight     214.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/n1
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.007(2)
_cell_length_b     16.958(5)
_cell_length_c     8.031(2)
_cell_angle_alpha     90.00
_cell_angle_beta     95.097(10)
_cell_angle_gamma     90.00
_cell_volume     1086.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2019
_cell_measurement_theta_min     2.82
_cell_measurement_theta_max     25.10
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.310
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.265
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9223
_exptl_absorpt_correction_T_max     0.9318
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6685
_diffrn_reflns_av_R_equivalents     0.0488
_diffrn_reflns_av_sigmaI/netI     0.0465
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     25.10
_diffrn_reflns_theta_full     25.10
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     7
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1910
_reflns_number_gt     1366
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0726
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1249
_refine_ls_wR_factor_ref     0.1517
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_restrained_S_all     1.082
_refine_ls_number_reflns     1910
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.323
_refine_diff_density_min     -0.254
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.95308(8) 0.89514(5) 0.33211(9) 0.0507(3) Uani d . 1 . .
    O O9 1.1091(3) 0.78594(14) 0.5555(3) 0.0697(7) Uani d . 1 . .
    C C13 0.7126(4) 1.0597(2) -0.0634(4) 0.0657(9) Uani d . 1 . .
    H H13 0.6673 1.0936 -0.1463 0.079 Uiso calc R 1 . .
    C C12 0.7805(4) 1.0894(2) 0.0841(4) 0.0681(9) Uani d . 1 . .
    H H12 0.7802 1.1435 0.1026 0.082 Uiso calc R 1 . .
    C C11 0.8499(4) 1.03928(19) 0.2066(4) 0.0580(8) Uani d . 1 . .
    H H11 0.8970 1.0599 0.3074 0.070 Uiso calc R 1 . .
    C C10 0.8500(3) 0.95873(17) 0.1806(3) 0.0440(6) Uani d . 1 . .
    C C2 0.7876(3) 0.86483(16) 0.4498(3) 0.0406(6) Uani d . 1 . .
    C C3 0.8173(3) 0.80788(15) 0.5752(3) 0.0452(7) Uani d . 1 . .
    C C4 0.6855(4) 0.78208(19) 0.6636(4) 0.0604(8) Uani d . 1 . .
    H H4 0.7058 0.7439 0.7460 0.073 Uiso calc R 1 . .
    C C5 0.5271(4) 0.8115(2) 0.6320(4) 0.0660(9) Uani d . 1 . .
    H H5 0.4401 0.7929 0.6906 0.079 Uiso calc R 1 . .
    C C14 0.7104(4) 0.9800(3) -0.0911(4) 0.0735(10) Uani d . 1 . .
    H H14 0.6627 0.9602 -0.1924 0.088 Uiso calc R 1 . .
    C C15 0.7787(4) 0.9287(2) 0.0311(4) 0.0624(8) Uani d . 1 . .
    H H15 0.7766 0.8746 0.0125 0.075 Uiso calc R 1 . .
    C C7 0.6253(3) 0.89590(18) 0.4229(4) 0.0505(7) Uani d . 1 . .
    H H7 0.6029 0.9353 0.3435 0.061 Uiso calc R 1 . .
    C C6 0.4983(4) 0.8686(2) 0.5132(4) 0.0608(8) Uani d . 1 . .
    H H6 0.3911 0.8895 0.4926 0.073 Uiso calc R 1 . .
    C C8 0.9816(4) 0.77186(18) 0.6176(4) 0.0604(8) Uani d . 1 . .
    H H8 0.9879 0.7340 0.7016 0.072 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C2 . 1.771(3) ?
    S1 C10 . 1.773(3) ?
    O9 C8 . 1.199(4) ?
    C13 C12 . 1.355(4) ?
    C13 C14 . 1.369(5) ?
    C13 H13 . 0.9300 ?
    C12 C11 . 1.379(4) ?
    C12 H12 . 0.9300 ?
    C11 C10 . 1.382(4) ?
    C11 H11 . 0.9300 ?
    C10 C15 . 1.380(4) ?
    C2 C3 . 1.400(4) ?
    C2 C7 . 1.401(4) ?
    C3 C4 . 1.394(4) ?
    C3 C8 . 1.463(4) ?
    C4 C5 . 1.365(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.365(5) ?
    C5 H5 . 0.9300 ?
    C14 C15 . 1.387(5) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C7 C6 . 1.380(4) ?
    C7 H7 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C8 H8 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 S1 C10 . . 102.59(12) ?
    C12 C13 C14 . . 120.5(3) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C13 C12 C11 . . 119.9(3) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C11 C10 . . 120.5(3) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C15 C10 C11 . . 119.3(3) ?
    C15 C10 S1 . . 120.3(2) ?
    C11 C10 S1 . . 120.3(2) ?
    C3 C2 C7 . . 117.8(3) ?
    C3 C2 S1 . . 119.8(2) ?
    C7 C2 S1 . . 122.4(2) ?
    C4 C3 C2 . . 119.6(3) ?
    C4 C3 C8 . . 117.2(3) ?
    C2 C3 C8 . . 123.2(3) ?
    C5 C4 C3 . . 121.6(3) ?
    C5 C4 H4 . . 119.2 ?
    C3 C4 H4 . . 119.2 ?
    C6 C5 C4 . . 119.1(3) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C13 C14 C15 . . 120.3(3) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C10 C15 C14 . . 119.4(3) ?
    C10 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    C6 C7 C2 . . 120.6(3) ?
    C6 C7 H7 . . 119.7 ?
    C2 C7 H7 . . 119.7 ?
    C5 C6 C7 . . 121.2(3) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    O9 C8 C3 . . 127.0(3) ?
    O9 C8 H8 . . 116.5 ?
    C3 C8 H8 . . 116.5 ?
data_Compound_5_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 O S'
_chemical_formula_sum     'C13 H10 O S'
_chemical_formula_weight     214.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/n1
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.007(2)
_cell_length_b     16.958(5)
_cell_length_c     8.031(2)
_cell_angle_alpha     90.00
_cell_angle_beta     95.097(10)
_cell_angle_gamma     90.00
_cell_volume     1086.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2019
_cell_measurement_theta_min     2.82
_cell_measurement_theta_max     25.10
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.310
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.265
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9223
_exptl_absorpt_correction_T_max     0.9318
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     ?
_diffrn_measurement_method     ?
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6685
_diffrn_reflns_av_R_equivalents     0.0488
_diffrn_reflns_av_sigmaI/netI     0.0465
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     25.10
_diffrn_reflns_theta_full     25.10
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     7
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1910
_reflns_number_gt     1366
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0725
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1257
_refine_ls_wR_factor_ref     0.1527
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     1910
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0904P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.013
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.323
_refine_diff_density_min     -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.04691(8) 0.10486(5) 0.66790(9) 0.0507(3) Uani d . 1 . .
    O O1 -0.1091(3) 0.21406(14) 0.4445(3) 0.0697(7) Uani d . 1 . .
    C C1 0.2874(4) -0.0596(2) 1.0634(4) 0.0657(9) Uani d . 1 . .
    H H1 0.3327 -0.0936 1.1464 0.079 Uiso calc R 1 . .
    C C2 0.2195(4) -0.0894(2) 0.9159(4) 0.0681(9) Uani d . 1 . .
    H H2 0.2198 -0.1435 0.8974 0.082 Uiso calc R 1 . .
    C C3 0.1501(4) -0.03928(19) 0.7934(4) 0.0580(8) Uani d . 1 . .
    H H3 0.1030 -0.0598 0.6926 0.070 Uiso calc R 1 . .
    C C4 0.1500(3) 0.04127(17) 0.8194(3) 0.0441(6) Uani d . 1 . .
    C C5 0.2124(3) 0.13516(16) 0.5502(3) 0.0407(6) Uani d . 1 . .
    C C6 0.1827(3) 0.19211(15) 0.4248(3) 0.0452(7) Uani d . 1 . .
    C C7 0.0184(4) 0.22814(18) 0.3825(4) 0.0604(8) Uani d . 1 . .
    H H7 0.0121 0.2660 0.2984 0.072 Uiso calc R 1 . .
    C C8 0.2213(4) 0.0713(2) 0.9689(4) 0.0624(8) Uani d . 1 . .
    H H8 0.2234 0.1254 0.9875 0.075 Uiso calc R 1 . .
    C C9 0.2897(4) 0.0200(3) 1.0912(4) 0.0734(10) Uani d . 1 . .
    H H9 0.3373 0.0398 1.1924 0.088 Uiso calc R 1 . .
    C C10 0.3145(4) 0.21791(19) 0.3364(4) 0.0604(8) Uani d . 1 . .
    H H10 0.2942 0.2561 0.2540 0.073 Uiso calc R 1 . .
    C C11 0.4729(4) 0.1885(2) 0.3680(4) 0.0660(9) Uani d . 1 . .
    H H11 0.5599 0.2071 0.3094 0.079 Uiso calc R 1 . .
    C C12 0.5017(4) 0.1314(2) 0.4868(4) 0.0609(8) Uani d . 1 . .
    H H12 0.6089 0.1104 0.5074 0.073 Uiso calc R 1 . .
    C C13 0.3747(3) 0.10408(18) 0.5771(4) 0.0505(7) Uani d . 1 . .
    H H13 0.3971 0.0647 0.6565 0.061 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C5 . 1.771(3) ?
    S1 C4 . 1.773(3) ?
    O1 C7 . 1.199(4) ?
    C1 C2 . 1.355(4) ?
    C1 C9 . 1.368(5) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.382(4) ?
    C3 H3 . 0.9300 ?
    C4 C8 . 1.380(4) ?
    C5 C6 . 1.400(4) ?
    C5 C13 . 1.401(4) ?
    C6 C10 . 1.394(4) ?
    C6 C7 . 1.463(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.387(5) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.365(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.365(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.380(4) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 S1 C4 . . 102.59(12) ?
    C2 C1 C9 . . 120.5(3) ?
    C2 C1 H1 . . 119.7 ?
    C9 C1 H1 . . 119.7 ?
    C1 C2 C3 . . 119.9(3) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C2 C3 C4 . . 120.4(3) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C8 C4 C3 . . 119.3(3) ?
    C8 C4 S1 . . 120.3(2) ?
    C3 C4 S1 . . 120.3(2) ?
    C6 C5 C13 . . 117.8(3) ?
    C6 C5 S1 . . 119.8(2) ?
    C13 C5 S1 . . 122.4(2) ?
    C10 C6 C5 . . 119.6(3) ?
    C10 C6 C7 . . 117.2(3) ?
    C5 C6 C7 . . 123.2(3) ?
    O1 C7 C6 . . 127.0(3) ?
    O1 C7 H7 . . 116.5 ?
    C6 C7 H7 . . 116.5 ?
    C4 C8 C9 . . 119.4(3) ?
    C4 C8 H8 . . 120.3 ?
    C9 C8 H8 . . 120.3 ?
    C1 C9 C8 . . 120.3(3) ?
    C1 C9 H9 . . 119.9 ?
    C8 C9 H9 . . 119.9 ?
    C11 C10 C6 . . 121.6(3) ?
    C11 C10 H10 . . 119.2 ?
    C6 C10 H10 . . 119.2 ?
    C12 C11 C10 . . 119.1(3) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C13 . . 121.2(3) ?
    C11 C12 H12 . . 119.4 ?
    C13 C12 H12 . . 119.4 ?
    C12 C13 C5 . . 120.6(3) ?
    C12 C13 H13 . . 119.7 ?
    C5 C13 H13 . . 119.7 ?
data_Compound_6_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 O3'
_chemical_formula_sum     'C12 H16 O3'
_chemical_formula_weight     208.25
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.894(4)
_cell_length_b     16.220(8)
_cell_length_c     7.742(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.214(14)
_cell_angle_gamma     90.00
_cell_volume     1116.9(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1463
_cell_measurement_theta_min     2.51
_cell_measurement_theta_max     21.93
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.238
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9623
_exptl_absorpt_correction_T_max     0.9767
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7217
_diffrn_reflns_av_R_equivalents     0.0427
_diffrn_reflns_av_sigmaI/netI     0.0423
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     8
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1944
_reflns_number_gt     1285
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0852
_refine_ls_R_factor_gt     0.0462
_refine_ls_wR_factor_gt     0.1222
_refine_ls_wR_factor_ref     0.1646
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     1944
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0956P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.307
_refine_diff_density_min     -0.331
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O10 0.27549(17) 0.40331(10) 0.09433(17) 0.0413(5) Uani d . 1 . .
    O O9 0.1882(2) 0.50089(10) -0.39245(19) 0.0577(6) Uani d . 1 . .
    H H9 0.1755 0.4652 -0.4661 0.087 Uiso calc R 1 . .
    O O14 0.18947(17) 0.36544(10) 0.36779(17) 0.0432(5) Uani d . 1 . .
    C C13 0.3372(3) 0.26728(15) 0.2005(3) 0.0506(7) Uani d . 1 . .
    H H13A 0.3497 0.2352 0.3037 0.076 Uiso calc R 1 . .
    H H13C 0.4266 0.2635 0.1317 0.076 Uiso calc R 1 . .
    H H13B 0.2531 0.2466 0.1356 0.076 Uiso calc R 1 . .
    C C11 0.3092(2) 0.35671(14) 0.2484(3) 0.0396(6) Uani d . 1 . .
    C C4 0.1317(2) 0.39187(13) 0.0277(3) 0.0351(6) Uani d . 1 . .
    C C3 0.1055(2) 0.42109(13) -0.1399(3) 0.0369(6) Uani d . 1 . .
    C C2 -0.0379(3) 0.41084(15) -0.2091(3) 0.0451(6) Uani d . 1 . .
    H H2 -0.0572 0.4301 -0.3201 0.054 Uiso calc R 1 . .
    C C1 -0.1536(3) 0.37279(15) -0.1182(3) 0.0478(6) Uani d . 1 . .
    C C7 -0.3093(3) 0.3633(2) -0.1979(4) 0.0766(9) Uani d . 1 . .
    H H7A -0.3491 0.3100 -0.1694 0.115 Uiso calc R 1 . .
    H H7B -0.3025 0.3686 -0.3211 0.115 Uiso calc R 1 . .
    H H7C -0.3745 0.4054 -0.1534 0.115 Uiso calc R 1 . .
    C C12 0.4460(3) 0.39724(18) 0.3284(3) 0.0576(7) Uani d . 1 . .
    H H12C 0.4229 0.4535 0.3563 0.086 Uiso calc R 1 . .
    H H12A 0.5278 0.3957 0.2480 0.086 Uiso calc R 1 . .
    H H12B 0.4739 0.3682 0.4317 0.086 Uiso calc R 1 . .
    C C5 0.0182(2) 0.35579(14) 0.1236(3) 0.0369(6) Uani d . 1 . .
    C C6 -0.1231(2) 0.34571(15) 0.0476(3) 0.0448(6) Uani d . 1 . .
    H H6 -0.1989 0.3201 0.1102 0.054 Uiso calc R 1 . .
    C C8 0.2320(3) 0.46348(15) -0.2347(3) 0.0442(6) Uani d . 1 . .
    H H8A 0.2748 0.5054 -0.1600 0.053 Uiso calc R 1 . .
    H H8B 0.3100 0.4233 -0.2583 0.053 Uiso calc R 1 . .
    C C15 0.0497(3) 0.33104(16) 0.3084(3) 0.0467(6) Uani d . 1 . .
    H H15B -0.0314 0.3501 0.3816 0.056 Uiso calc R 1 . .
    H H15A 0.0539 0.2714 0.3164 0.056 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O10 C4 . 1.390(3) ?
    O10 C11 . 1.443(3) ?
    O9 C8 . 1.417(3) ?
    O9 H9 . 0.8200 ?
    O14 C11 . 1.420(3) ?
    O14 C15 . 1.437(3) ?
    C13 C11 . 1.518(3) ?
    C13 H13A . 0.9600 ?
    C13 H13C . 0.9600 ?
    C13 H13B . 0.9600 ?
    C11 C12 . 1.513(3) ?
    C4 C5 . 1.385(3) ?
    C4 C3 . 1.400(3) ?
    C3 C2 . 1.392(3) ?
    C3 C8 . 1.511(3) ?
    C2 C1 . 1.393(3) ?
    C2 H2 . 0.9300 ?
    C1 C6 . 1.383(3) ?
    C1 C7 . 1.522(3) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C12 H12C . 0.9600 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C5 C6 . 1.395(3) ?
    C5 C15 . 1.511(3) ?
    C6 H6 . 0.9300 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 H15A . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 O10 C11 . . 115.15(16) ?
    C8 O9 H9 . . 109.5 ?
    C11 O14 C15 . . 113.77(16) ?
    C11 C13 H13A . . 109.5 ?
    C11 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    C11 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    H13C C13 H13B . . 109.5 ?
    O14 C11 O10 . . 109.39(17) ?
    O14 C11 C12 . . 107.08(18) ?
    O10 C11 C12 . . 105.97(18) ?
    O14 C11 C13 . . 112.25(19) ?
    O10 C11 C13 . . 109.41(17) ?
    C12 C11 C13 . . 112.5(2) ?
    C5 C4 O10 . . 121.95(19) ?
    C5 C4 C3 . . 121.4(2) ?
    O10 C4 C3 . . 116.65(19) ?
    C2 C3 C4 . . 117.7(2) ?
    C2 C3 C8 . . 123.4(2) ?
    C4 C3 C8 . . 118.88(19) ?
    C3 C2 C1 . . 122.4(2) ?
    C3 C2 H2 . . 118.8 ?
    C1 C2 H2 . . 118.8 ?
    C6 C1 C2 . . 117.8(2) ?
    C6 C1 C7 . . 121.3(2) ?
    C2 C1 C7 . . 120.8(2) ?
    C1 C7 H7A . . 109.5 ?
    C1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    H12C C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12C C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C4 C5 C6 . . 118.7(2) ?
    C4 C5 C15 . . 119.1(2) ?
    C6 C5 C15 . . 122.1(2) ?
    C1 C6 C5 . . 121.8(2) ?
    C1 C6 H6 . . 119.1 ?
    C5 C6 H6 . . 119.1 ?
    O9 C8 C3 . . 114.3(2) ?
    O9 C8 H8A . . 108.7 ?
    C3 C8 H8A . . 108.7 ?
    O9 C8 H8B . . 108.7 ?
    C3 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    O14 C15 C5 . . 110.92(18) ?
    O14 C15 H15B . . 109.5 ?
    C5 C15 H15B . . 109.5 ?
    O14 C15 H15A . . 109.5 ?
    C5 C15 H15A . . 109.5 ?
    H15B C15 H15A . . 108.0 ?
data_Compound_6_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 O3'
_chemical_formula_sum     'C12 H16 O3'
_chemical_formula_weight     208.25
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.894(4)
_cell_length_b     16.220(8)
_cell_length_c     7.742(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.214(14)
_cell_angle_gamma     90.00
_cell_volume     1116.9(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1463
_cell_measurement_theta_min     2.51
_cell_measurement_theta_max     21.93
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.238
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8479
_exptl_absorpt_correction_T_max     0.9767
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7217
_diffrn_reflns_av_R_equivalents     0.0427
_diffrn_reflns_av_sigmaI/netI     0.0423
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     8
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1944
_reflns_number_gt     1285
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0852
_refine_ls_R_factor_gt     0.0463
_refine_ls_wR_factor_gt     0.1261
_refine_ls_wR_factor_ref     0.1689
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     1944
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1061P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     6.481
_refine_ls_shift/su_mean     0.450
_refine_diff_density_max     0.309
_refine_diff_density_min     -0.331
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.27547(18) 0.40331(10) 0.09437(18) 0.0415(5) Uani d . 1 . .
    O O2 0.1881(2) 0.50078(10) -0.3929(2) 0.0578(6) Uani d . 1 . .
    H H2 0.1770 0.4651 -0.4668 0.087 Uiso calc R 1 . .
    O O3 0.18947(18) 0.36545(10) 0.36778(19) 0.0433(5) Uani d . 1 . .
    C C1 0.3372(3) 0.26728(16) 0.2005(3) 0.0507(7) Uani d . 1 . .
    H H1A 0.3499 0.2352 0.3037 0.076 Uiso calc R 1 . .
    H H1B 0.4265 0.2635 0.1316 0.076 Uiso calc R 1 . .
    H H1C 0.2531 0.2465 0.1358 0.076 Uiso calc R 1 . .
    C C2 0.3092(3) 0.35675(15) 0.2484(3) 0.0397(6) Uani d . 1 . .
    C C3 0.1317(3) 0.39191(14) 0.0278(3) 0.0353(6) Uani d . 1 . .
    C C4 0.1054(3) 0.42110(14) -0.1399(3) 0.0370(6) Uani d . 1 . .
    C C5 -0.0379(3) 0.41084(16) -0.2091(3) 0.0453(7) Uani d . 1 . .
    H H5 -0.0572 0.4301 -0.3201 0.054 Uiso calc R 1 . .
    C C6 -0.1537(3) 0.37284(17) -0.1182(3) 0.0480(7) Uani d . 1 . .
    C C7 -0.3094(3) 0.3634(2) -0.1979(4) 0.0767(10) Uani d . 1 . .
    H H7A -0.3482 0.3096 -0.1716 0.115 Uiso calc R 1 . .
    H H7B -0.3029 0.3700 -0.3208 0.115 Uiso calc R 1 . .
    H H7C -0.3752 0.4047 -0.1514 0.115 Uiso calc R 1 . .
    C C8 0.4459(3) 0.39727(19) 0.3285(3) 0.0577(8) Uani d . 1 . .
    H H8A 0.4230 0.4536 0.3560 0.087 Uiso calc R 1 . .
    H H8B 0.5279 0.3955 0.2484 0.087 Uiso calc R 1 . .
    H H8C 0.4735 0.3684 0.4321 0.087 Uiso calc R 1 . .
    C C9 0.0181(3) 0.35583(15) 0.1236(3) 0.0371(6) Uani d . 1 . .
    C C10 -0.1232(3) 0.34571(16) 0.0478(3) 0.0449(7) Uani d . 1 . .
    H H10 -0.1990 0.3200 0.1104 0.054 Uiso calc R 1 . .
    C C11 0.2320(3) 0.46342(16) -0.2348(3) 0.0445(7) Uani d . 1 . .
    H H11A 0.2748 0.5054 -0.1601 0.053 Uiso calc R 1 . .
    H H11B 0.3101 0.4232 -0.2581 0.053 Uiso calc R 1 . .
    C C12 0.0497(3) 0.33103(17) 0.3084(3) 0.0468(7) Uani d . 1 . .
    H H12A -0.0314 0.3501 0.3817 0.056 Uiso calc R 1 . .
    H H12B 0.0540 0.2714 0.3164 0.056 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C3 . 1.389(3) ?
    O1 C2 . 1.442(3) ?
    O2 C11 . 1.419(3) ?
    O2 H2 . 0.8201 ?
    O3 C2 . 1.420(3) ?
    O3 C12 . 1.437(3) ?
    C1 C2 . 1.519(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C8 . 1.513(3) ?
    C3 C9 . 1.386(3) ?
    C3 C4 . 1.400(3) ?
    C4 C5 . 1.391(3) ?
    C4 C11 . 1.511(3) ?
    C5 C6 . 1.393(4) ?
    C5 H5 . 0.9300 ?
    C6 C10 . 1.384(4) ?
    C6 C7 . 1.522(3) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 C10 . 1.395(3) ?
    C9 C12 . 1.511(3) ?
    C10 H10 . 0.9300 ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 O1 C2 . . 115.18(17) ?
    C11 O2 H2 . . 109.1 ?
    C2 O3 C12 . . 113.76(17) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.4 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.6 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O3 C2 O1 . . 109.42(18) ?
    O3 C2 C8 . . 107.05(19) ?
    O1 C2 C8 . . 106.0(2) ?
    O3 C2 C1 . . 112.2(2) ?
    O1 C2 C1 . . 109.41(18) ?
    C8 C2 C1 . . 112.5(2) ?
    C9 C3 O1 . . 122.0(2) ?
    C9 C3 C4 . . 121.3(2) ?
    O1 C3 C4 . . 116.7(2) ?
    C5 C4 C3 . . 117.8(2) ?
    C5 C4 C11 . . 123.4(2) ?
    C3 C4 C11 . . 118.8(2) ?
    C4 C5 C6 . . 122.4(2) ?
    C4 C5 H5 . . 118.8 ?
    C6 C5 H5 . . 118.8 ?
    C10 C6 C5 . . 117.8(2) ?
    C10 C6 C7 . . 121.3(3) ?
    C5 C6 C7 . . 120.9(2) ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.4 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C2 C8 H8A . . 109.5 ?
    C2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C2 C8 H8C . . 109.4 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C3 C9 C10 . . 118.8(2) ?
    C3 C9 C12 . . 119.1(2) ?
    C10 C9 C12 . . 122.1(2) ?
    C6 C10 C9 . . 121.8(2) ?
    C6 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    O2 C11 C4 . . 114.2(2) ?
    O2 C11 H11A . . 108.4 ?
    C4 C11 H11A . . 108.8 ?
    O2 C11 H11B . . 109.0 ?
    C4 C11 H11B . . 108.6 ?
    H11A C11 H11B . . 107.6 ?
    O3 C12 C9 . . 110.93(19) ?
    O3 C12 H12A . . 109.5 ?
    C9 C12 H12A . . 109.6 ?
    O3 C12 H12B . . 109.4 ?
    C9 C12 H12B . . 109.4 ?
    H12A C12 H12B . . 108.0 ?
data_Compound_7_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H18 N2 O3 S'
_chemical_formula_sum     'C13 H18 N2 O3 S'
_chemical_formula_weight     282.35
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     12.8651(14)
_cell_length_b     15.3291(14)
_cell_length_c     7.1435(8)
_cell_angle_alpha     90.00
_cell_angle_beta     93.379(4)
_cell_angle_gamma     90.00
_cell_volume     1406.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3155
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     24.47
_cell_measurement_temperature     300(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.236
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6654
_exptl_absorpt_correction_T_max     0.7452
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13591
_diffrn_reflns_av_R_equivalents     0.0494
_diffrn_reflns_av_sigmaI/netI     0.0346
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2482
_reflns_number_gt     1862
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0400
_refine_ls_wR_factor_gt     0.1082
_refine_ls_wR_factor_ref     0.1330
_refine_ls_goodness_of_fit_ref     1.079
_refine_ls_restrained_S_all     1.079
_refine_ls_number_reflns     2482
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0759P)²+0.1981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.318
_refine_diff_density_min     -0.358
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.33421(5) 0.08148(4) 0.13084(9) 0.0460(2) Uani d . 1 . .
    O O3 0.37111(16) -0.00654(12) 0.1230(3) 0.0638(6) Uani d . 1 . .
    O O2 0.28767(17) 0.11992(14) -0.0362(2) 0.0686(6) Uani d . 1 . .
    O O18 0.82865(16) 0.21154(14) 0.4203(4) 0.0801(7) Uani d . 1 . .
    N N16 0.69547(16) 0.30608(14) 0.3613(3) 0.0412(5) Uani d . 1 . .
    N N4 0.24633(16) 0.08330(12) 0.2859(3) 0.0410(5) Uani d . 1 . .
    C C19 0.8656(2) 0.36289(19) 0.4482(5) 0.0682(8) Uani d . 1 . .
    H H19A 0.8841 0.3659 0.5803 0.102 Uiso calc R 1 . .
    H H19B 0.8296 0.4152 0.4092 0.102 Uiso calc R 1 . .
    H H19C 0.9275 0.3570 0.3807 0.102 Uiso calc R 1 . .
    C C17 0.7967(2) 0.28616(18) 0.4089(4) 0.0494(6) Uani d . 1 . .
    C C13 0.61163(18) 0.25016(14) 0.3147(3) 0.0352(5) Uani d . 1 . .
    C C12 0.51548(18) 0.28784(14) 0.2663(3) 0.0381(5) Uani d . 1 . .
    H H12 0.5084 0.3482 0.2691 0.046 Uiso calc R 1 . .
    C C11 0.43124(18) 0.23701(14) 0.2145(3) 0.0400(6) Uani d . 1 . .
    H H11 0.3673 0.2630 0.1824 0.048 Uiso calc R 1 . .
    C C10 0.44080(19) 0.14621(14) 0.2096(3) 0.0388(6) Uani d . 1 . .
    C C5 0.1775(2) 0.15986(18) 0.2942(4) 0.0581(7) Uani d . 1 . .
    H H5A 0.1592 0.1809 0.1685 0.070 Uiso calc R 1 . .
    H H5B 0.2131 0.2064 0.3641 0.070 Uiso calc R 1 . .
    C C6 0.0804(2) 0.1340(2) 0.3889(6) 0.0772(10) Uani d . 1 . .
    H H6A 0.0419 0.0914 0.3120 0.093 Uiso calc R 1 . .
    H H6B 0.0364 0.1849 0.4007 0.093 Uiso calc R 1 . .
    C C7 0.1067(2) 0.0956(2) 0.5822(5) 0.0711(9) Uani d . 1 . .
    H H7A 0.1369 0.1405 0.6641 0.085 Uiso calc R 1 . .
    H H7B 0.0434 0.0752 0.6352 0.085 Uiso calc R 1 . .
    C C14 0.6206(2) 0.15967(15) 0.3121(4) 0.0464(6) Uani d . 1 . .
    H H14 0.6843 0.1336 0.3457 0.056 Uiso calc R 1 . .
    C C15 0.5362(2) 0.10891(16) 0.2602(4) 0.0469(6) Uani d . 1 . .
    H H15 0.5431 0.0485 0.2590 0.056 Uiso calc R 1 . .
    C C9 0.2776(2) 0.04738(16) 0.4722(3) 0.0469(6) Uani d . 1 . .
    H H9A 0.3165 0.0909 0.5459 0.056 Uiso calc R 1 . .
    H H9B 0.3222 -0.0030 0.4585 0.056 Uiso calc R 1 . .
    C C8 0.1820(2) 0.02099(18) 0.5717(4) 0.0565(7) Uani d . 1 . .
    H H8A 0.1480 -0.0273 0.5054 0.068 Uiso calc R 1 . .
    H H8B 0.2028 0.0015 0.6975 0.068 Uiso calc R 1 . .
    H H16 0.6805(19) 0.3588(17) 0.358(3) 0.040(7) Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.430(2) ?
    S1 O3 . 1.432(2) ?
    S1 N4 . 1.629(2) ?
    S1 C10 . 1.758(2) ?
    O18 C17 . 1.217(3) ?
    N16 C17 . 1.361(3) ?
    N16 C13 . 1.402(3) ?
    N16 H16 . 0.83(3) ?
    N4 C5 . 1.473(3) ?
    N4 C9 . 1.475(3) ?
    C19 C17 . 1.490(4) ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C13 C12 . 1.390(3) ?
    C13 C14 . 1.392(3) ?
    C12 C11 . 1.368(3) ?
    C12 H12 . 0.9300 ?
    C11 C10 . 1.398(3) ?
    C11 H11 . 0.9300 ?
    C10 C15 . 1.382(3) ?
    C5 C6 . 1.508(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.521(5) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.504(4) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C14 C15 . 1.370(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C9 C8 . 1.510(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 118.62(13) ?
    O2 S1 N4 . . 106.67(12) ?
    O3 S1 N4 . . 106.71(11) ?
    O2 S1 C10 . . 108.35(11) ?
    O3 S1 C10 . . 106.86(12) ?
    N4 S1 C10 . . 109.40(10) ?
    C17 N16 C13 . . 129.3(2) ?
    C17 N16 H16 . . 116.2(17) ?
    C13 N16 H16 . . 114.5(17) ?
    C5 N4 C9 . . 113.2(2) ?
    C5 N4 S1 . . 118.96(17) ?
    C9 N4 S1 . . 116.38(16) ?
    C17 C19 H19A . . 109.5 ?
    C17 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C17 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O18 C17 N16 . . 122.9(3) ?
    O18 C17 C19 . . 122.3(3) ?
    N16 C17 C19 . . 114.8(2) ?
    C12 C13 C14 . . 118.9(2) ?
    C12 C13 N16 . . 117.8(2) ?
    C14 C13 N16 . . 123.3(2) ?
    C11 C12 C13 . . 120.6(2) ?
    C11 C12 H12 . . 119.7 ?
    C13 C12 H12 . . 119.7 ?
    C12 C11 C10 . . 120.3(2) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C15 C10 C11 . . 118.9(2) ?
    C15 C10 S1 . . 120.92(18) ?
    C11 C10 S1 . . 120.12(19) ?
    N4 C5 C6 . . 109.0(2) ?
    N4 C5 H5A . . 109.9 ?
    C6 C5 H5A . . 109.9 ?
    N4 C5 H5B . . 109.9 ?
    C6 C5 H5B . . 109.9 ?
    H5A C5 H5B . . 108.3 ?
    C5 C6 C7 . . 111.3(3) ?
    C5 C6 H6A . . 109.4 ?
    C7 C6 H6A . . 109.4 ?
    C5 C6 H6B . . 109.4 ?
    C7 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C8 C7 C6 . . 111.0(3) ?
    C8 C7 H7A . . 109.4 ?
    C6 C7 H7A . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    C6 C7 H7B . . 109.4 ?
    H7A C7 H7B . . 108.0 ?
    C15 C14 C13 . . 120.3(2) ?
    C15 C14 H14 . . 119.9 ?
    C13 C14 H14 . . 119.9 ?
    C14 C15 C10 . . 120.9(2) ?
    C14 C15 H15 . . 119.5 ?
    C10 C15 H15 . . 119.5 ?
    N4 C9 C8 . . 109.8(2) ?
    N4 C9 H9A . . 109.7 ?
    C8 C9 H9A . . 109.7 ?
    N4 C9 H9B . . 109.7 ?
    C8 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    C7 C8 C9 . . 111.4(2) ?
    C7 C8 H8A . . 109.4 ?
    C9 C8 H8A . . 109.4 ?
    C7 C8 H8B . . 109.4 ?
    C9 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 108.0 ?
data_Compound_7_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H18 N2 O3 S'
_chemical_formula_sum     'C13 H18 N2 O3 S'
_chemical_formula_weight     282.35
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     12.8651(14)
_cell_length_b     15.3291(14)
_cell_length_c     7.1435(8)
_cell_angle_alpha     90.00
_cell_angle_beta     93.379(4)
_cell_angle_gamma     90.00
_cell_volume     1406.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3155
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     24.47
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.236
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6654
_exptl_absorpt_correction_T_max     0.7452
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13591
_diffrn_reflns_av_R_equivalents     0.0494
_diffrn_reflns_av_sigmaI/netI     0.0346
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2482
_reflns_number_gt     1862
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0631
_refine_ls_R_factor_gt     0.0400
_refine_ls_wR_factor_gt     0.1123
_refine_ls_wR_factor_ref     0.1384
_refine_ls_goodness_of_fit_ref     0.974
_refine_ls_restrained_S_all     0.974
_refine_ls_number_reflns     2482
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0911P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.178
_refine_ls_shift/su_mean     0.004
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.365
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.33423(5) 0.08148(4) 0.13084(9) 0.0460(2) Uani d . 1 . .
    O O1 0.37112(17) -0.00653(12) 0.1231(3) 0.0639(6) Uani d . 1 . .
    O O2 0.28768(17) 0.11992(14) -0.0363(2) 0.0686(6) Uani d . 1 . .
    O O3 0.82867(16) 0.21154(14) 0.4203(4) 0.0803(7) Uani d . 1 . .
    N N1 0.69540(15) 0.30618(12) 0.3612(3) 0.0411(5) Uani d . 1 . .
    H H1 0.6807 0.3609 0.3594 0.049 Uiso calc R 1 . .
    N N2 0.24632(16) 0.08331(12) 0.2859(3) 0.0411(5) Uani d . 1 . .
    C C1 0.8656(2) 0.3629(2) 0.4483(5) 0.0684(8) Uani d . 1 . .
    H H1A 0.8820 0.3672 0.5809 0.103 Uiso calc R 1 . .
    H H1B 0.8306 0.4151 0.4050 0.103 Uiso calc R 1 . .
    H H1C 0.9287 0.3560 0.3845 0.103 Uiso calc R 1 . .
    C C2 0.7967(2) 0.28618(18) 0.4089(4) 0.0495(6) Uani d . 1 . .
    C C3 0.61164(18) 0.25016(14) 0.3148(3) 0.0353(5) Uani d . 1 . .
    C C4 0.51545(18) 0.28786(14) 0.2662(3) 0.0382(5) Uani d . 1 . .
    H H4 0.5083 0.3482 0.2690 0.046 Uiso calc R 1 . .
    C C5 0.43120(18) 0.23700(15) 0.2145(3) 0.0401(6) Uani d . 1 . .
    H H5 0.3673 0.2630 0.1825 0.048 Uiso calc R 1 . .
    C C6 0.44078(19) 0.14622(14) 0.2096(3) 0.0390(6) Uani d . 1 . .
    C C7 0.2776(2) 0.04740(16) 0.4723(3) 0.0470(6) Uani d . 1 . .
    H H7A 0.3165 0.0909 0.5459 0.056 Uiso calc R 1 . .
    H H7B 0.3222 -0.0029 0.4585 0.056 Uiso calc R 1 . .
    C C8 0.1821(2) 0.02102(18) 0.5718(4) 0.0566(7) Uani d . 1 . .
    H H8A 0.1481 -0.0274 0.5056 0.068 Uiso calc R 1 . .
    H H8B 0.2029 0.0016 0.6977 0.068 Uiso calc R 1 . .
    C C9 0.1067(2) 0.0956(2) 0.5822(5) 0.0712(9) Uani d . 1 . .
    H H9A 0.1369 0.1405 0.6641 0.085 Uiso calc R 1 . .
    H H9B 0.0434 0.0752 0.6352 0.085 Uiso calc R 1 . .
    C C10 0.6206(2) 0.15966(15) 0.3122(4) 0.0465(6) Uani d . 1 . .
    H H10 0.6842 0.1336 0.3459 0.056 Uiso calc R 1 . .
    C C11 0.5362(2) 0.10888(16) 0.2602(4) 0.0470(6) Uani d . 1 . .
    H H11 0.5431 0.0485 0.2589 0.056 Uiso calc R 1 . .
    C C12 0.1775(2) 0.15985(18) 0.2943(4) 0.0583(7) Uani d . 1 . .
    H H12A 0.1593 0.1809 0.1686 0.070 Uiso calc R 1 . .
    H H12B 0.2131 0.2064 0.3643 0.070 Uiso calc R 1 . .
    C C13 0.0804(2) 0.1340(2) 0.3889(6) 0.0774(10) Uani d . 1 . .
    H H13A 0.0419 0.0914 0.3120 0.093 Uiso calc R 1 . .
    H H13B 0.0364 0.1849 0.4007 0.093 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.431(2) ?
    S1 O1 . 1.432(2) ?
    S1 N2 . 1.629(2) ?
    S1 C6 . 1.758(2) ?
    O3 C2 . 1.217(3) ?
    N1 C2 . 1.362(3) ?
    N1 C3 . 1.402(3) ?
    N1 H1 . 0.8600 ?
    N2 C12 . 1.473(3) ?
    N2 C7 . 1.474(3) ?
    C1 C2 . 1.491(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C3 C4 . 1.391(3) ?
    C3 C10 . 1.392(3) ?
    C4 C5 . 1.368(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.398(3) ?
    C5 H5 . 0.9300 ?
    C6 C11 . 1.383(3) ?
    C7 C8 . 1.510(4) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.504(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C13 . 1.521(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.369(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.508(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 118.62(13) ?
    O2 S1 N2 . . 106.68(12) ?
    O1 S1 N2 . . 106.71(11) ?
    O2 S1 C6 . . 108.34(11) ?
    O1 S1 C6 . . 106.87(12) ?
    N2 S1 C6 . . 109.39(10) ?
    C2 N1 C3 . . 129.2(2) ?
    C2 N1 H1 . . 115.4 ?
    C3 N1 H1 . . 115.4 ?
    C12 N2 C7 . . 113.2(2) ?
    C12 N2 S1 . . 118.96(17) ?
    C7 N2 S1 . . 116.37(16) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O3 C2 N1 . . 122.9(3) ?
    O3 C2 C1 . . 122.3(3) ?
    N1 C2 C1 . . 114.8(2) ?
    C4 C3 C10 . . 118.9(2) ?
    C4 C3 N1 . . 117.68(19) ?
    C10 C3 N1 . . 123.4(2) ?
    C5 C4 C3 . . 120.6(2) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 120.3(2) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C11 C6 C5 . . 118.9(2) ?
    C11 C6 S1 . . 120.89(18) ?
    C5 C6 S1 . . 120.13(19) ?
    N2 C7 C8 . . 109.8(2) ?
    N2 C7 H7A . . 109.7 ?
    C8 C7 H7A . . 109.7 ?
    N2 C7 H7B . . 109.7 ?
    C8 C7 H7B . . 109.7 ?
    H7A C7 H7B . . 108.2 ?
    C9 C8 C7 . . 111.4(2) ?
    C9 C8 H8A . . 109.4 ?
    C7 C8 H8A . . 109.4 ?
    C9 C8 H8B . . 109.4 ?
    C7 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 108.0 ?
    C8 C9 C13 . . 111.0(3) ?
    C8 C9 H9A . . 109.4 ?
    C13 C9 H9A . . 109.4 ?
    C8 C9 H9B . . 109.4 ?
    C13 C9 H9B . . 109.4 ?
    H9A C9 H9B . . 108.0 ?
    C11 C10 C3 . . 120.3(2) ?
    C11 C10 H10 . . 119.8 ?
    C3 C10 H10 . . 119.8 ?
    C10 C11 C6 . . 120.9(2) ?
    C10 C11 H11 . . 119.6 ?
    C6 C11 H11 . . 119.6 ?
    N2 C12 C13 . . 109.0(2) ?
    N2 C12 H12A . . 109.9 ?
    C13 C12 H12A . . 109.9 ?
    N2 C12 H12B . . 109.9 ?
    C13 C12 H12B . . 109.9 ?
    H12A C12 H12B . . 108.3 ?
    C12 C13 C9 . . 111.3(3) ?
    C12 C13 H13A . . 109.4 ?
    C9 C13 H13A . . 109.4 ?
    C12 C13 H13B . . 109.4 ?
    C9 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
data_Compound_8_APEX
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H21 N O3 S2'
_chemical_formula_sum     'C21 H21 N O3 S2'
_chemical_formula_iupac     ?
_chemical_formula_weight     399.51
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.7771(7)
_cell_length_b     11.4544(6)
_cell_length_c     14.9031(9)
_cell_angle_alpha     90
_cell_angle_beta     95.9450(10)
_cell_angle_gamma     90
_cell_volume     1999.6(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9992
_cell_measurement_theta_min     2.7483
_cell_measurement_theta_max     25.0381
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.41
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.287
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.84
_exptl_absorpt_correction_T_max     0.93
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     26025
_diffrn_reflns_av_R_equivalents     0.0243
_diffrn_reflns_av_sigmaI/netI     0.0141
_diffrn_reflns_theta_min     1.74
_diffrn_reflns_theta_max     25.08
_diffrn_reflns_theta_full     25.08
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     3551
_reflns_number_gt     3109
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0373
_refine_ls_R_factor_gt     0.0313
_refine_ls_wR_factor_gt     0.0791
_refine_ls_wR_factor_ref     0.0851
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     3551
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0372P)²+0.9990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.296
_refine_diff_density_min     -0.274
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.91971(4) 0.21669(4) 0.81440(3) 0.03634(13) Uani d . 1 . .
    S S2 0.78404(4) 0.40992(4) 0.79051(3) 0.03870(13) Uani d . 1 . .
    O O1 1.24609(11) 0.17686(12) 1.14080(8) 0.0502(3) Uani d . 1 . .
    O O2 0.71155(13) 0.47433(13) 0.84429(8) 0.0571(4) Uani d . 1 . .
    O O3 0.88781(11) 0.46575(12) 0.76918(9) 0.0536(4) Uani d . 1 . .
    N N1 0.80920(12) 0.28740(13) 0.84166(9) 0.0394(3) Uani d . 1 . .
    C C1 1.2362(2) 0.2417(2) 1.22155(13) 0.0635(6) Uani d . 1 . .
    H H1A 1.2431 0.3236 1.2094 0.095 Uiso calc R 1 . .
    H H1B 1.2956 0.2185 1.267 0.095 Uiso calc R 1 . .
    H H1C 1.1631 0.2267 1.2424 0.095 Uiso calc R 1 . .
    C C2 1.16706(14) 0.19384(16) 1.06907(11) 0.0386(4) Uani d . 1 . .
    C C3 1.18363(15) 0.12763(17) 0.99314(12) 0.0450(4) Uani d . 1 . .
    H H3A 1.2461 0.0778 0.9944 0.054 Uiso calc R 1 . .
    C C4 1.10890(15) 0.13527(17) 0.91682(12) 0.0435(4) Uani d . 1 . .
    H H4 1.121 0.0919 0.8659 0.052 Uiso calc R 1 . .
    C C5 1.01436(14) 0.20857(15) 0.91591(11) 0.0353(4) Uani d . 1 . .
    C C6 0.70321(14) 0.37950(15) 0.68654(10) 0.0354(4) Uani d . 1 . .
    C C7 0.75666(15) 0.34315(17) 0.61306(11) 0.0423(4) Uani d . 1 . .
    H H7 0.8358 0.3372 0.6174 0.051 Uiso calc R 1 . .
    C C8 0.69235(17) 0.31579(18) 0.53356(12) 0.0479(4) Uani d . 1 . .
    H H8 0.7288 0.2908 0.4846 0.058 Uiso calc R 1 . .
    C C9 0.57456(17) 0.32469(19) 0.52483(12) 0.0502(5) Uani d . 1 . .
    C C10 0.5053(2) 0.2921(3) 0.43719(15) 0.0783(7) Uani d . 1 . .
    H H10A 0.4393 0.2483 0.4499 0.117 Uiso calc R 1 . .
    H H10B 0.5511 0.2456 0.4013 0.117 Uiso calc R 1 . .
    H H10C 0.4814 0.3618 0.4048 0.117 Uiso calc R 1 . .
    C C11 0.99757(15) 0.27512(16) 0.99015(11) 0.0399(4) Uani d . 1 . .
    H H11 0.9349 0.3247 0.9887 0.048 Uiso calc R 1 . .
    C C12 1.07427(15) 0.26834(16) 1.06728(12) 0.0423(4) Uani d . 1 . .
    H H12 1.0634 0.3136 1.1175 0.051 Uiso calc R 1 . .
    C C13 0.86641(17) 0.06721(16) 0.80931(12) 0.0456(4) Uani d . 1 . .
    H H13A 0.9301 0.0132 0.8122 0.055 Uiso calc R 1 . .
    H H13B 0.824 0.0523 0.8605 0.055 Uiso calc R 1 . .
    C C14 0.79035(15) 0.04823(15) 0.72325(11) 0.0400(4) Uani d . 1 . .
    C C15 0.67372(16) 0.06473(18) 0.72001(13) 0.0505(5) Uani d . 1 . .
    H H15 0.6415 0.0884 0.7714 0.061 Uiso calc R 1 . .
    C C16 0.60467(17) 0.0460(2) 0.64022(15) 0.0598(6) Uani d . 1 . .
    H H16 0.5261 0.0564 0.6383 0.072 Uiso calc R 1 . .
    C C17 0.65223(18) 0.0120(2) 0.56390(14) 0.0586(5) Uani d . 1 . .
    H H17 0.6059 0.0001 0.5102 0.07 Uiso calc R 1 . .
    C C18 0.76801(18) -0.00444(19) 0.56687(13) 0.0542(5) Uani d . 1 . .
    H H18 0.7999 -0.0279 0.5153 0.065 Uiso calc R 1 . .
    C C19 0.83695(16) 0.01362(17) 0.64584(12) 0.0461(4) Uani d . 1 . .
    H H19 0.9153 0.0025 0.6473 0.055 Uiso calc R 1 . .
    C C20 0.52325(17) 0.3614(2) 0.59898(15) 0.0644(6) Uani d . 1 . .
    H H20 0.4442 0.368 0.5946 0.077 Uiso calc R 1 . .
    C C21 0.58601(16) 0.3883(2) 0.67931(13) 0.0547(5) Uani d . 1 . .
    H H21 0.5495 0.4123 0.7285 0.066 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N1 . 1.6200(15) ?
    S1 C5 . 1.7861(16) ?
    S1 C13 . 1.8226(19) ?
    S2 O2 . 1.4343(14) ?
    S2 O3 . 1.4435(13) ?
    S2 N1 . 1.6099(14) ?
    S2 C6 . 1.7673(16) ?
    O1 C2 . 1.357(2) ?
    O1 C1 . 1.430(2) ?
    C1 H1A . 0.96 ?
    C1 H1B . 0.96 ?
    C1 H1C . 0.96 ?
    C2 C12 . 1.385(2) ?
    C2 C3 . 1.393(2) ?
    C3 C4 . 1.367(2) ?
    C3 H3A . 0.93 ?
    C4 C5 . 1.393(2) ?
    C4 H4 . 0.93 ?
    C5 C11 . 1.375(2) ?
    C6 C21 . 1.377(2) ?
    C6 C7 . 1.383(2) ?
    C7 C8 . 1.375(2) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.384(3) ?
    C8 H8 . 0.93 ?
    C9 C20 . 1.379(3) ?
    C9 C10 . 1.513(3) ?
    C10 H10A . 0.96 ?
    C10 H10B . 0.96 ?
    C10 H10C . 0.96 ?
    C11 C12 . 1.389(2) ?
    C11 H11 . 0.93 ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.502(2) ?
    C13 H13A . 0.97 ?
    C13 H13B . 0.97 ?
    C14 C15 . 1.382(3) ?
    C14 C19 . 1.386(3) ?
    C15 C16 . 1.386(3) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.375(3) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.373(3) ?
    C17 H17 . 0.93 ?
    C18 C19 . 1.375(3) ?
    C18 H18 . 0.93 ?
    C19 H19 . 0.93 ?
    C20 C21 . 1.375(3) ?
    C20 H20 . 0.93 ?
    C21 H21 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 S1 C5 . . 105.11(8) ?
    N1 S1 C13 . . 101.42(9) ?
    C5 S1 C13 . . 99.69(8) ?
    O2 S2 O3 . . 117.49(9) ?
    O2 S2 N1 . . 105.95(8) ?
    O3 S2 N1 . . 111.84(8) ?
    O2 S2 C6 . . 107.08(8) ?
    O3 S2 C6 . . 106.60(8) ?
    N1 S2 C6 . . 107.41(8) ?
    C2 O1 C1 . . 118.66(15) ?
    S2 N1 S1 . . 115.49(8) ?
    O1 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    O1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C12 . . 125.39(16) ?
    O1 C2 C3 . . 114.82(15) ?
    C12 C2 C3 . . 119.78(16) ?
    C4 C3 C2 . . 120.59(16) ?
    C4 C3 H3A . . 119.7 ?
    C2 C3 H3A . . 119.7 ?
    C3 C4 C5 . . 119.44(16) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C11 C5 C4 . . 120.51(15) ?
    C11 C5 S1 . . 121.58(13) ?
    C4 C5 S1 . . 117.87(12) ?
    C21 C6 C7 . . 119.67(16) ?
    C21 C6 S2 . . 119.92(13) ?
    C7 C6 S2 . . 120.38(13) ?
    C8 C7 C6 . . 119.72(16) ?
    C8 C7 H7 . . 120.1 ?
    C6 C7 H7 . . 120.1 ?
    C7 C8 C9 . . 121.46(17) ?
    C7 C8 H8 . . 119.3 ?
    C9 C8 H8 . . 119.3 ?
    C20 C9 C8 . . 117.74(17) ?
    C20 C9 C10 . . 121.7(2) ?
    C8 C9 C10 . . 120.59(19) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C5 C11 C12 . . 119.99(16) ?
    C5 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C2 C12 C11 . . 119.66(16) ?
    C2 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C14 C13 S1 . . 110.11(12) ?
    C14 C13 H13A . . 109.6 ?
    S1 C13 H13A . . 109.6 ?
    C14 C13 H13B . . 109.6 ?
    S1 C13 H13B . . 109.6 ?
    H13A C13 H13B . . 108.2 ?
    C15 C14 C19 . . 119.20(16) ?
    C15 C14 C13 . . 120.83(17) ?
    C19 C14 C13 . . 119.97(17) ?
    C14 C15 C16 . . 120.09(18) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C17 C16 C15 . . 120.03(19) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C18 C17 C16 . . 120.04(19) ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C17 C18 C19 . . 120.24(19) ?
    C17 C18 H18 . . 119.9 ?
    C19 C18 H18 . . 119.9 ?
    C18 C19 C14 . . 120.41(18) ?
    C18 C19 H19 . . 119.8 ?
    C14 C19 H19 . . 119.8 ?
    C21 C20 C9 . . 121.69(18) ?
    C21 C20 H20 . . 119.2 ?
    C9 C20 H20 . . 119.2 ?
    C20 C21 C6 . . 119.72(17) ?
    C20 C21 H21 . . 120.1 ?
    C6 C21 H21 . . 120.1 ?
data_Compound_8_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H21 N O3 S2'
_chemical_formula_sum     'C21 H21 N O3 S2'
_chemical_formula_weight     399.51
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.7937(9)
_cell_length_b     11.4816(7)
_cell_length_c     14.9358(12)
_cell_angle_alpha     90.00
_cell_angle_beta     95.972(3)
_cell_angle_gamma     90.00
_cell_volume     2011.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3129
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     23.13
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorles
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.41
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.286
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8704
_exptl_absorpt_correction_T_max     0.8704
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12920
_diffrn_reflns_av_R_equivalents     0.0349
_diffrn_reflns_av_sigmaI/netI     0.0368
_diffrn_reflns_theta_min     1.74
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.04
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3546
_reflns_number_gt     2664
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0428
_refine_ls_wR_factor_gt     0.1225
_refine_ls_wR_factor_ref     0.1414
_refine_ls_goodness_of_fit_ref     1.124
_refine_ls_restrained_S_all     1.124
_refine_ls_number_reflns     3546
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0813P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.341
_refine_diff_density_min     -0.332
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.91969(5) 0.21665(5) 0.81432(4) 0.0375(2) Uani d . 1 . .
    S S3 0.78419(6) 0.40976(5) 0.79044(4) 0.0402(2) Uani d . 1 . .
    O O26 1.24615(15) 0.17768(16) 1.14026(12) 0.0512(5) Uani d . 1 . .
    O O4 0.88809(16) 0.46532(16) 0.76935(13) 0.0556(5) Uani d . 1 . .
    O O5 0.71164(17) 0.47438(17) 0.84434(12) 0.0589(6) Uani d . 1 . .
    N N2 0.80930(17) 0.28747(17) 0.84147(14) 0.0400(5) Uani d . 1 . .
    C C27 1.2366(3) 0.2421(3) 1.22105(19) 0.0652(9) Uani d . 1 . .
    H H27A 1.2449 0.3237 1.2094 0.098 Uiso calc R 1 . .
    H H27B 1.2952 0.2178 1.2666 0.098 Uiso calc R 1 . .
    H H27C 1.1632 0.2281 1.2414 0.098 Uiso calc R 1 . .
    C C23 1.1673(2) 0.1941(2) 1.06897(17) 0.0399(6) Uani d . 1 . .
    C C24 1.1835(2) 0.1282(2) 0.99287(17) 0.0464(7) Uani d . 1 . .
    H H24 1.2460 0.0786 0.9939 0.056 Uiso calc R 1 . .
    C C25 1.1088(2) 0.1358(2) 0.91676(17) 0.0453(7) Uani d . 1 . .
    H H25 1.1210 0.0924 0.8661 0.054 Uiso calc R 1 . .
    C C20 1.0144(2) 0.2087(2) 0.91535(16) 0.0349(6) Uani d . 1 . .
    C C6 0.7033(2) 0.3795(2) 0.68668(15) 0.0361(6) Uani d . 1 . .
    C C7 0.5863(2) 0.3880(3) 0.67936(19) 0.0566(8) Uani d . 1 . .
    H H7 0.5498 0.4125 0.7283 0.068 Uiso calc R 1 . .
    C C8 0.5234(2) 0.3601(3) 0.5991(2) 0.0682(9) Uani d . 1 . .
    H H8 0.4444 0.3658 0.5950 0.082 Uiso calc R 1 . .
    C C9 0.5746(2) 0.3239(2) 0.52474(18) 0.0507(7) Uani d . 1 . .
    C C12 0.5053(3) 0.2913(3) 0.4369(2) 0.0809(11) Uani d . 1 . .
    H H12A 0.4373 0.2513 0.4496 0.121 Uiso calc R 1 . .
    H H12B 0.5497 0.2413 0.4026 0.121 Uiso calc R 1 . .
    H H12C 0.4851 0.3606 0.4030 0.121 Uiso calc R 1 . .
    C C10 0.6923(2) 0.3151(2) 0.53404(18) 0.0494(7) Uani d . 1 . .
    H H10 0.7289 0.2899 0.4853 0.059 Uiso calc R 1 . .
    C C11 0.7563(2) 0.3426(2) 0.61328(17) 0.0432(6) Uani d . 1 . .
    H H11 0.8353 0.3365 0.6176 0.052 Uiso calc R 1 . .
    C C13 0.8663(2) 0.0672(2) 0.80893(17) 0.0467(7) Uani d . 1 . .
    H H13A 0.9299 0.0133 0.8120 0.056 Uiso calc R 1 . .
    H H13B 0.8237 0.0523 0.8599 0.056 Uiso calc R 1 . .
    C C14 0.7905(2) 0.0481(2) 0.72290(17) 0.0403(6) Uani d . 1 . .
    C C19 0.8364(2) 0.0135(2) 0.64557(18) 0.0474(7) Uani d . 1 . .
    H H19 0.9147 0.0020 0.6470 0.057 Uiso calc R 1 . .
    C C18 0.7677(3) -0.0041(2) 0.5667(2) 0.0564(8) Uani d . 1 . .
    H H18 0.7996 -0.0271 0.5151 0.068 Uiso calc R 1 . .
    C C17 0.6520(3) 0.0120(3) 0.5640(2) 0.0597(8) Uani d . 1 . .
    H H17 0.6057 0.0004 0.5104 0.072 Uiso calc R 1 . .
    C C16 0.6047(2) 0.0453(3) 0.6398(2) 0.0613(8) Uani d . 1 . .
    H H16 0.5263 0.0550 0.6380 0.074 Uiso calc R 1 . .
    C C15 0.6738(2) 0.0645(2) 0.71944(19) 0.0515(7) Uani d . 1 . .
    H H15 0.6416 0.0884 0.7706 0.062 Uiso calc R 1 . .
    C C21 0.9981(2) 0.2752(2) 0.99003(17) 0.0418(6) Uani d . 1 . .
    H H21 0.9354 0.3246 0.9887 0.050 Uiso calc R 1 . .
    C C22 1.0742(2) 0.2690(2) 1.06678(17) 0.0429(6) Uani d . 1 . .
    H H22 1.0634 0.3146 1.1166 0.051 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 N2 . 1.622(2) ?
    S1 C20 . 1.784(2) ?
    S1 C13 . 1.826(3) ?
    S3 O5 . 1.4401(19) ?
    S3 O4 . 1.4450(19) ?
    S3 N2 . 1.610(2) ?
    S3 C6 . 1.768(2) ?
    O26 C23 . 1.352(3) ?
    O26 C27 . 1.430(3) ?
    C27 H27A . 0.9600 ?
    C27 H27B . 0.9600 ?
    C27 H27C . 0.9600 ?
    C23 C22 . 1.392(3) ?
    C23 C24 . 1.395(4) ?
    C24 C25 . 1.367(3) ?
    C24 H24 . 0.9300 ?
    C25 C20 . 1.391(3) ?
    C25 H25 . 0.9300 ?
    C20 C21 . 1.382(3) ?
    C6 C7 . 1.376(3) ?
    C6 C11 . 1.384(3) ?
    C7 C8 . 1.380(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.383(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.383(4) ?
    C9 C12 . 1.519(4) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C10 C11 . 1.373(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C13 C14 . 1.503(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C19 . 1.384(4) ?
    C14 C15 . 1.385(4) ?
    C19 C18 . 1.374(4) ?
    C19 H19 . 0.9300 ?
    C18 C17 . 1.374(4) ?
    C18 H18 . 0.9300 ?
    C17 C16 . 1.367(4) ?
    C17 H17 . 0.9300 ?
    C16 C15 . 1.387(4) ?
    C16 H16 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C21 C22 . 1.383(3) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 S1 C20 . . 105.21(11) ?
    N2 S1 C13 . . 101.52(12) ?
    C20 S1 C13 . . 99.90(11) ?
    O5 S3 O4 . . 117.46(13) ?
    O5 S3 N2 . . 105.99(11) ?
    O4 S3 N2 . . 111.70(11) ?
    O5 S3 C6 . . 107.08(12) ?
    O4 S3 C6 . . 106.75(11) ?
    N2 S3 C6 . . 107.41(11) ?
    C23 O26 C27 . . 119.0(2) ?
    S3 N2 S1 . . 115.58(12) ?
    O26 C27 H27A . . 109.5 ?
    O26 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O26 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    O26 C23 C22 . . 125.5(2) ?
    O26 C23 C24 . . 115.1(2) ?
    C22 C23 C24 . . 119.4(2) ?
    C25 C24 C23 . . 120.8(2) ?
    C25 C24 H24 . . 119.6 ?
    C23 C24 H24 . . 119.6 ?
    C24 C25 C20 . . 119.8(2) ?
    C24 C25 H25 . . 120.1 ?
    C20 C25 H25 . . 120.1 ?
    C21 C20 C25 . . 119.9(2) ?
    C21 C20 S1 . . 121.81(19) ?
    C25 C20 S1 . . 118.25(19) ?
    C7 C6 C11 . . 119.4(2) ?
    C7 C6 S3 . . 120.0(2) ?
    C11 C6 S3 . . 120.51(19) ?
    C6 C7 C8 . . 119.8(3) ?
    C6 C7 H7 . . 120.1 ?
    C8 C7 H7 . . 120.1 ?
    C7 C8 C9 . . 121.8(3) ?
    C7 C8 H8 . . 119.1 ?
    C9 C8 H8 . . 119.1 ?
    C8 C9 C10 . . 117.3(3) ?
    C8 C9 C12 . . 121.8(3) ?
    C10 C9 C12 . . 120.9(3) ?
    C9 C12 H12A . . 109.5 ?
    C9 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C9 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C11 C10 C9 . . 121.7(3) ?
    C11 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C10 C11 C6 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C6 C11 H11 . . 120.0 ?
    C14 C13 S1 . . 110.29(17) ?
    C14 C13 H13A . . 109.6 ?
    S1 C13 H13A . . 109.6 ?
    C14 C13 H13B . . 109.6 ?
    S1 C13 H13B . . 109.6 ?
    H13A C13 H13B . . 108.1 ?
    C19 C14 C15 . . 118.8(2) ?
    C19 C14 C13 . . 120.4(2) ?
    C15 C14 C13 . . 120.8(2) ?
    C18 C19 C14 . . 120.7(3) ?
    C18 C19 H19 . . 119.6 ?
    C14 C19 H19 . . 119.6 ?
    C19 C18 C17 . . 120.1(3) ?
    C19 C18 H18 . . 119.9 ?
    C17 C18 H18 . . 119.9 ?
    C16 C17 C18 . . 120.1(3) ?
    C16 C17 H17 . . 119.9 ?
    C18 C17 H17 . . 119.9 ?
    C17 C16 C15 . . 120.1(3) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C14 C15 C16 . . 120.2(3) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C20 C21 C22 . . 120.5(2) ?
    C20 C21 H21 . . 119.7 ?
    C22 C21 H21 . . 119.7 ?
    C21 C22 C23 . . 119.6(2) ?
    C21 C22 H22 . . 120.2 ?
    C23 C22 H22 . . 120.2 ?
data_Compound_8_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H21 N O3 S2'
_chemical_formula_sum     'C21 H21 N O3 S2'
_chemical_formula_weight     399.51
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.7937(9)
_cell_length_b     11.4816(7)
_cell_length_c     14.9358(12)
_cell_angle_alpha     90.00
_cell_angle_beta     95.972(3)
_cell_angle_gamma     90.00
_cell_volume     2011.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3129
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     23.13
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.41
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.286
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8704
_exptl_absorpt_correction_T_max     0.8704
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12920
_diffrn_reflns_av_R_equivalents     0.0349
_diffrn_reflns_av_sigmaI/netI     0.0368
_diffrn_reflns_theta_min     1.74
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.04
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3546
_reflns_number_gt     2664
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0631
_refine_ls_R_factor_gt     0.0427
_refine_ls_wR_factor_gt     0.1232
_refine_ls_wR_factor_ref     0.1425
_refine_ls_goodness_of_fit_ref     1.097
_refine_ls_restrained_S_all     1.097
_refine_ls_number_reflns     3546
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0849P)²+0.0076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.161
_refine_ls_shift/su_mean     0.005
_refine_diff_density_max     0.341
_refine_diff_density_min     -0.331
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.78419(6) 0.40976(5) 0.79044(4) 0.0402(2) Uani d . 1 . .
    S S2 0.91969(5) 0.21664(5) 0.81432(4) 0.0374(2) Uani d . 1 . .
    O O1 1.24615(15) 0.17766(16) 1.14025(12) 0.0512(5) Uani d . 1 . .
    O O2 0.88808(16) 0.46531(16) 0.76934(13) 0.0556(5) Uani d . 1 . .
    O O3 0.71164(17) 0.47438(17) 0.84433(12) 0.0589(6) Uani d . 1 . .
    N N1 0.80930(17) 0.28746(17) 0.84147(14) 0.0400(5) Uani d . 1 . .
    C C1 0.5053(3) 0.2914(3) 0.4369(2) 0.0809(11) Uani d . 1 . .
    H H1A 0.4371 0.2517 0.4495 0.121 Uiso calc R 1 . .
    H H1B 0.5496 0.2412 0.4027 0.121 Uiso calc R 1 . .
    H H1C 0.4853 0.3607 0.4029 0.121 Uiso calc R 1 . .
    C C2 0.5746(2) 0.3240(2) 0.52474(18) 0.0507(7) Uani d . 1 . .
    C C3 0.5234(2) 0.3601(3) 0.5991(2) 0.0682(9) Uani d . 1 . .
    H H3 0.4444 0.3658 0.5950 0.082 Uiso calc R 1 . .
    C C4 0.5863(2) 0.3880(3) 0.67935(19) 0.0566(8) Uani d . 1 . .
    H H4 0.5498 0.4125 0.7283 0.068 Uiso calc R 1 . .
    C C5 0.7033(2) 0.3795(2) 0.68666(15) 0.0361(6) Uani d . 1 . .
    C C6 1.0144(2) 0.2087(2) 0.91536(16) 0.0349(6) Uani d . 1 . .
    C C7 0.9981(2) 0.2752(2) 0.99003(17) 0.0418(6) Uani d . 1 . .
    H H7 0.9354 0.3245 0.9887 0.050 Uiso calc R 1 . .
    C C8 1.0742(2) 0.2690(2) 1.06679(17) 0.0429(6) Uani d . 1 . .
    H H8 1.0634 0.3146 1.1167 0.052 Uiso calc R 1 . .
    C C9 1.1673(2) 0.1941(2) 1.06896(17) 0.0399(6) Uani d . 1 . .
    C C10 1.2366(3) 0.2421(3) 1.22106(19) 0.0652(9) Uani d . 1 . .
    H H10A 1.2449 0.3237 1.2094 0.098 Uiso calc R 1 . .
    H H10B 1.2952 0.2177 1.2666 0.098 Uiso calc R 1 . .
    H H10C 1.1632 0.2281 1.2414 0.098 Uiso calc R 1 . .
    C C11 0.8663(2) 0.0672(2) 0.80896(17) 0.0467(7) Uani d . 1 . .
    H H11A 0.9299 0.0133 0.8120 0.056 Uiso calc R 1 . .
    H H11B 0.8237 0.0523 0.8600 0.056 Uiso calc R 1 . .
    C C12 0.7905(2) 0.0481(2) 0.72291(17) 0.0403(6) Uani d . 1 . .
    C C13 0.6738(2) 0.0645(2) 0.71947(19) 0.0515(7) Uani d . 1 . .
    H H13 0.6416 0.0884 0.7707 0.062 Uiso calc R 1 . .
    C C14 0.6047(2) 0.0453(3) 0.6398(2) 0.0613(8) Uani d . 1 . .
    H H14 0.5263 0.0551 0.6380 0.074 Uiso calc R 1 . .
    C C15 0.6520(3) 0.0121(3) 0.5640(2) 0.0598(8) Uani d . 1 . .
    H H15 0.6056 0.0004 0.5104 0.072 Uiso calc R 1 . .
    C C16 0.7677(3) -0.0041(2) 0.5667(2) 0.0564(8) Uani d . 1 . .
    H H16 0.7996 -0.0271 0.5151 0.068 Uiso calc R 1 . .
    C C17 0.8365(2) 0.0135(2) 0.64559(18) 0.0474(7) Uani d . 1 . .
    H H17 0.9147 0.0020 0.6470 0.057 Uiso calc R 1 . .
    C C18 1.1088(2) 0.1358(2) 0.91676(17) 0.0453(7) Uani d . 1 . .
    H H18 1.1209 0.0924 0.8661 0.054 Uiso calc R 1 . .
    C C19 1.1835(2) 0.1282(2) 0.99286(17) 0.0464(7) Uani d . 1 . .
    H H19 1.2460 0.0786 0.9939 0.056 Uiso calc R 1 . .
    C C20 0.7563(2) 0.3427(2) 0.61328(17) 0.0432(6) Uani d . 1 . .
    H H20 0.8354 0.3365 0.6176 0.052 Uiso calc R 1 . .
    C C21 0.6923(2) 0.3152(2) 0.53404(18) 0.0494(7) Uani d . 1 . .
    H H21 0.7289 0.2900 0.4853 0.059 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O3 . 1.4400(19) ?
    S1 O2 . 1.4450(19) ?
    S1 N1 . 1.610(2) ?
    S1 C5 . 1.768(2) ?
    S2 N1 . 1.622(2) ?
    S2 C6 . 1.784(2) ?
    S2 C11 . 1.826(3) ?
    O1 C9 . 1.352(3) ?
    O1 C10 . 1.430(3) ?
    C1 C2 . 1.519(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.382(4) ?
    C2 C21 . 1.383(4) ?
    C3 C4 . 1.380(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.376(3) ?
    C4 H4 . 0.9300 ?
    C5 C20 . 1.383(3) ?
    C6 C7 . 1.382(3) ?
    C6 C18 . 1.391(3) ?
    C7 C8 . 1.383(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.392(3) ?
    C8 H8 . 0.9300 ?
    C9 C19 . 1.395(4) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C12 . 1.503(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C17 . 1.384(4) ?
    C12 C13 . 1.385(4) ?
    C13 C14 . 1.387(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.367(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.374(4) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.374(4) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.367(3) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.373(3) ?
    C20 H20 . 0.9300 ?
    C21 H21 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 S1 O2 . . 117.46(13) ?
    O3 S1 N1 . . 105.99(11) ?
    O2 S1 N1 . . 111.70(11) ?
    O3 S1 C5 . . 107.07(12) ?
    O2 S1 C5 . . 106.74(11) ?
    N1 S1 C5 . . 107.41(11) ?
    N1 S2 C6 . . 105.22(11) ?
    N1 S2 C11 . . 101.52(12) ?
    C6 S2 C11 . . 99.88(11) ?
    C9 O1 C10 . . 119.0(2) ?
    S1 N1 S2 . . 115.58(12) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 C21 . . 117.3(3) ?
    C3 C2 C1 . . 121.8(3) ?
    C21 C2 C1 . . 120.8(3) ?
    C4 C3 C2 . . 121.8(3) ?
    C4 C3 H3 . . 119.1 ?
    C2 C3 H3 . . 119.1 ?
    C5 C4 C3 . . 119.8(3) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C4 C5 C20 . . 119.4(2) ?
    C4 C5 S1 . . 120.0(2) ?
    C20 C5 S1 . . 120.49(19) ?
    C7 C6 C18 . . 119.9(2) ?
    C7 C6 S2 . . 121.82(19) ?
    C18 C6 S2 . . 118.24(19) ?
    C6 C7 C8 . . 120.5(2) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C7 C8 C9 . . 119.6(2) ?
    C7 C8 H8 . . 120.2 ?
    C9 C8 H8 . . 120.2 ?
    O1 C9 C8 . . 125.5(2) ?
    O1 C9 C19 . . 115.1(2) ?
    C8 C9 C19 . . 119.4(2) ?
    O1 C10 H10A . . 109.5 ?
    O1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    O1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C12 C11 S2 . . 110.27(17) ?
    C12 C11 H11A . . 109.6 ?
    S2 C11 H11A . . 109.6 ?
    C12 C11 H11B . . 109.6 ?
    S2 C11 H11B . . 109.6 ?
    H11A C11 H11B . . 108.1 ?
    C17 C12 C13 . . 118.8(2) ?
    C17 C12 C11 . . 120.4(2) ?
    C13 C12 C11 . . 120.8(2) ?
    C12 C13 C14 . . 120.2(3) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 120.1(3) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 120.1(3) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C17 C16 C15 . . 120.1(3) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C16 C17 C12 . . 120.7(3) ?
    C16 C17 H17 . . 119.7 ?
    C12 C17 H17 . . 119.7 ?
    C19 C18 C6 . . 119.8(2) ?
    C19 C18 H18 . . 120.1 ?
    C6 C18 H18 . . 120.1 ?
    C18 C19 C9 . . 120.8(2) ?
    C18 C19 H19 . . 119.6 ?
    C9 C19 H19 . . 119.6 ?
    C21 C20 C5 . . 120.0(2) ?
    C21 C20 H20 . . 120.0 ?
    C5 C20 H20 . . 120.0 ?
    C20 C21 C2 . . 121.7(3) ?
    C20 C21 H21 . . 119.1 ?
    C2 C21 H21 . . 119.1 ?
data_Compound_9_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 F2 O S'
_chemical_formula_sum     'C13 H10 F2 O S'
_chemical_formula_weight     252.27
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     Pca2(1)
_symmetry_space_group_name_Hall     'P 2c -2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y, z+1/2'
    'x+1/2, -y, z'
_cell_length_a     8.3649(16)
_cell_length_b     5.5063(10)
_cell_length_c     25.129(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1157.4(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2280
_cell_measurement_theta_min     3.70
_cell_measurement_theta_max     24.67
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.448
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.285
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7491
_exptl_absorpt_correction_T_max     0.8708
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6646
_diffrn_reflns_av_R_equivalents     0.0370
_diffrn_reflns_av_sigmaI/netI     0.0343
_diffrn_reflns_theta_min     1.62
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     28
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2013
_reflns_number_gt     1760
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0449
_refine_ls_R_factor_gt     0.0338
_refine_ls_wR_factor_gt     0.0886
_refine_ls_wR_factor_ref     0.1182
_refine_ls_goodness_of_fit_ref     1.190
_refine_ls_restrained_S_all     1.190
_refine_ls_number_reflns     2013
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0681P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.020
_refine_ls_shift/su_mean     0.004
_refine_diff_density_max     0.176
_refine_diff_density_min     -0.186
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.07(10)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.29434(9) 0.17051(14) 0.00059(3) 0.0413(2) Uani d . 1 . .
    F F1 0.5368(4) 0.3431(4) -0.21543(9) 0.0785(8) Uani d . 1 . .
    F F2 0.2986(4) 0.1816(5) 0.25419(9) 0.0833(10) Uani d . 1 . .
    O O1 0.3161(3) -0.0944(4) 0.01086(11) 0.0571(7) Uani d . 1 . .
    C C1 0.4817(5) 0.3033(8) -0.16523(14) 0.0539(10) Uani d . 1 . .
    C C2 0.5299(5) 0.0960(8) -0.13933(16) 0.0543(10) Uani d . 1 . .
    H H2 0.5982 -0.0150 -0.1555 0.065 Uiso calc R 1 . .
    C C3 0.4728(4) 0.0590(7) -0.08826(14) 0.0449(8) Uani d . 1 . .
    H H3 0.5015 -0.0808 -0.0698 0.054 Uiso calc R 1 . .
    C C4 0.3734(4) 0.2274(6) -0.06441(12) 0.0376(7) Uani d . 1 . .
    C C5 0.4491(4) 0.3284(6) 0.03887(13) 0.0389(8) Uani d . 1 . .
    H H5A 0.5535 0.2622 0.0305 0.047 Uiso calc R 1 . .
    H H5B 0.4491 0.5000 0.0301 0.047 Uiso calc R 1 . .
    C C6 0.4130(4) 0.2934(6) 0.09713(13) 0.0355(8) Uani d . 1 . .
    C C7 0.3139(4) 0.4548(6) 0.12431(16) 0.0447(8) Uani d . 1 . .
    H H7 0.2734 0.5894 0.1065 0.054 Uiso calc R 1 . .
    C C8 0.2746(5) 0.4194(8) 0.17711(15) 0.0534(9) Uani d . 1 . .
    H H8 0.2073 0.5264 0.1950 0.064 Uiso calc R 1 . .
    C C9 0.3383(5) 0.2213(8) 0.20225(15) 0.0501(9) Uani d . 1 . .
    C C10 0.3817(5) 0.4729(8) -0.14335(15) 0.0557(10) Uani d . 1 . .
    H H10 0.3514 0.6102 -0.1624 0.067 Uiso calc R 1 . .
    C C11 0.3270(5) 0.4339(7) -0.09210(16) 0.0495(9) Uani d . 1 . .
    H H11 0.2590 0.5461 -0.0762 0.059 Uiso calc R 1 . .
    C C12 0.4383(4) 0.0590(8) 0.17791(15) 0.0521(10) Uani d . 1 . .
    H H12 0.4804 -0.0725 0.1964 0.063 Uiso calc R 1 . .
    C C13 0.4747(4) 0.0967(7) 0.12502(16) 0.0468(9) Uani d . 1 . .
    H H13 0.5419 -0.0119 0.1076 0.056 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.493(3) ?
    S1 C4 . 1.790(3) ?
    S1 C5 . 1.832(3) ?
    F1 C1 . 1.361(4) ?
    F2 C9 . 1.364(5) ?
    C1 C10 . 1.369(6) ?
    C1 C2 . 1.375(6) ?
    C2 C3 . 1.384(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.382(5) ?
    C3 H3 . 0.9300 ?
    C4 C11 . 1.388(5) ?
    C5 C6 . 1.507(5) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C13 . 1.390(5) ?
    C6 C7 . 1.393(5) ?
    C7 C8 . 1.381(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.368(6) ?
    C8 H8 . 0.9300 ?
    C9 C12 . 1.369(6) ?
    C10 C11 . 1.384(6) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.379(5) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 C4 . . 106.50(16) ?
    O1 S1 C5 . . 106.67(15) ?
    C4 S1 C5 . . 97.76(15) ?
    F1 C1 C10 . . 118.0(4) ?
    F1 C1 C2 . . 118.2(4) ?
    C10 C1 C2 . . 123.7(4) ?
    C1 C2 C3 . . 117.4(4) ?
    C1 C2 H2 . . 121.3 ?
    C3 C2 H2 . . 121.3 ?
    C4 C3 C2 . . 120.7(3) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C11 . . 120.0(3) ?
    C3 C4 S1 . . 120.0(3) ?
    C11 C4 S1 . . 119.8(3) ?
    C6 C5 S1 . . 107.9(2) ?
    C6 C5 H5A . . 110.1 ?
    S1 C5 H5A . . 110.1 ?
    C6 C5 H5B . . 110.1 ?
    S1 C5 H5B . . 110.1 ?
    H5A C5 H5B . . 108.4 ?
    C13 C6 C7 . . 118.1(3) ?
    C13 C6 C5 . . 121.0(3) ?
    C7 C6 C5 . . 120.9(3) ?
    C8 C7 C6 . . 121.5(3) ?
    C8 C7 H7 . . 119.3 ?
    C6 C7 H7 . . 119.3 ?
    C9 C8 C7 . . 117.6(3) ?
    C9 C8 H8 . . 121.2 ?
    C7 C8 H8 . . 121.2 ?
    F2 C9 C12 . . 118.1(4) ?
    F2 C9 C8 . . 118.3(3) ?
    C12 C9 C8 . . 123.5(3) ?
    C1 C10 C11 . . 118.1(4) ?
    C1 C10 H10 . . 121.0 ?
    C11 C10 H10 . . 121.0 ?
    C10 C11 C4 . . 120.1(4) ?
    C10 C11 H11 . . 120.0 ?
    C4 C11 H11 . . 120.0 ?
    C9 C12 C13 . . 117.9(4) ?
    C9 C12 H12 . . 121.1 ?
    C13 C12 H12 . . 121.1 ?
    C12 C13 C6 . . 121.4(3) ?
    C12 C13 H13 . . 119.3 ?
    C6 C13 H13 . . 119.3 ?
data_Compound_10_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H12 N2 O'
_chemical_formula_sum     'C15 H12 N2 O'
_chemical_formula_weight     236.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/n1
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.5500(16)
_cell_length_b     11.186(3)
_cell_length_c     13.954(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.938(8)
_cell_angle_gamma     90.00
_cell_volume     1176.9(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1875
_cell_measurement_theta_min     2.92
_cell_measurement_theta_max     22.81
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.333
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9740
_exptl_absorpt_correction_T_max     0.9806
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7461
_diffrn_reflns_av_R_equivalents     0.0332
_diffrn_reflns_av_sigmaI/netI     0.0335
_diffrn_reflns_theta_min     2.33
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2066
_reflns_number_gt     1550
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0594
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.1017
_refine_ls_wR_factor_ref     0.1253
_refine_ls_goodness_of_fit_ref     1.227
_refine_ls_restrained_S_all     1.228
_refine_ls_number_reflns     2066
_refine_ls_number_parameters     169
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0626P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.012
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.137
_refine_diff_density_min     -0.203
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.50554(16) 0.37794(11) 0.09342(9) 0.0443(4) Uani d . 1 . .
    N N1 0.29539(19) 0.23506(13) 0.06062(10) 0.0369(4) Uani d . 1 . .
    N N2 0.3205(2) 0.39934(16) -0.03842(12) 0.0502(5) Uani d D 1 . .
    H H2B 0.229(2) 0.379(2) -0.0735(14) 0.075 Uiso d D 1 . .
    H H2A 0.368(3) 0.4663(13) -0.0538(15) 0.075 Uiso d D 1 . .
    C C1 0.5228(3) 0.05566(18) 0.25480(14) 0.0502(5) Uani d . 1 . .
    H H1 0.6304 0.0165 0.2667 0.060 Uiso calc R 1 . .
    C C2 0.4892(2) 0.11456(17) 0.16873(13) 0.0434(5) Uani d . 1 . .
    H H2 0.5742 0.1145 0.1228 0.052 Uiso calc R 1 . .
    C C3 0.3300(2) 0.17365(16) 0.15044(11) 0.0342(4) Uani d . 1 . .
    C C4 0.1537(2) 0.18899(16) -0.00154(12) 0.0368(4) Uani d . 1 . .
    C C5 -0.0219(2) 0.19900(16) 0.02550(13) 0.0401(5) Uani d . 1 . .
    C C6 -0.1551(3) 0.16093(18) -0.04081(14) 0.0495(5) Uani d . 1 . .
    H H6 -0.2730 0.1675 -0.0252 0.059 Uiso calc R 1 . .
    C C7 -0.1165(3) 0.11392(18) -0.12869(15) 0.0550(6) Uani d . 1 . .
    H H7 -0.2079 0.0897 -0.1716 0.066 Uiso calc R 1 . .
    C C8 0.3971(3) 0.05490(18) 0.32303(13) 0.0507(5) Uani d . 1 . .
    H H8 0.4193 0.0151 0.3809 0.061 Uiso calc R 1 . .
    C C9 0.2388(3) 0.11326(17) 0.30511(12) 0.0454(5) Uani d . 1 . .
    H H9 0.1552 0.1129 0.3518 0.054 Uiso calc R 1 . .
    C C10 0.1998(2) 0.17331(16) 0.21848(11) 0.0361(4) Uani d . 1 . .
    C C11 0.3809(2) 0.34055(16) 0.04112(12) 0.0342(4) Uani d . 1 . .
    C C12 0.1924(3) 0.13928(18) -0.08928(13) 0.0474(5) Uani d . 1 . .
    H H12 0.3099 0.1305 -0.1052 0.057 Uiso calc R 1 . .
    C C13 0.0569(3) 0.10278(18) -0.15299(14) 0.0539(6) Uani d . 1 . .
    H H13 0.0830 0.0708 -0.2121 0.065 Uiso calc R 1 . .
    C C14 -0.0683(3) 0.24309(17) 0.11938(14) 0.0461(5) Uani d . 1 . .
    H H14 -0.1752 0.2840 0.1218 0.055 Uiso calc R 1 . .
    C C15 0.0269(3) 0.23079(17) 0.20214(14) 0.0464(5) Uani d . 1 . .
    H H15 -0.0230 0.2627 0.2561 0.056 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C11 . 1.234(2) ?
    N1 C11 . 1.379(2) ?
    N1 C4 . 1.438(2) ?
    N1 C3 . 1.441(2) ?
    N2 C11 . 1.349(2) ?
    N2 H2B . 0.858(9) ?
    N2 H2A . 0.862(9) ?
    C1 C8 . 1.379(3) ?
    C1 C2 . 1.382(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.384(2) ?
    C2 H2 . 0.9300 ?
    C3 C10 . 1.401(2) ?
    C4 C12 . 1.389(3) ?
    C4 C5 . 1.401(3) ?
    C5 C6 . 1.398(3) ?
    C5 C14 . 1.459(3) ?
    C6 C7 . 1.379(3) ?
    C6 H6 . 0.9300 ?
    C7 C13 . 1.375(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.373(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.401(2) ?
    C9 H9 . 0.9300 ?
    C10 C15 . 1.462(3) ?
    C12 C13 . 1.382(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.336(2) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C11 N1 C4 . . 121.95(14) ?
    C11 N1 C3 . . 120.90(13) ?
    C4 N1 C3 . . 116.74(13) ?
    C11 N2 H2B . . 124.5(15) ?
    C11 N2 H2A . . 120.1(14) ?
    H2B N2 H2A . . 115.1(18) ?
    C8 C1 C2 . . 120.06(19) ?
    C8 C1 H1 . . 120.0 ?
    C2 C1 H1 . . 120.0 ?
    C1 C2 C3 . . 120.46(18) ?
    C1 C2 H2 . . 119.8 ?
    C3 C2 H2 . . 119.8 ?
    C2 C3 C10 . . 120.46(16) ?
    C2 C3 N1 . . 120.33(15) ?
    C10 C3 N1 . . 119.21(15) ?
    C12 C4 C5 . . 120.95(17) ?
    C12 C4 N1 . . 119.41(17) ?
    C5 C4 N1 . . 119.60(16) ?
    C6 C5 C4 . . 117.12(18) ?
    C6 C5 C14 . . 119.97(18) ?
    C4 C5 C14 . . 122.88(16) ?
    C7 C6 C5 . . 121.8(2) ?
    C7 C6 H6 . . 119.1 ?
    C5 C6 H6 . . 119.1 ?
    C13 C7 C6 . . 120.05(19) ?
    C13 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C9 C8 C1 . . 119.67(18) ?
    C9 C8 H8 . . 120.2 ?
    C1 C8 H8 . . 120.2 ?
    C8 C9 C10 . . 121.84(18) ?
    C8 C9 H9 . . 119.1 ?
    C10 C9 H9 . . 119.1 ?
    C9 C10 C3 . . 117.51(17) ?
    C9 C10 C15 . . 119.47(16) ?
    C3 C10 C15 . . 123.02(16) ?
    O1 C11 N2 . . 122.46(16) ?
    O1 C11 N1 . . 121.61(15) ?
    N2 C11 N1 . . 115.93(16) ?
    C13 C12 C4 . . 120.2(2) ?
    C13 C12 H12 . . 119.9 ?
    C4 C12 H12 . . 119.9 ?
    C7 C13 C12 . . 119.84(19) ?
    C7 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
    C15 C14 C5 . . 126.73(18) ?
    C15 C14 H14 . . 116.6 ?
    C5 C14 H14 . . 116.6 ?
    C14 C15 C10 . . 128.06(18) ?
    C14 C15 H15 . . 116.0 ?
    C10 C15 H15 . . 116.0 ?
data_Compound_11_APEX
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 I N O2 S'
_chemical_formula_sum     'C13 H10 I N O2 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     371.18
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4946(11)
_cell_length_b     7.7421(11)
_cell_length_c     11.4816(16)
_cell_angle_alpha     95.418(3)
_cell_angle_beta     103.879(3)
_cell_angle_gamma     96.985(3)
_cell_volume     636.65(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4101
_cell_measurement_theta_min     2.6726
_cell_measurement_theta_max     27.1162
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.936
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     2.671
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.56
_exptl_absorpt_correction_T_max     0.76
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     7653
_diffrn_reflns_av_R_equivalents     0.0247
_diffrn_reflns_av_sigmaI/netI     0.0285
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     27.34
_diffrn_reflns_theta_full     27.34
_diffrn_measured_fraction_theta_max     0.973
_diffrn_measured_fraction_theta_full     0.973
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2786
_reflns_number_gt     2492
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0324
_refine_ls_R_factor_gt     0.0275
_refine_ls_wR_factor_gt     0.0633
_refine_ls_wR_factor_ref     0.0659
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     2786
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0324P)²+0.3359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.407
_refine_diff_density_min     -0.425
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 1.32050(2) 1.17267(3) 1.412333(19) 0.04289(9) Uani d . 1 . .
    S S1 0.54670(9) 0.71959(11) 0.91681(7) 0.0413(2) Uani d . 1 . .
    O O1 -0.3387(3) 0.3512(4) 0.7134(3) 0.0599(7) Uani d . 1 . .
    O O2 -0.2470(3) 0.3193(4) 0.5501(2) 0.0598(7) Uani d . 1 . .
    N N1 -0.2198(3) 0.3702(3) 0.6568(3) 0.0395(6) Uani d . 1 . .
    C C1 1.0642(4) 1.0503(4) 1.2973(3) 0.0328(6) Uani d . 1 . .
    C C2 0.9027(4) 1.0497(4) 1.3363(3) 0.0395(7) Uani d . 1 . .
    H H2 0.9061 1.1044 1.4126 0.047 Uiso calc R 1 . .
    C C3 0.7356(4) 0.9660(4) 1.2595(3) 0.0395(7) Uani d . 1 . .
    H H3 0.6271 0.9657 1.2853 0.047 Uiso calc R 1 . .
    C C4 0.7265(4) 0.8831(4) 1.1456(3) 0.0312(6) Uani d . 1 . .
    C C5 0.5358(4) 0.7918(4) 1.0649(3) 0.0378(7) Uani d . 1 . .
    H H5A 0.4464 0.873 1.0613 0.045 Uiso calc R 1 . .
    H H5B 0.4926 0.692 1.1012 0.045 Uiso calc R 1 . .
    C C6 0.3162(4) 0.6227(4) 0.8469(3) 0.0332(6) Uani d . 1 . .
    C C7 0.1686(4) 0.6265(4) 0.9014(3) 0.0386(7) Uani d . 1 . .
    H H7 0.1882 0.6834 0.9794 0.046 Uiso calc R 1 . .
    C C8 -0.0077(4) 0.5444(4) 0.8379(3) 0.0357(7) Uani d . 1 . .
    H H8 -0.1072 0.5464 0.8729 0.043 Uiso calc R 1 . .
    C C9 -0.0341(4) 0.4602(4) 0.7227(3) 0.0328(6) Uani d . 1 . .
    C C10 0.8916(4) 0.8863(4) 1.1080(3) 0.0388(7) Uani d . 1 . .
    H H10 0.8891 0.8328 1.0315 0.047 Uiso calc R 1 . .
    C C11 1.0595(4) 0.9698(4) 1.1851(3) 0.0403(7) Uani d . 1 . .
    H H11 1.1688 0.9706 1.1602 0.048 Uiso calc R 1 . .
    C C12 0.2851(4) 0.5383(4) 0.7294(3) 0.0379(7) Uani d . 1 . .
    H H12 0.3835 0.5371 0.6932 0.046 Uiso calc R 1 . .
    C C13 0.1094(4) 0.4566(4) 0.6663(3) 0.0370(7) Uani d . 1 . .
    H H13 0.0882 0.4005 0.5879 0.044 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C1 . 2.106(3) ?
    S1 C6 . 1.760(3) ?
    S1 C5 . 1.763(3) ?
    O1 N1 . 1.225(3) ?
    O2 N1 . 1.211(4) ?
    N1 C9 . 1.468(3) ?
    C1 C11 . 1.368(5) ?
    C1 C2 . 1.388(4) ?
    C2 C3 . 1.389(4) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.384(4) ?
    C3 H3 . 0.93 ?
    C4 C10 . 1.404(4) ?
    C4 C5 . 1.548(4) ?
    C5 H5A . 0.97 ?
    C5 H5B . 0.97 ?
    C6 C12 . 1.395(4) ?
    C6 C7 . 1.397(4) ?
    C7 C8 . 1.388(4) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.376(4) ?
    C8 H8 . 0.93 ?
    C9 C13 . 1.384(4) ?
    C10 C11 . 1.394(4) ?
    C10 H10 . 0.93 ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.383(4) ?
    C12 H12 . 0.93 ?
    C13 H13 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 S1 C5 . . 102.67(14) ?
    O2 N1 O1 . . 123.8(3) ?
    O2 N1 C9 . . 118.4(3) ?
    O1 N1 C9 . . 117.8(3) ?
    C11 C1 C2 . . 120.6(3) ?
    C11 C1 I1 . . 119.4(2) ?
    C2 C1 I1 . . 120.0(2) ?
    C1 C2 C3 . . 119.0(3) ?
    C1 C2 H2 . . 120.5 ?
    C3 C2 H2 . . 120.5 ?
    C4 C3 C2 . . 121.7(3) ?
    C4 C3 H3 . . 119.1 ?
    C2 C3 H3 . . 119.1 ?
    C3 C4 C10 . . 118.2(3) ?
    C3 C4 C5 . . 119.0(2) ?
    C10 C4 C5 . . 122.7(3) ?
    C4 C5 S1 . . 112.32(18) ?
    C4 C5 H5A . . 109.1 ?
    S1 C5 H5A . . 109.1 ?
    C4 C5 H5B . . 109.1 ?
    S1 C5 H5B . . 109.1 ?
    H5A C5 H5B . . 107.9 ?
    C12 C6 C7 . . 119.9(3) ?
    C12 C6 S1 . . 115.8(2) ?
    C7 C6 S1 . . 124.3(2) ?
    C8 C7 C6 . . 119.4(3) ?
    C8 C7 H7 . . 120.3 ?
    C6 C7 H7 . . 120.3 ?
    C9 C8 C7 . . 119.6(3) ?
    C9 C8 H8 . . 120.2 ?
    C7 C8 H8 . . 120.2 ?
    C8 C9 C13 . . 122.1(3) ?
    C8 C9 N1 . . 119.4(3) ?
    C13 C9 N1 . . 118.4(3) ?
    C11 C10 C4 . . 120.1(3) ?
    C11 C10 H10 . . 120.0 ?
    C4 C10 H10 . . 120.0 ?
    C1 C11 C10 . . 120.3(3) ?
    C1 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C13 C12 C6 . . 120.6(3) ?
    C13 C12 H12 . . 119.7 ?
    C6 C12 H12 . . 119.7 ?
    C12 C13 C9 . . 118.4(3) ?
    C12 C13 H13 . . 120.8 ?
    C9 C13 H13 . . 120.8 ?
data_Compound_11_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 I N O2 S'
_chemical_formula_sum     'C13 H10 I N O2 S'
_chemical_formula_weight     371.18
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5076(15)
_cell_length_b     7.760(2)
_cell_length_c     11.507(3)
_cell_angle_alpha     95.317(8)
_cell_angle_beta     103.999(7)
_cell_angle_gamma     97.013(7)
_cell_volume     640.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1954
_cell_measurement_theta_min     2.67
_cell_measurement_theta_max     22.48
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.925
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     2.655
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.3502
_exptl_absorpt_correction_T_max     0.8787
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6315
_diffrn_reflns_av_R_equivalents     0.0381
_diffrn_reflns_av_sigmaI/netI     0.0447
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2224
_reflns_number_gt     1836
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0431
_refine_ls_R_factor_gt     0.0303
_refine_ls_wR_factor_gt     0.0723
_refine_ls_wR_factor_ref     0.0966
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     2224
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0532P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.069
_refine_diff_density_min     -0.552
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I9 1.32038(5) 1.17269(5) 1.41230(3) 0.04524(18) Uani d . 1 . .
    S S1 0.54650(19) 0.71990(19) 0.91683(13) 0.0426(4) Uani d . 1 . .
    N N16 -0.2196(6) 0.3702(6) 0.6576(4) 0.0414(11) Uani d . 1 . .
    C C6 1.0642(7) 1.0497(7) 1.2974(5) 0.0347(12) Uani d . 1 . .
    C C7 1.0591(7) 0.9687(7) 1.1848(5) 0.0414(13) Uani d . 1 . .
    H H7 1.1679 0.9692 1.1597 0.050 Uiso calc R 1 . .
    C C8 0.8917(7) 0.8862(7) 1.1091(5) 0.0394(13) Uani d . 1 . .
    H H8 0.8890 0.8317 1.0330 0.047 Uiso calc R 1 . .
    C C3 0.7270(7) 0.8839(6) 1.1454(5) 0.0312(11) Uani d . 1 . .
    C C2 0.5347(7) 0.7908(7) 1.0641(5) 0.0370(12) Uani d . 1 . .
    H H2A 0.4447 0.8711 1.0602 0.044 Uiso calc R 1 . .
    H H2B 0.4923 0.6908 1.1003 0.044 Uiso calc R 1 . .
    C C10 0.3168(7) 0.6231(6) 0.8477(5) 0.0320(11) Uani d . 1 . .
    C C11 0.1686(7) 0.6268(7) 0.9017(5) 0.0390(13) Uani d . 1 . .
    H H11 0.1878 0.6845 0.9792 0.047 Uiso calc R 1 . .
    C C12 -0.0060(7) 0.5443(7) 0.8390(5) 0.0376(12) Uani d . 1 . .
    H H12 -0.1050 0.5453 0.8744 0.045 Uiso calc R 1 . .
    C C13 -0.0336(7) 0.4603(6) 0.7237(5) 0.0335(12) Uani d . 1 . .
    C C14 0.1094(7) 0.4575(7) 0.6674(5) 0.0392(12) Uani d . 1 . .
    H H14 0.0876 0.4024 0.5890 0.047 Uiso calc R 1 . .
    C C15 0.2851(7) 0.5381(7) 0.7299(5) 0.0404(13) Uani d . 1 . .
    H H15 0.3831 0.5360 0.6937 0.048 Uiso calc R 1 . .
    C C4 0.7373(8) 0.9647(7) 1.2590(5) 0.0419(13) Uani d . 1 . .
    H H4 0.6296 0.9619 1.2856 0.050 Uiso calc R 1 . .
    C C5 0.9016(7) 1.0490(7) 1.3341(5) 0.0417(13) Uani d . 1 . .
    H H5 0.9039 1.1055 1.4095 0.050 Uiso calc R 1 . .
    O O17 -0.3386(6) 0.3506(6) 0.7142(4) 0.0602(12) Uani d . 1 . .
    O O18 -0.2465(6) 0.3196(6) 0.5506(4) 0.0627(12) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I9 C6 . 2.109(5) ?
    S1 C2 . 1.759(6) ?
    S1 C10 . 1.755(5) ?
    N16 O18 . 1.217(6) ?
    N16 O17 . 1.230(6) ?
    N16 C13 . 1.472(7) ?
    C6 C7 . 1.376(7) ?
    C6 C5 . 1.384(8) ?
    C7 C8 . 1.385(7) ?
    C7 H7 . 0.9300 ?
    C8 C3 . 1.396(7) ?
    C8 H8 . 0.9300 ?
    C3 C4 . 1.377(7) ?
    C3 C2 . 1.565(7) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C10 C15 . 1.403(7) ?
    C10 C11 . 1.401(7) ?
    C11 C12 . 1.378(7) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.379(7) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.383(7) ?
    C14 C15 . 1.380(7) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C4 C5 . 1.371(8) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 S1 C10 . . 102.2(2) ?
    O18 N16 O17 . . 124.0(5) ?
    O18 N16 C13 . . 118.3(5) ?
    O17 N16 C13 . . 117.8(5) ?
    C7 C6 C5 . . 119.8(5) ?
    C7 C6 I9 . . 119.5(4) ?
    C5 C6 I9 . . 120.7(4) ?
    C8 C7 C6 . . 119.9(5) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C7 C8 C3 . . 120.8(5) ?
    C7 C8 H8 . . 119.6 ?
    C3 C8 H8 . . 119.6 ?
    C4 C3 C8 . . 117.8(5) ?
    C4 C3 C2 . . 119.3(4) ?
    C8 C3 C2 . . 122.9(4) ?
    C3 C2 S1 . . 112.0(3) ?
    C3 C2 H2A . . 109.2 ?
    S1 C2 H2A . . 109.2 ?
    C3 C2 H2B . . 109.2 ?
    S1 C2 H2B . . 109.2 ?
    H2A C2 H2B . . 107.9 ?
    C15 C10 C11 . . 119.6(5) ?
    C15 C10 S1 . . 115.7(4) ?
    C11 C10 S1 . . 124.7(4) ?
    C12 C11 C10 . . 119.5(5) ?
    C12 C11 H11 . . 120.2 ?
    C10 C11 H11 . . 120.2 ?
    C11 C12 C13 . . 119.8(5) ?
    C11 C12 H12 . . 120.1 ?
    C13 C12 H12 . . 120.1 ?
    C12 C13 C14 . . 121.8(5) ?
    C12 C13 N16 . . 119.7(5) ?
    C14 C13 N16 . . 118.4(5) ?
    C15 C14 C13 . . 118.7(5) ?
    C15 C14 H14 . . 120.6 ?
    C13 C14 H14 . . 120.6 ?
    C14 C15 C10 . . 120.4(5) ?
    C14 C15 H15 . . 119.8 ?
    C10 C15 H15 . . 119.8 ?
    C5 C4 C3 . . 122.0(5) ?
    C5 C4 H4 . . 119.0 ?
    C3 C4 H4 . . 119.0 ?
    C4 C5 C6 . . 119.7(5) ?
    C4 C5 H5 . . 120.1 ?
    C6 C5 H5 . . 120.1 ?
data_Compound_11_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 I N O2 S'
_chemical_formula_sum     'C13 H10 I N O2 S'
_chemical_formula_weight     371.18
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5076(15)
_cell_length_b     7.760(2)
_cell_length_c     11.507(3)
_cell_angle_alpha     95.317(8)
_cell_angle_beta     103.999(7)
_cell_angle_gamma     97.013(7)
_cell_volume     640.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1954
_cell_measurement_theta_min     2.67
_cell_measurement_theta_max     22.48
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.925
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     2.655
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6912
_exptl_absorpt_correction_T_max     0.8787
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6315
_diffrn_reflns_av_R_equivalents     0.0381
_diffrn_reflns_av_sigmaI/netI     0.0447
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2224
_reflns_number_gt     1836
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0431
_refine_ls_R_factor_gt     0.0303
_refine_ls_wR_factor_gt     0.0724
_refine_ls_wR_factor_ref     0.0967
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_restrained_S_all     1.071
_refine_ls_number_reflns     2224
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0536P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.025
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     1.070
_refine_diff_density_min     -0.552
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 1.32038(5) 1.17269(5) 1.41230(3) 0.04524(18) Uani d . 1 . .
    S S1 0.54650(19) 0.71990(19) 0.91682(13) 0.0426(4) Uani d . 1 . .
    O O1 -0.2465(6) 0.3196(6) 0.5506(4) 0.0627(12) Uani d . 1 . .
    O O2 -0.3386(6) 0.3506(6) 0.7142(4) 0.0602(12) Uani d . 1 . .
    N N1 -0.2196(6) 0.3702(6) 0.6576(4) 0.0414(11) Uani d . 1 . .
    C C1 1.0642(7) 1.0497(7) 1.2974(5) 0.0347(12) Uani d . 1 . .
    C C2 1.0591(7) 0.9687(7) 1.1848(5) 0.0414(13) Uani d . 1 . .
    H H2 1.1679 0.9693 1.1597 0.050 Uiso calc R 1 . .
    C C3 0.8917(7) 0.8862(7) 1.1091(5) 0.0394(13) Uani d . 1 . .
    H H3 0.8890 0.8317 1.0331 0.047 Uiso calc R 1 . .
    C C4 0.7270(7) 0.8839(6) 1.1454(5) 0.0312(11) Uani d . 1 . .
    C C5 0.5347(7) 0.7908(7) 1.0641(5) 0.0370(12) Uani d . 1 . .
    H H5A 0.4447 0.8711 1.0603 0.044 Uiso calc R 1 . .
    H H5B 0.4923 0.6908 1.1003 0.044 Uiso calc R 1 . .
    C C6 0.3168(7) 0.6231(6) 0.8477(5) 0.0320(11) Uani d . 1 . .
    C C7 0.1686(7) 0.6268(7) 0.9017(5) 0.0390(13) Uani d . 1 . .
    H H7 0.1878 0.6845 0.9792 0.047 Uiso calc R 1 . .
    C C8 -0.0060(7) 0.5443(7) 0.8390(5) 0.0376(12) Uani d . 1 . .
    H H8 -0.1050 0.5453 0.8743 0.045 Uiso calc R 1 . .
    C C9 -0.0336(7) 0.4603(6) 0.7237(5) 0.0336(12) Uani d . 1 . .
    C C10 0.1094(7) 0.4575(7) 0.6674(5) 0.0393(12) Uani d . 1 . .
    H H10 0.0876 0.4024 0.5890 0.047 Uiso calc R 1 . .
    C C11 0.2851(7) 0.5381(7) 0.7299(5) 0.0404(13) Uani d . 1 . .
    H H11 0.3831 0.5360 0.6937 0.048 Uiso calc R 1 . .
    C C12 0.7373(8) 0.9647(7) 1.2590(5) 0.0419(13) Uani d . 1 . .
    H H12 0.6296 0.9619 1.2856 0.050 Uiso calc R 1 . .
    C C13 0.9016(7) 1.0490(7) 1.3341(5) 0.0417(13) Uani d . 1 . .
    H H13 0.9039 1.1055 1.4095 0.050 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C1 . 2.109(5) ?
    S1 C6 . 1.755(5) ?
    S1 C5 . 1.759(6) ?
    O1 N1 . 1.217(6) ?
    O2 N1 . 1.230(6) ?
    N1 C9 . 1.472(7) ?
    C1 C2 . 1.376(7) ?
    C1 C13 . 1.384(8) ?
    C2 C3 . 1.385(7) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.396(7) ?
    C3 H3 . 0.9300 ?
    C4 C12 . 1.377(7) ?
    C4 C5 . 1.565(7) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.401(7) ?
    C6 C11 . 1.403(7) ?
    C7 C8 . 1.378(7) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.379(7) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.382(7) ?
    C10 C11 . 1.380(7) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.371(8) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 S1 C5 . . 102.2(2) ?
    O1 N1 O2 . . 124.0(5) ?
    O1 N1 C9 . . 118.3(5) ?
    O2 N1 C9 . . 117.8(5) ?
    C2 C1 C13 . . 119.8(5) ?
    C2 C1 I1 . . 119.5(4) ?
    C13 C1 I1 . . 120.8(4) ?
    C1 C2 C3 . . 119.9(5) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C2 C3 C4 . . 120.8(5) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C12 C4 C3 . . 117.8(5) ?
    C12 C4 C5 . . 119.3(4) ?
    C3 C4 C5 . . 122.9(4) ?
    C4 C5 S1 . . 112.0(3) ?
    C4 C5 H5A . . 109.2 ?
    S1 C5 H5A . . 109.2 ?
    C4 C5 H5B . . 109.2 ?
    S1 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    C7 C6 C11 . . 119.6(5) ?
    C7 C6 S1 . . 124.6(4) ?
    C11 C6 S1 . . 115.7(4) ?
    C8 C7 C6 . . 119.5(5) ?
    C8 C7 H7 . . 120.2 ?
    C6 C7 H7 . . 120.2 ?
    C7 C8 C9 . . 119.8(5) ?
    C7 C8 H8 . . 120.1 ?
    C9 C8 H8 . . 120.1 ?
    C10 C9 C8 . . 121.8(5) ?
    C10 C9 N1 . . 118.4(5) ?
    C8 C9 N1 . . 119.7(5) ?
    C9 C10 C11 . . 118.8(5) ?
    C9 C10 H10 . . 120.6 ?
    C11 C10 H10 . . 120.6 ?
    C10 C11 C6 . . 120.4(5) ?
    C10 C11 H11 . . 119.8 ?
    C6 C11 H11 . . 119.8 ?
    C13 C12 C4 . . 122.0(5) ?
    C13 C12 H12 . . 119.0 ?
    C4 C12 H12 . . 119.0 ?
    C12 C13 C1 . . 119.7(5) ?
    C12 C13 H13 . . 120.1 ?
    C1 C13 H13 . . 120.1 ?
data_Compound_12_APEX
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H5 N O3 S'
_chemical_formula_sum     'C7 H5 N O3 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     183.18
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.5830(12)
_cell_length_b     6.9252(8)
_cell_length_c     11.8518(15)
_cell_angle_alpha     90
_cell_angle_beta     103.815(3)
_cell_angle_gamma     90
_cell_volume     763.78(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2150
_cell_measurement_theta_min     3.4334
_cell_measurement_theta_max     25.6741
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.593
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.384
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.6636
_exptl_absorpt_correction_T_max     0.7453
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     5166
_diffrn_reflns_av_R_equivalents     0.0216
_diffrn_reflns_av_sigmaI/netI     0.0191
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     25.78
_diffrn_reflns_theta_full     25.78
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     1473
_reflns_number_gt     1283
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0364
_refine_ls_R_factor_gt     0.0308
_refine_ls_wR_factor_gt     0.0767
_refine_ls_wR_factor_ref     0.0806
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     1473
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0346P)²+0.3571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.275
_refine_diff_density_min     -0.312
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.71048(5) 0.77117(7) 0.34633(4) 0.03726(16) Uani d . 1 . .
    O O1 0.58436(15) 0.6573(2) 0.33741(13) 0.0569(4) Uani d . 1 . .
    O O2 0.74426(16) 0.8307(2) 0.24099(11) 0.0533(4) Uani d . 1 . .
    O O3 1.01830(14) 0.69119(19) 0.60358(10) 0.0418(3) Uani d . 1 . .
    N N1 0.85064(16) 0.6592(2) 0.43101(13) 0.0393(4) Uani d . 1 . .
    H H1 0.8815 0.5501 0.4121 0.047 Uiso calc R 1 . .
    C C1 0.7808(2) 1.2299(3) 0.62054(18) 0.0486(5) Uani d . 1 . .
    H H1A 0.7988 1.3211 0.6799 0.058 Uiso calc R 1 . .
    C C2 0.8669(2) 1.0675(3) 0.62928(15) 0.0404(4) Uani d . 1 . .
    H H2 0.9433 1.0489 0.6934 0.049 Uiso calc R 1 . .
    C C3 0.83630(18) 0.9339(2) 0.54028(14) 0.0320(4) Uani d . 1 . .
    C C4 0.72226(19) 0.9636(3) 0.44499(15) 0.0339(4) Uani d . 1 . .
    C C5 0.91367(19) 0.7512(2) 0.53243(15) 0.0327(4) Uani d . 1 . .
    C C6 0.6680(2) 1.2579(3) 0.52409(19) 0.0512(5) Uani d . 1 . .
    H H6 0.612 1.3686 0.5198 0.061 Uiso calc R 1 . .
    C C7 0.6362(2) 1.1259(3) 0.43402(18) 0.0464(5) Uani d . 1 . .
    H H7 0.5608 1.1454 0.3693 0.056 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4236(14) ?
    S1 O1 . 1.4258(15) ?
    S1 N1 . 1.6640(15) ?
    S1 C4 . 1.7585(18) ?
    O3 C5 . 1.219(2) ?
    N1 C5 . 1.367(2) ?
    N1 H1 . 0.86 ?
    C1 C2 . 1.384(3) ?
    C1 C6 . 1.387(3) ?
    C1 H1A . 0.93 ?
    C2 C3 . 1.381(2) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.387(2) ?
    C3 C5 . 1.480(2) ?
    C4 C7 . 1.381(3) ?
    C6 C7 . 1.383(3) ?
    C6 H6 . 0.93 ?
    C7 H7 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 117.48(9) ?
    O2 S1 N1 . . 110.13(9) ?
    O1 S1 N1 . . 109.56(9) ?
    O2 S1 C4 . . 111.82(9) ?
    O1 S1 C4 . . 112.78(9) ?
    N1 S1 C4 . . 92.16(8) ?
    C5 N1 S1 . . 115.88(12) ?
    C5 N1 H1 . . 122.1 ?
    S1 N1 H1 . . 122.1 ?
    C2 C1 C6 . . 120.58(19) ?
    C2 C1 H1A . . 119.7 ?
    C6 C1 H1A . . 119.7 ?
    C3 C2 C1 . . 118.25(18) ?
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C2 C3 C4 . . 120.34(16) ?
    C2 C3 C5 . . 127.05(16) ?
    C4 C3 C5 . . 112.61(15) ?
    C7 C4 C3 . . 122.25(17) ?
    C7 C4 S1 . . 127.72(14) ?
    C3 C4 S1 . . 110.02(13) ?
    O3 C5 N1 . . 124.53(16) ?
    O3 C5 C3 . . 126.13(16) ?
    N1 C5 C3 . . 109.33(14) ?
    C7 C6 C1 . . 121.89(18) ?
    C7 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    C4 C7 C6 . . 116.68(18) ?
    C4 C7 H7 . . 121.7 ?
    C6 C7 H7 . . 121.7 ?
data_Compound_12_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H5 N O3 S'
_chemical_formula_sum     'C7 H5 N O3 S'
_chemical_formula_weight     183.18
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.6083(16)
_cell_length_b     6.9347(10)
_cell_length_c     11.882(2)
_cell_angle_alpha     90.00
_cell_angle_beta     103.834(6)
_cell_angle_gamma     90.00
_cell_volume     768.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1234
_cell_measurement_theta_min     3.43
_cell_measurement_theta_max     21.50
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.583
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.381
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8322
_exptl_absorpt_correction_T_max     0.9812
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4799
_diffrn_reflns_av_R_equivalents     0.0347
_diffrn_reflns_av_sigmaI/netI     0.0358
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1346
_reflns_number_gt     1025
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0590
_refine_ls_R_factor_gt     0.0386
_refine_ls_wR_factor_gt     0.1067
_refine_ls_wR_factor_ref     0.1375
_refine_ls_goodness_of_fit_ref     1.171
_refine_ls_restrained_S_all     1.171
_refine_ls_number_reflns     1346
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'mixed'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0766P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.236
_refine_diff_density_min     -0.305
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.21039(8) 0.22889(11) 0.84628(7) 0.0398(3) Uani d . 1 . .
    O O1 0.2438(2) 0.1694(3) 0.74080(18) 0.0563(7) Uani d . 1 . .
    O O2 0.0848(2) 0.3425(3) 0.8371(2) 0.0600(7) Uani d . 1 . .
    N N1 0.3503(3) 0.3404(4) 0.9311(2) 0.0425(7) Uani d . 1 . .
    O O3 0.5180(2) 0.3087(3) 1.10339(17) 0.0441(6) Uani d . 1 . .
    C C1 0.2220(3) 0.0374(4) 0.9451(2) 0.0361(7) Uani d . 1 . .
    C C2 0.1361(3) -0.1255(4) 0.9339(3) 0.0486(8) Uani d . 1 . .
    H H2 0.0612 -0.1454 0.8691 0.058 Uiso calc R 1 . .
    C C3 0.1674(4) -0.2569(5) 1.0240(3) 0.0544(10) Uani d . 1 . .
    H H3 0.1113 -0.3672 1.0197 0.065 Uiso calc R 1 . .
    C C4 0.2804(4) -0.2292(5) 1.1211(3) 0.0499(9) Uani d . 1 . .
    H H4 0.2978 -0.3200 1.1804 0.060 Uiso calc R 1 . .
    C C5 0.4128(3) 0.2489(4) 1.0322(2) 0.0333(7) Uani d . 1 . .
    C C6 0.3354(3) 0.0660(4) 1.0399(2) 0.0330(7) Uani d . 1 . .
    C C7 0.3663(3) -0.0680(4) 1.1294(3) 0.0435(8) Uani d . 1 . .
    H H7 0.4429 -0.0495 1.1932 0.052 Uiso calc R 1 . .
    H H1 0.376(3) 0.446(4) 0.913(3) 0.047(10) Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.423(2) ?
    S1 O1 . 1.427(2) ?
    S1 N1 . 1.665(2) ?
    S1 C1 . 1.758(3) ?
    N1 C5 . 1.364(4) ?
    N1 H1 . 0.82(3) ?
    O3 C5 . 1.224(3) ?
    C1 C6 . 1.382(4) ?
    C1 C2 . 1.386(4) ?
    C2 C3 . 1.383(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.395(5) ?
    C3 H3 . 0.9300 ?
    C4 C7 . 1.379(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.484(4) ?
    C6 C7 . 1.390(4) ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 117.24(14) ?
    O2 S1 N1 . . 109.65(15) ?
    O1 S1 N1 . . 110.33(15) ?
    O2 S1 C1 . . 112.72(15) ?
    O1 S1 C1 . . 112.09(13) ?
    N1 S1 C1 . . 91.92(13) ?
    C5 N1 S1 . . 116.0(2) ?
    C5 N1 H1 . . 124(2) ?
    S1 N1 H1 . . 120(2) ?
    C6 C1 C2 . . 122.0(3) ?
    C6 C1 S1 . . 110.3(2) ?
    C2 C1 S1 . . 127.6(2) ?
    C3 C2 C1 . . 116.7(3) ?
    C3 C2 H2 . . 121.7 ?
    C1 C2 H2 . . 121.7 ?
    C2 C3 C4 . . 122.1(3) ?
    C2 C3 H3 . . 119.0 ?
    C4 C3 H3 . . 119.0 ?
    C7 C4 C3 . . 120.3(3) ?
    C7 C4 H4 . . 119.8 ?
    C3 C4 H4 . . 119.8 ?
    O3 C5 N1 . . 124.6(2) ?
    O3 C5 C6 . . 126.1(3) ?
    N1 C5 C6 . . 109.3(2) ?
    C1 C6 C7 . . 120.7(3) ?
    C1 C6 C5 . . 112.4(2) ?
    C7 C6 C5 . . 126.9(3) ?
    C4 C7 C6 . . 118.2(3) ?
    C4 C7 H7 . . 120.9 ?
    C6 C7 H7 . . 120.9 ?
data_Compound_12_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H5 N O3 S'
_chemical_formula_sum     'C7 H0 N O3 S'
_chemical_formula_weight     178.14
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.6083(16)
_cell_length_b     6.9347(10)
_cell_length_c     11.882(2)
_cell_angle_alpha     90.00
_cell_angle_beta     103.834(6)
_cell_angle_gamma     90.00
_cell_volume     768.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1234
_cell_measurement_theta_min     3.43
_cell_measurement_theta_max     21.50
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.539
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     356
_exptl_absorpt_coefficient_mu     0.380
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8599
_exptl_absorpt_correction_T_max     0.9813
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4799
_diffrn_reflns_av_R_equivalents     0.0347
_diffrn_reflns_av_sigmaI/netI     0.0358
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1346
_reflns_number_gt     1025
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0798
_refine_ls_R_factor_gt     0.0593
_refine_ls_wR_factor_gt     0.1663
_refine_ls_wR_factor_ref     0.1968
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     1346
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1150P)²+0.9183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.025
_refine_ls_shift/su_mean     0.006
_refine_diff_density_max     0.588
_refine_diff_density_min     -0.467
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.21050(11) 0.22887(16) 0.84648(9) 0.0402(4) Uani d . 1 . .
    O O1 0.2443(4) 0.1688(5) 0.7411(3) 0.0571(10) Uani d . 1 . .
    O O2 0.0844(3) 0.3423(5) 0.8376(3) 0.0613(10) Uani d . 1 . .
    O O3 0.3507(4) 0.3425(5) 0.9303(3) 0.0625(10) Uani d . 1 . .
    N N1 0.5181(3) 0.3091(4) 1.1032(2) 0.0289(7) Uani d . 1 . .
    C C1 0.2217(4) 0.0375(6) 0.9452(3) 0.0370(10) Uani d . 1 . .
    C C2 0.1361(5) -0.1235(7) 0.9337(4) 0.0496(12) Uani d . 1 . .
    H H2 0.0610 -0.1428 0.8690 0.060 Uiso calc R 1 . .
    C C3 0.1681(6) -0.2572(7) 1.0247(5) 0.0555(14) Uani d . 1 . .
    H H3 0.1125 -0.3680 1.0203 0.067 Uiso calc R 1 . .
    C C4 0.2805(5) -0.2290(7) 1.1214(4) 0.0501(12) Uani d . 1 . .
    H H4 0.2979 -0.3194 1.1809 0.060 Uiso calc R 1 . .
    C C5 0.4136(5) 0.2491(5) 1.0326(3) 0.0355(10) Uani d . 1 . .
    C C6 0.3351(4) 0.0658(5) 1.0399(3) 0.0337(9) Uani d . 1 . .
    C C7 0.3660(5) -0.0686(6) 1.1297(4) 0.0448(11) Uani d . 1 . .
    H H7 0.4425 -0.0501 1.1935 0.054 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.428(3) ?
    S1 O1 . 1.428(3) ?
    S1 O3 . 1.669(3) ?
    S1 C1 . 1.758(4) ?
    O3 C5 . 1.383(5) ?
    N1 C5 . 1.217(5) ?
    C1 C2 . 1.374(6) ?
    C1 C6 . 1.381(6) ?
    C2 C3 . 1.402(7) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.389(7) ?
    C3 H3 . 0.9300 ?
    C4 C7 . 1.372(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.491(5) ?
    C6 C7 . 1.394(6) ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 117.6(2) ?
    O2 S1 O3 . . 109.5(2) ?
    O1 S1 O3 . . 109.9(2) ?
    O2 S1 C1 . . 112.4(2) ?
    O1 S1 C1 . . 111.98(19) ?
    O3 S1 C1 . . 92.66(18) ?
    C5 O3 S1 . . 115.1(3) ?
    C2 C1 C6 . . 122.3(4) ?
    C2 C1 S1 . . 127.4(3) ?
    C6 C1 S1 . . 110.3(3) ?
    C1 C2 C3 . . 116.4(4) ?
    C1 C2 H2 . . 121.8 ?
    C3 C2 H2 . . 121.8 ?
    C4 C3 C2 . . 121.9(4) ?
    C4 C3 H3 . . 119.1 ?
    C2 C3 H3 . . 119.1 ?
    C7 C4 C3 . . 120.5(4) ?
    C7 C4 H4 . . 119.8 ?
    C3 C4 H4 . . 119.8 ?
    N1 C5 O3 . . 124.1(4) ?
    N1 C5 C6 . . 126.6(4) ?
    O3 C5 C6 . . 109.3(3) ?
    C1 C6 C7 . . 120.7(4) ?
    C1 C6 C5 . . 112.7(4) ?
    C7 C6 C5 . . 126.6(4) ?
    C4 C7 C6 . . 118.2(4) ?
    C4 C7 H7 . . 120.9 ?
    C6 C7 H7 . . 120.9 ?
data_Compound_13_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H5 I N2 O2'
_chemical_formula_sum     'C6 H5 I N2 O2'
_chemical_formula_weight     264.02
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.7617(15)
_cell_length_b     12.912(3)
_cell_length_c     15.663(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.141(6)
_cell_angle_gamma     90.00
_cell_volume     1563.5(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3493
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     26.02
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.40
_exptl_crystal_density_diffrn     2.243
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     992
_exptl_absorpt_coefficient_mu     4.046
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.2633
_exptl_absorpt_correction_T_max     0.2945
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9846
_diffrn_reflns_av_R_equivalents     0.0298
_diffrn_reflns_av_sigmaI/netI     0.0296
_diffrn_reflns_theta_min     3.05
_diffrn_reflns_theta_max     25.18
_diffrn_reflns_theta_full     25.18
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2796
_reflns_number_gt     2258
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0380
_refine_ls_R_factor_gt     0.0256
_refine_ls_wR_factor_gt     0.0522
_refine_ls_wR_factor_ref     0.0561
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2796
_refine_ls_number_parameters     215
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0212P)²+1.3049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.832
_refine_diff_density_min     -0.651
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.39584(4) 0.67281(2) 0.153677(16) 0.05022(11) Uani d . 1 . .
    I I2 0.82449(4) 0.87837(2) 0.219736(16) 0.05021(11) Uani d . 1 . .
    N N1 0.3357(5) 0.8471(3) 0.2986(2) 0.0481(9) Uani d D 1 . .
    H H1A 0.301(5) 0.850(4) 0.2450(8) 0.063(15) Uiso d D 1 . .
    H H1B 0.301(6) 0.893(3) 0.333(3) 0.079(18) Uiso d D 1 . .
    O O1 0.7446(4) 0.5151(3) 0.52627(18) 0.0624(9) Uani d . 1 . .
    O O2 0.7598(5) 0.4463(3) 0.4020(2) 0.0767(11) Uani d . 1 . .
    N N4 1.0047(6) 0.6712(3) 0.3079(3) 0.0582(11) Uani d D 1 . .
    H H4A 0.964(7) 0.678(5) 0.2553(12) 0.10(2) Uiso d D 1 . .
    H H4B 1.062(5) 0.618(2) 0.328(3) 0.068(17) Uiso d D 1 . .
    C C10 0.4198(5) 0.7641(3) 0.3335(2) 0.0342(9) Uani d . 1 . .
    N N2 0.7104(4) 0.5151(3) 0.4481(2) 0.0477(9) Uani d . 1 . .
    O O3 0.7340(5) 1.0189(3) 0.5397(2) 0.0691(10) Uani d . 1 . .
    O O4 0.8666(4) 0.9236(3) 0.63678(18) 0.0688(10) Uani d . 1 . .
    C C1 0.4690(5) 0.6788(3) 0.2852(2) 0.0339(9) Uani d . 1 . .
    C C2 0.5637(5) 0.5972(3) 0.3222(2) 0.0371(9) Uani d . 1 . .
    H H2A 0.5976 0.5426 0.2889 0.044 Uiso calc R 1 . .
    C C3 0.6070(5) 0.5984(3) 0.4097(2) 0.0358(9) Uani d . 1 . .
    C C4 0.5562(5) 0.6793(3) 0.4600(2) 0.0406(10) Uani d . 1 . .
    H H4D 0.5840 0.6786 0.5190 0.049 Uiso calc R 1 . .
    C C5 0.4657(5) 0.7593(3) 0.4225(2) 0.0398(10) Uani d . 1 . .
    H H5 0.4325 0.8132 0.4568 0.048 Uiso calc R 1 . .
    C C6 0.9654(5) 0.7407(3) 0.3682(2) 0.0391(10) Uani d . 1 . .
    C C7 0.8817(5) 0.8341(3) 0.3476(2) 0.0345(9) Uani d . 1 . .
    C C8 0.8343(5) 0.8999(3) 0.4107(2) 0.0352(9) Uani d . 1 . .
    H H8 0.7751 0.9609 0.3962 0.042 Uiso calc R 1 . .
    C C9 0.8755(5) 0.8745(3) 0.4961(2) 0.0364(9) Uani d . 1 . .
    N N3 0.8213(5) 0.9431(3) 0.5614(2) 0.0478(9) Uani d . 1 . .
    C C11 0.9651(5) 0.7839(3) 0.5185(2) 0.0422(10) Uani d . 1 . .
    H H11 0.9949 0.7680 0.5758 0.051 Uiso calc R 1 . .
    C C12 1.0087(5) 0.7185(3) 0.4556(3) 0.0455(10) Uani d . 1 . .
    H H12 1.0685 0.6579 0.4706 0.055 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C1 . 2.089(3) ?
    I2 C7 . 2.092(4) ?
    N1 C10 . 1.345(5) ?
    N1 H1A . 0.858(5) ?
    N1 H1B . 0.859(5) ?
    O1 N2 . 1.229(4) ?
    O2 N2 . 1.229(4) ?
    N4 C6 . 1.358(5) ?
    N4 H4A . 0.860(5) ?
    N4 H4B . 0.859(5) ?
    C10 C5 . 1.408(5) ?
    C10 C1 . 1.409(5) ?
    N2 C3 . 1.441(5) ?
    O3 N3 . 1.221(5) ?
    O4 N3 . 1.228(4) ?
    C1 C2 . 1.382(5) ?
    C2 C3 . 1.382(5) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.387(6) ?
    C4 C5 . 1.353(5) ?
    C4 H4D . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.393(5) ?
    C6 C12 . 1.408(5) ?
    C7 C8 . 1.379(5) ?
    C8 C9 . 1.385(5) ?
    C8 H8 . 0.9300 ?
    C9 C11 . 1.390(6) ?
    C9 N3 . 1.444(5) ?
    C11 C12 . 1.363(6) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 N1 H1A . . 122(3) ?
    C10 N1 H1B . . 118(4) ?
    H1A N1 H1B . . 119(5) ?
    C6 N4 H4A . . 121(4) ?
    C6 N4 H4B . . 115(3) ?
    H4A N4 H4B . . 124(5) ?
    N1 C10 C5 . . 120.6(4) ?
    N1 C10 C1 . . 123.3(3) ?
    C5 C10 C1 . . 116.1(4) ?
    O2 N2 O1 . . 122.3(4) ?
    O2 N2 C3 . . 119.1(3) ?
    O1 N2 C3 . . 118.6(4) ?
    C2 C1 C10 . . 122.1(3) ?
    C2 C1 I1 . . 118.2(3) ?
    C10 C1 I1 . . 119.7(3) ?
    C1 C2 C3 . . 118.7(3) ?
    C1 C2 H2A . . 120.6 ?
    C3 C2 H2A . . 120.6 ?
    C2 C3 C4 . . 121.1(4) ?
    C2 C3 N2 . . 118.8(3) ?
    C4 C3 N2 . . 120.1(3) ?
    C5 C4 C3 . . 119.4(4) ?
    C5 C4 H4D . . 120.3 ?
    C3 C4 H4D . . 120.3 ?
    C4 C5 C10 . . 122.6(4) ?
    C4 C5 H5 . . 118.7 ?
    C10 C5 H5 . . 118.7 ?
    N4 C6 C7 . . 122.7(4) ?
    N4 C6 C12 . . 119.5(4) ?
    C7 C6 C12 . . 117.9(4) ?
    C8 C7 C6 . . 121.0(3) ?
    C8 C7 I2 . . 118.1(3) ?
    C6 C7 I2 . . 120.9(3) ?
    C7 C8 C9 . . 119.5(4) ?
    C7 C8 H8 . . 120.2 ?
    C9 C8 H8 . . 120.2 ?
    C8 C9 C11 . . 120.7(4) ?
    C8 C9 N3 . . 118.8(4) ?
    C11 C9 N3 . . 120.6(3) ?
    O3 N3 O4 . . 122.4(4) ?
    O3 N3 C9 . . 119.0(3) ?
    O4 N3 C9 . . 118.6(4) ?
    C12 C11 C9 . . 119.3(4) ?
    C12 C11 H11 . . 120.4 ?
    C9 C11 H11 . . 120.4 ?
    C11 C12 C6 . . 121.6(4) ?
    C11 C12 H12 . . 119.2 ?
    C6 C12 H12 . . 119.2 ?
data_Compound_13_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     '(C5 H3 I N2 O3), (C7 H3 I N2 O)'
_chemical_formula_sum     'C6 H0 I N2 O2'
_chemical_formula_weight     258.98
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/c1
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.7617(15)
_cell_length_b     12.912(3)
_cell_length_c     15.663(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.141(6)
_cell_angle_gamma     90.00
_cell_volume     1563.5(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3493
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     26.02
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.40
_exptl_crystal_density_diffrn     2.200
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     952
_exptl_absorpt_coefficient_mu     4.044
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.2634
_exptl_absorpt_correction_T_max     0.2946
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9857
_diffrn_reflns_av_R_equivalents     0.0298
_diffrn_reflns_av_sigmaI/netI     0.0296
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     25.18
_diffrn_reflns_theta_full     25.18
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2799
_reflns_number_gt     2259
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0459
_refine_ls_R_factor_gt     0.0330
_refine_ls_wR_factor_gt     0.0877
_refine_ls_wR_factor_ref     0.1043
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     2799
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0571P)²+3.6546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.014
_refine_ls_shift/su_mean     0.002
_refine_diff_density_max     0.966
_refine_diff_density_min     -0.760
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.39577(6) 0.67279(4) 0.15371(2) 0.04982(17) Uani d . 1 . .
    I I2 -0.17547(6) 0.87836(4) 0.21971(2) 0.04987(17) Uani d . 1 . .
    O O1 0.3317(7) 0.8477(4) 0.2977(3) 0.0669(14) Uani d . 1 . .
    O O2 0.7466(7) 0.5151(4) 0.5263(3) 0.0623(13) Uani d . 1 . .
    O O3 0.7616(8) 0.4462(4) 0.4021(3) 0.0768(17) Uani d . 1 . .
    O O4 0.0061(8) 0.6701(5) 0.3072(4) 0.0798(18) Uani d . 1 . .
    N N1 0.4183(7) 0.7641(5) 0.3335(4) 0.0506(14) Uani d . 1 . .
    N N2 0.7117(7) 0.5153(5) 0.4482(3) 0.0468(13) Uani d . 1 . .
    N N3 -0.2632(8) 1.0182(5) 0.5402(3) 0.0504(14) Uani d . 1 . .
    N N4 -0.1327(7) 0.9236(5) 0.6364(3) 0.0505(14) Uani d . 1 . .
    C C1 0.4682(7) 0.6783(5) 0.2854(3) 0.0340(13) Uani d . 1 . .
    C C2 0.5646(8) 0.5967(5) 0.3228(4) 0.0378(14) Uani d . 1 . .
    H H2 0.5990 0.5422 0.2895 0.045 Uiso calc R 1 . .
    C C3 0.6079(7) 0.5979(5) 0.4095(4) 0.0361(13) Uani d . 1 . .
    C C4 0.5570(8) 0.6785(5) 0.4605(4) 0.0416(15) Uani d . 1 . .
    H H4 0.5854 0.6777 0.5195 0.050 Uiso calc R 1 . .
    C C5 0.4639(8) 0.7595(5) 0.4224(4) 0.0393(14) Uani d . 1 . .
    H H5 0.4299 0.8131 0.4568 0.047 Uiso calc R 1 . .
    C C6 -0.0336(7) 0.7401(5) 0.3681(4) 0.0389(14) Uani d . 1 . .
    C C7 -0.1180(7) 0.8340(5) 0.3476(4) 0.0350(13) Uani d . 1 . .
    C C8 -0.1647(7) 0.8999(5) 0.4107(3) 0.0353(13) Uani d . 1 . .
    H H8 -0.2230 0.9612 0.3961 0.042 Uiso calc R 1 . .
    C C9 -0.1246(7) 0.8743(5) 0.4961(4) 0.0374(13) Uani d . 1 . .
    C C10 -0.1781(8) 0.9428(5) 0.5614(3) 0.0328(13) Uani d . 1 . .
    C C11 -0.0337(8) 0.7833(5) 0.5183(4) 0.0428(15) Uani d . 1 . .
    H H11 -0.0030 0.7675 0.5756 0.051 Uiso calc R 1 . .
    C C12 0.0092(8) 0.7185(5) 0.4559(4) 0.0454(15) Uani d . 1 . .
    H H12 0.0686 0.6577 0.4711 0.054 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C1 . 2.089(5) ?
    I2 C7 . 2.093(6) ?
    O1 N1 . 1.364(8) ?
    O2 N2 . 1.230(7) ?
    O3 N2 . 1.232(7) ?
    O4 C6 . 1.369(8) ?
    N1 C1 . 1.413(8) ?
    N1 C5 . 1.408(8) ?
    N2 C3 . 1.438(8) ?
    N3 C10 . 1.206(8) ?
    N4 C10 . 1.221(7) ?
    C1 C2 . 1.391(8) ?
    C2 C3 . 1.368(8) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.391(9) ?
    C4 C5 . 1.376(9) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.401(8) ?
    C6 C12 . 1.414(9) ?
    C7 C8 . 1.378(8) ?
    C8 C9 . 1.385(8) ?
    C8 H8 . 0.9300 ?
    C9 C11 . 1.399(9) ?
    C9 C10 . 1.441(8) ?
    C11 C12 . 1.351(9) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 N1 C1 . . 123.3(5) ?
    O1 N1 C5 . . 120.7(6) ?
    C1 N1 C5 . . 116.0(5) ?
    O2 N2 O3 . . 121.9(6) ?
    O2 N2 C3 . . 119.1(5) ?
    O3 N2 C3 . . 119.0(5) ?
    C2 C1 N1 . . 122.1(5) ?
    C2 C1 I1 . . 118.5(4) ?
    N1 C1 I1 . . 119.4(4) ?
    C3 C2 C1 . . 119.0(5) ?
    C3 C2 H2 . . 120.5 ?
    C1 C2 H2 . . 120.5 ?
    C2 C3 C4 . . 121.4(6) ?
    C2 C3 N2 . . 119.2(5) ?
    C4 C3 N2 . . 119.3(5) ?
    C3 C4 C5 . . 119.0(6) ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 H4 . . 120.5 ?
    C4 C5 N1 . . 122.5(6) ?
    C4 C5 H5 . . 118.8 ?
    N1 C5 H5 . . 118.8 ?
    O4 C6 C7 . . 122.8(6) ?
    O4 C6 C12 . . 119.9(6) ?
    C7 C6 C12 . . 117.3(5) ?
    C8 C7 C6 . . 121.2(5) ?
    C8 C7 I2 . . 118.1(4) ?
    C6 C7 I2 . . 120.7(4) ?
    C7 C8 C9 . . 119.7(6) ?
    C7 C8 H8 . . 120.2 ?
    C9 C8 H8 . . 120.2 ?
    C8 C9 C11 . . 120.3(6) ?
    C8 C9 C10 . . 119.0(6) ?
    C11 C9 C10 . . 120.7(5) ?
    N3 C10 N4 . . 122.2(6) ?
    N3 C10 C9 . . 119.0(5) ?
    N4 C10 C9 . . 118.8(6) ?
    C12 C11 C9 . . 119.5(6) ?
    C12 C11 H11 . . 120.3 ?
    C9 C11 H11 . . 120.3 ?
    C11 C12 C6 . . 122.0(6) ?
    C11 C12 H12 . . 119.0 ?
    C6 C12 H12 . . 119.0 ?
data_Compound_14_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H14 N2 O2 S'
_chemical_formula_sum     'C15 H14 N2 O2 S'
_chemical_formula_weight     286.34
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     P2(1)2(1)2(1)
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'
_cell_length_a     7.7598(10)
_cell_length_b     9.9684(13)
_cell_length_c     18.231(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1410.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3129
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     23.12
_cell_measurement_temperature     300(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.349
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.232
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7762
_exptl_absorpt_correction_T_max     0.8928
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8867
_diffrn_reflns_av_R_equivalents     0.0414
_diffrn_reflns_av_sigmaI/netI     0.0433
_diffrn_reflns_theta_min     3.33
_diffrn_reflns_theta_max     25.08
_diffrn_reflns_theta_full     25.08
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     21
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2472
_reflns_number_gt     1992
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0539
_refine_ls_R_factor_gt     0.0372
_refine_ls_wR_factor_gt     0.0759
_refine_ls_wR_factor_ref     0.0814
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     2472
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.187
_refine_diff_density_min     -0.201
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     0.43(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.14933(8) 0.31893(7) 0.72679(3) 0.03844(18) Uani d . 1 . .
    O O19 0.1780(3) 0.40556(19) 1.04551(9) 0.0553(5) Uani d . 1 . .
    O O2 0.1842(3) 0.44623(19) 0.69310(10) 0.0546(6) Uani d . 1 . .
    N N3 -0.0175(3) 0.2413(2) 0.70470(11) 0.0482(6) Uani d . 1 . .
    N N5 -0.2980(3) 0.3529(3) 0.72921(16) 0.0817(9) Uani d . 1 . .
    C C20 0.0861(4) 0.3247(3) 1.09773(14) 0.0612(8) Uani d . 1 . .
    H H20A -0.0350 0.3282 1.0872 0.092 Uiso calc R 1 . .
    H H20B 0.1066 0.3584 1.1463 0.092 Uiso calc R 1 . .
    H H20C 0.1254 0.2336 1.0946 0.092 Uiso calc R 1 . .
    C C16 0.1661(3) 0.3757(3) 0.97230(13) 0.0393(6) Uani d . 1 . .
    C C17 0.0742(3) 0.2686(3) 0.94382(13) 0.0379(6) Uani d . 1 . .
    H H17 0.0165 0.2097 0.9748 0.046 Uiso calc R 1 . .
    C C18 0.0695(3) 0.2503(2) 0.86843(13) 0.0372(6) Uani d . 1 . .
    H H18 0.0085 0.1786 0.8486 0.045 Uiso calc R 1 . .
    C C13 0.1551(3) 0.3383(2) 0.82300(12) 0.0345(6) Uani d . 1 . .
    C C6 0.3144(3) 0.2015(3) 0.70575(13) 0.0420(7) Uani d . 1 . .
    H H6A 0.4244 0.2377 0.7214 0.050 Uiso calc R 1 . .
    H H6B 0.2940 0.1196 0.7331 0.050 Uiso calc R 1 . .
    C C7 0.3238(3) 0.1686(2) 0.62547(12) 0.0354(6) Uani d . 1 . .
    C C8 0.2464(3) 0.0549(3) 0.59824(14) 0.0434(6) Uani d . 1 . .
    H H8 0.1858 -0.0014 0.6296 0.052 Uiso calc R 1 . .
    C C9 0.2582(4) 0.0238(3) 0.52452(15) 0.0466(7) Uani d . 1 . .
    H H9 0.2067 -0.0539 0.5068 0.056 Uiso calc R 1 . .
    C C10 0.3457(4) 0.1070(3) 0.47724(14) 0.0484(7) Uani d . 1 . .
    H H10 0.3530 0.0857 0.4277 0.058 Uiso calc R 1 . .
    C C15 0.2529(4) 0.4642(3) 0.92658(14) 0.0449(7) Uani d . 1 . .
    H H15 0.3146 0.5355 0.9464 0.054 Uiso calc R 1 . .
    C C14 0.2473(3) 0.4459(3) 0.85180(15) 0.0440(6) Uani d . 1 . .
    H H14 0.3046 0.5049 0.8207 0.053 Uiso calc R 1 . .
    C C12 0.4112(3) 0.2525(3) 0.57734(14) 0.0444(7) Uani d . 1 . .
    H H12 0.4630 0.3303 0.5949 0.053 Uiso calc R 1 . .
    C C11 0.4218(4) 0.2212(3) 0.50332(15) 0.0487(8) Uani d . 1 . .
    H H11 0.4807 0.2778 0.4715 0.058 Uiso calc R 1 . .
    C C4 -0.1661(4) 0.3047(3) 0.71876(14) 0.0524(7) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.436(2) ?
    S1 N3 . 1.561(2) ?
    S1 C13 . 1.765(2) ?
    S1 C6 . 1.777(2) ?
    O19 C16 . 1.370(3) ?
    O19 C20 . 1.437(3) ?
    N3 C4 . 1.340(4) ?
    N5 C4 . 1.146(3) ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C16 C17 . 1.385(3) ?
    C16 C15 . 1.388(4) ?
    C17 C18 . 1.387(3) ?
    C17 H17 . 0.9300 ?
    C18 C13 . 1.378(3) ?
    C18 H18 . 0.9300 ?
    C13 C14 . 1.391(3) ?
    C6 C7 . 1.502(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.375(3) ?
    C7 C12 . 1.389(3) ?
    C8 C9 . 1.382(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.375(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.368(4) ?
    C10 H10 . 0.9300 ?
    C15 C14 . 1.376(3) ?
    C15 H15 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C12 C11 . 1.387(4) ?
    C12 H12 . 0.9300 ?
    C11 H11 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 N3 . . 118.95(12) ?
    O2 S1 C13 . . 108.88(11) ?
    N3 S1 C13 . . 109.38(12) ?
    O2 S1 C6 . . 110.73(12) ?
    N3 S1 C6 . . 102.46(12) ?
    C13 S1 C6 . . 105.55(12) ?
    C16 O19 C20 . . 119.4(2) ?
    C4 N3 S1 . . 115.52(19) ?
    O19 C20 H20A . . 109.5 ?
    O19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O19 C16 C17 . . 124.5(2) ?
    O19 C16 C15 . . 114.5(2) ?
    C17 C16 C15 . . 121.0(2) ?
    C18 C17 C16 . . 119.1(2) ?
    C18 C17 H17 . . 120.4 ?
    C16 C17 H17 . . 120.4 ?
    C17 C18 C13 . . 119.9(2) ?
    C17 C18 H18 . . 120.0 ?
    C13 C18 H18 . . 120.0 ?
    C18 C13 C14 . . 120.8(2) ?
    C18 C13 S1 . . 121.01(19) ?
    C14 C13 S1 . . 118.19(18) ?
    C7 C6 S1 . . 112.91(17) ?
    C7 C6 H6A . . 109.0 ?
    S1 C6 H6A . . 109.0 ?
    C7 C6 H6B . . 109.0 ?
    S1 C6 H6B . . 109.0 ?
    H6A C6 H6B . . 107.8 ?
    C8 C7 C12 . . 118.8(2) ?
    C8 C7 C6 . . 120.7(2) ?
    C12 C7 C6 . . 120.5(2) ?
    C9 C8 C7 . . 120.5(2) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C10 C9 C8 . . 120.4(3) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 119.8(2) ?
    C9 C10 H10 . . 120.1 ?
    C11 C10 H10 . . 120.1 ?
    C14 C15 C16 . . 119.7(2) ?
    C14 C15 H15 . . 120.2 ?
    C16 C15 H15 . . 120.2 ?
    C15 C14 C13 . . 119.5(2) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C11 C12 C7 . . 120.5(2) ?
    C11 C12 H12 . . 119.7 ?
    C7 C12 H12 . . 119.7 ?
    C10 C11 C12 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    N5 C4 N3 . . 176.2(3) ?
data_Compound_14_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H14 N2 O2 S'
_chemical_formula_sum     'C15 H14 N2 O2 S'
_chemical_formula_weight     286.34
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     P2(1)2(1)2(1)
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'
_cell_length_a     7.7598(10)
_cell_length_b     9.9684(13)
_cell_length_c     18.231(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1410.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3129
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     23.12
_cell_measurement_temperature     300(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.349
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.232
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7762
_exptl_absorpt_correction_T_max     0.8928
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8867
_diffrn_reflns_av_R_equivalents     0.0414
_diffrn_reflns_av_sigmaI/netI     0.0433
_diffrn_reflns_theta_min     3.33
_diffrn_reflns_theta_max     25.08
_diffrn_reflns_theta_full     25.08
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     21
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2472
_reflns_number_gt     1992
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0539
_refine_ls_R_factor_gt     0.0372
_refine_ls_wR_factor_gt     0.0759
_refine_ls_wR_factor_ref     0.0814
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     2472
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.187
_refine_diff_density_min     -0.201
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     0.43(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.14933(8) 0.31893(7) 0.72679(3) 0.03844(18) Uani d . 1 . .
    O O19 0.1780(3) 0.40556(19) 1.04551(9) 0.0553(5) Uani d . 1 . .
    O O2 0.1842(3) 0.44623(19) 0.69310(10) 0.0546(6) Uani d . 1 . .
    N N3 -0.0175(3) 0.2413(2) 0.70470(11) 0.0482(6) Uani d . 1 . .
    N N5 -0.2980(3) 0.3529(3) 0.72921(16) 0.0817(9) Uani d . 1 . .
    C C20 0.0861(4) 0.3247(3) 1.09773(14) 0.0612(8) Uani d . 1 . .
    H H20A -0.0350 0.3282 1.0872 0.092 Uiso calc R 1 . .
    H H20B 0.1066 0.3584 1.1463 0.092 Uiso calc R 1 . .
    H H20C 0.1254 0.2336 1.0946 0.092 Uiso calc R 1 . .
    C C16 0.1661(3) 0.3757(3) 0.97230(13) 0.0393(6) Uani d . 1 . .
    C C17 0.0742(3) 0.2686(3) 0.94382(13) 0.0379(6) Uani d . 1 . .
    H H17 0.0165 0.2097 0.9748 0.046 Uiso calc R 1 . .
    C C18 0.0695(3) 0.2503(2) 0.86843(13) 0.0372(6) Uani d . 1 . .
    H H18 0.0085 0.1786 0.8486 0.045 Uiso calc R 1 . .
    C C13 0.1551(3) 0.3383(2) 0.82300(12) 0.0345(6) Uani d . 1 . .
    C C6 0.3144(3) 0.2015(3) 0.70575(13) 0.0420(7) Uani d . 1 . .
    H H6A 0.4244 0.2377 0.7214 0.050 Uiso calc R 1 . .
    H H6B 0.2940 0.1196 0.7331 0.050 Uiso calc R 1 . .
    C C7 0.3238(3) 0.1686(2) 0.62547(12) 0.0354(6) Uani d . 1 . .
    C C8 0.2464(3) 0.0549(3) 0.59824(14) 0.0434(6) Uani d . 1 . .
    H H8 0.1858 -0.0014 0.6296 0.052 Uiso calc R 1 . .
    C C9 0.2582(4) 0.0238(3) 0.52452(15) 0.0466(7) Uani d . 1 . .
    H H9 0.2067 -0.0539 0.5068 0.056 Uiso calc R 1 . .
    C C10 0.3457(4) 0.1070(3) 0.47724(14) 0.0484(7) Uani d . 1 . .
    H H10 0.3530 0.0857 0.4277 0.058 Uiso calc R 1 . .
    C C15 0.2529(4) 0.4642(3) 0.92658(14) 0.0449(7) Uani d . 1 . .
    H H15 0.3146 0.5355 0.9464 0.054 Uiso calc R 1 . .
    C C14 0.2473(3) 0.4459(3) 0.85180(15) 0.0440(6) Uani d . 1 . .
    H H14 0.3046 0.5049 0.8207 0.053 Uiso calc R 1 . .
    C C12 0.4112(3) 0.2525(3) 0.57734(14) 0.0444(7) Uani d . 1 . .
    H H12 0.4630 0.3303 0.5949 0.053 Uiso calc R 1 . .
    C C11 0.4218(4) 0.2212(3) 0.50332(15) 0.0487(8) Uani d . 1 . .
    H H11 0.4807 0.2778 0.4715 0.058 Uiso calc R 1 . .
    C C4 -0.1661(4) 0.3047(3) 0.71876(14) 0.0524(7) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.436(2) ?
    S1 N3 . 1.561(2) ?
    S1 C13 . 1.765(2) ?
    S1 C6 . 1.777(2) ?
    O19 C16 . 1.370(3) ?
    O19 C20 . 1.437(3) ?
    N3 C4 . 1.340(4) ?
    N5 C4 . 1.146(3) ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C16 C17 . 1.385(3) ?
    C16 C15 . 1.388(4) ?
    C17 C18 . 1.387(3) ?
    C17 H17 . 0.9300 ?
    C18 C13 . 1.378(3) ?
    C18 H18 . 0.9300 ?
    C13 C14 . 1.391(3) ?
    C6 C7 . 1.502(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.375(3) ?
    C7 C12 . 1.389(3) ?
    C8 C9 . 1.382(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.375(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.368(4) ?
    C10 H10 . 0.9300 ?
    C15 C14 . 1.376(3) ?
    C15 H15 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C12 C11 . 1.387(4) ?
    C12 H12 . 0.9300 ?
    C11 H11 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 N3 . . 118.95(12) ?
    O2 S1 C13 . . 108.88(11) ?
    N3 S1 C13 . . 109.38(12) ?
    O2 S1 C6 . . 110.73(12) ?
    N3 S1 C6 . . 102.46(12) ?
    C13 S1 C6 . . 105.55(12) ?
    C16 O19 C20 . . 119.4(2) ?
    C4 N3 S1 . . 115.52(19) ?
    O19 C20 H20A . . 109.5 ?
    O19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O19 C16 C17 . . 124.5(2) ?
    O19 C16 C15 . . 114.5(2) ?
    C17 C16 C15 . . 121.0(2) ?
    C18 C17 C16 . . 119.1(2) ?
    C18 C17 H17 . . 120.4 ?
    C16 C17 H17 . . 120.4 ?
    C17 C18 C13 . . 119.9(2) ?
    C17 C18 H18 . . 120.0 ?
    C13 C18 H18 . . 120.0 ?
    C18 C13 C14 . . 120.8(2) ?
    C18 C13 S1 . . 121.01(19) ?
    C14 C13 S1 . . 118.19(18) ?
    C7 C6 S1 . . 112.91(17) ?
    C7 C6 H6A . . 109.0 ?
    S1 C6 H6A . . 109.0 ?
    C7 C6 H6B . . 109.0 ?
    S1 C6 H6B . . 109.0 ?
    H6A C6 H6B . . 107.8 ?
    C8 C7 C12 . . 118.8(2) ?
    C8 C7 C6 . . 120.7(2) ?
    C12 C7 C6 . . 120.5(2) ?
    C9 C8 C7 . . 120.5(2) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C10 C9 C8 . . 120.4(3) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 119.8(2) ?
    C9 C10 H10 . . 120.1 ?
    C11 C10 H10 . . 120.1 ?
    C14 C15 C16 . . 119.7(2) ?
    C14 C15 H15 . . 120.2 ?
    C16 C15 H15 . . 120.2 ?
    C15 C14 C13 . . 119.5(2) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C11 C12 C7 . . 120.5(2) ?
    C11 C12 H12 . . 119.7 ?
    C7 C12 H12 . . 119.7 ?
    C10 C11 C12 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    N5 C4 N3 . . 176.2(3) ?
data_Compound_14_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H14 N2 O2 S'
_chemical_formula_sum     'C15 H14 N2 O2 S'
_chemical_formula_weight     288.36
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     P2(1)2(1)2(1)
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'
_cell_length_a     7.7592(10)
_cell_length_b     9.9677(13)
_cell_length_c     18.230(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1409.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3129
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     23.12
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.232
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.7762
_exptl_absorpt_correction_T_max     0.8928
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8816
_diffrn_reflns_av_R_equivalents     0.0410
_diffrn_reflns_av_sigmaI/netI     0.0429
_diffrn_reflns_theta_min     2.23
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     19
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2458
_reflns_number_gt     1984
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0574
_refine_ls_R_factor_gt     0.0397
_refine_ls_wR_factor_gt     0.0917
_refine_ls_wR_factor_ref     0.1126
_refine_ls_goodness_of_fit_ref     1.136
_refine_ls_restrained_S_all     1.136
_refine_ls_number_reflns     2458
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0524P)²+0.2488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.070
_refine_ls_shift/su_mean     0.006
_refine_diff_density_max     0.152
_refine_diff_density_min     -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     0.43(12)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.14932(11) 0.31891(9) 0.72682(4) 0.0374(2) Uani d . 1 . .
    O O1 0.1782(4) 0.4052(3) 1.04528(12) 0.0546(7) Uani d . 1 . .
    O O2 0.1822(4) 0.4455(3) 0.69252(14) 0.0544(7) Uani d . 1 . .
    H H2 0.2623 0.4830 0.7135 0.082 Uiso calc R 1 . .
    N N1 -0.0176(4) 0.2436(3) 0.70515(15) 0.0487(8) Uani d . 1 . .
    H H1 -0.0143 0.1655 0.6852 0.058 Uiso calc R 1 . .
    N N2 -0.2979(4) 0.3532(5) 0.7290(2) 0.0800(12) Uani d . 1 . .
    C C1 0.3451(5) 0.1060(4) 0.47732(19) 0.0477(9) Uani d . 1 . .
    H H1A 0.3527 0.0845 0.4278 0.057 Uiso calc R 1 . .
    C C2 0.2579(5) 0.0229(4) 0.5241(2) 0.0458(9) Uani d . 1 . .
    H H2A 0.2065 -0.0548 0.5063 0.055 Uiso calc R 1 . .
    C C3 0.2461(5) 0.0540(3) 0.59781(19) 0.0431(8) Uani d . 1 . .
    H H3 0.1855 -0.0023 0.6293 0.052 Uiso calc R 1 . .
    C C4 0.3240(4) 0.1687(3) 0.62498(17) 0.0355(7) Uani d . 1 . .
    C C5 0.3147(4) 0.2019(4) 0.70568(17) 0.0412(9) Uani d . 1 . .
    H H5A 0.4247 0.2384 0.7212 0.049 Uiso calc R 1 . .
    H H5B 0.2948 0.1199 0.7331 0.049 Uiso calc R 1 . .
    C C6 0.1549(4) 0.3382(3) 0.82328(16) 0.0341(7) Uani d . 1 . .
    C C7 0.0698(4) 0.2497(3) 0.86932(17) 0.0369(8) Uani d . 1 . .
    H H7 0.0097 0.1774 0.8497 0.044 Uiso calc R 1 . .
    C C8 0.0738(4) 0.2685(3) 0.94418(17) 0.0370(8) Uani d . 1 . .
    H H8 0.0155 0.2099 0.9752 0.044 Uiso calc R 1 . .
    C C9 0.1653(5) 0.3753(3) 0.97274(17) 0.0382(8) Uani d . 1 . .
    C C10 0.0868(5) 0.3244(5) 1.09696(18) 0.0589(10) Uani d . 1 . .
    H H10A -0.0341 0.3261 1.0857 0.088 Uiso calc R 1 . .
    H H10B 0.1047 0.3590 1.1455 0.088 Uiso calc R 1 . .
    H H10C 0.1281 0.2337 1.0945 0.088 Uiso calc R 1 . .
    C C11 0.4215(5) 0.2213(4) 0.5032(2) 0.0491(10) Uani d . 1 . .
    H H11 0.4797 0.2779 0.4711 0.059 Uiso calc R 1 . .
    C C12 0.4115(4) 0.2529(4) 0.57708(19) 0.0438(9) Uani d . 1 . .
    H H12 0.4636 0.3305 0.5946 0.053 Uiso calc R 1 . .
    C C13 -0.1663(5) 0.3050(4) 0.71875(18) 0.0512(9) Uani d . 1 . .
    C C14 0.2524(5) 0.4634(4) 0.92723(19) 0.0450(9) Uani d . 1 . .
    H H14 0.3142 0.5345 0.9472 0.054 Uiso calc R 1 . .
    C C15 0.2474(4) 0.4457(4) 0.85222(19) 0.0423(8) Uani d . 1 . .
    H H15 0.3050 0.5049 0.8213 0.051 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.431(3) ?
    S1 N1 . 1.548(3) ?
    S1 C6 . 1.769(3) ?
    S1 C5 . 1.777(3) ?
    O1 C9 . 1.359(4) ?
    O1 C10 . 1.428(4) ?
    O2 H2 . 0.8200 ?
    N1 C13 . 1.330(5) ?
    N1 H1 . 0.8600 ?
    N2 C13 . 1.144(5) ?
    C1 C11 . 1.376(5) ?
    C1 C2 . 1.368(5) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.382(5) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.385(5) ?
    C3 H3 . 0.9300 ?
    C4 C12 . 1.388(5) ?
    C4 C5 . 1.509(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.385(4) ?
    C6 C15 . 1.394(4) ?
    C7 C8 . 1.378(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.381(5) ?
    C8 H8 . 0.9300 ?
    C9 C14 . 1.384(5) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C12 . 1.386(5) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C14 C15 . 1.379(5) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 N1 . . 117.71(17) ?
    O2 S1 C6 . . 109.52(16) ?
    N1 S1 C6 . . 109.07(16) ?
    O2 S1 C5 . . 110.81(17) ?
    N1 S1 C5 . . 103.34(17) ?
    C6 S1 C5 . . 105.60(16) ?
    C9 O1 C10 . . 118.8(3) ?
    S1 O2 H2 . . 109.5 ?
    C13 N1 S1 . . 117.1(3) ?
    C13 N1 H1 . . 121.4 ?
    S1 N1 H1 . . 121.4 ?
    C11 C1 C2 . . 120.3(3) ?
    C11 C1 H1A . . 119.8 ?
    C2 C1 H1A . . 119.8 ?
    C3 C2 C1 . . 120.2(3) ?
    C3 C2 H2A . . 119.9 ?
    C1 C2 H2A . . 119.9 ?
    C2 C3 C4 . . 120.3(3) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C12 . . 119.2(3) ?
    C3 C4 C5 . . 120.6(3) ?
    C12 C4 C5 . . 120.3(3) ?
    C4 C5 S1 . . 112.9(2) ?
    C4 C5 H5A . . 109.0 ?
    S1 C5 H5A . . 109.0 ?
    C4 C5 H5B . . 109.0 ?
    S1 C5 H5B . . 109.0 ?
    H5A C5 H5B . . 107.8 ?
    C7 C6 C15 . . 120.4(3) ?
    C7 C6 S1 . . 121.4(2) ?
    C15 C6 S1 . . 118.2(2) ?
    C8 C7 C6 . . 120.2(3) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
    C7 C8 C9 . . 119.3(3) ?
    C7 C8 H8 . . 120.3 ?
    C9 C8 H8 . . 120.3 ?
    O1 C9 C14 . . 114.1(3) ?
    O1 C9 C8 . . 125.0(3) ?
    C14 C9 C8 . . 120.9(3) ?
    O1 C10 H10A . . 109.5 ?
    O1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    O1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C1 C11 C12 . . 119.9(3) ?
    C1 C11 H11 . . 120.1 ?
    C12 C11 H11 . . 120.1 ?
    C11 C12 C4 . . 120.1(3) ?
    C11 C12 H12 . . 119.9 ?
    C4 C12 H12 . . 119.9 ?
    N2 C13 N1 . . 177.0(4) ?
    C15 C14 C9 . . 120.0(3) ?
    C15 C14 H14 . . 120.0 ?
    C9 C14 H14 . . 120.0 ?
    C14 C15 C6 . . 119.2(3) ?
    C14 C15 H15 . . 120.4 ?
    C6 C15 H15 . . 120.4 ?
data_Compound_15_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H17 N3 O4 S2, C3 H6 O'
_chemical_formula_sum     'C17 H23 N3 O5 S2'
_chemical_formula_weight     413.50
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.811(4)
_cell_length_b     17.503(10)
_cell_length_c     15.892(9)
_cell_angle_alpha     90.00
_cell_angle_beta     103.305(17)
_cell_angle_gamma     90.00
_cell_volume     2114(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     137
_cell_measurement_theta_min     3.48
_cell_measurement_theta_max     22.54
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.299
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     872
_exptl_absorpt_coefficient_mu     0.283
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6649
_exptl_absorpt_correction_T_max     0.7452
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19952
_diffrn_reflns_av_R_equivalents     0.0439
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     1.76
_diffrn_reflns_theta_max     25.09
_diffrn_reflns_theta_full     25.09
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3694
_reflns_number_gt     2806
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0453
_refine_ls_wR_factor_gt     0.1248
_refine_ls_wR_factor_ref     0.1418
_refine_ls_goodness_of_fit_ref     1.120
_refine_ls_restrained_S_all     1.120
_refine_ls_number_reflns     3694
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0858P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.365
_refine_diff_density_min     -0.275
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.019(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.28837(8) 0.63439(3) 0.46309(4) 0.0404(2) Uani d . 1 . .
    S S6 -0.04773(9) 0.64674(4) 0.31660(4) 0.0556(3) Uani d . 1 . .
    O O18 0.0932(2) 1.00041(8) 0.75637(10) 0.0517(5) Uani d . 1 . .
    N N4 -0.1225(3) 0.58031(10) 0.46378(12) 0.0435(5) Uani d . 1 . .
    O O3 -0.3655(2) 0.66530(9) 0.37768(10) 0.0490(5) Uani d . 1 . .
    O O17 -0.0133(3) 0.99439(11) 0.60986(12) 0.0919(8) Uani d . 1 . .
    O O2 -0.4001(2) 0.59171(10) 0.50589(11) 0.0551(5) Uani d . 1 . .
    C C22 -0.0274(7) 1.1278(2) 0.7235(3) 0.145(2) Uani d . 1 . .
    H H22A -0.0660 1.1191 0.6625 0.217 Uiso calc R 1 . .
    H H22B -0.0033 1.1811 0.7340 0.217 Uiso calc R 1 . .
    H H22C -0.1180 1.1121 0.7517 0.217 Uiso calc R 1 . .
    O O24 0.4299(4) 0.79797(16) 0.62932(17) 0.1176(10) Uani d . 1 . .
    C C19 0.2825(7) 1.0937(2) 0.7105(2) 0.1193(17) Uani d . 1 . .
    H H20B 0.3843 1.0646 0.7377 0.179 Uiso calc R 1 . .
    H H19C 0.3126 1.1469 0.7114 0.179 Uiso calc R 1 . .
    H H19A 0.2416 1.0771 0.6517 0.179 Uiso calc R 1 . .
    C C20 0.1385(4) 1.08189(13) 0.75896(17) 0.0620(8) Uani d . 1 . .
    C C16 0.0248(4) 0.96523(14) 0.68011(15) 0.0504(6) Uani d . 1 . .
    N N15 0.0047(3) 0.89072(10) 0.69721(11) 0.0424(5) Uani d . 1 . .
    H H15 0.0381 0.8772 0.7505 0.051 Uiso calc R 1 . .
    C C12 -0.0642(3) 0.83270(12) 0.63812(13) 0.0368(5) Uani d . 1 . .
    C C13 -0.0826(3) 0.76149(13) 0.67259(14) 0.0469(6) Uani d . 1 . .
    H H13 -0.0486 0.7540 0.7320 0.056 Uiso calc R 1 . .
    C C14 -0.1507(3) 0.70191(13) 0.61948(14) 0.0478(6) Uani d . 1 . .
    H H14 -0.1628 0.6542 0.6433 0.057 Uiso calc R 1 . .
    C C9 -0.2019(3) 0.71180(12) 0.53041(13) 0.0368(5) Uani d . 1 . .
    C C5 -0.0217(3) 0.58938(12) 0.40788(15) 0.0406(6) Uani d . 1 . .
    N N9 0.1271(3) 0.54800(11) 0.41620(13) 0.0480(5) Uani d . 1 . .
    H H9 0.1607 0.5158 0.4576 0.058 Uiso calc R 1 . .
    C C8 0.2219(3) 0.56063(16) 0.35420(17) 0.0571(7) Uani d . 1 . .
    H H8 0.3268 0.5359 0.3532 0.069 Uiso calc R 1 . .
    C C7 0.1465(4) 0.61199(18) 0.2962(2) 0.0675(8) Uani d . 1 . .
    H H7 0.1924 0.6276 0.2499 0.081 Uiso calc R 1 . .
    C C11 -0.1154(3) 0.84304(13) 0.54868(15) 0.0488(6) Uani d . 1 . .
    H H11 -0.1033 0.8907 0.5248 0.059 Uiso calc R 1 . .
    C C10 -0.1838(3) 0.78245(13) 0.49567(15) 0.0484(6) Uani d . 1 . .
    H H10 -0.2178 0.7895 0.4362 0.058 Uiso calc R 1 . .
    C C21 0.2082(4) 1.09676(15) 0.85507(17) 0.0667(8) Uani d . 1 . .
    H H21B 0.1190 1.0844 0.8855 0.100 Uiso calc R 1 . .
    H H21C 0.2396 1.1497 0.8640 0.100 Uiso calc R 1 . .
    H H21A 0.3101 1.0656 0.8764 0.100 Uiso calc R 1 . .
    C C23 0.3811(4) 0.8226(2) 0.5564(2) 0.0817(10) Uani d . 1 . .
    C C25 0.3123(5) 0.7697(2) 0.4830(2) 0.0972(12) Uani d . 1 . .
    H H25B 0.3283 0.7178 0.5029 0.146 Uiso calc R 1 . .
    H H25C 0.3749 0.7778 0.4384 0.146 Uiso calc R 1 . .
    H H25A 0.1893 0.7794 0.4604 0.146 Uiso calc R 1 . .
    C C26 0.3885(7) 0.9041(3) 0.5367(4) 0.149(2) Uani d . 1 . .
    H H26C 0.2712 0.9239 0.5188 0.223 Uiso calc R 1 . .
    H H26A 0.4490 0.9109 0.4910 0.223 Uiso calc R 1 . .
    H H26B 0.4503 0.9309 0.5873 0.223 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4337(18) ?
    S1 O3 . 1.4566(17) ?
    S1 N4 . 1.602(2) ?
    S1 C9 . 1.762(2) ?
    S6 C7 . 1.733(3) ?
    S6 C5 . 1.737(2) ?
    O18 C16 . 1.355(3) ?
    O18 C20 . 1.468(3) ?
    N4 C5 . 1.325(3) ?
    O17 C16 . 1.201(3) ?
    C22 C20 . 1.518(5) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    O24 C23 . 1.213(4) ?
    C19 C20 . 1.516(5) ?
    C19 H20B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C20 C21 . 1.521(4) ?
    C16 N15 . 1.349(3) ?
    N15 C12 . 1.404(3) ?
    N15 H15 . 0.8600 ?
    C12 C13 . 1.382(3) ?
    C12 C11 . 1.397(3) ?
    C13 C14 . 1.370(3) ?
    C13 H13 . 0.9300 ?
    C14 C9 . 1.390(3) ?
    C14 H14 . 0.9300 ?
    C9 C10 . 1.375(3) ?
    C5 N9 . 1.350(3) ?
    N9 C8 . 1.380(3) ?
    N9 H9 . 0.8600 ?
    C8 C7 . 1.325(4) ?
    C8 H8 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C11 C10 . 1.383(3) ?
    C11 H11 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C23 C26 . 1.465(5) ?
    C23 C25 . 1.489(5) ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
    C25 H25A . 0.9600 ?
    C26 H26C . 0.9600 ?
    C26 H26A . 0.9600 ?
    C26 H26B . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 118.00(11) ?
    O2 S1 N4 . . 105.56(11) ?
    O3 S1 N4 . . 112.71(10) ?
    O2 S1 C9 . . 107.61(11) ?
    O3 S1 C9 . . 107.38(10) ?
    N4 S1 C9 . . 104.71(10) ?
    C7 S6 C5 . . 90.82(13) ?
    C16 O18 C20 . . 120.64(19) ?
    C5 N4 S1 . . 121.92(16) ?
    C20 C22 H22A . . 109.5 ?
    C20 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C20 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C20 C19 H20B . . 109.5 ?
    C20 C19 H19C . . 109.5 ?
    H20B C19 H19C . . 109.5 ?
    C20 C19 H19A . . 109.5 ?
    H20B C19 H19A . . 109.5 ?
    H19C C19 H19A . . 109.5 ?
    O18 C20 C19 . . 108.7(2) ?
    O18 C20 C22 . . 108.9(3) ?
    C19 C20 C22 . . 114.1(3) ?
    O18 C20 C21 . . 102.9(2) ?
    C19 C20 C21 . . 110.5(3) ?
    C22 C20 C21 . . 111.1(3) ?
    O17 C16 N15 . . 125.6(2) ?
    O17 C16 O18 . . 126.9(2) ?
    N15 C16 O18 . . 107.43(19) ?
    C16 N15 C12 . . 127.54(19) ?
    C16 N15 H15 . . 116.2 ?
    C12 N15 H15 . . 116.2 ?
    C13 C12 C11 . . 119.3(2) ?
    C13 C12 N15 . . 116.49(19) ?
    C11 C12 N15 . . 124.3(2) ?
    C14 C13 C12 . . 120.2(2) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 120.8(2) ?
    C13 C14 H14 . . 119.6 ?
    C9 C14 H14 . . 119.6 ?
    C10 C9 C14 . . 119.2(2) ?
    C10 C9 S1 . . 120.56(17) ?
    C14 C9 S1 . . 120.19(17) ?
    N4 C5 N9 . . 120.1(2) ?
    N4 C5 S6 . . 130.96(18) ?
    N9 C5 S6 . . 108.93(18) ?
    C5 N9 C8 . . 115.8(2) ?
    C5 N9 H9 . . 122.1 ?
    C8 N9 H9 . . 122.1 ?
    C7 C8 N9 . . 112.3(2) ?
    C7 C8 H8 . . 123.8 ?
    N9 C8 H8 . . 123.8 ?
    C8 C7 S6 . . 112.1(2) ?
    C8 C7 H7 . . 124.0 ?
    S6 C7 H7 . . 124.0 ?
    C10 C11 C12 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C9 C10 C11 . . 120.4(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C20 C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C20 C21 H21A . . 109.5 ?
    H21B C21 H21A . . 109.5 ?
    H21C C21 H21A . . 109.5 ?
    O24 C23 C26 . . 122.1(4) ?
    O24 C23 C25 . . 120.4(4) ?
    C26 C23 C25 . . 117.6(4) ?
    C23 C25 H25B . . 109.5 ?
    C23 C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C23 C25 H25A . . 109.5 ?
    H25B C25 H25A . . 109.5 ?
    H25C C25 H25A . . 109.5 ?
    C23 C26 H26C . . 109.5 ?
    C23 C26 H26A . . 109.5 ?
    H26C C26 H26A . . 109.5 ?
    C23 C26 H26B . . 109.5 ?
    H26C C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
data_Compound_15_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H17 N3 O4 S2, C3 H6 O'
_chemical_formula_sum     'C17 H23 N3 O5 S2'
_chemical_formula_weight     413.50
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.811(4)
_cell_length_b     17.503(10)
_cell_length_c     15.892(9)
_cell_angle_alpha     90.00
_cell_angle_beta     103.305(17)
_cell_angle_gamma     90.00
_cell_volume     2114(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     137
_cell_measurement_theta_min     3.48
_cell_measurement_theta_max     22.54
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.299
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     872
_exptl_absorpt_coefficient_mu     0.283
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.6649
_exptl_absorpt_correction_T_max     0.7452
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19952
_diffrn_reflns_av_R_equivalents     0.0439
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     1.76
_diffrn_reflns_theta_max     25.09
_diffrn_reflns_theta_full     25.09
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3694
_reflns_number_gt     2806
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0453
_refine_ls_wR_factor_gt     0.1248
_refine_ls_wR_factor_ref     0.1418
_refine_ls_goodness_of_fit_ref     1.120
_refine_ls_restrained_S_all     1.120
_refine_ls_number_reflns     3694
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0858P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.365
_refine_diff_density_min     -0.275
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.019(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.28837(8) 0.63439(3) 0.46309(4) 0.0404(2) Uani d . 1 . .
    S S6 -0.04773(9) 0.64674(4) 0.31660(4) 0.0556(3) Uani d . 1 . .
    O O18 0.0932(2) 1.00041(8) 0.75637(10) 0.0517(5) Uani d . 1 . .
    N N4 -0.1225(3) 0.58031(10) 0.46378(12) 0.0435(5) Uani d . 1 . .
    O O3 -0.3655(2) 0.66530(9) 0.37768(10) 0.0490(5) Uani d . 1 . .
    O O17 -0.0133(3) 0.99439(11) 0.60986(12) 0.0919(8) Uani d . 1 . .
    O O2 -0.4001(2) 0.59171(10) 0.50589(11) 0.0551(5) Uani d . 1 . .
    C C22 -0.0274(7) 1.1278(2) 0.7235(3) 0.145(2) Uani d . 1 . .
    H H22A -0.0660 1.1191 0.6625 0.217 Uiso calc R 1 . .
    H H22B -0.0033 1.1811 0.7340 0.217 Uiso calc R 1 . .
    H H22C -0.1180 1.1121 0.7517 0.217 Uiso calc R 1 . .
    O O24 0.4299(4) 0.79797(16) 0.62932(17) 0.1176(10) Uani d . 1 . .
    C C19 0.2825(7) 1.0937(2) 0.7105(2) 0.1193(17) Uani d . 1 . .
    H H20B 0.3843 1.0646 0.7377 0.179 Uiso calc R 1 . .
    H H19C 0.3126 1.1469 0.7114 0.179 Uiso calc R 1 . .
    H H19A 0.2416 1.0771 0.6517 0.179 Uiso calc R 1 . .
    C C20 0.1385(4) 1.08189(13) 0.75896(17) 0.0620(8) Uani d . 1 . .
    C C16 0.0248(4) 0.96523(14) 0.68011(15) 0.0504(6) Uani d . 1 . .
    N N15 0.0047(3) 0.89072(10) 0.69721(11) 0.0424(5) Uani d . 1 . .
    H H15 0.0381 0.8772 0.7505 0.051 Uiso calc R 1 . .
    C C12 -0.0642(3) 0.83270(12) 0.63812(13) 0.0368(5) Uani d . 1 . .
    C C13 -0.0826(3) 0.76149(13) 0.67259(14) 0.0469(6) Uani d . 1 . .
    H H13 -0.0486 0.7540 0.7320 0.056 Uiso calc R 1 . .
    C C14 -0.1507(3) 0.70191(13) 0.61948(14) 0.0478(6) Uani d . 1 . .
    H H14 -0.1628 0.6542 0.6433 0.057 Uiso calc R 1 . .
    C C9 -0.2019(3) 0.71180(12) 0.53041(13) 0.0368(5) Uani d . 1 . .
    C C5 -0.0217(3) 0.58938(12) 0.40788(15) 0.0406(6) Uani d . 1 . .
    N N9 0.1271(3) 0.54800(11) 0.41620(13) 0.0480(5) Uani d . 1 . .
    H H9 0.1607 0.5158 0.4576 0.058 Uiso calc R 1 . .
    C C8 0.2219(3) 0.56063(16) 0.35420(17) 0.0571(7) Uani d . 1 . .
    H H8 0.3268 0.5359 0.3532 0.069 Uiso calc R 1 . .
    C C7 0.1465(4) 0.61199(18) 0.2962(2) 0.0675(8) Uani d . 1 . .
    H H7 0.1924 0.6276 0.2499 0.081 Uiso calc R 1 . .
    C C11 -0.1154(3) 0.84304(13) 0.54868(15) 0.0488(6) Uani d . 1 . .
    H H11 -0.1033 0.8907 0.5248 0.059 Uiso calc R 1 . .
    C C10 -0.1838(3) 0.78245(13) 0.49567(15) 0.0484(6) Uani d . 1 . .
    H H10 -0.2178 0.7895 0.4362 0.058 Uiso calc R 1 . .
    C C21 0.2082(4) 1.09676(15) 0.85507(17) 0.0667(8) Uani d . 1 . .
    H H21B 0.1190 1.0844 0.8855 0.100 Uiso calc R 1 . .
    H H21C 0.2396 1.1497 0.8640 0.100 Uiso calc R 1 . .
    H H21A 0.3101 1.0656 0.8764 0.100 Uiso calc R 1 . .
    C C23 0.3811(4) 0.8226(2) 0.5564(2) 0.0817(10) Uani d . 1 . .
    C C25 0.3123(5) 0.7697(2) 0.4830(2) 0.0972(12) Uani d . 1 . .
    H H25B 0.3283 0.7178 0.5029 0.146 Uiso calc R 1 . .
    H H25C 0.3749 0.7778 0.4384 0.146 Uiso calc R 1 . .
    H H25A 0.1893 0.7794 0.4604 0.146 Uiso calc R 1 . .
    C C26 0.3885(7) 0.9041(3) 0.5367(4) 0.149(2) Uani d . 1 . .
    H H26C 0.2712 0.9239 0.5188 0.223 Uiso calc R 1 . .
    H H26A 0.4490 0.9109 0.4910 0.223 Uiso calc R 1 . .
    H H26B 0.4503 0.9309 0.5873 0.223 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4337(18) ?
    S1 O3 . 1.4566(17) ?
    S1 N4 . 1.602(2) ?
    S1 C9 . 1.762(2) ?
    S6 C7 . 1.733(3) ?
    S6 C5 . 1.737(2) ?
    O18 C16 . 1.355(3) ?
    O18 C20 . 1.468(3) ?
    N4 C5 . 1.325(3) ?
    O17 C16 . 1.201(3) ?
    C22 C20 . 1.518(5) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    O24 C23 . 1.213(4) ?
    C19 C20 . 1.516(5) ?
    C19 H20B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C20 C21 . 1.521(4) ?
    C16 N15 . 1.349(3) ?
    N15 C12 . 1.404(3) ?
    N15 H15 . 0.8600 ?
    C12 C13 . 1.382(3) ?
    C12 C11 . 1.397(3) ?
    C13 C14 . 1.370(3) ?
    C13 H13 . 0.9300 ?
    C14 C9 . 1.390(3) ?
    C14 H14 . 0.9300 ?
    C9 C10 . 1.375(3) ?
    C5 N9 . 1.350(3) ?
    N9 C8 . 1.380(3) ?
    N9 H9 . 0.8600 ?
    C8 C7 . 1.325(4) ?
    C8 H8 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C11 C10 . 1.383(3) ?
    C11 H11 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C23 C26 . 1.465(5) ?
    C23 C25 . 1.489(5) ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
    C25 H25A . 0.9600 ?
    C26 H26C . 0.9600 ?
    C26 H26A . 0.9600 ?
    C26 H26B . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 118.00(11) ?
    O2 S1 N4 . . 105.56(11) ?
    O3 S1 N4 . . 112.71(10) ?
    O2 S1 C9 . . 107.61(11) ?
    O3 S1 C9 . . 107.38(10) ?
    N4 S1 C9 . . 104.71(10) ?
    C7 S6 C5 . . 90.82(13) ?
    C16 O18 C20 . . 120.64(19) ?
    C5 N4 S1 . . 121.92(16) ?
    C20 C22 H22A . . 109.5 ?
    C20 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C20 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C20 C19 H20B . . 109.5 ?
    C20 C19 H19C . . 109.5 ?
    H20B C19 H19C . . 109.5 ?
    C20 C19 H19A . . 109.5 ?
    H20B C19 H19A . . 109.5 ?
    H19C C19 H19A . . 109.5 ?
    O18 C20 C19 . . 108.7(2) ?
    O18 C20 C22 . . 108.9(3) ?
    C19 C20 C22 . . 114.1(3) ?
    O18 C20 C21 . . 102.9(2) ?
    C19 C20 C21 . . 110.5(3) ?
    C22 C20 C21 . . 111.1(3) ?
    O17 C16 N15 . . 125.6(2) ?
    O17 C16 O18 . . 126.9(2) ?
    N15 C16 O18 . . 107.43(19) ?
    C16 N15 C12 . . 127.54(19) ?
    C16 N15 H15 . . 116.2 ?
    C12 N15 H15 . . 116.2 ?
    C13 C12 C11 . . 119.3(2) ?
    C13 C12 N15 . . 116.49(19) ?
    C11 C12 N15 . . 124.3(2) ?
    C14 C13 C12 . . 120.2(2) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 120.8(2) ?
    C13 C14 H14 . . 119.6 ?
    C9 C14 H14 . . 119.6 ?
    C10 C9 C14 . . 119.2(2) ?
    C10 C9 S1 . . 120.56(17) ?
    C14 C9 S1 . . 120.19(17) ?
    N4 C5 N9 . . 120.1(2) ?
    N4 C5 S6 . . 130.96(18) ?
    N9 C5 S6 . . 108.93(18) ?
    C5 N9 C8 . . 115.8(2) ?
    C5 N9 H9 . . 122.1 ?
    C8 N9 H9 . . 122.1 ?
    C7 C8 N9 . . 112.3(2) ?
    C7 C8 H8 . . 123.8 ?
    N9 C8 H8 . . 123.8 ?
    C8 C7 S6 . . 112.1(2) ?
    C8 C7 H7 . . 124.0 ?
    S6 C7 H7 . . 124.0 ?
    C10 C11 C12 . . 120.0(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C9 C10 C11 . . 120.4(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C20 C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C20 C21 H21A . . 109.5 ?
    H21B C21 H21A . . 109.5 ?
    H21C C21 H21A . . 109.5 ?
    O24 C23 C26 . . 122.1(4) ?
    O24 C23 C25 . . 120.4(4) ?
    C26 C23 C25 . . 117.6(4) ?
    C23 C25 H25B . . 109.5 ?
    C23 C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C23 C25 H25A . . 109.5 ?
    H25B C25 H25A . . 109.5 ?
    H25C C25 H25A . . 109.5 ?
    C23 C26 H26C . . 109.5 ?
    C23 C26 H26A . . 109.5 ?
    H26C C26 H26A . . 109.5 ?
    C23 C26 H26B . . 109.5 ?
    H26C C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
data_Compound_15_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H23 N3 O5 S2'
_chemical_formula_sum     'C17 H23 N3 O5 S2'
_chemical_formula_weight     413.50
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)/n1
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.811(4)
_cell_length_b     17.503(10)
_cell_length_c     15.892(9)
_cell_angle_alpha     90.00
_cell_angle_beta     103.305(17)
_cell_angle_gamma     90.00
_cell_volume     2114(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     654
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     19.39
_cell_measurement_temperature     300(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.229
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.280
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9079
_exptl_absorpt_correction_T_max     0.9640
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19952
_diffrn_reflns_av_R_equivalents     0.0439
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     1.76
_diffrn_reflns_theta_max     25.09
_diffrn_reflns_theta_full     25.09
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3694
_reflns_number_gt     2806
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0692
_refine_ls_R_factor_gt     0.0517
_refine_ls_wR_factor_gt     0.1686
_refine_ls_wR_factor_ref     0.2000
_refine_ls_goodness_of_fit_ref     0.814
_refine_ls_restrained_S_all     0.814
_refine_ls_number_reflns     3694
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     10.903
_refine_ls_shift/su_mean     0.714
_refine_diff_density_max     0.473
_refine_diff_density_min     -0.289
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.018(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.28837(11) 0.63441(5) 0.46312(5) 0.0401(4) Uani d . 1 . .
    S S2 -0.04779(13) 0.64676(6) 0.31651(7) 0.0553(4) Uani d . 1 . .
    O O4 0.0930(4) 1.00042(13) 0.75657(14) 0.0519(7) Uani d . 1 . .
    N N1 -0.1221(4) 0.58038(16) 0.46378(19) 0.0455(8) Uani d . 1 . .
    O O2 -0.3657(3) 0.66520(14) 0.37762(15) 0.0494(7) Uani d . 1 . .
    O O3 -0.0125(6) 0.99437(17) 0.60986(19) 0.0925(13) Uani d . 1 . .
    O O1 -0.4001(3) 0.59177(14) 0.50607(16) 0.0557(7) Uani d . 1 . .
    C C21 -0.0298(12) 1.1273(3) 0.7249(5) 0.145(4) Uani d . 1 . .
    H H21A -0.0577 1.1263 0.6628 0.218 Uiso calc R 1 . .
    H H21B -0.0128 1.1792 0.7445 0.218 Uiso calc R 1 . .
    H H21C -0.1247 1.1050 0.7455 0.218 Uiso calc R 1 . .
    O O5 0.4307(7) 0.7978(2) 0.6291(2) 0.1149(14) Uani d . 1 . .
    C C1 0.2845(10) 1.0934(3) 0.7102(3) 0.117(3) Uani d . 1 . .
    H H1A 0.3854 1.0635 0.7369 0.176 Uiso calc R 1 . .
    H H1B 0.3166 1.1464 0.7118 0.176 Uiso calc R 1 . .
    H H1C 0.2428 1.0775 0.6512 0.176 Uiso calc R 1 . .
    C C2 0.1381(7) 1.0819(2) 0.7594(3) 0.0622(12) Uani d . 1 . .
    C C3 0.0246(5) 0.9654(2) 0.6801(2) 0.0502(9) Uani d . 1 . .
    N N3 0.0045(4) 0.89061(15) 0.69727(16) 0.0411(7) Uani d . 1 . .
    H H4 0.0375 0.8770 0.7506 0.049 Uiso calc R 1 . .
    C C5 -0.0640(4) 0.83285(18) 0.6381(2) 0.0374(8) Uani d . 1 . .
    C C6 -0.0830(5) 0.76141(19) 0.6731(2) 0.0472(9) Uani d . 1 . .
    H H6 -0.0497 0.7540 0.7326 0.057 Uiso calc R 1 . .
    C C7 -0.1510(5) 0.7017(2) 0.6196(2) 0.0483(9) Uani d . 1 . .
    H H7 -0.1633 0.6540 0.6432 0.058 Uiso calc R 1 . .
    C C8 -0.2019(4) 0.71193(19) 0.53025(19) 0.0370(8) Uani d . 1 . .
    C C9 -0.0216(5) 0.58954(17) 0.4079(2) 0.0401(8) Uani d . 1 . .
    N N2 0.1269(4) 0.54796(16) 0.41667(17) 0.0461(7) Uani d . 1 . .
    H H10 0.1607 0.5161 0.4584 0.055 Uiso calc R 1 . .
    C C11 0.2223(5) 0.5601(2) 0.3534(3) 0.0575(10) Uani d . 1 . .
    H H11 0.3267 0.5351 0.3521 0.069 Uiso calc R 1 . .
    C C12 0.1463(6) 0.6116(3) 0.2956(3) 0.0667(12) Uani d . 1 . .
    H H12 0.1917 0.6272 0.2492 0.080 Uiso calc R 1 . .
    C C13 -0.1153(5) 0.8431(2) 0.5488(2) 0.0481(9) Uani d . 1 . .
    H H13 -0.1032 0.8907 0.5247 0.058 Uiso calc R 1 . .
    C C14 -0.1844(5) 0.7823(2) 0.4958(2) 0.0483(9) Uani d . 1 . .
    H H14 -0.2191 0.7894 0.4363 0.058 Uiso calc R 1 . .
    C C15 0.2085(7) 1.0968(2) 0.8541(2) 0.0674(12) Uani d . 1 . .
    H H15A 0.1197 1.0849 0.8849 0.101 Uiso calc R 1 . .
    H H15B 0.2409 1.1496 0.8627 0.101 Uiso calc R 1 . .
    H H15C 0.3100 1.0653 0.8752 0.101 Uiso calc R 1 . .
    C C16 0.3815(7) 0.8227(3) 0.5563(4) 0.0819(14) Uani d . 1 . .
    C C17 0.3128(8) 0.7700(4) 0.4832(3) 0.0964(17) Uani d . 1 . .
    H H17A 0.3212 0.7183 0.5039 0.145 Uiso calc R 1 . .
    H H17B 0.3809 0.7756 0.4404 0.145 Uiso calc R 1 . .
    H H17C 0.1920 0.7821 0.4580 0.145 Uiso calc R 1 . .
    C C19 0.3884(7) 0.9044(3) 0.5353(3) 0.1110(15) Uani d . 1 . .
    H H19A 0.2710 0.9245 0.5193 0.167 Uiso calc R 1 . .
    H H19B 0.4446 0.9105 0.4880 0.167 Uiso calc R 1 . .
    H H19C 0.4540 0.9315 0.5848 0.167 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.435(3) ?
    S1 O2 . 1.457(3) ?
    S1 N1 . 1.605(3) ?
    S1 C8 . 1.762(3) ?
    S2 C9 . 1.737(3) ?
    S2 C12 . 1.737(4) ?
    O4 C3 . 1.356(4) ?
    O4 C2 . 1.467(4) ?
    N1 C9 . 1.324(5) ?
    O3 C3 . 1.200(4) ?
    C21 C2 . 1.524(8) ?
    C21 H21A . 0.9603 ?
    C21 H21B . 0.9603 ?
    C21 H21C . 0.9603 ?
    O5 C16 . 1.212(6) ?
    C1 C2 . 1.540(8) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C15 . 1.501(5) ?
    C3 N3 . 1.353(4) ?
    N3 C5 . 1.400(4) ?
    N3 H4 . 0.8600 ?
    C5 C6 . 1.390(5) ?
    C5 C13 . 1.396(4) ?
    C6 C7 . 1.375(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.395(5) ?
    C7 H7 . 0.9300 ?
    C8 C14 . 1.368(5) ?
    C9 N2 . 1.349(4) ?
    N2 C11 . 1.398(5) ?
    N2 H10 . 0.8600 ?
    C11 C12 . 1.327(6) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.387(5) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 H15A . 0.9602 ?
    C15 H15B . 0.9602 ?
    C15 H15C . 0.9602 ?
    C16 C17 . 1.484(7) ?
    C16 C19 . 1.472(7) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C19 H19A . 0.9601 ?
    C19 H19B . 0.9601 ?
    C19 H19C . 0.9601 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . 117.96(16) ?
    O1 S1 N1 . . 105.68(17) ?
    O2 S1 N1 . . 112.66(16) ?
    O1 S1 C8 . . 107.63(15) ?
    O2 S1 C8 . . 107.37(15) ?
    N1 S1 C8 . . 104.66(16) ?
    C9 S2 C12 . . 90.89(18) ?
    C3 O4 C2 . . 120.6(3) ?
    C9 N1 S1 . . 121.9(2) ?
    C2 C21 H21A . . 109.9 ?
    C2 C21 H21B . . 109.8 ?
    H21A C21 H21B . . 109.4 ?
    C2 C21 H21C . . 108.8 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.4 ?
    C2 C1 H1A . . 108.8 ?
    C2 C1 H1B . . 110.0 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.6 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O4 C2 C15 . . 103.3(3) ?
    O4 C2 C21 . . 108.4(4) ?
    C15 C2 C21 . . 110.9(5) ?
    O4 C2 C1 . . 108.2(4) ?
    C15 C2 C1 . . 110.0(4) ?
    C21 C2 C1 . . 115.3(6) ?
    O3 C3 N3 . . 125.6(3) ?
    O3 C3 O4 . . 127.1(3) ?
    N3 C3 O4 . . 107.3(3) ?
    C3 N3 C5 . . 127.4(3) ?
    C3 N3 H4 . . 116.3 ?
    C5 N3 H4 . . 116.3 ?
    C6 C5 C13 . . 119.4(3) ?
    C6 C5 N3 . . 116.1(3) ?
    C13 C5 N3 . . 124.5(3) ?
    C7 C6 C5 . . 119.9(3) ?
    C7 C6 H6 . . 120.1 ?
    C5 C6 H6 . . 120.0 ?
    C6 C7 C8 . . 120.7(3) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.7 ?
    C14 C8 C7 . . 119.5(3) ?
    C14 C8 S1 . . 120.7(2) ?
    C7 C8 S1 . . 119.8(3) ?
    N1 C9 N2 . . 119.6(3) ?
    N1 C9 S2 . . 131.1(3) ?
    N2 C9 S2 . . 109.3(3) ?
    C9 N2 C11 . . 115.5(3) ?
    C9 N2 H10 . . 122.2 ?
    C11 N2 H10 . . 122.3 ?
    C12 C11 N2 . . 111.9(4) ?
    C12 C11 H11 . . 124.2 ?
    N2 C11 H11 . . 123.9 ?
    C11 C12 S2 . . 112.3(3) ?
    C11 C12 H12 . . 123.7 ?
    S2 C12 H12 . . 123.9 ?
    C14 C13 C5 . . 120.0(3) ?
    C14 C13 H13 . . 120.0 ?
    C5 C13 H13 . . 120.0 ?
    C8 C14 C13 . . 120.6(3) ?
    C8 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.8 ?
    C2 C15 H15A . . 109.4 ?
    C2 C15 H15B . . 109.4 ?
    H15A C15 H15B . . 109.5 ?
    C2 C15 H15C . . 109.6 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.4 ?
    O5 C16 C17 . . 120.1(5) ?
    O5 C16 C19 . . 123.1(5) ?
    C17 C16 C19 . . 116.8(5) ?
    C16 C17 H17A . . 109.6 ?
    C16 C17 H17B . . 109.2 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.6 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C16 C19 H19A . . 109.5 ?
    C16 C19 H19B . . 109.1 ?
    H19A C19 H19B . . 109.5 ?
    C16 C19 H19C . . 109.9 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
data_Compound_16_APEX
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H10 N4 O2 S, H2 O'
_chemical_formula_sum     'C7 H12 N4 O3 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     232.27
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21 1'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.6095(10)
_cell_length_b     7.3299(15)
_cell_length_c     12.491(2)
_cell_angle_alpha     90
_cell_angle_beta     93.297(5)
_cell_angle_gamma     90
_cell_volume     512.74(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     58
_cell_measurement_theta_min     4.7817
_cell_measurement_theta_max     20.3137
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     244
_exptl_absorpt_coefficient_mu     0.310
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.85
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     3017
_diffrn_reflns_av_R_equivalents     0.0188
_diffrn_reflns_av_sigmaI/netI     0.0334
_diffrn_reflns_theta_min     1.63
_diffrn_reflns_theta_max     25.83
_diffrn_reflns_theta_full     25.83
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     1940
_reflns_number_gt     1825
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0337
_refine_ls_R_factor_gt     0.0305
_refine_ls_wR_factor_gt     0.0704
_refine_ls_wR_factor_ref     0.0725
_refine_ls_goodness_of_fit_ref     1.134
_refine_ls_restrained_S_all     1.132
_refine_ls_number_reflns     1940
_refine_ls_number_parameters     168
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0366P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.212
_refine_diff_density_min     -0.222
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.02(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement     'APEX2 v2010.1-2 (Bruker AXS)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.25231(9) 0.67472(7) 0.29318(4) 0.02799(14) Uani d . 1 . .
    O O2 0.4569(3) 0.7875(2) 0.32229(13) 0.0390(4) Uani d . 1 . .
    O O3 0.0204(3) 0.7536(2) 0.31138(13) 0.0383(4) Uani d . 1 . .
    C C4 0.2552(4) 0.6311(3) 0.15512(18) 0.0288(5) Uani d . 1 . .
    C C5 0.4389(4) 0.6951(4) 0.09561(17) 0.0328(5) Uani d . 1 . .
    H H5 0.5701 0.7519 0.1302 0.039 Uiso calc R 1 . .
    C C6 0.4292(4) 0.6755(4) -0.01354(17) 0.0365(5) Uani d . 1 . .
    H H6 0.5534 0.7197 -0.0524 0.044 Uiso calc R 1 . .
    C C7 0.2341(4) 0.5897(3) -0.06721(19) 0.0328(5) Uani d . 1 . .
    C C8 0.0541(4) 0.5205(3) -0.00646(19) 0.0353(6) Uani d . 1 . .
    H H8 -0.0739 0.4591 -0.0407 0.042 Uiso calc R 1 . .
    C C9 0.0620(4) 0.5410(3) 0.10280(19) 0.0348(5) Uani d . 1 . .
    H H9 -0.0607 0.4952 0.142 0.042 Uiso calc R 1 . .
    N N10 0.2172(5) 0.5763(4) -0.17744(19) 0.0485(6) Uani d D 1 . .
    H H10A 0.114(4) 0.498(3) -0.206(2) 0.049(9) Uiso d D 1 . .
    H H10B 0.345(3) 0.599(5) -0.212(2) 0.065(11) Uiso d D 1 . .
    N N11 0.2506(3) 0.4835(3) 0.35355(14) 0.0315(4) Uani d . 1 . .
    C C12 0.4486(4) 0.3789(3) 0.36231(17) 0.0312(5) Uani d . 1 . .
    N N13 0.6673(4) 0.4356(3) 0.34474(19) 0.0442(5) Uani d D 1 . .
    H H13A 0.693(4) 0.5519(11) 0.338(2) 0.039(7) Uiso d D 1 . .
    H H13B 0.785(4) 0.359(3) 0.355(2) 0.064(10) Uiso d D 1 . .
    N N14 0.4182(4) 0.2065(3) 0.38980(19) 0.0451(6) Uani d D 1 . .
    H H14A 0.275(2) 0.168(4) 0.401(2) 0.048(8) Uiso d D 1 . .
    H H14B 0.541(3) 0.141(3) 0.410(2) 0.056(9) Uiso d D 1 . .
    O O15 0.9224(4) 0.0654(3) 0.43379(15) 0.0429(4) Uani d D 1 . .
    H H15A 0.906(5) 0.036(4) 0.4964(9) 0.058(10) Uiso d D 1 . .
    H H15B 0.949(6) -0.033(2) 0.406(2) 0.067(11) Uiso d D 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4443(18) ?
    S1 O3 . 1.4535(17) ?
    S1 N11 . 1.592(2) ?
    S1 C4 . 1.755(2) ?
    C4 C5 . 1.386(3) ?
    C4 C9 . 1.399(3) ?
    C5 C6 . 1.369(3) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.400(3) ?
    C6 H6 . 0.93 ?
    C7 N10 . 1.378(3) ?
    C7 C8 . 1.393(3) ?
    C8 C9 . 1.371(3) ?
    C8 H8 . 0.93 ?
    C9 H9 . 0.93 ?
    N10 H10A . 0.873(5) ?
    N10 H10B . 0.870(5) ?
    N11 C12 . 1.349(3) ?
    C12 N14 . 1.323(3) ?
    C12 N13 . 1.326(3) ?
    N13 H13A . 0.869(5) ?
    N13 H13B . 0.871(5) ?
    N14 H14A . 0.870(5) ?
    N14 H14B . 0.867(5) ?
    O15 H15A . 0.821(5) ?
    O15 H15B . 0.822(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 116.00(10) ?
    O2 S1 N11 . . 114.29(10) ?
    O3 S1 N11 . . 104.25(10) ?
    O2 S1 C4 . . 107.43(10) ?
    O3 S1 C4 . . 106.57(10) ?
    N11 S1 C4 . . 107.82(10) ?
    C5 C4 C9 . . 119.3(2) ?
    C5 C4 S1 . . 120.97(16) ?
    C9 C4 S1 . . 119.62(17) ?
    C6 C5 C4 . . 120.7(2) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C7 . . 120.6(2) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    N10 C7 C8 . . 120.5(2) ?
    N10 C7 C6 . . 121.2(2) ?
    C8 C7 C6 . . 118.3(2) ?
    C9 C8 C7 . . 121.3(2) ?
    C9 C8 H8 . . 119.4 ?
    C7 C8 H8 . . 119.4 ?
    C8 C9 C4 . . 119.8(2) ?
    C8 C9 H9 . . 120.1 ?
    C4 C9 H9 . . 120.1 ?
    C7 N10 H10A . . 117.4(19) ?
    C7 N10 H10B . . 118.(2) ?
    H10A N10 H10B . . 118.(3) ?
    C12 N11 S1 . . 120.75(16) ?
    N14 C12 N13 . . 118.5(2) ?
    N14 C12 N11 . . 116.5(2) ?
    N13 C12 N11 . . 125.0(2) ?
    C12 N13 H13A . . 119.0(18) ?
    C12 N13 H13B . . 119.(2) ?
    H13A N13 H13B . . 121.(3) ?
    C12 N14 H14A . . 119.(2) ?
    C12 N14 H14B . . 120.(2) ?
    H14A N14 H14B . . 120.(3) ?
    H15A O15 H15B . . 102.(3) ?
data_Compound_16_CCDC
_audit_creation_method     'APEX2 v2010.1-2'
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H10 N4 O2 S, H2 O'
_chemical_formula_sum     'C7 H12 N4 O3 S'
_chemical_formula_iupac     ?
_chemical_formula_weight     232.27
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21 1'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.6095(10)
_cell_length_b     7.3299(15)
_cell_length_c     12.491(2)
_cell_angle_alpha     90
_cell_angle_beta     93.297(5)
_cell_angle_gamma     90
_cell_volume     512.74(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     58
_cell_measurement_theta_min     4.7817
_cell_measurement_theta_max     20.3137
_cell_measurement_temperature     291.(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     244
_exptl_absorpt_coefficient_mu     0.310
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.85
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     3017
_diffrn_reflns_av_R_equivalents     0.0188
_diffrn_reflns_av_sigmaI/netI     0.0334
_diffrn_reflns_theta_min     1.63
_diffrn_reflns_theta_max     25.83
_diffrn_reflns_theta_full     25.83
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     1940
_reflns_number_gt     1825
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0337
_refine_ls_R_factor_gt     0.0305
_refine_ls_wR_factor_gt     0.0704
_refine_ls_wR_factor_ref     0.0725
_refine_ls_goodness_of_fit_ref     1.134
_refine_ls_restrained_S_all     1.132
_refine_ls_number_reflns     1940
_refine_ls_number_parameters     168
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0366P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.212
_refine_diff_density_min     -0.222
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.02(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement     'APEX2 v2010.1-2 (Bruker AXS)'
_computing_data_reduction     'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.25231(9) 0.67472(7) 0.29318(4) 0.02799(14) Uani d . 1 . .
    O O2 0.4569(3) 0.7875(2) 0.32229(13) 0.0390(4) Uani d . 1 . .
    O O3 0.0204(3) 0.7536(2) 0.31138(13) 0.0383(4) Uani d . 1 . .
    C C4 0.2552(4) 0.6311(3) 0.15512(18) 0.0288(5) Uani d . 1 . .
    C C5 0.4389(4) 0.6951(4) 0.09561(17) 0.0328(5) Uani d . 1 . .
    H H5 0.5701 0.7519 0.1302 0.039 Uiso calc R 1 . .
    C C6 0.4292(4) 0.6755(4) -0.01354(17) 0.0365(5) Uani d . 1 . .
    H H6 0.5534 0.7197 -0.0524 0.044 Uiso calc R 1 . .
    C C7 0.2341(4) 0.5897(3) -0.06721(19) 0.0328(5) Uani d . 1 . .
    C C8 0.0541(4) 0.5205(3) -0.00646(19) 0.0353(6) Uani d . 1 . .
    H H8 -0.0739 0.4591 -0.0407 0.042 Uiso calc R 1 . .
    C C9 0.0620(4) 0.5410(3) 0.10280(19) 0.0348(5) Uani d . 1 . .
    H H9 -0.0607 0.4952 0.142 0.042 Uiso calc R 1 . .
    N N10 0.2172(5) 0.5763(4) -0.17744(19) 0.0485(6) Uani d D 1 . .
    H H10A 0.114(4) 0.498(3) -0.206(2) 0.049(9) Uiso d D 1 . .
    H H10B 0.345(3) 0.599(5) -0.212(2) 0.065(11) Uiso d D 1 . .
    N N11 0.2506(3) 0.4835(3) 0.35355(14) 0.0315(4) Uani d . 1 . .
    C C12 0.4486(4) 0.3789(3) 0.36231(17) 0.0312(5) Uani d . 1 . .
    N N13 0.6673(4) 0.4356(3) 0.34474(19) 0.0442(5) Uani d D 1 . .
    H H13A 0.693(4) 0.5519(11) 0.338(2) 0.039(7) Uiso d D 1 . .
    H H13B 0.785(4) 0.359(3) 0.355(2) 0.064(10) Uiso d D 1 . .
    N N14 0.4182(4) 0.2065(3) 0.38980(19) 0.0451(6) Uani d D 1 . .
    H H14A 0.275(2) 0.168(4) 0.401(2) 0.048(8) Uiso d D 1 . .
    H H14B 0.541(3) 0.141(3) 0.410(2) 0.056(9) Uiso d D 1 . .
    O O15 0.9224(4) 0.0654(3) 0.43379(15) 0.0429(4) Uani d D 1 . .
    H H15A 0.906(5) 0.036(4) 0.4964(9) 0.058(10) Uiso d D 1 . .
    H H15B 0.949(6) -0.033(2) 0.406(2) 0.067(11) Uiso d D 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4443(18) ?
    S1 O3 . 1.4535(17) ?
    S1 N11 . 1.592(2) ?
    S1 C4 . 1.755(2) ?
    C4 C5 . 1.386(3) ?
    C4 C9 . 1.399(3) ?
    C5 C6 . 1.369(3) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.400(3) ?
    C6 H6 . 0.93 ?
    C7 N10 . 1.378(3) ?
    C7 C8 . 1.393(3) ?
    C8 C9 . 1.371(3) ?
    C8 H8 . 0.93 ?
    C9 H9 . 0.93 ?
    N10 H10A . 0.873(5) ?
    N10 H10B . 0.870(5) ?
    N11 C12 . 1.349(3) ?
    C12 N14 . 1.323(3) ?
    C12 N13 . 1.326(3) ?
    N13 H13A . 0.869(5) ?
    N13 H13B . 0.871(5) ?
    N14 H14A . 0.870(5) ?
    N14 H14B . 0.867(5) ?
    O15 H15A . 0.821(5) ?
    O15 H15B . 0.822(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 116.00(10) ?
    O2 S1 N11 . . 114.29(10) ?
    O3 S1 N11 . . 104.25(10) ?
    O2 S1 C4 . . 107.43(10) ?
    O3 S1 C4 . . 106.57(10) ?
    N11 S1 C4 . . 107.82(10) ?
    C5 C4 C9 . . 119.3(2) ?
    C5 C4 S1 . . 120.97(16) ?
    C9 C4 S1 . . 119.62(17) ?
    C6 C5 C4 . . 120.7(2) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C7 . . 120.6(2) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    N10 C7 C8 . . 120.5(2) ?
    N10 C7 C6 . . 121.2(2) ?
    C8 C7 C6 . . 118.3(2) ?
    C9 C8 C7 . . 121.3(2) ?
    C9 C8 H8 . . 119.4 ?
    C7 C8 H8 . . 119.4 ?
    C8 C9 C4 . . 119.8(2) ?
    C8 C9 H9 . . 120.1 ?
    C4 C9 H9 . . 120.1 ?
    C7 N10 H10A . . 117.4(19) ?
    C7 N10 H10B . . 118.(2) ?
    H10A N10 H10B . . 118.(3) ?
    C12 N11 S1 . . 120.75(16) ?
    N14 C12 N13 . . 118.5(2) ?
    N14 C12 N11 . . 116.5(2) ?
    N13 C12 N11 . . 125.0(2) ?
    C12 N13 H13A . . 119.0(18) ?
    C12 N13 H13B . . 119.(2) ?
    H13A N13 H13B . . 121.(3) ?
    C12 N14 H14A . . 119.(2) ?
    C12 N14 H14B . . 120.(2) ?
    H14A N14 H14B . . 120.(3) ?
    H15A O15 H15B . . 102.(3) ?
data_Compound_16_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     '(C7 H10 N4 O2 S), (H2 O)'
_chemical_formula_sum     'C7 H12 N4 O3 S'
_chemical_formula_weight     232.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)1
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.6245(17)
_cell_length_b     7.354(3)
_cell_length_c     12.521(5)
_cell_angle_alpha     90.00
_cell_angle_beta     93.445(13)
_cell_angle_gamma     90.00
_cell_volume     517.0(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     654
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     19.39
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.492
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     244
_exptl_absorpt_coefficient_mu     0.308
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9079
_exptl_absorpt_correction_T_max     0.9640
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3381
_diffrn_reflns_av_R_equivalents     0.0388
_diffrn_reflns_av_sigmaI/netI     0.0701
_diffrn_reflns_theta_min     3.21
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1776
_reflns_number_gt     1427
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0614
_refine_ls_R_factor_gt     0.0458
_refine_ls_wR_factor_gt     0.0850
_refine_ls_wR_factor_ref     0.0920
_refine_ls_goodness_of_fit_ref     0.999
_refine_ls_restrained_S_all     0.998
_refine_ls_number_reflns     1776
_refine_ls_number_parameters     161
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.240
_refine_diff_density_min     -0.277
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.25(12)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.25269(16) 0.67473(12) 0.29322(7) 0.0311(3) Uani d . 1 . .
    O O2 0.4567(5) 0.7871(4) 0.3221(2) 0.0404(7) Uani d . 1 . .
    O O3 0.0207(4) 0.7534(4) 0.3117(2) 0.0393(7) Uani d . 1 . .
    C C4 0.2550(6) 0.6314(4) 0.1553(3) 0.0277(9) Uani d . 1 . .
    C C5 0.4377(6) 0.6955(6) 0.0954(3) 0.0334(9) Uani d . 1 . .
    H H5 0.5683 0.7530 0.1297 0.040 Uiso calc R 1 . .
    C C6 0.4281(6) 0.6752(7) -0.0132(3) 0.0372(9) Uani d . 1 . .
    H H6 0.5522 0.7190 -0.0518 0.045 Uiso calc R 1 . .
    C C7 0.2344(7) 0.5896(5) -0.0670(3) 0.0347(10) Uani d . 1 . .
    C C8 0.0542(7) 0.5210(5) -0.0057(3) 0.0377(10) Uani d . 1 . .
    H H8 -0.0747 0.4608 -0.0397 0.045 Uiso calc R 1 . .
    C C9 0.0641(6) 0.5406(5) 0.1026(3) 0.0354(10) Uani d . 1 . .
    H H9 -0.0571 0.4934 0.1417 0.042 Uiso calc R 1 . .
    N N10 0.2171(7) 0.5772(6) -0.1769(3) 0.0503(10) Uani d D 1 . .
    H H10A 0.125(6) 0.493(4) -0.206(3) 0.060 Uiso d D 1 . .
    H H10B 0.345(7) 0.596(7) -0.214(4) 0.060 Uiso d . 1 . .
    N N11 0.2500(5) 0.4831(4) 0.3533(2) 0.0325(8) Uani d . 1 . .
    C C12 0.4486(7) 0.3796(5) 0.3620(3) 0.0321(10) Uani d . 1 . .
    N N13 0.6678(7) 0.4350(6) 0.3451(3) 0.0462(10) Uani d . 1 . .
    H H13A 0.693(8) 0.540(7) 0.336(4) 0.055 Uiso d . 1 . .
    H H13B 0.794(8) 0.354(6) 0.351(3) 0.055 Uiso d . 1 . .
    N N14 0.4174(7) 0.2067(5) 0.3900(3) 0.0484(11) Uani d . 1 . .
    H H14A 0.280(7) 0.156(7) 0.396(3) 0.058 Uiso d . 1 . .
    H H14B 0.537(7) 0.135(6) 0.401(3) 0.058 Uiso d . 1 . .
    O O15 0.9215(6) 0.0652(4) 0.4337(3) 0.0474(9) Uani d . 1 . .
    H H15A 0.945(8) -0.021(7) 0.403(4) 0.057 Uiso d . 1 . .
    H H15B 0.905(7) 0.038(6) 0.498(4) 0.057 Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.443(3) ?
    S1 O3 . 1.458(3) ?
    S1 N11 . 1.598(3) ?
    S1 C4 . 1.757(4) ?
    C4 C5 . 1.391(5) ?
    C4 C9 . 1.396(5) ?
    C5 C6 . 1.365(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.397(5) ?
    C6 H6 . 0.9300 ?
    C7 N10 . 1.377(5) ?
    C7 C8 . 1.402(5) ?
    C8 C9 . 1.361(5) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    N10 H10A . 0.872(5) ?
    N10 H10B . 0.89(4) ?
    N11 C12 . 1.351(5) ?
    C12 N13 . 1.328(5) ?
    C12 N14 . 1.334(5) ?
    N13 H13A . 0.80(5) ?
    N13 H13B . 0.93(4) ?
    N14 H14A . 0.86(4) ?
    N14 H14B . 0.86(4) ?
    O15 H15A . 0.76(5) ?
    O15 H15B . 0.84(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O3 . . 116.02(16) ?
    O2 S1 N11 . . 114.66(17) ?
    O3 S1 N11 . . 103.96(16) ?
    O2 S1 C4 . . 107.32(16) ?
    O3 S1 C4 . . 106.72(16) ?
    N11 S1 C4 . . 107.66(16) ?
    C5 C4 C9 . . 118.7(3) ?
    C5 C4 S1 . . 121.2(3) ?
    C9 C4 S1 . . 120.0(3) ?
    C6 C5 C4 . . 120.9(3) ?
    C6 C5 H5 . . 119.6 ?
    C4 C5 H5 . . 119.6 ?
    C5 C6 C7 . . 120.9(3) ?
    C5 C6 H6 . . 119.6 ?
    C7 C6 H6 . . 119.6 ?
    N10 C7 C6 . . 121.2(4) ?
    N10 C7 C8 . . 120.9(4) ?
    C6 C7 C8 . . 117.8(4) ?
    C9 C8 C7 . . 121.3(3) ?
    C9 C8 H8 . . 119.3 ?
    C7 C8 H8 . . 119.3 ?
    C8 C9 C4 . . 120.4(3) ?
    C8 C9 H9 . . 119.8 ?
    C4 C9 H9 . . 119.8 ?
    C7 N10 H10A . . 118(3) ?
    C7 N10 H10B . . 120(3) ?
    H10A N10 H10B . . 112(4) ?
    C12 N11 S1 . . 120.3(3) ?
    N13 C12 N14 . . 118.2(4) ?
    N13 C12 N11 . . 125.8(4) ?
    N14 C12 N11 . . 115.9(4) ?
    C12 N13 H13A . . 120(3) ?
    C12 N13 H13B . . 120(3) ?
    H13A N13 H13B . . 120(4) ?
    C12 N14 H14A . . 125(3) ?
    C12 N14 H14B . . 121(3) ?
    H14A N14 H14B . . 115(5) ?
    H15A O15 H15B . . 109(5) ?
data_Compound_16_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     '(C7 H6 N3 O3 S), (O)'
_chemical_formula_sum     'C7 H8 N4 O S'
_chemical_formula_weight     196.23
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P12(1)1
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.6245(17)
_cell_length_b     7.354(3)
_cell_length_c     12.521(5)
_cell_angle_alpha     90.00
_cell_angle_beta     93.445(13)
_cell_angle_gamma     90.00
_cell_volume     517.0(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     654
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     19.39
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.261
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     204
_exptl_absorpt_coefficient_mu     0.282
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9079
_exptl_absorpt_correction_T_max     0.9640
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3392
_diffrn_reflns_av_R_equivalents     0.1452
_diffrn_reflns_av_sigmaI/netI     0.1447
_diffrn_reflns_theta_min     1.63
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1777
_reflns_number_gt     1247
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1073
_refine_ls_R_factor_gt     0.0865
_refine_ls_wR_factor_gt     0.2132
_refine_ls_wR_factor_ref     0.2280
_refine_ls_goodness_of_fit_ref     0.993
_refine_ls_restrained_S_all     0.992
_refine_ls_number_reflns     1777
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.048
_refine_ls_shift/su_mean     0.005
_refine_diff_density_max     0.472
_refine_diff_density_min     -0.632
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     0.9(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.2528(3) 0.1633(2) 0.29341(14) 0.0305(5) Uani d . 1 . .
    O O1S 0.9229(10) -0.2237(8) 0.4347(5) 0.0463(16) Uani d . 1 . .
    O O1 0.2494(11) 0.3545(9) 0.3539(5) 0.0543(17) Uani d . 1 . .
    O O2 0.0217(10) 0.0856(7) 0.3121(4) 0.0401(15) Uani d . 1 . .
    O O3 0.4579(9) 0.0512(7) 0.3228(4) 0.0384(14) Uani d . 1 . .
    N N1 0.2179(14) 0.2629(12) -0.1792(6) 0.052(2) Uani d . 1 . .
    N N2 0.4151(14) 0.6325(10) 0.3908(6) 0.0477(19) Uani d . 1 . .
    N N3 0.4273(14) 0.1626(14) -0.0142(6) 0.058(2) Uani d . 1 . .
    H H3 0.5423 0.1227 -0.0499 0.070 Uiso calc R 1 . .
    C C1 0.2329(14) 0.2485(11) -0.0676(6) 0.0337(19) Uani d . 1 . .
    C C2 0.0544(15) 0.3172(11) -0.0060(7) 0.041(2) Uani d . 1 . .
    H H2 -0.0731 0.3792 -0.0399 0.049 Uiso calc R 1 . .
    C C3 0.0619(14) 0.2959(12) 0.1032(7) 0.038(2) Uani d . 1 . .
    H H3A -0.0607 0.3410 0.1423 0.046 Uiso calc R 1 . .
    C C4 0.2542(13) 0.2064(9) 0.1551(6) 0.0284(18) Uani d . 1 . .
    C C5 0.4503(14) 0.4594(10) 0.3620(6) 0.0309(19) Uani d . 1 . .
    C C6 0.6662(11) 0.4018(11) 0.3456(6) 0.0286(17) Uani d . 1 . .
    H H6A 0.7947 0.4811 0.3540 0.034 Uiso calc R 1 . .
    H H6B 0.6905 0.2817 0.3256 0.034 Uiso calc R 1 . .
    C C7 0.4359(13) 0.1413(11) 0.0960(6) 0.0338(18) Uani d . 1 . .
    H H7 0.5653 0.0826 0.1305 0.041 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O3 . 1.447(6) ?
    S1 O2 . 1.452(6) ?
    S1 O1 . 1.598(6) ?
    S1 C4 . 1.760(7) ?
    O1 C5 . 1.367(9) ?
    N1 C1 . 1.398(11) ?
    N2 C5 . 1.341(10) ?
    N3 C7 . 1.386(10) ?
    N3 C1 . 1.398(11) ?
    N3 H3 . 0.8600 ?
    C1 C2 . 1.397(11) ?
    C2 C3 . 1.375(11) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.394(11) ?
    C3 H3A . 0.9300 ?
    C4 C7 . 1.383(10) ?
    C5 C6 . 1.314(10) ?
    C6 H6A . 0.9300 ?
    C6 H6B . 0.9300 ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 S1 O2 . . 116.3(3) ?
    O3 S1 O1 . . 114.4(3) ?
    O2 S1 O1 . . 103.5(3) ?
    O3 S1 C4 . . 107.6(3) ?
    O2 S1 C4 . . 106.6(3) ?
    O1 S1 C4 . . 108.0(3) ?
    C5 O1 S1 . . 119.9(5) ?
    C7 N3 C1 . . 120.5(7) ?
    C7 N3 H3 . . 119.8 ?
    C1 N3 H3 . . 119.8 ?
    C2 C1 N1 . . 121.5(7) ?
    C2 C1 N3 . . 117.8(7) ?
    N1 C1 N3 . . 120.7(7) ?
    C3 C2 C1 . . 121.9(7) ?
    C3 C2 H2 . . 119.1 ?
    C1 C2 H2 . . 119.1 ?
    C2 C3 C4 . . 119.6(7) ?
    C2 C3 H3A . . 120.2 ?
    C4 C3 H3A . . 120.2 ?
    C7 C4 C3 . . 119.5(7) ?
    C7 C4 S1 . . 120.8(6) ?
    C3 C4 S1 . . 119.6(6) ?
    C6 C5 N2 . . 120.0(7) ?
    C6 C5 O1 . . 125.1(7) ?
    N2 C5 O1 . . 114.9(7) ?
    C5 C6 H6A . . 120.0 ?
    C5 C6 H6B . . 120.0 ?
    H6A C6 H6B . . 120.0 ?
    C4 C7 N3 . . 120.7(7) ?
    C4 C7 H7 . . 119.6 ?
    N3 C7 H7 . . 119.6 ?
data_Compound_17_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H15 O P, C7 H7 N S,'
_chemical_formula_sum     'C25 H22 N O P S'
_chemical_formula_weight     415.47
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2699(10)
_cell_length_b     11.1605(10)
_cell_length_c     11.1911(12)
_cell_angle_alpha     85.945(3)
_cell_angle_beta     67.750(3)
_cell_angle_gamma     70.671(3)
_cell_volume     1118.07(19)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3717
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     24.96
_cell_measurement_temperature     300(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.234
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.232
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9029
_exptl_absorpt_correction_T_max     0.9772
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11052
_diffrn_reflns_av_R_equivalents     0.0348
_diffrn_reflns_av_sigmaI/netI     0.0373
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3900
_reflns_number_gt     3000
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0568
_refine_ls_R_factor_gt     0.0390
_refine_ls_wR_factor_gt     0.0941
_refine_ls_wR_factor_ref     0.1104
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     3900
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0495P)²+0.3084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.238
_refine_diff_density_min     -0.250
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S28 0.00829(8) 0.95834(6) 0.80459(7) 0.0636(2) Uani d . 1 . .
    P P1 0.36152(6) 0.31286(5) 0.14058(5) 0.03709(16) Uani d . 1 . .
    O O2 0.52104(15) 0.30422(14) 0.07712(14) 0.0476(4) Uani d . 1 . .
    N N29 0.2043(3) 0.8500(2) 0.9086(2) 0.0619(6) Uani d . 1 . .
    H H29A 0.278(4) 0.799(3) 0.910(3) 0.093 Uiso d . 1 . .
    H H29B 0.164(4) 0.917(3) 0.957(3) 0.093 Uiso d . 1 . .
    C C12 0.2106(3) 0.1851(3) -0.1505(3) 0.0656(7) Uani d . 1 . .
    H H12 0.1820 0.1574 -0.2102 0.079 Uiso calc R 1 . .
    C C11 0.1127(3) 0.2848(3) -0.0629(2) 0.0613(7) Uani d . 1 . .
    H H11 0.0179 0.3248 -0.0636 0.074 Uiso calc R 1 . .
    C C10 0.1537(2) 0.3266(2) 0.0264(2) 0.0508(6) Uani d . 1 . .
    H H10 0.0864 0.3944 0.0854 0.061 Uiso calc R 1 . .
    C C9 0.2952(2) 0.2675(2) 0.02846(19) 0.0403(5) Uani d . 1 . .
    C C15 0.3317(2) 0.21045(19) 0.27353(19) 0.0389(5) Uani d . 1 . .
    C C20 0.3980(3) 0.2117(2) 0.3615(2) 0.0465(5) Uani d . 1 . .
    H H20 0.4567 0.2630 0.3494 0.056 Uiso calc R 1 . .
    C C19 0.3770(3) 0.1368(2) 0.4665(2) 0.0580(7) Uani d . 1 . .
    H H19 0.4205 0.1387 0.5254 0.070 Uiso calc R 1 . .
    C C18 0.2920(3) 0.0598(2) 0.4840(2) 0.0627(7) Uani d . 1 . .
    H H18 0.2787 0.0089 0.5542 0.075 Uiso calc R 1 . .
    C C3 0.2430(2) 0.47108(19) 0.21007(18) 0.0384(5) Uani d . 1 . .
    C C4 0.1000(2) 0.4958(2) 0.3044(2) 0.0501(6) Uani d . 1 . .
    H H4 0.0618 0.4296 0.3331 0.060 Uiso calc R 1 . .
    C C5 0.0151(3) 0.6191(2) 0.3551(2) 0.0604(7) Uani d . 1 . .
    H H5 -0.0803 0.6359 0.4179 0.072 Uiso calc R 1 . .
    C C6 0.0719(3) 0.7170(2) 0.3124(2) 0.0642(7) Uani d . 1 . .
    H H6 0.0148 0.7996 0.3469 0.077 Uiso calc R 1 . .
    C C7 0.2115(3) 0.6933(2) 0.2196(3) 0.0656(7) Uani d . 1 . .
    H H7 0.2488 0.7599 0.1908 0.079 Uiso calc R 1 . .
    C C8 0.2976(3) 0.5706(2) 0.1685(2) 0.0522(6) Uani d . 1 . .
    H H8 0.3928 0.5550 0.1056 0.063 Uiso calc R 1 . .
    C C13 0.3503(3) 0.1263(3) -0.1501(3) 0.0722(8) Uani d . 1 . .
    H H13 0.4165 0.0585 -0.2095 0.087 Uiso calc R 1 . .
    C C14 0.3935(3) 0.1671(2) -0.0619(2) 0.0591(6) Uani d . 1 . .
    H H14 0.4891 0.1272 -0.0630 0.071 Uiso calc R 1 . .
    C C16 0.2453(3) 0.1333(2) 0.2928(2) 0.0544(6) Uani d . 1 . .
    H H16 0.1997 0.1320 0.2355 0.065 Uiso calc R 1 . .
    C C17 0.2267(3) 0.0577(3) 0.3981(3) 0.0678(7) Uani d . 1 . .
    H H17 0.1694 0.0052 0.4104 0.081 Uiso calc R 1 . .
    C C24 0.3296(4) 0.4823(3) 0.6075(3) 0.0861(9) Uani d . 1 . .
    H H24 0.3681 0.4044 0.5609 0.103 Uiso calc R 1 . .
    C C25 0.3361(3) 0.4885(3) 0.7265(3) 0.0746(8) Uani d . 1 . .
    H H25 0.3786 0.4146 0.7611 0.089 Uiso calc R 1 . .
    C C26 0.2798(3) 0.6039(2) 0.7955(2) 0.0561(6) Uani d . 1 . .
    H H26 0.2855 0.6072 0.8761 0.067 Uiso calc R 1 . .
    C C21 0.2148(2) 0.7154(2) 0.7463(2) 0.0455(5) Uani d . 1 . .
    C C27 0.1491(2) 0.8390(2) 0.8232(2) 0.0469(5) Uani d . 1 . .
    C C23 0.2667(4) 0.5904(4) 0.5575(3) 0.0883(10) Uani d . 1 . .
    H H23 0.2632 0.5859 0.4761 0.106 Uiso calc R 1 . .
    C C22 0.2074(3) 0.7076(3) 0.6262(3) 0.0670(7) Uani d . 1 . .
    H H22 0.1630 0.7805 0.5916 0.080 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S28 C27 . 1.680(2) ?
    P1 O2 . 1.4905(15) ?
    P1 C9 . 1.805(2) ?
    P1 C3 . 1.805(2) ?
    P1 C15 . 1.806(2) ?
    N29 C27 . 1.312(3) ?
    N29 H29A . 0.78(3) ?
    N29 H29B . 0.84(3) ?
    C12 C13 . 1.367(4) ?
    C12 C11 . 1.371(4) ?
    C12 H12 . 0.9300 ?
    C11 C10 . 1.381(3) ?
    C11 H11 . 0.9300 ?
    C10 C9 . 1.392(3) ?
    C10 H10 . 0.9300 ?
    C9 C14 . 1.392(3) ?
    C15 C16 . 1.381(3) ?
    C15 C20 . 1.396(3) ?
    C20 C19 . 1.384(3) ?
    C20 H20 . 0.9300 ?
    C19 C18 . 1.373(4) ?
    C19 H19 . 0.9300 ?
    C18 C17 . 1.369(4) ?
    C18 H18 . 0.9300 ?
    C3 C8 . 1.381(3) ?
    C3 C4 . 1.395(3) ?
    C4 C5 . 1.385(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.378(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.366(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.382(3) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C13 C14 . 1.382(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C16 C17 . 1.391(3) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
    C24 C23 . 1.360(5) ?
    C24 C25 . 1.367(4) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.378(3) ?
    C25 H25 . 0.9300 ?
    C26 C21 . 1.388(3) ?
    C26 H26 . 0.9300 ?
    C21 C22 . 1.385(3) ?
    C21 C27 . 1.488(3) ?
    C23 C22 . 1.390(4) ?
    C23 H23 . 0.9300 ?
    C22 H22 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 P1 C9 . . 111.58(9) ?
    O2 P1 C3 . . 111.93(9) ?
    C9 P1 C3 . . 108.62(9) ?
    O2 P1 C15 . . 111.96(9) ?
    C9 P1 C15 . . 107.14(10) ?
    C3 P1 C15 . . 105.29(9) ?
    C27 N29 H29A . . 121(2) ?
    C27 N29 H29B . . 118(2) ?
    H29A N29 H29B . . 120(3) ?
    C13 C12 C11 . . 120.0(2) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C11 C10 . . 120.6(2) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C11 C10 C9 . . 120.2(2) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C10 C9 C14 . . 118.4(2) ?
    C10 C9 P1 . . 124.38(17) ?
    C14 C9 P1 . . 117.21(17) ?
    C16 C15 C20 . . 119.06(19) ?
    C16 C15 P1 . . 123.23(16) ?
    C20 C15 P1 . . 117.70(16) ?
    C19 C20 C15 . . 120.3(2) ?
    C19 C20 H20 . . 119.8 ?
    C15 C20 H20 . . 119.8 ?
    C18 C19 C20 . . 120.0(2) ?
    C18 C19 H19 . . 120.0 ?
    C20 C19 H19 . . 120.0 ?
    C17 C18 C19 . . 120.1(2) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 H18 . . 120.0 ?
    C8 C3 C4 . . 119.2(2) ?
    C8 C3 P1 . . 118.24(16) ?
    C4 C3 P1 . . 122.51(17) ?
    C5 C4 C3 . . 119.8(2) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C6 C5 C4 . . 120.0(2) ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C7 C6 C5 . . 120.4(2) ?
    C7 C6 H6 . . 119.8 ?
    C5 C6 H6 . . 119.8 ?
    C6 C7 C8 . . 120.2(2) ?
    C6 C7 H7 . . 119.9 ?
    C8 C7 H7 . . 119.9 ?
    C3 C8 C7 . . 120.4(2) ?
    C3 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C12 C13 C14 . . 120.3(2) ?
    C12 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C13 C14 C9 . . 120.5(2) ?
    C13 C14 H14 . . 119.7 ?
    C9 C14 H14 . . 119.7 ?
    C15 C16 C17 . . 119.8(2) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C18 C17 C16 . . 120.7(2) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C23 C24 C25 . . 119.8(3) ?
    C23 C24 H24 . . 120.1 ?
    C25 C24 H24 . . 120.1 ?
    C24 C25 C26 . . 120.2(3) ?
    C24 C25 H25 . . 119.9 ?
    C26 C25 H25 . . 119.9 ?
    C25 C26 C21 . . 120.9(2) ?
    C25 C26 H26 . . 119.5 ?
    C21 C26 H26 . . 119.5 ?
    C22 C21 C26 . . 118.3(2) ?
    C22 C21 C27 . . 120.9(2) ?
    C26 C21 C27 . . 120.7(2) ?
    N29 C27 C21 . . 116.8(2) ?
    N29 C27 S28 . . 121.30(18) ?
    C21 C27 S28 . . 121.86(17) ?
    C24 C23 C22 . . 121.0(3) ?
    C24 C23 H23 . . 119.5 ?
    C22 C23 H23 . . 119.5 ?
    C21 C22 C23 . . 119.8(3) ?
    C21 C22 H22 . . 120.1 ?
    C23 C22 H22 . . 120.1 ?
data_Compound_17_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     '(C7 H7 N S), (C18 H15 O P)'
_chemical_formula_sum     'C25 H22 N O P S'
_chemical_formula_weight     415.47
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2699(10)
_cell_length_b     11.1605(10)
_cell_length_c     11.1911(12)
_cell_angle_alpha     85.945(3)
_cell_angle_beta     67.750(3)
_cell_angle_gamma     70.671(3)
_cell_volume     1118.07(19)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3717
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     24.96
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.234
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.232
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.9029
_exptl_absorpt_correction_T_max     0.9772
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11064
_diffrn_reflns_av_R_equivalents     0.0348
_diffrn_reflns_av_sigmaI/netI     0.0373
_diffrn_reflns_theta_min     1.94
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3902
_reflns_number_gt     3000
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0594
_refine_ls_R_factor_gt     0.0400
_refine_ls_wR_factor_gt     0.1145
_refine_ls_wR_factor_ref     0.1462
_refine_ls_goodness_of_fit_ref     1.008
_refine_ls_restrained_S_all     1.008
_refine_ls_number_reflns     3902
_refine_ls_number_parameters     268
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     'mixed'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0955P)²+0.1430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.044
_refine_ls_shift/su_mean     0.008
_refine_diff_density_max     0.268
_refine_diff_density_min     -0.293
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.00828(8) 0.95842(7) -0.19544(8) 0.0627(3) Uani d . 1 . .
    P P1 0.36154(6) 0.31287(5) 0.14058(5) 0.0362(2) Uani d . 1 . .
    O O1 0.52110(17) 0.30414(16) 0.07717(15) 0.0467(4) Uani d . 1 . .
    N N1 0.2045(3) 0.8498(2) -0.0915(3) 0.0606(6) Uani d D 1 . .
    H H@2 0.285(2) 0.798(2) -0.090(3) 0.091 Uiso d D 1 . .
    H H@1 0.168(3) 0.9166(19) -0.043(3) 0.091 Uiso d D 1 . .
    C C1 0.2110(4) 0.1848(3) -0.1506(3) 0.0648(8) Uani d . 1 . .
    H H1 0.1825 0.1570 -0.2102 0.078 Uiso calc R 1 . .
    C C2 0.1128(3) 0.2845(3) -0.0630(3) 0.0609(7) Uani d . 1 . .
    H H2 0.0180 0.3242 -0.0638 0.073 Uiso calc R 1 . .
    C C3 0.1537(3) 0.3264(3) 0.0264(2) 0.0503(6) Uani d . 1 . .
    H H3 0.0864 0.3943 0.0853 0.060 Uiso calc R 1 . .
    C C4 0.2954(3) 0.2674(2) 0.0285(2) 0.0396(5) Uani d . 1 . .
    C C5 0.3317(2) 0.2103(2) 0.2735(2) 0.0384(5) Uani d . 1 . .
    C C6 0.3982(3) 0.2117(2) 0.3614(2) 0.0460(6) Uani d . 1 . .
    H H6 0.4568 0.2631 0.3492 0.055 Uiso calc R 1 . .
    C C7 0.3771(3) 0.1366(3) 0.4667(2) 0.0573(7) Uani d . 1 . .
    H H7 0.4204 0.1384 0.5257 0.069 Uiso calc R 1 . .
    C C8 0.2922(3) 0.0596(3) 0.4838(3) 0.0615(8) Uani d . 1 . .
    H H8 0.2790 0.0087 0.5539 0.074 Uiso calc R 1 . .
    C C9 0.2431(2) 0.4710(2) 0.2101(2) 0.0378(5) Uani d . 1 . .
    C C10 0.1001(3) 0.4957(2) 0.3045(2) 0.0493(6) Uani d . 1 . .
    H H10 0.0619 0.4295 0.3332 0.059 Uiso calc R 1 . .
    C C11 0.0151(3) 0.6191(3) 0.3553(3) 0.0597(7) Uani d . 1 . .
    H H11 -0.0802 0.6358 0.4182 0.072 Uiso calc R 1 . .
    C C12 0.0718(3) 0.7172(3) 0.3125(3) 0.0628(8) Uani d . 1 . .
    H H12 0.0146 0.7999 0.3468 0.075 Uiso calc R 1 . .
    C C13 0.2118(3) 0.6934(3) 0.2198(3) 0.0647(8) Uani d . 1 . .
    H H13 0.2494 0.7599 0.1913 0.078 Uiso calc R 1 . .
    C C14 0.2975(3) 0.5707(2) 0.1684(2) 0.0514(6) Uani d . 1 . .
    H H14 0.3926 0.5552 0.1053 0.062 Uiso calc R 1 . .
    C C15 0.3506(4) 0.1261(3) -0.1503(3) 0.0711(9) Uani d . 1 . .
    H H15 0.4169 0.0583 -0.2097 0.085 Uiso calc R 1 . .
    C C16 0.3938(3) 0.1671(3) -0.0621(3) 0.0583(7) Uani d . 1 . .
    H H16 0.4894 0.1273 -0.0633 0.070 Uiso calc R 1 . .
    C C17 0.2454(3) 0.1332(3) 0.2927(3) 0.0534(7) Uani d . 1 . .
    H H17 0.1997 0.1318 0.2354 0.064 Uiso calc R 1 . .
    C C18 0.2270(4) 0.0574(3) 0.3981(3) 0.0669(8) Uani d . 1 . .
    H H18 0.1698 0.0048 0.4104 0.080 Uiso calc R 1 . .
    C C19 0.3295(4) 0.4824(4) -0.3927(4) 0.0855(11) Uani d . 1 . .
    H H19 0.3675 0.4045 -0.4394 0.103 Uiso calc R 1 . .
    C C20 0.3365(4) 0.4882(3) -0.2736(3) 0.0743(9) Uani d . 1 . .
    H H20 0.3793 0.4143 -0.2392 0.089 Uiso calc R 1 . .
    C C21 0.2801(3) 0.6039(2) -0.2046(3) 0.0557(7) Uani d . 1 . .
    H H21 0.2858 0.6072 -0.1240 0.067 Uiso calc R 1 . .
    C C22 0.2148(3) 0.7154(2) -0.2536(2) 0.0451(6) Uani d . 1 . .
    C C23 0.1491(3) 0.8393(2) -0.1768(2) 0.0463(6) Uani d . 1 . .
    C C24 0.2667(4) 0.5905(4) -0.4427(3) 0.0868(11) Uani d . 1 . .
    H H24 0.2634 0.5860 -0.5241 0.104 Uiso calc R 1 . .
    C C25 0.2075(3) 0.7078(3) -0.3741(3) 0.0661(8) Uani d . 1 . .
    H H25 0.1631 0.7808 -0.4087 0.079 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C23 . 1.679(2) ?
    P1 O1 . 1.4906(16) ?
    P1 C9 . 1.804(2) ?
    P1 C4 . 1.805(2) ?
    P1 C5 . 1.806(2) ?
    N1 C23 . 1.312(3) ?
    N1 H@2 . 0.843(10) ?
    N1 H@1 . 0.844(10) ?
    C1 C15 . 1.366(4) ?
    C1 C2 . 1.370(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.383(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.393(3) ?
    C3 H3 . 0.9300 ?
    C4 C16 . 1.392(3) ?
    C5 C17 . 1.381(3) ?
    C5 C6 . 1.397(3) ?
    C6 C7 . 1.388(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.371(4) ?
    C7 H7 . 0.9300 ?
    C8 C18 . 1.367(4) ?
    C8 H8 . 0.9300 ?
    C9 C14 . 1.382(3) ?
    C9 C10 . 1.396(3) ?
    C10 C11 . 1.386(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.380(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.367(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.382(4) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.381(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.391(4) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 C24 . 1.359(5) ?
    C19 C20 . 1.370(5) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.380(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.389(4) ?
    C21 H21 . 0.9300 ?
    C22 C25 . 1.388(4) ?
    C22 C23 . 1.489(4) ?
    C24 C25 . 1.392(5) ?
    C24 H24 . 0.9300 ?
    C25 H25 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 P1 C9 . . 111.94(10) ?
    O1 P1 C4 . . 111.57(10) ?
    C9 P1 C4 . . 108.71(10) ?
    O1 P1 C5 . . 111.91(10) ?
    C9 P1 C5 . . 105.33(10) ?
    C4 P1 C5 . . 107.06(11) ?
    C23 N1 H@2 . . 123(2) ?
    C23 N1 H@1 . . 120(2) ?
    H@2 N1 H@1 . . 116(3) ?
    C15 C1 C2 . . 120.1(3) ?
    C15 C1 H1 . . 120.0 ?
    C2 C1 H1 . . 120.0 ?
    C1 C2 C3 . . 120.5(3) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 120.2(2) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C16 . . 118.3(2) ?
    C3 C4 P1 . . 124.37(18) ?
    C16 C4 P1 . . 117.32(18) ?
    C17 C5 C6 . . 119.1(2) ?
    C17 C5 P1 . . 123.27(18) ?
    C6 C5 P1 . . 117.58(18) ?
    C7 C6 C5 . . 120.2(2) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C8 C7 C6 . . 120.0(3) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C18 C8 C7 . . 120.3(2) ?
    C18 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C14 C9 C10 . . 119.2(2) ?
    C14 C9 P1 . . 118.32(17) ?
    C10 C9 P1 . . 122.51(19) ?
    C11 C10 C9 . . 119.8(2) ?
    C11 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C12 C11 C10 . . 120.1(2) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 120.3(3) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 120.2(3) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 120.5(2) ?
    C13 C14 H14 . . 119.7 ?
    C9 C14 H14 . . 119.7 ?
    C1 C15 C16 . . 120.2(3) ?
    C1 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C4 . . 120.6(3) ?
    C15 C16 H16 . . 119.7 ?
    C4 C16 H16 . . 119.7 ?
    C5 C17 C18 . . 119.8(2) ?
    C5 C17 H17 . . 120.1 ?
    C18 C17 H17 . . 120.1 ?
    C8 C18 C17 . . 120.7(3) ?
    C8 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
    C24 C19 C20 . . 119.9(3) ?
    C24 C19 H19 . . 120.1 ?
    C20 C19 H19 . . 120.1 ?
    C19 C20 C21 . . 120.0(3) ?
    C19 C20 H20 . . 120.0 ?
    C21 C20 H20 . . 120.0 ?
    C20 C21 C22 . . 121.0(3) ?
    C20 C21 H21 . . 119.5 ?
    C22 C21 H21 . . 119.5 ?
    C25 C22 C21 . . 118.3(3) ?
    C25 C22 C23 . . 120.8(2) ?
    C21 C22 C23 . . 120.9(2) ?
    N1 C23 C22 . . 116.6(2) ?
    N1 C23 S1 . . 121.5(2) ?
    C22 C23 S1 . . 121.87(18) ?
    C19 C24 C25 . . 121.1(3) ?
    C19 C24 H24 . . 119.5 ?
    C25 C24 H24 . . 119.5 ?
    C22 C25 C24 . . 119.7(3) ?
    C22 C25 H25 . . 120.2 ?
    C24 C25 H25 . . 120.2 ?
data_Compound_18_APEX
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N O2 S'
_chemical_formula_sum     'C13 H13 N O2 S'
_chemical_formula_weight     247.30
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.259(3)
_cell_length_b     11.050(4)
_cell_length_c     13.380(5)
_cell_angle_alpha     67.808(8)
_cell_angle_beta     87.291(8)
_cell_angle_gamma     67.435(7)
_cell_volume     1288.4(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6965
_cell_measurement_theta_min     2.3811
_cell_measurement_theta_max     24.3695
_cell_measurement_temperature     291(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.275
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.240
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min     0.78
_exptl_absorpt_correction_T_max     0.94
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX II DUO'
_diffrn_measurement_method     'φ & ω  scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     23008
_diffrn_reflns_av_R_equivalents     0.0393
_diffrn_reflns_av_sigmaI/netI     0.0299
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     25.65
_diffrn_reflns_theta_full     25.65
_diffrn_measured_fraction_theta_max     0.941
_diffrn_measured_fraction_theta_full     0.941
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4600
_reflns_number_gt     3117
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0949
_refine_ls_R_factor_gt     0.0619
_refine_ls_wR_factor_gt     0.1961
_refine_ls_wR_factor_ref     0.2657
_refine_ls_goodness_of_fit_ref     1.104
_refine_ls_restrained_S_all     1.109
_refine_ls_number_reflns     4600
_refine_ls_number_parameters     333
_refine_ls_number_restraints     30
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1686P)²+0.2365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.372
_refine_diff_density_min     -0.440
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     ?
_computing_cell_refinement     ?
_computing_data_reduction     ?
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1A 0.20036(14) 0.42400(11) 0.11580(12) 0.0794(5) Uani d PD 0.85 A 1
    O O2A 0.1773(4) 0.3848(4) 0.0299(4) 0.1042(12) Uani d PD 0.85 A 1
    O O3A 0.2814(4) 0.3131(3) 0.2164(3) 0.0877(10) Uani d PD 0.85 A 1
    N N4A 0.0420(4) 0.5094(4) 0.1407(4) 0.0852(11) Uani d PD 0.85 A 1
    H H4A 0.0081 0.5482 0.0731 0.128 Uiso d PRD 0.85 A 1
    S S1B 0.2538(10) 0.3996(10) 0.1608(8) 0.0751(19) Uiso d PD 0.15 A 2
    O O2B 0.142(2) 0.395(3) 0.101(2) 0.103(7) Uiso d PD 0.15 A 2
    O O3B 0.384(2) 0.281(2) 0.2015(19) 0.113(7) Uiso d PD 0.15 A 2
    N N4B 0.191(2) 0.443(2) 0.2605(14) 0.080(5) Uiso d PD 0.15 A 2
    H H4B 0.2683 0.3816 0.3048 0.121 Uiso d PRD 0.15 A 2
    C C5 0.0092(5) 0.5767(4) 0.2165(4) 0.0944(13) Uani d D 1 . .
    C C6 -0.1227(7) 0.6922(6) 0.1955(5) 0.1273(19) Uani d . 1 A .
    H H6 -0.1812 0.7294 0.1311 0.153 Uiso calc R 1 . .
    C C7 -0.1628(7) 0.7496(6) 0.2749(6) 0.139(2) Uani d . 1 . .
    H H7 -0.2512 0.8231 0.2651 0.167 Uiso calc R 1 A .
    C C8 -0.0728(8) 0.6978(7) 0.3660(5) 0.138(2) Uani d . 1 A .
    H H8 -0.0983 0.7355 0.4189 0.165 Uiso calc R 1 . .
    C C9 0.0527(7) 0.5918(6) 0.3782(5) 0.1205(17) Uani d . 1 . .
    H H9 0.1151 0.5594 0.4396 0.145 Uiso calc R 1 A .
    C C10 0.0940(5) 0.5295(6) 0.3078(5) 0.1074(15) Uani d D 1 A .
    H H10 0.1809 0.4527 0.3216 0.129 Uiso d R 1 . .
    C C11A 0.2825(6) 0.5444(5) 0.0630(4) 0.0744(19) Uani d PGD 0.85 A 1
    C C12A 0.3931(6) 0.5318(4) 0.1276(3) 0.085(2) Uani d PGD 0.85 A 1
    H H12A 0.4264 0.4565 0.1950 0.102 Uiso calc PR 0.85 A 1
    C C13A 0.4537(4) 0.6316(5) 0.0916(4) 0.0887(15) Uani d PGD 0.85 A 1
    H H13A 0.5277 0.6231 0.1349 0.106 Uiso calc PR 0.85 A 1
    C C14A 0.4038(5) 0.7440(4) -0.0090(5) 0.0920(16) Uani d PGD 0.85 A 1
    C C15A 0.2933(6) 0.7567(5) -0.0736(3) 0.104(2) Uani d PGD 0.85 A 1
    H H15A 0.2600 0.8320 -0.1409 0.125 Uiso calc PR 0.85 A 1
    C C16A 0.2327(5) 0.6569(6) -0.0376(4) 0.0897(19) Uani d PGD 0.85 A 1
    H H16A 0.1587 0.6654 -0.0808 0.108 Uiso calc PR 0.85 A 1
    C C17A 0.4636(8) 0.8606(8) -0.0505(8) 0.140(3) Uani d PDU 0.85 A 1
    H H17A 0.4937 0.8738 0.0101 0.210 Uiso calc PR 0.85 A 1
    H H17B 0.3911 0.9483 -0.0980 0.210 Uiso calc PR 0.85 A 1
    H H17C 0.5431 0.8324 -0.0894 0.210 Uiso calc PR 0.85 A 1
    C C11B 0.284(3) 0.548(3) 0.0854(18) 0.031(5) Uiso d PGD 0.15 A 2
    C C12B 0.408(3) 0.555(3) 0.1164(15) 0.060(8) Uiso d PGD 0.15 A 2
    H H12B 0.4585 0.4925 0.1841 0.072 Uiso calc PR 0.15 A 2
    C C13B 0.456(3) 0.655(3) 0.0463(18) 0.074(9) Uiso d PGD 0.15 A 2
    H H13B 0.5383 0.6594 0.0671 0.089 Uiso calc PR 0.15 A 2
    C C14B 0.380(3) 0.748(3) -0.0550(16) 0.087(11) Uiso d PGD 0.15 A 2
    C C15B 0.256(3) 0.742(3) -0.0860(17) 0.105(14) Uiso d PGD 0.15 A 2
    H H15B 0.2053 0.8042 -0.1537 0.126 Uiso calc PR 0.15 A 2
    C C16B 0.208(3) 0.642(3) -0.016(2) 0.085(12) Uiso d PGD 0.15 A 2
    H H16B 0.1254 0.6373 -0.0366 0.102 Uiso calc PR 0.15 A 2
    C C17B 0.429(3) 0.867(3) -0.129(2) 0.097(9) Uiso d PD 0.15 A 2
    H H17D 0.3863 0.9496 -0.1125 0.146 Uiso calc PR 0.15 A 2
    H H17E 0.4015 0.8906 -0.2041 0.146 Uiso calc PR 0.15 A 2
    H H17F 0.5309 0.8325 -0.1170 0.146 Uiso calc PR 0.15 A 2
    S S18 0.47506(9) 0.21890(9) 0.50060(8) 0.0703(4) Uani d . 1 . .
    O O19 0.4133(3) 0.3707(3) 0.4496(3) 0.0923(9) Uani d . 1 . .
    O O20 0.3851(3) 0.1422(3) 0.5255(3) 0.0873(8) Uani d . 1 . .
    N N21 0.5778(3) 0.1580(4) 0.4202(3) 0.0746(9) Uani d . 1 . .
    H H21 0.588(5) 0.075(4) 0.438(4) 0.089 Uiso d . 1 . .
    C C22 0.7029(4) 0.1844(4) 0.3923(3) 0.0693(9) Uani d . 1 . .
    C C23 0.8226(4) 0.0736(5) 0.3889(3) 0.0872(12) Uani d . 1 . .
    H H23 0.8206 -0.0154 0.4061 0.105 Uiso calc R 1 . .
    C C24 0.9449(5) 0.0940(6) 0.3602(4) 0.1098(16) Uani d . 1 . .
    H H24 1.0249 0.0184 0.3577 0.132 Uiso calc R 1 . .
    C C25 0.9518(6) 0.2230(7) 0.3353(5) 0.1157(17) Uani d . 1 . .
    H H25 1.0354 0.2355 0.3157 0.139 Uiso calc R 1 . .
    C C26 0.8355(7) 0.3323(7) 0.3394(4) 0.1127(16) Uani d . 1 . .
    H H26 0.8404 0.4195 0.3250 0.135 Uiso calc R 1 . .
    C C27 0.7089(5) 0.3164(5) 0.3649(4) 0.0944(12) Uani d . 1 . .
    H H27 0.6282 0.3939 0.3636 0.113 Uiso calc R 1 . .
    C C28 0.5841(3) 0.1697(3) 0.6181(3) 0.0567(7) Uani d . 1 . .
    C C29 0.6398(4) 0.0303(4) 0.6901(3) 0.0692(9) Uani d . 1 . .
    H H29 0.6152 -0.0369 0.6792 0.083 Uiso calc R 1 . .
    C C30 0.7324(4) -0.0089(4) 0.7785(3) 0.0785(10) Uani d . 1 . .
    H H30 0.7685 -0.1030 0.8281 0.094 Uiso calc R 1 . .
    C C31 0.7728(4) 0.0881(4) 0.7953(3) 0.0745(10) Uani d . 1 . .
    C C32 0.7152(5) 0.2273(4) 0.7233(3) 0.0873(12) Uani d . 1 . .
    H H32 0.7391 0.2943 0.7350 0.105 Uiso calc R 1 . .
    C C33 0.6219(4) 0.2700(4) 0.6332(3) 0.0784(11) Uani d . 1 . .
    H H33 0.5853 0.3642 0.5839 0.094 Uiso calc R 1 . .
    C C34 0.8804(5) 0.0425(7) 0.8902(4) 0.1181(18) Uani d . 1 . .
    H H34A 0.8837 0.1253 0.8960 0.177 Uiso calc R 1 . .
    H H34B 0.9725 -0.0150 0.8785 0.177 Uiso calc R 1 . .
    H H34C 0.8529 -0.0116 0.9561 0.177 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1A O2A . 1.431(4) ?
    S1A O3A . 1.444(3) ?
    S1A N4A . 1.628(4) ?
    S1A C11A . 1.754(4) ?
    N4A C5 . 1.429(6) ?
    N4A H4A . 0.8631 ?
    S1B O3B . 1.412(16) ?
    S1B O2B . 1.450(16) ?
    S1B N4B . 1.608(15) ?
    S1B C11B . 1.71(2) ?
    N4B C10 . 1.405(16) ?
    N4B H4B . 0.8753 ?
    N4B H10 . 0.8606 ?
    C5 C10 . 1.338(6) ?
    C5 C6 . 1.407(8) ?
    C6 C7 . 1.402(8) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.356(8) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.332(8) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.330(7) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11A C12A . 1.3900 ?
    C11A C16A . 1.3900 ?
    C12A C13A . 1.3900 ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.3900 ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.3900 ?
    C14A C17A . 1.542(7) ?
    C15A C16A . 1.3900 ?
    C15A H15A . 0.9300 ?
    C16A H16A . 0.9300 ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C11B C12B . 1.3900 ?
    C11B C16B . 1.3900 ?
    C12B C13B . 1.3900 ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.3900 ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.3900 ?
    C14B C17B . 1.562(17) ?
    C15B C16B . 1.3900 ?
    C15B H15B . 0.9300 ?
    C16B H16B . 0.9300 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    S18 O20 . 1.428(3) ?
    S18 O19 . 1.429(3) ?
    S18 N21 . 1.617(3) ?
    S18 C28 . 1.753(3) ?
    N21 C22 . 1.425(5) ?
    N21 H21 . 0.82(4) ?
    C22 C23 . 1.375(5) ?
    C22 C27 . 1.389(6) ?
    C23 C24 . 1.370(6) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.366(8) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.350(8) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.386(7) ?
    C26 H26 . 0.9300 ?
    C27 H27 . 0.9300 ?
    C28 C29 . 1.372(5) ?
    C28 C33 . 1.388(4) ?
    C29 C30 . 1.376(5) ?
    C29 H29 . 0.9300 ?
    C30 C31 . 1.380(5) ?
    C30 H30 . 0.9300 ?
    C31 C32 . 1.371(5) ?
    C31 C34 . 1.518(6) ?
    C32 C33 . 1.387(5) ?
    C32 H32 . 0.9300 ?
    C33 H33 . 0.9300 ?
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2A S1A O3A . . 118.6(2) ?
    O2A S1A N4A . . 105.0(2) ?
    O3A S1A N4A . . 108.8(2) ?
    O2A S1A C11A . . 106.8(3) ?
    O3A S1A C11A . . 109.0(2) ?
    N4A S1A C11A . . 108.2(2) ?
    C5 N4A S1A . . 126.2(3) ?
    C5 N4A H4A . . 126.2 ?
    S1A N4A H4A . . 92.9 ?
    O3B S1B O2B . . 120.5(15) ?
    O3B S1B N4B . . 107.7(13) ?
    O2B S1B N4B . . 109.2(14) ?
    O3B S1B C11B . . 110.0(15) ?
    O2B S1B C11B . . 108.6(14) ?
    N4B S1B C11B . . 98.6(13) ?
    C10 N4B S1B . . 154.4(16) ?
    C10 N4B H4B . . 112.1 ?
    S1B N4B H4B . . 92.8 ?
    C10 N4B H10 . . 40.1 ?
    S1B N4B H10 . . 164.6 ?
    H4B N4B H10 . . 72.1 ?
    C10 C5 C6 . . 119.8(5) ?
    C10 C5 N4A . . 122.9(4) ?
    C6 C5 N4A . . 117.2(5) ?
    C7 C6 C5 . . 117.8(6) ?
    C7 C6 H6 . . 121.1 ?
    C5 C6 H6 . . 121.1 ?
    C8 C7 C6 . . 120.0(5) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C9 C8 C7 . . 118.7(6) ?
    C9 C8 H8 . . 120.7 ?
    C7 C8 H8 . . 120.7 ?
    C10 C9 C8 . . 123.9(6) ?
    C10 C9 H9 . . 118.1 ?
    C8 C9 H9 . . 118.1 ?
    C9 C10 C5 . . 119.8(5) ?
    C9 C10 N4B . . 155.9(10) ?
    C5 C10 N4B . . 83.6(9) ?
    C9 C10 H10 . . 120.7 ?
    C5 C10 H10 . . 119.5 ?
    N4B C10 H10 . . 36.6 ?
    C12A C11A C16A . . 120.0 ?
    C12A C11A S1A . . 118.5(3) ?
    C16A C11A S1A . . 121.4(3) ?
    C13A C12A C11A . . 120.0 ?
    C13A C12A H12A . . 120.0 ?
    C11A C12A H12A . . 120.0 ?
    C14A C13A C12A . . 120.0 ?
    C14A C13A H13A . . 120.0 ?
    C12A C13A H13A . . 120.0 ?
    C13A C14A C15A . . 120.0 ?
    C13A C14A C17A . . 121.9(5) ?
    C15A C14A C17A . . 118.0(5) ?
    C16A C15A C14A . . 120.0 ?
    C16A C15A H15A . . 120.0 ?
    C14A C15A H15A . . 120.0 ?
    C15A C16A C11A . . 120.0 ?
    C15A C16A H16A . . 120.0 ?
    C11A C16A H16A . . 120.0 ?
    C14A C17A H17A . . 109.5 ?
    C14A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C14A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C12B C11B C16B . . 120.0 ?
    C12B C11B S1B . . 117.0(15) ?
    C16B C11B S1B . . 121.4(15) ?
    C11B C12B C13B . . 120.0 ?
    C11B C12B H12B . . 120.0 ?
    C13B C12B H12B . . 120.0 ?
    C14B C13B C12B . . 120.0 ?
    C14B C13B H13B . . 120.0 ?
    C12B C13B H13B . . 120.0 ?
    C15B C14B C13B . . 120.0 ?
    C15B C14B C17B . . 120.7(17) ?
    C13B C14B C17B . . 119.2(17) ?
    C14B C15B C16B . . 120.0 ?
    C14B C15B H15B . . 120.0 ?
    C16B C15B H15B . . 120.0 ?
    C15B C16B C11B . . 120.0 ?
    C15B C16B H16B . . 120.0 ?
    C11B C16B H16B . . 120.0 ?
    C14B C17B H17D . . 109.5 ?
    C14B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C14B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    O20 S18 O19 . . 119.48(17) ?
    O20 S18 N21 . . 103.58(17) ?
    O19 S18 N21 . . 108.41(19) ?
    O20 S18 C28 . . 109.63(17) ?
    O19 S18 C28 . . 108.35(16) ?
    N21 S18 C28 . . 106.64(15) ?
    C22 N21 S18 . . 122.5(2) ?
    C22 N21 H21 . . 115(3) ?
    S18 N21 H21 . . 107(3) ?
    C23 C22 C27 . . 118.5(4) ?
    C23 C22 N21 . . 117.8(4) ?
    C27 C22 N21 . . 123.7(4) ?
    C24 C23 C22 . . 120.2(5) ?
    C24 C23 H23 . . 119.9 ?
    C22 C23 H23 . . 119.9 ?
    C25 C24 C23 . . 121.4(5) ?
    C25 C24 H24 . . 119.3 ?
    C23 C24 H24 . . 119.3 ?
    C26 C25 C24 . . 119.1(5) ?
    C26 C25 H25 . . 120.5 ?
    C24 C25 H25 . . 120.5 ?
    C25 C26 C27 . . 121.0(5) ?
    C25 C26 H26 . . 119.5 ?
    C27 C26 H26 . . 119.5 ?
    C26 C27 C22 . . 119.8(5) ?
    C26 C27 H27 . . 120.1 ?
    C22 C27 H27 . . 120.1 ?
    C29 C28 C33 . . 120.6(3) ?
    C29 C28 S18 . . 119.7(2) ?
    C33 C28 S18 . . 119.6(3) ?
    C28 C29 C30 . . 119.3(3) ?
    C28 C29 H29 . . 120.4 ?
    C30 C29 H29 . . 120.4 ?
    C29 C30 C31 . . 121.5(4) ?
    C29 C30 H30 . . 119.2 ?
    C31 C30 H30 . . 119.2 ?
    C32 C31 C30 . . 118.5(3) ?
    C32 C31 C34 . . 120.3(4) ?
    C30 C31 C34 . . 121.2(4) ?
    C31 C32 C33 . . 121.3(3) ?
    C31 C32 H32 . . 119.4 ?
    C33 C32 H32 . . 119.4 ?
    C32 C33 C28 . . 118.8(3) ?
    C32 C33 H33 . . 120.6 ?
    C28 C33 H33 . . 120.6 ?
    C31 C34 H34A . . 109.5 ?
    C31 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C31 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2A S1A N4A C5 . . . . -176.5(4) ?
    O3A S1A N4A C5 . . . . 55.6(4) ?
    C11A S1A N4A C5 . . . . -62.7(4) ?
    O3B S1B N4B C10 . . . . 174(4) ?
    O2B S1B N4B C10 . . . . -53(4) ?
    C11B S1B N4B C10 . . . . 60(4) ?
    S1A N4A C5 C10 . . . . -30.7(7) ?
    S1A N4A C5 C6 . . . . 153.1(4) ?
    C10 C5 C6 C7 . . . . -3.0(8) ?
    N4A C5 C6 C7 . . . . 173.3(5) ?
    C5 C6 C7 C8 . . . . 3.0(10) ?
    C6 C7 C8 C9 . . . . -0.4(11) ?
    C7 C8 C9 C10 . . . . -2.4(11) ?
    C8 C9 C10 C5 . . . . 2.4(10) ?
    C8 C9 C10 N4B . . . . 166(2) ?
    C6 C5 C10 C9 . . . . 0.4(8) ?
    N4A C5 C10 C9 . . . . -175.7(5) ?
    C6 C5 C10 N4B . . . . -173.1(10) ?
    N4A C5 C10 N4B . . . . 10.8(10) ?
    S1B N4B C10 C9 . . . . -146(2) ?
    S1B N4B C10 C5 . . . . 20(4) ?
    O2A S1A C11A C12A . . . . -138.6(3) ?
    O3A S1A C11A C12A . . . . -9.3(4) ?
    N4A S1A C11A C12A . . . . 108.8(3) ?
    O2A S1A C11A C16A . . . . 46.2(4) ?
    O3A S1A C11A C16A . . . . 175.4(3) ?
    N4A S1A C11A C16A . . . . -66.4(3) ?
    C16A C11A C12A C13A . . . . 0.0 ?
    S1A C11A C12A C13A . . . . -175.3(4) ?
    C11A C12A C13A C14A . . . . 0.0 ?
    C12A C13A C14A C15A . . . . 0.0 ?
    C12A C13A C14A C17A . . . . 177.5(5) ?
    C13A C14A C15A C16A . . . . 0.0 ?
    C17A C14A C15A C16A . . . . -177.6(5) ?
    C14A C15A C16A C11A . . . . 0.0 ?
    C12A C11A C16A C15A . . . . 0.0 ?
    S1A C11A C16A C15A . . . . 175.2(4) ?
    O3B S1B C11B C12B . . . . -32(2) ?
    O2B S1B C11B C12B . . . . -165.7(17) ?
    N4B S1B C11B C12B . . . . 80.6(17) ?
    O3B S1B C11B C16B . . . . 133.5(18) ?
    O2B S1B C11B C16B . . . . 0(2) ?
    N4B S1B C11B C16B . . . . -114.0(17) ?
    C16B C11B C12B C13B . . . . 0.0 ?
    S1B C11B C12B C13B . . . . 165.5(19) ?
    C11B C12B C13B C14B . . . . 0.0 ?
    C12B C13B C14B C15B . . . . 0.0 ?
    C12B C13B C14B C17B . . . . 176(3) ?
    C13B C14B C15B C16B . . . . 0.0 ?
    C17B C14B C15B C16B . . . . -176(3) ?
    C14B C15B C16B C11B . . . . 0.0 ?
    C12B C11B C16B C15B . . . . 0.0 ?
    S1B C11B C16B C15B . . . . -165(2) ?
    O20 S18 N21 C22 . . . . -167.2(3) ?
    O19 S18 N21 C22 . . . . 65.0(3) ?
    C28 S18 N21 C22 . . . . -51.5(3) ?
    S18 N21 C22 C23 . . . . 138.4(3) ?
    S18 N21 C22 C27 . . . . -43.9(5) ?
    C27 C22 C23 C24 . . . . 0.8(6) ?
    N21 C22 C23 C24 . . . . 178.6(4) ?
    C22 C23 C24 C25 . . . . 0.5(7) ?
    C23 C24 C25 C26 . . . . 0.2(9) ?
    C24 C25 C26 C27 . . . . -2.2(9) ?
    C25 C26 C27 C22 . . . . 3.5(8) ?
    C23 C22 C27 C26 . . . . -2.7(6) ?
    N21 C22 C27 C26 . . . . 179.6(4) ?
    O20 S18 C28 C29 . . . . 38.7(3) ?
    O19 S18 C28 C29 . . . . 170.7(3) ?
    N21 S18 C28 C29 . . . . -72.8(3) ?
    O20 S18 C28 C33 . . . . -146.1(3) ?
    O19 S18 C28 C33 . . . . -14.1(4) ?
    N21 S18 C28 C33 . . . . 102.4(3) ?
    C33 C28 C29 C30 . . . . 0.8(6) ?
    S18 C28 C29 C30 . . . . 175.9(3) ?
    C28 C29 C30 C31 . . . . -1.3(6) ?
    C29 C30 C31 C32 . . . . 2.0(6) ?
    C29 C30 C31 C34 . . . . -177.1(4) ?
    C30 C31 C32 C33 . . . . -2.1(6) ?
    C34 C31 C32 C33 . . . . 176.9(4) ?
    C31 C32 C33 C28 . . . . 1.7(6) ?
    C29 C28 C33 C32 . . . . -1.0(6) ?
    S18 C28 C33 C32 . . . . -176.1(3) ?
data_Compound_18_CCDC
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N O2 S'
_chemical_formula_sum     'C13 H13 N O2 S'
_chemical_formula_weight     247.30
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2890(11)
_cell_length_b     11.0563(12)
_cell_length_c     13.4402(15)
_cell_angle_alpha     67.823(3)
_cell_angle_beta     87.573(4)
_cell_angle_gamma     67.616(3)
_cell_volume     1299.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5366
_cell_measurement_theta_min     2.53
_cell_measurement_theta_max     24.65
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.264
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.238
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8903
_exptl_absorpt_correction_T_max     0.8903
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12851
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_av_sigmaI/netI     0.0325
_diffrn_reflns_theta_min     2.86
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4544
_reflns_number_gt     3364
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0722
_refine_ls_R_factor_gt     0.0550
_refine_ls_wR_factor_gt     0.1528
_refine_ls_wR_factor_ref     0.1737
_refine_ls_goodness_of_fit_ref     1.012
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     4544
_refine_ls_number_parameters     333
_refine_ls_number_restraints     30
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1035P)²+0.2796P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.252
_refine_diff_density_min     -0.404
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1A 0.20015(11) 0.42407(8) 0.11615(9) 0.0804(3) Uani d PD 0.85 A 1
    O O2A 0.1771(3) 0.3842(3) 0.0303(3) 0.1086(9) Uani d PD 0.85 A 1
    O O3A 0.2814(3) 0.3134(3) 0.2163(2) 0.0912(8) Uani d PD 0.85 A 1
    N N4A 0.0413(3) 0.5097(3) 0.1408(3) 0.0875(8) Uani d PD 0.85 A 1
    H H4A 0.0075 0.5485 0.0732 0.131 Uiso d PRD 0.85 A 1
    S S1B 0.2538(7) 0.3989(8) 0.1617(6) 0.0738(13) Uiso d PD 0.15 A 2
    O O2B 0.1418(18) 0.403(2) 0.0960(15) 0.108(5) Uiso d PD 0.15 A 2
    O O3B 0.3793(16) 0.2769(15) 0.2076(12) 0.101(5) Uiso d PD 0.15 A 2
    N N4B 0.1907(16) 0.4415(16) 0.2611(11) 0.084(4) Uiso d PD 0.15 A 2
    H H4B 0.2677 0.3802 0.3054 0.126 Uiso d PRD 0.15 A 2
    C C5 0.0088(4) 0.5769(3) 0.2161(3) 0.0946(10) Uani d D 1 . .
    C C6 -0.1234(5) 0.6920(5) 0.1949(4) 0.1306(13) Uani d . 1 A .
    H H6 -0.1820 0.7284 0.1308 0.157 Uiso calc R 1 . .
    C C7 -0.1638(5) 0.7499(5) 0.2741(4) 0.1409(16) Uani d . 1 . .
    H H7 -0.2519 0.8231 0.2641 0.169 Uiso calc R 1 A .
    C C8 -0.0732(6) 0.6984(5) 0.3653(4) 0.1407(16) Uani d . 1 A .
    H H8 -0.0981 0.7369 0.4174 0.169 Uiso calc R 1 . .
    C C9 0.0519(5) 0.5918(5) 0.3785(4) 0.1245(13) Uani d . 1 . .
    H H9 0.1132 0.5580 0.4406 0.149 Uiso calc R 1 A .
    C C10 0.0941(4) 0.5305(4) 0.3062(4) 0.1085(11) Uani d D 1 A .
    H H10 0.1809 0.4537 0.3200 0.130 Uiso d R 1 . .
    C C11A 0.2814(4) 0.5458(4) 0.0635(3) 0.0717(15) Uani d PGD 0.85 A 1
    C C12A 0.3936(4) 0.5321(3) 0.1267(2) 0.0774(12) Uani d PGD 0.85 A 1
    H H12A 0.4279 0.4566 0.1936 0.093 Uiso calc PR 0.85 A 1
    C C13A 0.4547(3) 0.6314(4) 0.0901(3) 0.0926(11) Uani d PGD 0.85 A 1
    H H13A 0.5298 0.6222 0.1324 0.111 Uiso calc PR 0.85 A 1
    C C14A 0.4036(3) 0.7443(3) -0.0098(4) 0.0930(11) Uani d PGD 0.85 A 1
    C C15A 0.2913(4) 0.7579(3) -0.0731(2) 0.1015(13) Uani d PGD 0.85 A 1
    H H15A 0.2571 0.8335 -0.1399 0.122 Uiso calc PR 0.85 A 1
    C C16A 0.2303(4) 0.6587(4) -0.0364(3) 0.0955(15) Uani d PGD 0.85 A 1
    H H16A 0.1552 0.6678 -0.0788 0.115 Uiso calc PR 0.85 A 1
    C C17A 0.4640(6) 0.8593(5) -0.0516(5) 0.143(2) Uani d PDU 0.85 A 1
    H H17A 0.4943 0.8731 0.0084 0.215 Uiso calc PR 0.85 A 1
    H H17B 0.3923 0.9468 -0.0996 0.215 Uiso calc PR 0.85 A 1
    H H17C 0.5432 0.8300 -0.0898 0.215 Uiso calc PR 0.85 A 1
    C C11B 0.293(3) 0.543(2) 0.0859(16) 0.044(5) Uiso d PGD 0.15 A 2
    C C12B 0.408(3) 0.562(2) 0.1180(12) 0.094(10) Uiso d PGD 0.15 A 2
    H H12B 0.4566 0.5048 0.1869 0.113 Uiso calc PR 0.15 A 2
    C C13B 0.450(2) 0.665(3) 0.0470(14) 0.084(8) Uiso d PGD 0.15 A 2
    H H13B 0.5270 0.6781 0.0685 0.101 Uiso calc PR 0.15 A 2
    C C14B 0.377(2) 0.750(2) -0.0560(12) 0.079(7) Uiso d PGD 0.15 A 2
    C C15B 0.262(2) 0.732(2) -0.0880(12) 0.079(7) Uiso d PGD 0.15 A 2
    H H15B 0.2129 0.7884 -0.1569 0.095 Uiso calc PR 0.15 A 2
    C C16B 0.220(2) 0.628(3) -0.0171(18) 0.063(6) Uiso d PGD 0.15 A 2
    H H16B 0.1425 0.6152 -0.0385 0.076 Uiso calc PR 0.15 A 2
    C C17B 0.424(3) 0.867(2) -0.1305(18) 0.108(8) Uiso d PD 0.15 A 2
    H H17D 0.3813 0.9504 -0.1142 0.162 Uiso calc PR 0.15 A 2
    H H17E 0.3946 0.8905 -0.2046 0.162 Uiso calc PR 0.15 A 2
    H H17F 0.5251 0.8339 -0.1192 0.162 Uiso calc PR 0.15 A 2
    S S18 0.47516(6) 0.21883(7) 0.50060(6) 0.0710(2) Uani d . 1 . .
    O O19 0.4129(2) 0.3703(2) 0.45041(18) 0.0956(6) Uani d . 1 . .
    O O20 0.38487(18) 0.1421(2) 0.52602(18) 0.0875(6) Uani d . 1 . .
    N N21 0.5786(2) 0.1583(3) 0.41986(19) 0.0748(6) Uani d . 1 . .
    H H21 0.583(3) 0.078(3) 0.435(2) 0.090 Uiso d . 1 . .
    C C22 0.7038(3) 0.1843(3) 0.39199(18) 0.0702(7) Uani d . 1 . .
    C C23 0.8225(3) 0.0741(3) 0.3889(2) 0.0882(8) Uani d . 1 . .
    H H23 0.8203 -0.0149 0.4068 0.106 Uiso calc R 1 . .
    C C24 0.9449(4) 0.0939(5) 0.3598(3) 0.1137(12) Uani d . 1 . .
    H H24 1.0243 0.0189 0.3566 0.136 Uiso calc R 1 . .
    C C25 0.9503(4) 0.2241(5) 0.3353(3) 0.1194(13) Uani d . 1 . .
    H H25 1.0332 0.2376 0.3160 0.143 Uiso calc R 1 . .
    C C26 0.8345(5) 0.3319(5) 0.3397(3) 0.1155(12) Uani d . 1 . .
    H H26 0.8389 0.4194 0.3247 0.139 Uiso calc R 1 . .
    C C27 0.7077(4) 0.3158(4) 0.3662(3) 0.0957(9) Uani d . 1 . .
    H H27 0.6276 0.3922 0.3664 0.115 Uiso calc R 1 . .
    C C28 0.5846(2) 0.1698(2) 0.61768(19) 0.0588(5) Uani d . 1 . .
    C C29 0.6400(3) 0.0302(3) 0.6903(2) 0.0710(6) Uani d . 1 . .
    H H29 0.6151 -0.0370 0.6797 0.085 Uiso calc R 1 . .
    C C30 0.7321(3) -0.0090(3) 0.7783(2) 0.0788(7) Uani d . 1 . .
    H H30 0.7685 -0.1032 0.8273 0.095 Uiso calc R 1 . .
    C C31 0.7725(3) 0.0881(3) 0.7960(2) 0.0777(7) Uani d . 1 . .
    C C32 0.7150(3) 0.2275(3) 0.7228(3) 0.0888(9) Uani d . 1 . .
    H H32 0.7396 0.2946 0.7337 0.107 Uiso calc R 1 . .
    C C33 0.6219(3) 0.2695(3) 0.6339(2) 0.0781(7) Uani d . 1 . .
    H H33 0.5846 0.3638 0.5852 0.094 Uiso calc R 1 . .
    C C34 0.8796(4) 0.0418(5) 0.8906(3) 0.1205(13) Uani d . 1 . .
    H H34A 0.8801 0.1241 0.8990 0.181 Uiso calc R 1 . .
    H H34B 0.9720 -0.0118 0.8775 0.181 Uiso calc R 1 . .
    H H34C 0.8546 -0.0162 0.9554 0.181 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1A O2A . 1.438(3) ?
    S1A O3A . 1.443(3) ?
    S1A N4A . 1.640(3) ?
    S1A C11A . 1.761(2) ?
    N4A C5 . 1.428(4) ?
    N4A H4A . 0.8657 ?
    S1B O3B . 1.407(13) ?
    S1B O2B . 1.460(15) ?
    S1B N4B . 1.611(12) ?
    S1B C11B . 1.719(14) ?
    N4B C10 . 1.406(13) ?
    N4B H4B . 0.8773 ?
    N4B H10 . 0.8481 ?
    C5 C10 . 1.333(4) ?
    C5 C6 . 1.411(5) ?
    C6 C7 . 1.411(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.364(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.335(6) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.352(5) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9333 ?
    C11A C12A . 1.3900 ?
    C11A C16A . 1.3900 ?
    C12A C13A . 1.3900 ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.3900 ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.3900 ?
    C14A C17A . 1.534(5) ?
    C15A C16A . 1.3900 ?
    C15A H15A . 0.9300 ?
    C16A H16A . 0.9300 ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C11B C12B . 1.3900 ?
    C11B C16B . 1.3900 ?
    C12B C13B . 1.3900 ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.3900 ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.3900 ?
    C14B C17B . 1.537(15) ?
    C15B C16B . 1.3900 ?
    C15B H15B . 0.9300 ?
    C16B H16B . 0.9300 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    S18 O19 . 1.427(2) ?
    S18 O20 . 1.4332(19) ?
    S18 N21 . 1.633(2) ?
    S18 C28 . 1.754(2) ?
    N21 C22 . 1.429(3) ?
    N21 H21 . 0.81(3) ?
    C22 C23 . 1.370(4) ?
    C22 C27 . 1.378(4) ?
    C23 C24 . 1.376(4) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.372(5) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.345(6) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.396(5) ?
    C26 H26 . 0.9300 ?
    C27 H27 . 0.9300 ?
    C28 C29 . 1.379(3) ?
    C28 C33 . 1.386(3) ?
    C29 C30 . 1.370(4) ?
    C29 H29 . 0.9300 ?
    C30 C31 . 1.388(4) ?
    C30 H30 . 0.9300 ?
    C31 C32 . 1.379(4) ?
    C31 C34 . 1.514(4) ?
    C32 C33 . 1.379(4) ?
    C32 H32 . 0.9300 ?
    C33 H33 . 0.9300 ?
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2A S1A O3A . . 118.41(15) ?
    O2A S1A N4A . . 105.11(17) ?
    O3A S1A N4A . . 108.96(17) ?
    O2A S1A C11A . . 107.0(2) ?
    O3A S1A C11A . . 109.04(17) ?
    N4A S1A C11A . . 107.90(18) ?
    C5 N4A S1A . . 126.2(2) ?
    C5 N4A H4A . . 126.2 ?
    S1A N4A H4A . . 92.8 ?
    O3B S1B O2B . . 122.3(11) ?
    O3B S1B N4B . . 105.4(9) ?
    O2B S1B N4B . . 110.0(10) ?
    O3B S1B C11B . . 110.2(12) ?
    O2B S1B C11B . . 106.1(12) ?
    N4B S1B C11B . . 100.8(10) ?
    C10 N4B S1B . . 153.6(12) ?
    C10 N4B H4B . . 112.8 ?
    S1B N4B H4B . . 92.6 ?
    C10 N4B H10 . . 40.1 ?
    S1B N4B H10 . . 164.4 ?
    H4B N4B H10 . . 72.8 ?
    C10 C5 C6 . . 120.2(4) ?
    C10 C5 N4A . . 122.7(3) ?
    C6 C5 N4A . . 117.0(4) ?
    C7 C6 C5 . . 117.8(4) ?
    C7 C6 H6 . . 121.1 ?
    C5 C6 H6 . . 121.1 ?
    C8 C7 C6 . . 119.9(4) ?
    C8 C7 H7 . . 120.1 ?
    C6 C7 H7 . . 120.1 ?
    C9 C8 C7 . . 118.9(4) ?
    C9 C8 H8 . . 120.5 ?
    C7 C8 H8 . . 120.5 ?
    C8 C9 C10 . . 123.5(5) ?
    C8 C9 H9 . . 118.3 ?
    C10 C9 H9 . . 118.3 ?
    C5 C10 C9 . . 119.7(4) ?
    C5 C10 N4B . . 84.4(7) ?
    C9 C10 N4B . . 155.6(7) ?
    C5 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 120.6 ?
    N4B C10 H10 . . 35.8 ?
    C12A C11A C16A . . 120.0 ?
    C12A C11A S1A . . 118.6(2) ?
    C16A C11A S1A . . 121.3(2) ?
    C13A C12A C11A . . 120.0 ?
    C13A C12A H12A . . 120.0 ?
    C11A C12A H12A . . 120.0 ?
    C12A C13A C14A . . 120.0 ?
    C12A C13A H13A . . 120.0 ?
    C14A C13A H13A . . 120.0 ?
    C13A C14A C15A . . 120.0 ?
    C13A C14A C17A . . 121.8(4) ?
    C15A C14A C17A . . 118.2(4) ?
    C16A C15A C14A . . 120.0 ?
    C16A C15A H15A . . 120.0 ?
    C14A C15A H15A . . 120.0 ?
    C15A C16A C11A . . 120.0 ?
    C15A C16A H16A . . 120.0 ?
    C11A C16A H16A . . 120.0 ?
    C14A C17A H17A . . 109.5 ?
    C14A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C14A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C12B C11B C16B . . 120.0 ?
    C12B C11B S1B . . 121.6(15) ?
    C16B C11B S1B . . 117.6(15) ?
    C11B C12B C13B . . 120.0 ?
    C11B C12B H12B . . 120.0 ?
    C13B C12B H12B . . 120.0 ?
    C12B C13B C14B . . 120.0 ?
    C12B C13B H13B . . 120.0 ?
    C14B C13B H13B . . 120.0 ?
    C13B C14B C15B . . 120.0 ?
    C13B C14B C17B . . 118.3(15) ?
    C15B C14B C17B . . 121.7(15) ?
    C16B C15B C14B . . 120.0 ?
    C16B C15B H15B . . 120.0 ?
    C14B C15B H15B . . 120.0 ?
    C15B C16B C11B . . 120.0 ?
    C15B C16B H16B . . 120.0 ?
    C11B C16B H16B . . 120.0 ?
    C14B C17B H17D . . 109.5 ?
    C14B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C14B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    O19 S18 O20 . . 119.00(12) ?
    O19 S18 N21 . . 108.65(13) ?
    O20 S18 N21 . . 104.34(12) ?
    O19 S18 C28 . . 108.23(12) ?
    O20 S18 C28 . . 109.50(12) ?
    N21 S18 C28 . . 106.42(11) ?
    C22 N21 S18 . . 123.11(18) ?
    C22 N21 H21 . . 118(2) ?
    S18 N21 H21 . . 106(2) ?
    C23 C22 C27 . . 119.5(3) ?
    C23 C22 N21 . . 118.1(3) ?
    C27 C22 N21 . . 122.4(3) ?
    C22 C23 C24 . . 120.6(3) ?
    C22 C23 H23 . . 119.7 ?
    C24 C23 H23 . . 119.7 ?
    C25 C24 C23 . . 120.2(4) ?
    C25 C24 H24 . . 119.9 ?
    C23 C24 H24 . . 119.9 ?
    C26 C25 C24 . . 119.3(3) ?
    C26 C25 H25 . . 120.4 ?
    C24 C25 H25 . . 120.4 ?
    C25 C26 C27 . . 121.7(4) ?
    C25 C26 H26 . . 119.1 ?
    C27 C26 H26 . . 119.1 ?
    C22 C27 C26 . . 118.6(4) ?
    C22 C27 H27 . . 120.7 ?
    C26 C27 H27 . . 120.7 ?
    C29 C28 C33 . . 120.0(2) ?
    C29 C28 S18 . . 119.86(17) ?
    C33 C28 S18 . . 120.02(19) ?
    C30 C29 C28 . . 119.6(2) ?
    C30 C29 H29 . . 120.2 ?
    C28 C29 H29 . . 120.2 ?
    C29 C30 C31 . . 121.7(3) ?
    C29 C30 H30 . . 119.1 ?
    C31 C30 H30 . . 119.1 ?
    C32 C31 C30 . . 117.8(3) ?
    C32 C31 C34 . . 121.1(3) ?
    C30 C31 C34 . . 121.1(3) ?
    C33 C32 C31 . . 121.5(2) ?
    C33 C32 H32 . . 119.3 ?
    C31 C32 H32 . . 119.3 ?
    C32 C33 C28 . . 119.4(3) ?
    C32 C33 H33 . . 120.3 ?
    C28 C33 H33 . . 120.3 ?
    C31 C34 H34A . . 109.5 ?
    C31 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C31 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2A S1A N4A C5 . . . . -176.5(3) ?
    O3A S1A N4A C5 . . . . 55.6(3) ?
    C11A S1A N4A C5 . . . . -62.7(3) ?
    O3B S1B N4B C10 . . . . 174(2) ?
    O2B S1B N4B C10 . . . . -53(3) ?
    C11B S1B N4B C10 . . . . 59(3) ?
    S1A N4A C5 C10 . . . . -30.2(4) ?
    S1A N4A C5 C6 . . . . 153.4(3) ?
    C10 C5 C6 C7 . . . . -3.1(6) ?
    N4A C5 C6 C7 . . . . 173.4(4) ?
    C5 C6 C7 C8 . . . . 2.8(7) ?
    C6 C7 C8 C9 . . . . -1.0(8) ?
    C7 C8 C9 C10 . . . . -0.6(8) ?
    C6 C5 C10 C9 . . . . 1.6(5) ?
    N4A C5 C10 C9 . . . . -174.7(3) ?
    C6 C5 C10 N4B . . . . -174.3(7) ?
    N4A C5 C10 N4B . . . . 9.4(7) ?
    C8 C9 C10 C5 . . . . 0.3(7) ?
    C8 C9 C10 N4B . . . . 170.4(17) ?
    S1B N4B C10 C5 . . . . 23(3) ?
    S1B N4B C10 C9 . . . . -147.9(17) ?
    O2A S1A C11A C12A . . . . -137.1(2) ?
    O3A S1A C11A C12A . . . . -7.9(3) ?
    N4A S1A C11A C12A . . . . 110.3(2) ?
    O2A S1A C11A C16A . . . . 46.7(3) ?
    O3A S1A C11A C16A . . . . 175.8(2) ?
    N4A S1A C11A C16A . . . . -66.0(3) ?
    C16A C11A C12A C13A . . . . 0.0 ?
    S1A C11A C12A C13A . . . . -176.3(3) ?
    C11A C12A C13A C14A . . . . 0.0 ?
    C12A C13A C14A C15A . . . . 0.0 ?
    C12A C13A C14A C17A . . . . 177.7(4) ?
    C13A C14A C15A C16A . . . . 0.0 ?
    C17A C14A C15A C16A . . . . -177.8(4) ?
    C14A C15A C16A C11A . . . . 0.0 ?
    C12A C11A C16A C15A . . . . 0.0 ?
    S1A C11A C16A C15A . . . . 176.2(3) ?
    O3B S1B C11B C12B . . . . -37.1(15) ?
    O2B S1B C11B C12B . . . . -171.4(14) ?
    N4B S1B C11B C12B . . . . 73.8(14) ?
    O3B S1B C11B C16B . . . . 132.6(14) ?
    O2B S1B C11B C16B . . . . -1.7(17) ?
    N4B S1B C11B C16B . . . . -116.4(13) ?
    C16B C11B C12B C13B . . . . 0.0 ?
    S1B C11B C12B C13B . . . . 169.5(18) ?
    C11B C12B C13B C14B . . . . 0.0 ?
    C12B C13B C14B C15B . . . . 0.0 ?
    C12B C13B C14B C17B . . . . 178(2) ?
    C13B C14B C15B C16B . . . . 0.0 ?
    C17B C14B C15B C16B . . . . -178(2) ?
    C14B C15B C16B C11B . . . . 0.0 ?
    C12B C11B C16B C15B . . . . 0.0 ?
    S1B C11B C16B C15B . . . . -169.9(18) ?
    O19 S18 N21 C22 . . . . 65.2(2) ?
    O20 S18 N21 C22 . . . . -166.9(2) ?
    C28 S18 N21 C22 . . . . -51.1(2) ?
    S18 N21 C22 C23 . . . . 138.1(2) ?
    S18 N21 C22 C27 . . . . -43.3(3) ?
    C27 C22 C23 C24 . . . . -0.4(4) ?
    N21 C22 C23 C24 . . . . 178.2(3) ?
    C22 C23 C24 C25 . . . . 1.3(5) ?
    C23 C24 C25 C26 . . . . -0.4(6) ?
    C24 C25 C26 C27 . . . . -1.4(6) ?
    C23 C22 C27 C26 . . . . -1.3(4) ?
    N21 C22 C27 C26 . . . . -179.9(3) ?
    C25 C26 C27 C22 . . . . 2.2(6) ?
    O19 S18 C28 C29 . . . . 169.83(19) ?
    O20 S18 C28 C29 . . . . 38.7(2) ?
    N21 S18 C28 C29 . . . . -73.6(2) ?
    O19 S18 C28 C33 . . . . -14.0(2) ?
    O20 S18 C28 C33 . . . . -145.2(2) ?
    N21 S18 C28 C33 . . . . 102.6(2) ?
    C33 C28 C29 C30 . . . . 0.0(4) ?
    S18 C28 C29 C30 . . . . 176.11(19) ?
    C28 C29 C30 C31 . . . . -0.6(4) ?
    C29 C30 C31 C32 . . . . 1.0(4) ?
    C29 C30 C31 C34 . . . . -177.1(3) ?
    C30 C31 C32 C33 . . . . -0.9(4) ?
    C34 C31 C32 C33 . . . . 177.2(3) ?
    C31 C32 C33 C28 . . . . 0.3(4) ?
    C29 C28 C33 C32 . . . . 0.2(4) ?
    S18 C28 C33 C32 . . . . -176.0(2) ?
data_Compound_18_Manual
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N O2 S'
_chemical_formula_sum     'C13 H13 N O2 S'
_chemical_formula_weight     247.30
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2890(11)
_cell_length_b     11.0563(12)
_cell_length_c     13.4402(15)
_cell_angle_alpha     67.823(3)
_cell_angle_beta     87.573(4)
_cell_angle_gamma     67.616(3)
_cell_volume     1299.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5366
_cell_measurement_theta_min     2.53
_cell_measurement_theta_max     24.65
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.264
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.238
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8903
_exptl_absorpt_correction_T_max     0.8903
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12851
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_av_sigmaI/netI     0.0325
_diffrn_reflns_theta_min     2.86
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4544
_reflns_number_gt     3364
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0722
_refine_ls_R_factor_gt     0.0550
_refine_ls_wR_factor_gt     0.1528
_refine_ls_wR_factor_ref     0.1737
_refine_ls_goodness_of_fit_ref     1.012
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     4544
_refine_ls_number_parameters     333
_refine_ls_number_restraints     30
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1035P)²+0.2796P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.252
_refine_diff_density_min     -0.404
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1A 0.20015(11) 0.42407(8) 0.11615(9) 0.0804(3) Uani d PD 0.85 A 1
    O O2A 0.1771(3) 0.3842(3) 0.0303(3) 0.1086(9) Uani d PD 0.85 A 1
    O O3A 0.2814(3) 0.3134(3) 0.2163(2) 0.0912(8) Uani d PD 0.85 A 1
    N N4A 0.0413(3) 0.5097(3) 0.1408(3) 0.0875(8) Uani d PD 0.85 A 1
    H H4A 0.0075 0.5485 0.0732 0.131 Uiso d PRD 0.85 A 1
    S S1B 0.2538(7) 0.3989(8) 0.1617(6) 0.0738(13) Uiso d PD 0.15 A 2
    O O2B 0.1418(18) 0.403(2) 0.0960(15) 0.108(5) Uiso d PD 0.15 A 2
    O O3B 0.3793(16) 0.2769(15) 0.2076(12) 0.101(5) Uiso d PD 0.15 A 2
    N N4B 0.1907(16) 0.4415(16) 0.2611(11) 0.084(4) Uiso d PD 0.15 A 2
    H H4B 0.2677 0.3802 0.3054 0.126 Uiso d PRD 0.15 A 2
    C C5 0.0088(4) 0.5769(3) 0.2161(3) 0.0946(10) Uani d D 1 . .
    C C6 -0.1234(5) 0.6920(5) 0.1949(4) 0.1306(13) Uani d . 1 A .
    H H6 -0.1820 0.7284 0.1308 0.157 Uiso calc R 1 . .
    C C7 -0.1638(5) 0.7499(5) 0.2741(4) 0.1409(16) Uani d . 1 . .
    H H7 -0.2519 0.8231 0.2641 0.169 Uiso calc R 1 A .
    C C8 -0.0732(6) 0.6984(5) 0.3653(4) 0.1407(16) Uani d . 1 A .
    H H8 -0.0981 0.7369 0.4174 0.169 Uiso calc R 1 . .
    C C9 0.0519(5) 0.5918(5) 0.3785(4) 0.1245(13) Uani d . 1 . .
    H H9 0.1132 0.5580 0.4406 0.149 Uiso calc R 1 A .
    C C10 0.0941(4) 0.5305(4) 0.3062(4) 0.1085(11) Uani d D 1 A .
    H H10 0.1809 0.4537 0.3200 0.130 Uiso d R 1 . .
    C C11A 0.2814(4) 0.5458(4) 0.0635(3) 0.0717(15) Uani d PGD 0.85 A 1
    C C12A 0.3936(4) 0.5321(3) 0.1267(2) 0.0774(12) Uani d PGD 0.85 A 1
    H H12A 0.4279 0.4566 0.1936 0.093 Uiso calc PR 0.85 A 1
    C C13A 0.4547(3) 0.6314(4) 0.0901(3) 0.0926(11) Uani d PGD 0.85 A 1
    H H13A 0.5298 0.6222 0.1324 0.111 Uiso calc PR 0.85 A 1
    C C14A 0.4036(3) 0.7443(3) -0.0098(4) 0.0930(11) Uani d PGD 0.85 A 1
    C C15A 0.2913(4) 0.7579(3) -0.0731(2) 0.1015(13) Uani d PGD 0.85 A 1
    H H15A 0.2571 0.8335 -0.1399 0.122 Uiso calc PR 0.85 A 1
    C C16A 0.2303(4) 0.6587(4) -0.0364(3) 0.0955(15) Uani d PGD 0.85 A 1
    H H16A 0.1552 0.6678 -0.0788 0.115 Uiso calc PR 0.85 A 1
    C C17A 0.4640(6) 0.8593(5) -0.0516(5) 0.143(2) Uani d PDU 0.85 A 1
    H H17A 0.4943 0.8731 0.0084 0.215 Uiso calc PR 0.85 A 1
    H H17B 0.3923 0.9468 -0.0996 0.215 Uiso calc PR 0.85 A 1
    H H17C 0.5432 0.8300 -0.0898 0.215 Uiso calc PR 0.85 A 1
    C C11B 0.293(3) 0.543(2) 0.0859(16) 0.044(5) Uiso d PGD 0.15 A 2
    C C12B 0.408(3) 0.562(2) 0.1180(12) 0.094(10) Uiso d PGD 0.15 A 2
    H H12B 0.4566 0.5048 0.1869 0.113 Uiso calc PR 0.15 A 2
    C C13B 0.450(2) 0.665(3) 0.0470(14) 0.084(8) Uiso d PGD 0.15 A 2
    H H13B 0.5270 0.6781 0.0685 0.101 Uiso calc PR 0.15 A 2
    C C14B 0.377(2) 0.750(2) -0.0560(12) 0.079(7) Uiso d PGD 0.15 A 2
    C C15B 0.262(2) 0.732(2) -0.0880(12) 0.079(7) Uiso d PGD 0.15 A 2
    H H15B 0.2129 0.7884 -0.1569 0.095 Uiso calc PR 0.15 A 2
    C C16B 0.220(2) 0.628(3) -0.0171(18) 0.063(6) Uiso d PGD 0.15 A 2
    H H16B 0.1425 0.6152 -0.0385 0.076 Uiso calc PR 0.15 A 2
    C C17B 0.424(3) 0.867(2) -0.1305(18) 0.108(8) Uiso d PD 0.15 A 2
    H H17D 0.3813 0.9504 -0.1142 0.162 Uiso calc PR 0.15 A 2
    H H17E 0.3946 0.8905 -0.2046 0.162 Uiso calc PR 0.15 A 2
    H H17F 0.5251 0.8339 -0.1192 0.162 Uiso calc PR 0.15 A 2
    S S18 0.47516(6) 0.21883(7) 0.50060(6) 0.0710(2) Uani d . 1 . .
    O O19 0.4129(2) 0.3703(2) 0.45041(18) 0.0956(6) Uani d . 1 . .
    O O20 0.38487(18) 0.1421(2) 0.52602(18) 0.0875(6) Uani d . 1 . .
    N N21 0.5786(2) 0.1583(3) 0.41986(19) 0.0748(6) Uani d . 1 . .
    H H21 0.583(3) 0.078(3) 0.435(2) 0.090 Uiso d . 1 . .
    C C22 0.7038(3) 0.1843(3) 0.39199(18) 0.0702(7) Uani d . 1 . .
    C C23 0.8225(3) 0.0741(3) 0.3889(2) 0.0882(8) Uani d . 1 . .
    H H23 0.8203 -0.0149 0.4068 0.106 Uiso calc R 1 . .
    C C24 0.9449(4) 0.0939(5) 0.3598(3) 0.1137(12) Uani d . 1 . .
    H H24 1.0243 0.0189 0.3566 0.136 Uiso calc R 1 . .
    C C25 0.9503(4) 0.2241(5) 0.3353(3) 0.1194(13) Uani d . 1 . .
    H H25 1.0332 0.2376 0.3160 0.143 Uiso calc R 1 . .
    C C26 0.8345(5) 0.3319(5) 0.3397(3) 0.1155(12) Uani d . 1 . .
    H H26 0.8389 0.4194 0.3247 0.139 Uiso calc R 1 . .
    C C27 0.7077(4) 0.3158(4) 0.3662(3) 0.0957(9) Uani d . 1 . .
    H H27 0.6276 0.3922 0.3664 0.115 Uiso calc R 1 . .
    C C28 0.5846(2) 0.1698(2) 0.61768(19) 0.0588(5) Uani d . 1 . .
    C C29 0.6400(3) 0.0302(3) 0.6903(2) 0.0710(6) Uani d . 1 . .
    H H29 0.6151 -0.0370 0.6797 0.085 Uiso calc R 1 . .
    C C30 0.7321(3) -0.0090(3) 0.7783(2) 0.0788(7) Uani d . 1 . .
    H H30 0.7685 -0.1032 0.8273 0.095 Uiso calc R 1 . .
    C C31 0.7725(3) 0.0881(3) 0.7960(2) 0.0777(7) Uani d . 1 . .
    C C32 0.7150(3) 0.2275(3) 0.7228(3) 0.0888(9) Uani d . 1 . .
    H H32 0.7396 0.2946 0.7337 0.107 Uiso calc R 1 . .
    C C33 0.6219(3) 0.2695(3) 0.6339(2) 0.0781(7) Uani d . 1 . .
    H H33 0.5846 0.3638 0.5852 0.094 Uiso calc R 1 . .
    C C34 0.8796(4) 0.0418(5) 0.8906(3) 0.1205(13) Uani d . 1 . .
    H H34A 0.8801 0.1241 0.8990 0.181 Uiso calc R 1 . .
    H H34B 0.9720 -0.0118 0.8775 0.181 Uiso calc R 1 . .
    H H34C 0.8546 -0.0162 0.9554 0.181 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1A O2A . 1.438(3) ?
    S1A O3A . 1.443(3) ?
    S1A N4A . 1.640(3) ?
    S1A C11A . 1.761(2) ?
    N4A C5 . 1.428(4) ?
    N4A H4A . 0.8657 ?
    S1B O3B . 1.407(13) ?
    S1B O2B . 1.460(15) ?
    S1B N4B . 1.611(12) ?
    S1B C11B . 1.719(14) ?
    N4B C10 . 1.406(13) ?
    N4B H4B . 0.8773 ?
    N4B H10 . 0.8481 ?
    C5 C10 . 1.333(4) ?
    C5 C6 . 1.411(5) ?
    C6 C7 . 1.411(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.364(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.335(6) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.352(5) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9333 ?
    C11A C12A . 1.3900 ?
    C11A C16A . 1.3900 ?
    C12A C13A . 1.3900 ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.3900 ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.3900 ?
    C14A C17A . 1.534(5) ?
    C15A C16A . 1.3900 ?
    C15A H15A . 0.9300 ?
    C16A H16A . 0.9300 ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C11B C12B . 1.3900 ?
    C11B C16B . 1.3900 ?
    C12B C13B . 1.3900 ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.3900 ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.3900 ?
    C14B C17B . 1.537(15) ?
    C15B C16B . 1.3900 ?
    C15B H15B . 0.9300 ?
    C16B H16B . 0.9300 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    S18 O19 . 1.427(2) ?
    S18 O20 . 1.4332(19) ?
    S18 N21 . 1.633(2) ?
    S18 C28 . 1.754(2) ?
    N21 C22 . 1.429(3) ?
    N21 H21 . 0.81(3) ?
    C22 C23 . 1.370(4) ?
    C22 C27 . 1.378(4) ?
    C23 C24 . 1.376(4) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.372(5) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.345(6) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.396(5) ?
    C26 H26 . 0.9300 ?
    C27 H27 . 0.9300 ?
    C28 C29 . 1.379(3) ?
    C28 C33 . 1.386(3) ?
    C29 C30 . 1.370(4) ?
    C29 H29 . 0.9300 ?
    C30 C31 . 1.388(4) ?
    C30 H30 . 0.9300 ?
    C31 C32 . 1.379(4) ?
    C31 C34 . 1.514(4) ?
    C32 C33 . 1.379(4) ?
    C32 H32 . 0.9300 ?
    C33 H33 . 0.9300 ?
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2A S1A O3A . . 118.41(15) ?
    O2A S1A N4A . . 105.11(17) ?
    O3A S1A N4A . . 108.96(17) ?
    O2A S1A C11A . . 107.0(2) ?
    O3A S1A C11A . . 109.04(17) ?
    N4A S1A C11A . . 107.90(18) ?
    C5 N4A S1A . . 126.2(2) ?
    C5 N4A H4A . . 126.2 ?
    S1A N4A H4A . . 92.8 ?
    O3B S1B O2B . . 122.3(11) ?
    O3B S1B N4B . . 105.4(9) ?
    O2B S1B N4B . . 110.0(10) ?
    O3B S1B C11B . . 110.2(12) ?
    O2B S1B C11B . . 106.1(12) ?
    N4B S1B C11B . . 100.8(10) ?
    C10 N4B S1B . . 153.6(12) ?
    C10 N4B H4B . . 112.8 ?
    S1B N4B H4B . . 92.6 ?
    C10 N4B H10 . . 40.1 ?
    S1B N4B H10 . . 164.4 ?
    H4B N4B H10 . . 72.8 ?
    C10 C5 C6 . . 120.2(4) ?
    C10 C5 N4A . . 122.7(3) ?
    C6 C5 N4A . . 117.0(4) ?
    C7 C6 C5 . . 117.8(4) ?
    C7 C6 H6 . . 121.1 ?
    C5 C6 H6 . . 121.1 ?
    C8 C7 C6 . . 119.9(4) ?
    C8 C7 H7 . . 120.1 ?
    C6 C7 H7 . . 120.1 ?
    C9 C8 C7 . . 118.9(4) ?
    C9 C8 H8 . . 120.5 ?
    C7 C8 H8 . . 120.5 ?
    C8 C9 C10 . . 123.5(5) ?
    C8 C9 H9 . . 118.3 ?
    C10 C9 H9 . . 118.3 ?
    C5 C10 C9 . . 119.7(4) ?
    C5 C10 N4B . . 84.4(7) ?
    C9 C10 N4B . . 155.6(7) ?
    C5 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 120.6 ?
    N4B C10 H10 . . 35.8 ?
    C12A C11A C16A . . 120.0 ?
    C12A C11A S1A . . 118.6(2) ?
    C16A C11A S1A . . 121.3(2) ?
    C13A C12A C11A . . 120.0 ?
    C13A C12A H12A . . 120.0 ?
    C11A C12A H12A . . 120.0 ?
    C12A C13A C14A . . 120.0 ?
    C12A C13A H13A . . 120.0 ?
    C14A C13A H13A . . 120.0 ?
    C13A C14A C15A . . 120.0 ?
    C13A C14A C17A . . 121.8(4) ?
    C15A C14A C17A . . 118.2(4) ?
    C16A C15A C14A . . 120.0 ?
    C16A C15A H15A . . 120.0 ?
    C14A C15A H15A . . 120.0 ?
    C15A C16A C11A . . 120.0 ?
    C15A C16A H16A . . 120.0 ?
    C11A C16A H16A . . 120.0 ?
    C14A C17A H17A . . 109.5 ?
    C14A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C14A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C12B C11B C16B . . 120.0 ?
    C12B C11B S1B . . 121.6(15) ?
    C16B C11B S1B . . 117.6(15) ?
    C11B C12B C13B . . 120.0 ?
    C11B C12B H12B . . 120.0 ?
    C13B C12B H12B . . 120.0 ?
    C12B C13B C14B . . 120.0 ?
    C12B C13B H13B . . 120.0 ?
    C14B C13B H13B . . 120.0 ?
    C13B C14B C15B . . 120.0 ?
    C13B C14B C17B . . 118.3(15) ?
    C15B C14B C17B . . 121.7(15) ?
    C16B C15B C14B . . 120.0 ?
    C16B C15B H15B . . 120.0 ?
    C14B C15B H15B . . 120.0 ?
    C15B C16B C11B . . 120.0 ?
    C15B C16B H16B . . 120.0 ?
    C11B C16B H16B . . 120.0 ?
    C14B C17B H17D . . 109.5 ?
    C14B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C14B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    O19 S18 O20 . . 119.00(12) ?
    O19 S18 N21 . . 108.65(13) ?
    O20 S18 N21 . . 104.34(12) ?
    O19 S18 C28 . . 108.23(12) ?
    O20 S18 C28 . . 109.50(12) ?
    N21 S18 C28 . . 106.42(11) ?
    C22 N21 S18 . . 123.11(18) ?
    C22 N21 H21 . . 118(2) ?
    S18 N21 H21 . . 106(2) ?
    C23 C22 C27 . . 119.5(3) ?
    C23 C22 N21 . . 118.1(3) ?
    C27 C22 N21 . . 122.4(3) ?
    C22 C23 C24 . . 120.6(3) ?
    C22 C23 H23 . . 119.7 ?
    C24 C23 H23 . . 119.7 ?
    C25 C24 C23 . . 120.2(4) ?
    C25 C24 H24 . . 119.9 ?
    C23 C24 H24 . . 119.9 ?
    C26 C25 C24 . . 119.3(3) ?
    C26 C25 H25 . . 120.4 ?
    C24 C25 H25 . . 120.4 ?
    C25 C26 C27 . . 121.7(4) ?
    C25 C26 H26 . . 119.1 ?
    C27 C26 H26 . . 119.1 ?
    C22 C27 C26 . . 118.6(4) ?
    C22 C27 H27 . . 120.7 ?
    C26 C27 H27 . . 120.7 ?
    C29 C28 C33 . . 120.0(2) ?
    C29 C28 S18 . . 119.86(17) ?
    C33 C28 S18 . . 120.02(19) ?
    C30 C29 C28 . . 119.6(2) ?
    C30 C29 H29 . . 120.2 ?
    C28 C29 H29 . . 120.2 ?
    C29 C30 C31 . . 121.7(3) ?
    C29 C30 H30 . . 119.1 ?
    C31 C30 H30 . . 119.1 ?
    C32 C31 C30 . . 117.8(3) ?
    C32 C31 C34 . . 121.1(3) ?
    C30 C31 C34 . . 121.1(3) ?
    C33 C32 C31 . . 121.5(2) ?
    C33 C32 H32 . . 119.3 ?
    C31 C32 H32 . . 119.3 ?
    C32 C33 C28 . . 119.4(3) ?
    C32 C33 H33 . . 120.3 ?
    C28 C33 H33 . . 120.3 ?
    C31 C34 H34A . . 109.5 ?
    C31 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C31 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2A S1A N4A C5 . . . . -176.5(3) ?
    O3A S1A N4A C5 . . . . 55.6(3) ?
    C11A S1A N4A C5 . . . . -62.7(3) ?
    O3B S1B N4B C10 . . . . 174(2) ?
    O2B S1B N4B C10 . . . . -53(3) ?
    C11B S1B N4B C10 . . . . 59(3) ?
    S1A N4A C5 C10 . . . . -30.2(4) ?
    S1A N4A C5 C6 . . . . 153.4(3) ?
    C10 C5 C6 C7 . . . . -3.1(6) ?
    N4A C5 C6 C7 . . . . 173.4(4) ?
    C5 C6 C7 C8 . . . . 2.8(7) ?
    C6 C7 C8 C9 . . . . -1.0(8) ?
    C7 C8 C9 C10 . . . . -0.6(8) ?
    C6 C5 C10 C9 . . . . 1.6(5) ?
    N4A C5 C10 C9 . . . . -174.7(3) ?
    C6 C5 C10 N4B . . . . -174.3(7) ?
    N4A C5 C10 N4B . . . . 9.4(7) ?
    C8 C9 C10 C5 . . . . 0.3(7) ?
    C8 C9 C10 N4B . . . . 170.4(17) ?
    S1B N4B C10 C5 . . . . 23(3) ?
    S1B N4B C10 C9 . . . . -147.9(17) ?
    O2A S1A C11A C12A . . . . -137.1(2) ?
    O3A S1A C11A C12A . . . . -7.9(3) ?
    N4A S1A C11A C12A . . . . 110.3(2) ?
    O2A S1A C11A C16A . . . . 46.7(3) ?
    O3A S1A C11A C16A . . . . 175.8(2) ?
    N4A S1A C11A C16A . . . . -66.0(3) ?
    C16A C11A C12A C13A . . . . 0.0 ?
    S1A C11A C12A C13A . . . . -176.3(3) ?
    C11A C12A C13A C14A . . . . 0.0 ?
    C12A C13A C14A C15A . . . . 0.0 ?
    C12A C13A C14A C17A . . . . 177.7(4) ?
    C13A C14A C15A C16A . . . . 0.0 ?
    C17A C14A C15A C16A . . . . -177.8(4) ?
    C14A C15A C16A C11A . . . . 0.0 ?
    C12A C11A C16A C15A . . . . 0.0 ?
    S1A C11A C16A C15A . . . . 176.2(3) ?
    O3B S1B C11B C12B . . . . -37.1(15) ?
    O2B S1B C11B C12B . . . . -171.4(14) ?
    N4B S1B C11B C12B . . . . 73.8(14) ?
    O3B S1B C11B C16B . . . . 132.6(14) ?
    O2B S1B C11B C16B . . . . -1.7(17) ?
    N4B S1B C11B C16B . . . . -116.4(13) ?
    C16B C11B C12B C13B . . . . 0.0 ?
    S1B C11B C12B C13B . . . . 169.5(18) ?
    C11B C12B C13B C14B . . . . 0.0 ?
    C12B C13B C14B C15B . . . . 0.0 ?
    C12B C13B C14B C17B . . . . 178(2) ?
    C13B C14B C15B C16B . . . . 0.0 ?
    C17B C14B C15B C16B . . . . -178(2) ?
    C14B C15B C16B C11B . . . . 0.0 ?
    C12B C11B C16B C15B . . . . 0.0 ?
    S1B C11B C16B C15B . . . . -169.9(18) ?
    O19 S18 N21 C22 . . . . 65.2(2) ?
    O20 S18 N21 C22 . . . . -166.9(2) ?
    C28 S18 N21 C22 . . . . -51.1(2) ?
    S18 N21 C22 C23 . . . . 138.1(2) ?
    S18 N21 C22 C27 . . . . -43.3(3) ?
    C27 C22 C23 C24 . . . . -0.4(4) ?
    N21 C22 C23 C24 . . . . 178.2(3) ?
    C22 C23 C24 C25 . . . . 1.3(5) ?
    C23 C24 C25 C26 . . . . -0.4(6) ?
    C24 C25 C26 C27 . . . . -1.4(6) ?
    C23 C22 C27 C26 . . . . -1.3(4) ?
    N21 C22 C27 C26 . . . . -179.9(3) ?
    C25 C26 C27 C22 . . . . 2.2(6) ?
    O19 S18 C28 C29 . . . . 169.83(19) ?
    O20 S18 C28 C29 . . . . 38.7(2) ?
    N21 S18 C28 C29 . . . . -73.6(2) ?
    O19 S18 C28 C33 . . . . -14.0(2) ?
    O20 S18 C28 C33 . . . . -145.2(2) ?
    N21 S18 C28 C33 . . . . 102.6(2) ?
    C33 C28 C29 C30 . . . . 0.0(4) ?
    S18 C28 C29 C30 . . . . 176.11(19) ?
    C28 C29 C30 C31 . . . . -0.6(4) ?
    C29 C30 C31 C32 . . . . 1.0(4) ?
    C29 C30 C31 C34 . . . . -177.1(3) ?
    C30 C31 C32 C33 . . . . -0.9(4) ?
    C34 C31 C32 C33 . . . . 177.2(3) ?
    C31 C32 C33 C28 . . . . 0.3(4) ?
    C29 C28 C33 C32 . . . . 0.2(4) ?
    S18 C28 C33 C32 . . . . -176.0(2) ?
data_Compound_18_X2S
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H12 N O2 S, 'C13 H12 N O2 S'
_chemical_formula_sum     'C13 H12 N O2 S'
_chemical_formula_weight     246.30
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2890(11)
_cell_length_b     11.0563(12)
_cell_length_c     13.4402(15)
_cell_angle_alpha     67.823(3)
_cell_angle_beta     87.573(4)
_cell_angle_gamma     67.616(3)
_cell_volume     1299.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5366
_cell_measurement_theta_min     2.53
_cell_measurement_theta_max     24.65
_cell_measurement_temperature     300(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.258
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     516
_exptl_absorpt_coefficient_mu     0.238
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min     0.8903
_exptl_absorpt_correction_T_max     0.8903
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     300(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'micro-focus sealed tube'
_diffrn_radiation_monochromator     'doubly curved silicon crystal'
_diffrn_measurement_device_type     'Bruker SMART X2S'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12857
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_av_sigmaI/netI     0.0325
_diffrn_reflns_theta_min     1.65
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4545
_reflns_number_gt     3364
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0975
_refine_ls_R_factor_gt     0.0767
_refine_ls_wR_factor_gt     0.2011
_refine_ls_wR_factor_ref     0.2269
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     4545
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1107P)²+1.0378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.143
_refine_ls_shift/su_mean     0.006
_refine_diff_density_max     0.975
_refine_diff_density_min     -0.567
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker GIS'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Bruker APEX2'
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.79831(13) 0.57698(11) 0.88214(11) 0.0918(4) Uani d . 1 . .
    S S2 0.52478(9) 0.78104(10) 0.49944(8) 0.0697(3) Uani d . 1 . .
    O O1 0.7163(4) 0.6829(3) 0.7873(3) 0.1073(11) Uani d . 1 . .
    O O2 0.8242(4) 0.6160(4) 0.9678(4) 0.1296(15) Uani d . 1 . .
    O O3 0.6151(3) 0.8583(3) 0.4736(3) 0.0858(8) Uani d . 1 . .
    O O4 0.5872(3) 0.6296(3) 0.5500(3) 0.0935(9) Uani d . 1 . .
    C C13 0.5389(8) 0.1403(7) 1.0562(8) 0.186(4) Uani d . 1 . .
    H H13A 0.4397 0.1812 1.0314 0.279 Uiso calc R 1 . .
    H H13B 0.5525 0.1004 1.1339 0.279 Uiso calc R 1 . .
    H H13C 0.5873 0.0670 1.0301 0.279 Uiso calc R 1 . .
    C C2 0.7088(7) 0.2478(6) 1.0726(4) 0.1151(19) Uani d . 1 . .
    H H2 0.7434 0.1748 1.1406 0.138 Uiso calc R 1 . .
    C C1 0.5981(6) 0.2550(5) 1.0137(5) 0.1072(17) Uani d . 1 . .
    C C26 0.7708(5) 0.3463(5) 1.0336(4) 0.0965(14) Uani d . 1 . .
    H H26 0.8462 0.3396 1.0741 0.116 Uiso calc R 1 . .
    C C3 0.7170(4) 0.4541(4) 0.9329(3) 0.0707(9) Uani d . 1 . .
    N N1 0.9588(4) 0.4898(5) 0.8599(4) 0.1038(13) Uani d . 1 . .
    C C4 0.9911(5) 0.4226(5) 0.7834(5) 0.0920(14) Uani d . 1 . .
    C C5 0.9062(6) 0.4700(6) 0.6953(5) 0.1073(16) Uani d . 1 . .
    H H5 0.8186 0.5448 0.6829 0.129 Uiso calc R 1 . .
    C C6 0.9472(7) 0.4084(7) 0.6212(5) 0.1229(18) Uani d . 1 . .
    H H6 0.8856 0.4415 0.5594 0.147 Uiso calc R 1 . .
    C C7 1.0751(9) 0.3005(7) 0.6359(6) 0.140(2) Uani d . 1 . .
    H H7 1.1015 0.2618 0.5840 0.168 Uiso calc R 1 . .
    C C8 1.1231(7) 0.3085(7) 0.8056(5) 0.130(2) Uani d . 1 . .
    H H8 1.1814 0.2728 0.8697 0.156 Uiso calc R 1 . .
    C C9 1.1638(8) 0.2501(7) 0.7268(6) 0.140(2) Uani d . 1 . .
    H H9 1.2519 0.1766 0.7374 0.168 Uiso calc R 1 . .
    C C10 0.6054(4) 0.4643(4) 0.8753(4) 0.0830(11) Uani d . 1 . .
    H H10 0.5685 0.5389 0.8083 0.100 Uiso calc R 1 . .
    C C11 0.5463(5) 0.3654(6) 0.9149(5) 0.1037(15) Uani d . 1 . .
    H H11 0.4704 0.3734 0.8741 0.124 Uiso calc R 1 . .
    C C12 0.1212(6) 0.9585(7) 0.1090(4) 0.1196(19) Uani d . 1 . .
    H H12A 0.1239 0.8764 0.0984 0.179 Uiso calc R 1 . .
    H H12B 0.1436 1.0203 0.0448 0.179 Uiso calc R 1 . .
    H H12C 0.0282 1.0081 0.1236 0.179 Uiso calc R 1 . .
    C C14 0.2283(4) 0.9120(5) 0.2037(3) 0.0752(10) Uani d . 1 . .
    C C15 0.2857(5) 0.7728(5) 0.2767(4) 0.0869(12) Uani d . 1 . .
    H H15 0.2615 0.7057 0.2653 0.104 Uiso calc R 1 . .
    C C16 0.3777(5) 0.7304(4) 0.3658(3) 0.0781(11) Uani d . 1 . .
    H H16 0.4145 0.6361 0.4145 0.094 Uiso calc R 1 . .
    C C17 0.4155(3) 0.8304(3) 0.3824(3) 0.0573(8) Uani d . 1 . .
    N N2 0.4216(4) 0.8407(5) 0.5805(3) 0.0737(9) Uani d . 1 . .
    C C18 0.2963(4) 0.8157(4) 0.6082(3) 0.0693(9) Uani d . 1 . .
    C C19 0.1779(5) 0.9257(5) 0.6117(4) 0.0874(12) Uani d . 1 . .
    H H19 0.1804 1.0145 0.5942 0.105 Uiso calc R 1 . .
    C C20 0.0554(5) 0.9062(7) 0.6407(4) 0.1120(17) Uani d . 1 . .
    H H20 -0.0235 0.9812 0.6444 0.134 Uiso calc R 1 . .
    C C21 0.0489(7) 0.7766(8) 0.6643(5) 0.1175(19) Uani d . 1 . .
    H H21 -0.0344 0.7637 0.6827 0.141 Uiso calc R 1 . .
    C C22 0.2679(4) 1.0088(4) 0.2214(3) 0.0778(10) Uani d . 1 . .
    H H22 0.2314 1.1029 0.1723 0.093 Uiso calc R 1 . .
    C C23 0.3601(4) 0.9697(4) 0.3098(3) 0.0693(9) Uani d . 1 . .
    H H23 0.3849 1.0369 0.3204 0.083 Uiso calc R 1 . .
    C C24 0.1651(7) 0.6686(7) 0.6603(5) 0.1138(17) Uani d . 1 . .
    H H24 0.1608 0.5809 0.6756 0.137 Uiso calc R 1 . .
    C C25 0.2919(5) 0.6846(5) 0.6337(4) 0.0942(13) Uani d . 1 . .
    H H25 0.3719 0.6081 0.6334 0.113 Uiso calc R 1 . .
    H H2A 0.408(5) 0.915(4) 0.564(3) 0.074(15) Uiso d . 1 . .
    H H1A 1.031(6) 0.452(6) 0.921(5) 0.14(2) Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.385(3) ?
    S1 O2 . 1.439(4) ?
    S1 N1 . 1.646(5) ?
    S1 C3 . 1.769(4) ?
    S2 O4 . 1.428(3) ?
    S2 O3 . 1.438(3) ?
    S2 N2 . 1.631(4) ?
    S2 C17 . 1.753(4) ?
    C13 C1 . 1.522(8) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C2 C1 . 1.375(8) ?
    C2 C26 . 1.392(8) ?
    C2 H2 . 0.9300 ?
    C1 C11 . 1.371(8) ?
    C26 C3 . 1.379(6) ?
    C26 H26 . 0.9300 ?
    C3 C10 . 1.357(6) ?
    N1 C4 . 1.442(6) ?
    N1 H1A . 0.98(6) ?
    C4 C5 . 1.308(7) ?
    C4 C8 . 1.404(8) ?
    C5 C6 . 1.375(8) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.357(8) ?
    C6 H6 . 0.9300 ?
    C7 C9 . 1.353(9) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.409(9) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.373(7) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C14 . 1.515(6) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C14 C15 . 1.378(6) ?
    C14 C22 . 1.378(6) ?
    C15 C16 . 1.372(6) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.393(5) ?
    C16 H16 . 0.9300 ?
    C17 C23 . 1.376(5) ?
    N2 C18 . 1.425(5) ?
    N2 H2A . 0.72(4) ?
    C18 C19 . 1.369(6) ?
    C18 C25 . 1.377(6) ?
    C19 C20 . 1.375(6) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.373(8) ?
    C20 H20 . 0.9300 ?
    C21 C24 . 1.347(8) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.376(5) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.396(7) ?
    C24 H24 . 0.9300 ?
    C25 H25 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . 118.8(2) ?
    O1 S1 N1 . . 111.7(3) ?
    O2 S1 N1 . . 103.1(2) ?
    O1 S1 C3 . . 107.0(2) ?
    O2 S1 C3 . . 108.6(2) ?
    N1 S1 C3 . . 107.18(19) ?
    O4 S2 O3 . . 119.07(18) ?
    O4 S2 N2 . . 108.3(2) ?
    O3 S2 N2 . . 104.57(18) ?
    O4 S2 C17 . . 108.50(17) ?
    O3 S2 C17 . . 109.26(17) ?
    N2 S2 C17 . . 106.48(17) ?
    C1 C13 H13A . . 109.5 ?
    C1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C1 C2 C26 . . 122.0(5) ?
    C1 C2 H2 . . 119.0 ?
    C26 C2 H2 . . 119.0 ?
    C11 C1 C2 . . 118.1(5) ?
    C11 C1 C13 . . 121.4(7) ?
    C2 C1 C13 . . 120.5(6) ?
    C3 C26 C2 . . 117.9(5) ?
    C3 C26 H26 . . 121.1 ?
    C2 C26 H26 . . 121.1 ?
    C10 C3 C26 . . 120.5(4) ?
    C10 C3 S1 . . 121.6(3) ?
    C26 C3 S1 . . 117.8(3) ?
    C4 N1 S1 . . 125.1(4) ?
    C4 N1 H1A . . 117(3) ?
    S1 N1 H1A . . 113(4) ?
    C5 C4 C8 . . 121.8(5) ?
    C5 C4 N1 . . 122.1(5) ?
    C8 C4 N1 . . 116.1(6) ?
    C4 C5 C6 . . 119.6(6) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C7 C6 C5 . . 121.8(7) ?
    C7 C6 H6 . . 119.1 ?
    C5 C6 H6 . . 119.1 ?
    C9 C7 C6 . . 119.3(6) ?
    C9 C7 H7 . . 120.4 ?
    C6 C7 H7 . . 120.4 ?
    C4 C8 C9 . . 117.3(6) ?
    C4 C8 H8 . . 121.3 ?
    C9 C8 H8 . . 121.3 ?
    C7 C9 C8 . . 120.2(6) ?
    C7 C9 H9 . . 119.9 ?
    C8 C9 H9 . . 119.9 ?
    C3 C10 C11 . . 120.7(4) ?
    C3 C10 H10 . . 119.7 ?
    C11 C10 H10 . . 119.7 ?
    C1 C11 C10 . . 120.7(5) ?
    C1 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
    C14 C12 H12A . . 109.5 ?
    C14 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C14 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C15 C14 C22 . . 118.0(4) ?
    C15 C14 C12 . . 121.1(4) ?
    C22 C14 C12 . . 120.9(4) ?
    C16 C15 C14 . . 121.7(4) ?
    C16 C15 H15 . . 119.1 ?
    C14 C15 H15 . . 119.1 ?
    C15 C16 C17 . . 119.3(4) ?
    C15 C16 H16 . . 120.4 ?
    C17 C16 H16 . . 120.4 ?
    C23 C17 C16 . . 119.8(4) ?
    C23 C17 S2 . . 120.0(3) ?
    C16 C17 S2 . . 120.1(3) ?
    C18 N2 S2 . . 123.5(3) ?
    C18 N2 H2A . . 111(4) ?
    S2 N2 H2A . . 108(4) ?
    C19 C18 C25 . . 119.4(4) ?
    C19 C18 N2 . . 118.4(4) ?
    C25 C18 N2 . . 122.2(4) ?
    C18 C19 C20 . . 120.7(5) ?
    C18 C19 H19 . . 119.7 ?
    C20 C19 H19 . . 119.7 ?
    C21 C20 C19 . . 120.4(5) ?
    C21 C20 H20 . . 119.8 ?
    C19 C20 H20 . . 119.8 ?
    C24 C21 C20 . . 118.9(5) ?
    C24 C21 H21 . . 120.5 ?
    C20 C21 H21 . . 120.5 ?
    C23 C22 C14 . . 121.7(4) ?
    C23 C22 H22 . . 119.1 ?
    C14 C22 H22 . . 119.1 ?
    C22 C23 C17 . . 119.5(3) ?
    C22 C23 H23 . . 120.2 ?
    C17 C23 H23 . . 120.2 ?
    C21 C24 C25 . . 121.8(5) ?
    C21 C24 H24 . . 119.1 ?
    C25 C24 H24 . . 119.1 ?
    C18 C25 C24 . . 118.7(5) ?
    C18 C25 H25 . . 120.6 ?
    C24 C25 H25 . . 120.6 ?
data_global
_journal_date_recd_electronic     2010-04-30
_journal_date_accepted     2010-10-20
_journal_name_full     'Journal of Applied Crystallography'
_journal_year     2011
_journal_volume     44
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     SC
_journal_coeditor_code     KK5074
_publ_contact_author_name     'Simon E. Lawrence'
_publ_contact_author_address
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland
;
_publ_contact_author_email     s.lawrence@ucc.ie
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Evaluation of the Bruker SMART X2S: crystallography for the
non-specialist.
;
loop_
    _publ_author_name
    _publ_author_address
    'Kevin S. Eccles'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Stephen P. Stokes'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Carla A. Daly'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Nicola M. Barry'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Sharon P. McSweeney'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Damian J. O'Neill'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Dawn M. Kelly'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'W. Brian Jennings'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Orla M. Ni Dhubhghaill'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Humphrey A. Moynihan'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
    'Anita R. Maguire'
;
Department of Chemistry & School of Pharmacy,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland
;
    'Simon E. Lawrence'
;
Department of Chemistry,
Analytical and Biological Chemistry Research Facility,
University College Cork,
Cork,
Ireland.
;
