##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and 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 is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2013-05-28
_journal_date_accepted     2013-06-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     o1049
_journal_page_last     o1049
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681301547X
_journal_coeditor_code     RZ5071
_publ_contact_author_name     'Yousuf, S. '
_publ_contact_author_address
;
      H.E.J Research Institute of Chemistry,
      International Cenetr for Chemical and Biological Sciences,
      University of Karachi,
      Karachi-75270, Pakistan
;
_publ_contact_author_email     'dr.sammer.yousuf@gmail.com'
_publ_contact_author_fax     '+92-21 34819018-9'
_publ_contact_author_phone     '+92-21 34824924'
_publ_section_title
;
Ethyl 4-acetyl-5-anilino-3-methylthiophene-2-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yahia Nasser Mabkhot '
;
Additional correspondence author, email: yahia@ksu.edu.sa.
;
;     Department of Chemistry, College of Science,
      King Saud University,
      PO Box 2455, Riyadh 11451, Saudi Arabia
;
    'Fatima Alatibi' ?
;     Department of Chemistry, College of Science,
      King Saud University,
      PO Box 2455, Riyadh 11451, Saudi Arabia
;
    'Assem Barakat' ?
;     Department of Chemistry, College of Science,
      King Saud University,
      PO Box 2455, Riyadh 11451, Saudi Arabia
      Department of Chemistry, Faculty of Science,
      Alexandria University,  PO Box 426,
      Ibrahimia 21321 Alexandria, Egypt.
;
    'M. Iqbal Choudhary' ?
;     H.E.J. Research Institute of Chemistry,
      International Center for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
      Department of Chemistry, College of Science,
      King Saud University,
      PO Box 2455, Riyadh 11451, Saudi Arabia
;
    'Sammer Yousuf' ?
;     H.E.J. Research Institute of Chemistry,
      International Center for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 4-acetyl-5-anilino-3-methylthiophene-2-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H17 N O3 S'
_chemical_formula_sum     'C16 H17 N O3 S'
_chemical_formula_iupac     'C16 H17 N O3 S'
_chemical_formula_weight     303.37
_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     7.9443(6)
_cell_length_b     9.5038(7)
_cell_length_c     11.8706(9)
_cell_angle_alpha     66.759(2)
_cell_angle_beta     89.754(2)
_cell_angle_gamma     66.785(2)
_cell_volume     744.60(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2619
_cell_measurement_theta_min     2.46
_cell_measurement_theta_max     25.84
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'Yellow'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.353
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     320
_exptl_absorpt_coefficient_mu     0.227
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.9049
_exptl_absorpt_correction_T_max     0.9497
_exptl_special_details     ?
_diffrn_ambient_temperature     273(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 SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10410
_diffrn_reflns_av_R_equivalents     0.0279
_diffrn_reflns_av_sigmaI/netI     0.0324
_diffrn_reflns_theta_min     1.90
_diffrn_reflns_theta_max     28.33
_diffrn_reflns_theta_full     28.33
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     3699
_reflns_number_gt     2848
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0646
_refine_ls_R_factor_gt     0.0480
_refine_ls_wR_factor_gt     0.1143
_refine_ls_wR_factor_ref     0.1255
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.049
_refine_ls_number_reflns     3699
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0954P] 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     0.300
_refine_diff_density_min     -0.246
_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     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.48333(6) 0.26835(5) -0.00730(4) 0.04325(15) Uani d . 1 1 . .
    O O1 0.8347(2) 0.01329(18) -0.22852(13) 0.0685(4) Uani d . 1 1 . .
    O O2 0.6413(2) -0.06433(17) 0.34080(12) 0.0704(5) Uani d . 1 1 . .
    O O3 0.41944(19) 0.19842(16) 0.23323(11) 0.0546(3) Uani d . 1 1 . .
    N N1 0.5630(2) 0.2832(2) -0.23190(14) 0.0483(4) Uani d . 1 1 . .
    C C2 0.6046(2) 0.1930(2) -0.10687(15) 0.0404(4) Uani d . 1 1 . .
    C C3 0.7453(2) 0.0270(2) -0.04358(15) 0.0407(4) Uani d . 1 1 . .
    C C4 0.7482(2) -0.0370(2) 0.08869(15) 0.0394(4) Uani d . 1 1 . .
    C C5 0.6149(2) 0.0774(2) 0.12066(15) 0.0419(4) Uani d . 1 1 . .
    C C6 0.5653(3) 0.0580(2) 0.24344(16) 0.0475(4) Uani d . 1 1 . .
    C C7 0.3506(3) 0.1937(3) 0.34727(19) 0.0634(6) Uani d . 1 1 . .
    H H7A 0.4503 0.1639 0.4111 0.076 Uiso calc R 1 1 . .
    H H7B 0.2996 0.1109 0.3776 0.076 Uiso calc R 1 1 . .
    C C8 0.2028(3) 0.3670(3) 0.3158(2) 0.0728(6) Uani d . 1 1 . .
    H H8A 0.1526 0.3702 0.3889 0.109 Uiso calc R 1 1 . .
    H H8B 0.1054 0.3948 0.2524 0.109 Uiso calc R 1 1 . .
    H H8C 0.2553 0.4475 0.2858 0.109 Uiso calc R 1 1 . .
    C C9 0.8800(3) -0.2083(2) 0.18489(17) 0.0539(5) Uani d . 1 1 . .
    H H9A 0.8528 -0.2197 0.2661 0.081 Uiso calc R 1 1 . .
    H H9B 1.0055 -0.2205 0.1820 0.081 Uiso calc R 1 1 . .
    H H9C 0.8659 -0.2944 0.1682 0.081 Uiso calc R 1 1 . .
    C C10 0.8559(2) -0.0600(2) -0.11438(17) 0.0466(4) Uani d . 1 1 . .
    C C11 0.9989(3) -0.2421(3) -0.0534(2) 0.0605(5) Uani d . 1 1 . .
    H H11A 1.0558 -0.2749 -0.1159 0.091 Uiso calc R 1 1 . .
    H H11B 0.9394 -0.3133 -0.0102 0.091 Uiso calc R 1 1 . .
    H H11C 1.0925 -0.2538 0.0049 0.091 Uiso calc R 1 1 . .
    C C12 0.4166(2) 0.4428(2) -0.30492(15) 0.0435(4) Uani d . 1 1 . .
    C C13 0.3570(3) 0.5761(2) -0.27179(18) 0.0536(5) Uani d . 1 1 . .
    H H13A 0.4097 0.5614 -0.1958 0.064 Uiso calc R 1 1 . .
    C C14 0.2190(3) 0.7316(2) -0.3516(2) 0.0640(6) Uani d . 1 1 . .
    H H14A 0.1781 0.8210 -0.3286 0.077 Uiso calc R 1 1 . .
    C C15 0.1418(3) 0.7551(3) -0.4643(2) 0.0665(6) Uani d . 1 1 . .
    H H15A 0.0501 0.8603 -0.5181 0.080 Uiso calc R 1 1 . .
    C C16 0.2008(3) 0.6224(3) -0.49714(19) 0.0653(6) Uani d . 1 1 . .
    H H16A 0.1484 0.6380 -0.5735 0.078 Uiso calc R 1 1 . .
    C C17 0.3366(3) 0.4667(2) -0.41818(17) 0.0540(5) Uani d . 1 1 . .
    H H17A 0.3750 0.3772 -0.4409 0.065 Uiso calc R 1 1 . .
    H H1A 0.627(3) 0.228(3) -0.267(2) 0.058(6) Uiso d . 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0447(3) 0.0347(2) 0.0357(2) -0.00843(18) 0.00177(18) -0.00958(17)
    O1 0.0810(10) 0.0576(9) 0.0452(8) -0.0093(8) 0.0116(7) -0.0217(7)
    O2 0.0924(11) 0.0462(8) 0.0366(7) -0.0056(7) 0.0057(7) -0.0072(6)
    O3 0.0653(8) 0.0428(7) 0.0390(7) -0.0107(6) 0.0109(6) -0.0139(6)
    N1 0.0532(9) 0.0401(8) 0.0330(8) -0.0071(7) 0.0017(7) -0.0105(6)
    C2 0.0419(9) 0.0394(9) 0.0344(8) -0.0161(7) 0.0013(7) -0.0119(7)
    C3 0.0382(9) 0.0379(8) 0.0387(9) -0.0121(7) 0.0011(7) -0.0136(7)
    C4 0.0379(8) 0.0348(8) 0.0369(8) -0.0121(7) -0.0019(7) -0.0105(7)
    C5 0.0459(9) 0.0357(8) 0.0331(8) -0.0132(7) -0.0013(7) -0.0084(7)
    C6 0.0573(11) 0.0370(9) 0.0381(9) -0.0144(8) 0.0025(8) -0.0121(7)
    C7 0.0785(15) 0.0569(12) 0.0454(11) -0.0198(11) 0.0207(10) -0.0223(10)
    C8 0.0731(15) 0.0667(14) 0.0759(16) -0.0192(12) 0.0235(13) -0.0386(13)
    C9 0.0515(11) 0.0418(10) 0.0426(10) -0.0044(8) -0.0029(8) -0.0090(8)
    C10 0.0447(10) 0.0452(10) 0.0461(10) -0.0156(8) 0.0045(8) -0.0194(8)
    C11 0.0581(12) 0.0510(11) 0.0601(13) -0.0085(9) 0.0104(10) -0.0268(10)
    C12 0.0440(9) 0.0390(9) 0.0351(9) -0.0153(7) 0.0041(7) -0.0065(7)
    C13 0.0664(13) 0.0430(10) 0.0415(10) -0.0210(9) -0.0020(9) -0.0107(8)
    C14 0.0776(15) 0.0396(10) 0.0563(13) -0.0154(10) 0.0040(11) -0.0126(9)
    C15 0.0637(13) 0.0466(11) 0.0528(12) -0.0064(10) -0.0046(10) -0.0034(9)
    C16 0.0684(14) 0.0613(13) 0.0417(11) -0.0148(11) -0.0086(10) -0.0112(10)
    C17 0.0619(12) 0.0493(10) 0.0368(10) -0.0146(9) 0.0011(8) -0.0140(8)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.7182(18) ?
    S1 C5 . 1.7422(16) ?
    O1 C10 . 1.230(2) ?
    O2 C6 . 1.202(2) ?
    O3 C6 . 1.339(2) ?
    O3 C7 . 1.449(2) ?
    N1 C2 . 1.350(2) ?
    N1 C12 . 1.409(2) ?
    N1 H1A . 0.82(2) ?
    C2 C3 . 1.409(2) ?
    C3 C4 . 1.439(2) ?
    C3 C10 . 1.460(2) ?
    C4 C5 . 1.365(2) ?
    C4 C9 . 1.500(2) ?
    C5 C6 . 1.468(2) ?
    C7 C8 . 1.491(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 C11 . 1.509(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.379(3) ?
    C12 C17 . 1.384(3) ?
    C13 C14 . 1.382(3) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.371(3) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.372(3) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.374(3) ?
    C16 H16A . 0.9300 ?
    C17 H17A . 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 C5 . . 91.06(8) ?
    C6 O3 C7 . . 116.03(14) ?
    C2 N1 C12 . . 129.39(17) ?
    C2 N1 H1A . . 111.3(15) ?
    C12 N1 H1A . . 118.8(15) ?
    N1 C2 C3 . . 124.72(16) ?
    N1 C2 S1 . . 122.77(13) ?
    C3 C2 S1 . . 112.47(12) ?
    C2 C3 C4 . . 111.16(15) ?
    C2 C3 C10 . . 119.78(15) ?
    C4 C3 C10 . . 128.91(15) ?
    C5 C4 C3 . . 112.44(14) ?
    C5 C4 C9 . . 121.66(16) ?
    C3 C4 C9 . . 125.89(16) ?
    C4 C5 C6 . . 129.30(15) ?
    C4 C5 S1 . . 112.85(13) ?
    C6 C5 S1 . . 117.80(13) ?
    O2 C6 O3 . . 123.37(17) ?
    O2 C6 C5 . . 126.39(17) ?
    O3 C6 C5 . . 110.24(14) ?
    O3 C7 C8 . . 106.38(17) ?
    O3 C7 H7A . . 110.5 ?
    C8 C7 H7A . . 110.5 ?
    O3 C7 H7B . . 110.5 ?
    C8 C7 H7B . . 110.5 ?
    H7A C7 H7B . . 108.6 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C4 C9 H9A . . 109.5 ?
    C4 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C4 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O1 C10 C3 . . 120.70(17) ?
    O1 C10 C11 . . 116.71(17) ?
    C3 C10 C11 . . 122.59(17) ?
    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 . . 119.32(16) ?
    C13 C12 N1 . . 123.40(16) ?
    C17 C12 N1 . . 117.20(17) ?
    C12 C13 C14 . . 119.95(18) ?
    C12 C13 H13A . . 120.0 ?
    C14 C13 H13A . . 120.0 ?
    C15 C14 C13 . . 120.5(2) ?
    C15 C14 H14A . . 119.8 ?
    C13 C14 H14A . . 119.8 ?
    C14 C15 C16 . . 119.61(19) ?
    C14 C15 H15A . . 120.2 ?
    C16 C15 H15A . . 120.2 ?
    C15 C16 C17 . . 120.50(19) ?
    C15 C16 H16A . . 119.7 ?
    C17 C16 H16A . . 119.7 ?
    C16 C17 C12 . . 120.15(19) ?
    C16 C17 H17A . . 119.9 ?
    C12 C17 H17A . . 119.9 ?
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
    C12 N1 C2 C3 . . . . 174.03(18) ?
    C12 N1 C2 S1 . . . . -3.6(3) ?
    C5 S1 C2 N1 . . . . 176.62(16) ?
    C5 S1 C2 C3 . . . . -1.28(14) ?
    N1 C2 C3 C4 . . . . -176.94(17) ?
    S1 C2 C3 C4 . . . . 0.91(19) ?
    N1 C2 C3 C10 . . . . -1.0(3) ?
    S1 C2 C3 C10 . . . . 176.89(13) ?
    C2 C3 C4 C5 . . . . 0.1(2) ?
    C10 C3 C4 C5 . . . . -175.39(17) ?
    C2 C3 C4 C9 . . . . -179.55(16) ?
    C10 C3 C4 C9 . . . . 4.9(3) ?
    C3 C4 C5 C6 . . . . 176.08(18) ?
    C9 C4 C5 C6 . . . . -4.2(3) ?
    C3 C4 C5 S1 . . . . -1.09(19) ?
    C9 C4 C5 S1 . . . . 178.60(14) ?
    C2 S1 C5 C4 . . . . 1.37(14) ?
    C2 S1 C5 C6 . . . . -176.16(15) ?
    C7 O3 C6 O2 . . . . -2.5(3) ?
    C7 O3 C6 C5 . . . . 177.47(16) ?
    C4 C5 C6 O2 . . . . 3.2(3) ?
    S1 C5 C6 O2 . . . . -179.74(17) ?
    C4 C5 C6 O3 . . . . -176.76(17) ?
    S1 C5 C6 O3 . . . . 0.3(2) ?
    C6 O3 C7 C8 . . . . 174.54(18) ?
    C2 C3 C10 O1 . . . . 4.0(3) ?
    C4 C3 C10 O1 . . . . 179.20(18) ?
    C2 C3 C10 C11 . . . . -175.38(17) ?
    C4 C3 C10 C11 . . . . -0.2(3) ?
    C2 N1 C12 C13 . . . . 39.8(3) ?
    C2 N1 C12 C17 . . . . -143.5(2) ?
    C17 C12 C13 C14 . . . . -0.1(3) ?
    N1 C12 C13 C14 . . . . 176.61(18) ?
    C12 C13 C14 C15 . . . . -0.7(3) ?
    C13 C14 C15 C16 . . . . 0.8(4) ?
    C14 C15 C16 C17 . . . . -0.2(4) ?
    C15 C16 C17 C12 . . . . -0.6(3) ?
    C13 C12 C17 C16 . . . . 0.7(3) ?
    N1 C12 C17 C16 . . . . -176.19(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1A O1 . 0.82(3) 1.93(3) 2.607(3) 140(2) yes
