##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-11-19
_journal_date_accepted     2011-01-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o305
_journal_page_last     o305
_journal_paper_category     QO
_journal_coeditor_code     BT5412
_publ_contact_author_name     ' M.N. Ponnuswamy '
_publ_contact_author_address
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai - 600 025
    India
;
_publ_contact_author_email     'mnpsy2004@yahoo.com'
_publ_contact_author_fax     '+9144 22352494'
_publ_contact_author_phone     '+9144 22300122'
_publ_section_title
;
Diethyl
1,1-dioxo-3,5-bis(pyridin-2-yl)-1λ⁶,4-thiomorpholine-2,6-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Sugumar'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'N. Edayadulla'
;
Department of Natural Products Chemistry,
School of Chemistry,
Madurai Kamaraj University,
Madurai 625 021
India
;
    'P. Ramesh'
;
Department of Natural Products Chemistry,
School of Chemistry,
Madurai Kamaraj University,
Madurai 625 021
India
;
    'P. Ramesh'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'M. N. Ponnuswamy'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diethyl
1,1-dioxo-3,5-bis(pyridin-2-yl)-1λ⁶,4-thiomorpholine-2,6-dicarboxylate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C20 H23 N3 O6 S'
_chemical_formula_sum     'C20 H23 N3 O6 S'
_chemical_formula_iupac     'C20 H23 N3 O6 S'
_chemical_formula_weight     433.47
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
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'
_cell_length_a     20.7258(13)
_cell_length_b     8.3921(5)
_cell_length_c     24.4923(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4260.0(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4535
_cell_measurement_theta_min     1.66
_cell_measurement_theta_max     28.25
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1824
_exptl_absorpt_coefficient_mu     0.193
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.962
_exptl_absorpt_correction_T_max     0.970
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEXII area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22898
_diffrn_reflns_av_R_equivalents     0.0274
_diffrn_reflns_av_sigmaI/netI     0.0365
_diffrn_reflns_theta_min     1.66
_diffrn_reflns_theta_max     28.25
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     27
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     32
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     0
_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     9897
_reflns_number_gt     7453
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0631
_refine_ls_R_factor_gt     0.0415
_refine_ls_wR_factor_gt     0.1005
_refine_ls_wR_factor_ref     0.1128
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     9897
_refine_ls_number_parameters     553
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0624P)²+0.0627P] 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     0.291
_refine_diff_density_min     -0.174
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 4584 Friedel pairs'
_refine_ls_abs_structure_Flack     0.14(6)
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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) 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_disorder_assembly
    _atom_site_disorder_group
    S S1A 0.07796(3) 0.29281(10) 0.17383(2) 0.03724(14) Uani d . 1 . .
    O O1A -0.08829(9) 0.1886(3) 0.18546(9) 0.0567(5) Uani d . 1 . .
    O O2A -0.02641(10) 0.0197(3) 0.13848(9) 0.0649(6) Uani d . 1 . .
    O O3A 0.05012(9) 0.4478(2) 0.16522(8) 0.0481(5) Uani d . 1 . .
    O O4A 0.10104(11) 0.2054(3) 0.12711(8) 0.0491(5) Uani d . 1 . .
    O O5A 0.17481(10) 0.5395(2) 0.26684(9) 0.0538(5) Uani d . 1 . .
    O O6A 0.08102(10) 0.4278(3) 0.29336(10) 0.0538(6) Uani d . 1 . .
    N N1A 0.10848(11) 0.0586(3) 0.27062(12) 0.0374(6) Uani d . 1 . .
    H H1A 0.0979(17) 0.092(4) 0.3042(15) 0.060(11) Uiso d . 1 . .
    C C2A 0.05581(12) 0.0218(3) 0.23411(11) 0.0368(5) Uani d . 1 . .
    H H2A 0.0731 -0.0398 0.2034 0.044 Uiso calc R 1 . .
    C C3A 0.02173(12) 0.1721(3) 0.21064(10) 0.0347(5) Uani d . 1 . .
    H H3A 0.0037 0.2344 0.2409 0.042 Uiso calc R 1 . .
    C C4A 0.14360(13) 0.3100(3) 0.22123(10) 0.0364(6) Uani d . 1 . .
    H H4A 0.1811 0.3493 0.2010 0.044 Uiso calc R 1 . .
    C C5A 0.16188(12) 0.1416(3) 0.24529(11) 0.0351(6) Uani d . 1 . .
    H H5A 0.1774 0.0755 0.2150 0.042 Uiso calc R 1 . .
    C C6A 0.00661(13) -0.0803(3) 0.26320(11) 0.0420(6) Uani d . 1 . .
    C C10A -0.04476(19) -0.3286(4) 0.27768(18) 0.0736(10) Uani d . 1 . .
    H H10A -0.0497 -0.4367 0.2703 0.088 Uiso calc R 1 . .
    C C9A -0.0819(2) -0.2545(4) 0.3169(3) 0.0729(17) Uani d . 1 . .
    H H9A -0.1135 -0.3112 0.3356 0.088 Uiso calc R 1 . .
    C C8A -0.07184(18) -0.0963(5) 0.32788(15) 0.0717(10) Uani d . 1 . .
    H H8A -0.0965 -0.0486 0.3551 0.086 Uiso calc R 1 . .
    N N7A -0.02839(13) -0.0069(3) 0.30152(10) 0.0577(7) Uani d . 1 . .
    C C12A -0.03341(13) 0.1183(3) 0.17295(12) 0.0440(6) Uani d . 1 . .
    C C13A -0.14618(16) 0.1198(5) 0.16069(16) 0.0735(11) Uani d . 1 . .
    H H13A -0.1359 0.0752 0.1252 0.088 Uiso calc R 1 . .
    H H13B -0.1789 0.2013 0.1559 0.088 Uiso calc R 1 . .
    C C14A -0.17102(18) -0.0106(5) 0.19873(18) 0.0800(11) Uani d . 1 . .
    H H14A -0.1410 -0.0978 0.1991 0.120 Uiso calc R 1 . .
    H H14B -0.2122 -0.0475 0.1860 0.120 Uiso calc R 1 . .
    H H14C -0.1755 0.0314 0.2350 0.120 Uiso calc R 1 . .
    C C15A 0.12790(15) 0.4312(4) 0.26447(14) 0.0424(7) Uani d . 1 . .
    C C16A 0.16830(19) 0.6658(4) 0.30708(18) 0.0735(11) Uani d . 1 . .
    H H16A 0.1500 0.6239 0.3406 0.088 Uiso calc R 1 . .
    H H16B 0.1401 0.7489 0.2934 0.088 Uiso calc R 1 . .
    C C17A 0.2328(3) 0.7300(6) 0.3173(3) 0.115(2) Uani d . 1 . .
    H H17A 0.2590 0.6500 0.3344 0.172 Uiso calc R 1 . .
    H H17B 0.2297 0.8211 0.3408 0.172 Uiso calc R 1 . .
    H H17C 0.2522 0.7611 0.2833 0.172 Uiso calc R 1 . .
    C C18A 0.21738(12) 0.1620(3) 0.28544(10) 0.0354(5) Uani d . 1 . .
    C C19A 0.28099(13) 0.1448(3) 0.26942(12) 0.0452(6) Uani d . 1 . .
    H H19A 0.2910 0.1166 0.2337 0.054 Uiso calc R 1 . .
    C C20A 0.32921(14) 0.1699(4) 0.30700(13) 0.0557(8) Uani d . 1 . .
    H H20A 0.3722 0.1605 0.2967 0.067 Uiso calc R 1 . .
    C C21A 0.31343(18) 0.2091(5) 0.36023(16) 0.0567(8) Uani d . 1 . .
    H H21A 0.3450 0.2258 0.3866 0.068 Uiso calc R 1 . .
    C C22A 0.24882(18) 0.2220(6) 0.3722(2) 0.0659(12) Uani d . 1 . .
    H H22A 0.2376 0.2470 0.4080 0.079 Uiso calc R 1 . .
    C C11A -0.00059(17) -0.2393(4) 0.2500(2) 0.0585(13) Uani d . 1 . .
    H H11A 0.0244 -0.2849 0.2226 0.070 Uiso calc R 1 . .
    N N23A 0.20096(12) 0.2015(4) 0.33639(12) 0.0539(6) Uani d . 1 . .
    S S1B 0.16804(3) 0.70742(10) 0.10968(2) 0.03664(14) Uani d . 1 . .
    O O1B 0.07041(10) 0.4650(2) 0.01390(9) 0.0517(5) Uani d . 1 . .
    O O2B 0.16626(10) 0.5726(3) -0.00902(9) 0.0503(6) Uani d . 1 . .
    O O3B 0.19608(9) 0.5531(2) 0.11852(8) 0.0470(5) Uani d . 1 . .
    O O4B 0.14445(11) 0.7948(3) 0.15549(8) 0.0495(5) Uani d . 1 . .
    O O5B 0.33391(9) 0.8084(3) 0.09752(8) 0.0561(5) Uani d . 1 . .
    O O6B 0.27294(11) 0.9824(3) 0.14422(9) 0.0645(6) Uani d . 1 . .
    N N1B 0.13666(12) 0.9403(3) 0.01219(12) 0.0375(6) Uani d . 1 . .
    H H1B 0.1533(11) 0.885(3) -0.0151(10) 0.016(6) Uiso d . 1 . .
    C C2B 0.08363(12) 0.8566(3) 0.03772(11) 0.0364(6) Uani d . 1 . .
    H H2B 0.0675 0.9231 0.0676 0.044 Uiso calc R 1 . .
    C C3B 0.10241(12) 0.6909(3) 0.06219(11) 0.0350(5) Uani d . 1 . .
    H H3B 0.0649 0.6509 0.0824 0.042 Uiso calc R 1 . .
    C C4B 0.22467(12) 0.8277(3) 0.07248(10) 0.0360(5) Uani d . 1 . .
    H H4B 0.2426 0.7655 0.0422 0.043 Uiso calc R 1 . .
    C C5B 0.18996(12) 0.9771(3) 0.04946(10) 0.0368(5) Uani d . 1 . .
    H H5B 0.1725 1.0379 0.0803 0.044 Uiso calc R 1 . .
    C C6B 0.02908(13) 0.8343(3) -0.00298(10) 0.0379(6) Uani d . 1 . .
    N N7B 0.04684(13) 0.7879(4) -0.05309(11) 0.0515(6) Uani d . 1 . .
    C C8B -0.00031(19) 0.7602(4) -0.0897(2) 0.0568(11) Uani d . 1 . .
    H H8B 0.0112 0.7298 -0.1249 0.068 Uiso calc R 1 . .
    C C9B -0.0645(2) 0.7749(5) -0.07749(18) 0.0585(10) Uani d . 1 . .
    H H9B -0.0957 0.7527 -0.1037 0.070 Uiso calc R 1 . .
    C C10B -0.08203(15) 0.8230(4) -0.02585(14) 0.0591(8) Uani d . 1 . .
    H H10B -0.1253 0.8341 -0.0166 0.071 Uiso calc R 1 . .
    C C11B -0.03454(13) 0.8544(4) 0.01173(12) 0.0488(7) Uani d . 1 . .
    H H11B -0.0452 0.8888 0.0467 0.059 Uiso calc R 1 . .
    C C12B 0.11816(14) 0.5696(4) 0.01801(13) 0.0367(6) Uani d . 1 . .
    C C13B 0.07553(18) 0.3485(4) -0.02997(18) 0.0738(11) Uani d . 1 . .
    H H13C 0.1073 0.2679 -0.0208 0.089 Uiso calc R 1 . .
    H H13D 0.0886 0.4002 -0.0636 0.089 Uiso calc R 1 . .
    C C14B 0.0110(2) 0.2750(6) -0.0364(2) 0.1052(19) Uani d . 1 . .
    H H14D -0.0049 0.2424 -0.0014 0.158 Uiso calc R 1 . .
    H H14E 0.0142 0.1838 -0.0600 0.158 Uiso calc R 1 . .
    H H14F -0.0181 0.3512 -0.0522 0.158 Uiso calc R 1 . .
    C C15B 0.27901(12) 0.8812(3) 0.10983(11) 0.0425(6) Uani d . 1 . .
    C C16B 0.39240(16) 0.8787(5) 0.12212(16) 0.0777(12) Uani d . 1 . .
    H H16C 0.4253 0.7975 0.1264 0.093 Uiso calc R 1 . .
    H H16D 0.3824 0.9215 0.1579 0.093 Uiso calc R 1 . .
    C C17B 0.41688(19) 1.0101(5) 0.08536(18) 0.0843(12) Uani d . 1 . .
    H H17D 0.4262 0.9672 0.0499 0.126 Uiso calc R 1 . .
    H H17E 0.4554 1.0550 0.1007 0.126 Uiso calc R 1 . .
    H H17F 0.3846 1.0915 0.0822 0.126 Uiso calc R 1 . .
    C C18B 0.23894(13) 1.0806(3) 0.02030(11) 0.0411(6) Uani d . 1 . .
    N N23B 0.27697(14) 1.0074(3) -0.01583(10) 0.0572(7) Uani d . 1 . .
    C C22B 0.32086(19) 1.0969(4) -0.04148(16) 0.0744(10) Uani d . 1 . .
    H H22B 0.3487 1.0465 -0.0658 0.089 Uiso calc R 1 . .
    C C21B 0.3276(2) 1.2571(5) -0.0344(2) 0.0787(17) Uani d . 1 . .
    H H21B 0.3576 1.3150 -0.0545 0.094 Uiso calc R 1 . .
    C C20B 0.28872(18) 1.3298(4) 0.0032(2) 0.0831(13) Uani d . 1 . .
    H H20B 0.2926 1.4386 0.0097 0.100 Uiso calc R 1 . .
    C C19B 0.24368(18) 1.2407(4) 0.0315(2) 0.0593(13) Uani d . 1 . .
    H H19B 0.2172 1.2880 0.0575 0.071 Uiso calc R 1 . .
_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
    S1A O3A . 1.439(2) ?
    S1A O4A . 1.441(2) ?
    S1A C3A . 1.788(3) ?
    S1A C4A . 1.794(3) ?
    O1A C12A . 1.318(3) ?
    O1A C13A . 1.463(4) ?
    O2A C12A . 1.191(3) ?
    O5A C15A . 1.332(4) ?
    O5A C16A . 1.454(4) ?
    O6A C15A . 1.202(4) ?
    N1A C2A . 1.445(4) ?
    N1A C5A . 1.447(3) ?
    N1A H1A . 0.90(4) ?
    C2A C6A . 1.511(4) ?
    C2A C3A . 1.556(4) ?
    C2A H2A . 0.9800 ?
    C3A C12A . 1.537(4) ?
    C3A H3A . 0.9800 ?
    C4A C15A . 1.504(4) ?
    C4A C5A . 1.577(4) ?
    C4A H4A . 0.9800 ?
    C5A C18A . 1.523(3) ?
    C5A H5A . 0.9800 ?
    C6A N7A . 1.337(4) ?
    C6A C11A . 1.381(4) ?
    C10A C11A . 1.364(5) ?
    C10A C9A . 1.379(6) ?
    C10A H10A . 0.9300 ?
    C9A C8A . 1.371(5) ?
    C9A H9A . 0.9300 ?
    C8A N7A . 1.338(4) ?
    C8A H8A . 0.9300 ?
    C13A C14A . 1.527(6) ?
    C13A H13A . 0.9700 ?
    C13A H13B . 0.9700 ?
    C14A H14A . 0.9600 ?
    C14A H14B . 0.9600 ?
    C14A H14C . 0.9600 ?
    C16A C17A . 1.464(6) ?
    C16A H16A . 0.9700 ?
    C16A H16B . 0.9700 ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C18A N23A . 1.335(4) ?
    C18A C19A . 1.383(4) ?
    C19A C20A . 1.375(4) ?
    C19A H19A . 0.9300 ?
    C20A C21A . 1.384(5) ?
    C20A H20A . 0.9300 ?
    C21A C22A . 1.375(5) ?
    C21A H21A . 0.9300 ?
    C22A N23A . 1.335(5) ?
    C22A H22A . 0.9300 ?
    C11A H11A . 0.9300 ?
    S1B O4B . 1.427(2) ?
    S1B O3B . 1.4356(19) ?
    S1B C3B . 1.795(3) ?
    S1B C4B . 1.796(3) ?
    O1B C12B . 1.327(3) ?
    O1B C13B . 1.456(4) ?
    O2B C12B . 1.197(3) ?
    O5B C15B . 1.326(3) ?
    O5B C16B . 1.477(4) ?
    O6B C15B . 1.202(3) ?
    N1B C2B . 1.447(4) ?
    N1B C5B . 1.466(4) ?
    N1B H1B . 0.88(2) ?
    C2B C6B . 1.519(4) ?
    C2B C3B . 1.563(4) ?
    C2B H2B . 0.9800 ?
    C3B C12B . 1.521(4) ?
    C3B H3B . 0.9800 ?
    C4B C15B . 1.519(4) ?
    C4B C5B . 1.552(4) ?
    C4B H4B . 0.9800 ?
    C5B C18B . 1.515(4) ?
    C5B H5B . 0.9800 ?
    C6B N7B . 1.339(4) ?
    C6B C11B . 1.377(4) ?
    N7B C8B . 1.346(5) ?
    C8B C9B . 1.368(5) ?
    C8B H8B . 0.9300 ?
    C9B C10B . 1.377(6) ?
    C9B H9B . 0.9300 ?
    C10B C11B . 1.373(4) ?
    C10B H10B . 0.9300 ?
    C11B H11B . 0.9300 ?
    C13B C14B . 1.481(5) ?
    C13B H13C . 0.9700 ?
    C13B H13D . 0.9700 ?
    C14B H14D . 0.9600 ?
    C14B H14E . 0.9600 ?
    C14B H14F . 0.9600 ?
    C16B C17B . 1.511(6) ?
    C16B H16C . 0.9700 ?
    C16B H16D . 0.9700 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    C18B N23B . 1.335(4) ?
    C18B C19B . 1.375(4) ?
    N23B C22B . 1.336(4) ?
    C22B C21B . 1.362(5) ?
    C22B H22B . 0.9300 ?
    C21B C20B . 1.367(6) ?
    C21B H21B . 0.9300 ?
    C20B C19B . 1.382(5) ?
    C20B H20B . 0.9300 ?
    C19B H19B . 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
    O3A S1A O4A . . 118.48(13) ?
    O3A S1A C3A . . 108.96(12) ?
    O4A S1A C3A . . 109.18(13) ?
    O3A S1A C4A . . 109.05(13) ?
    O4A S1A C4A . . 107.63(13) ?
    C3A S1A C4A . . 102.32(12) ?
    C12A O1A C13A . . 115.8(2) ?
    C15A O5A C16A . . 117.4(3) ?
    C2A N1A C5A . . 114.5(2) ?
    C2A N1A H1A . . 117(2) ?
    C5A N1A H1A . . 115(2) ?
    N1A C2A C6A . . 109.8(2) ?
    N1A C2A C3A . . 113.5(2) ?
    C6A C2A C3A . . 109.1(2) ?
    N1A C2A H2A . . 108.1 ?
    C6A C2A H2A . . 108.1 ?
    C3A C2A H2A . . 108.1 ?
    C12A C3A C2A . . 108.8(2) ?
    C12A C3A S1A . . 110.37(18) ?
    C2A C3A S1A . . 110.48(17) ?
    C12A C3A H3A . . 109.1 ?
    C2A C3A H3A . . 109.1 ?
    S1A C3A H3A . . 109.1 ?
    C15A C4A C5A . . 113.3(2) ?
    C15A C4A S1A . . 110.23(19) ?
    C5A C4A S1A . . 110.61(19) ?
    C15A C4A H4A . . 107.5 ?
    C5A C4A H4A . . 107.5 ?
    S1A C4A H4A . . 107.5 ?
    N1A C5A C18A . . 110.8(2) ?
    N1A C5A C4A . . 114.1(2) ?
    C18A C5A C4A . . 108.8(2) ?
    N1A C5A H5A . . 107.7 ?
    C18A C5A H5A . . 107.7 ?
    C4A C5A H5A . . 107.7 ?
    N7A C6A C11A . . 123.4(3) ?
    N7A C6A C2A . . 115.9(2) ?
    C11A C6A C2A . . 120.7(3) ?
    C11A C10A C9A . . 118.2(4) ?
    C11A C10A H10A . . 120.9 ?
    C9A C10A H10A . . 120.9 ?
    C8A C9A C10A . . 119.2(4) ?
    C8A C9A H9A . . 120.4 ?
    C10A C9A H9A . . 120.4 ?
    N7A C8A C9A . . 123.4(4) ?
    N7A C8A H8A . . 118.3 ?
    C9A C8A H8A . . 118.3 ?
    C6A N7A C8A . . 116.5(3) ?
    O2A C12A O1A . . 125.5(3) ?
    O2A C12A C3A . . 122.6(2) ?
    O1A C12A C3A . . 111.8(2) ?
    O1A C13A C14A . . 107.9(3) ?
    O1A C13A H13A . . 110.1 ?
    C14A C13A H13A . . 110.1 ?
    O1A C13A H13B . . 110.1 ?
    C14A C13A H13B . . 110.1 ?
    H13A C13A H13B . . 108.4 ?
    C13A C14A H14A . . 109.5 ?
    C13A C14A H14B . . 109.5 ?
    H14A C14A H14B . . 109.5 ?
    C13A C14A H14C . . 109.5 ?
    H14A C14A H14C . . 109.5 ?
    H14B C14A H14C . . 109.5 ?
    O6A C15A O5A . . 125.4(3) ?
    O6A C15A C4A . . 125.0(3) ?
    O5A C15A C4A . . 109.5(3) ?
    O5A C16A C17A . . 107.4(4) ?
    O5A C16A H16A . . 110.2 ?
    C17A C16A H16A . . 110.2 ?
    O5A C16A H16B . . 110.2 ?
    C17A C16A H16B . . 110.2 ?
    H16A C16A H16B . . 108.5 ?
    C16A C17A H17A . . 109.5 ?
    C16A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C16A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    N23A C18A C19A . . 122.3(2) ?
    N23A C18A C5A . . 116.0(2) ?
    C19A C18A C5A . . 121.7(2) ?
    C20A C19A C18A . . 119.1(3) ?
    C20A C19A H19A . . 120.4 ?
    C18A C19A H19A . . 120.4 ?
    C19A C20A C21A . . 119.7(3) ?
    C19A C20A H20A . . 120.2 ?
    C21A C20A H20A . . 120.2 ?
    C22A C21A C20A . . 116.7(4) ?
    C22A C21A H21A . . 121.6 ?
    C20A C21A H21A . . 121.6 ?
    N23A C22A C21A . . 125.0(4) ?
    N23A C22A H22A . . 117.5 ?
    C21A C22A H22A . . 117.5 ?
    C10A C11A C6A . . 119.1(4) ?
    C10A C11A H11A . . 120.4 ?
    C6A C11A H11A . . 120.4 ?
    C18A N23A C22A . . 117.2(3) ?
    O4B S1B O3B . . 118.95(13) ?
    O4B S1B C3B . . 106.83(13) ?
    O3B S1B C3B . . 109.55(13) ?
    O4B S1B C4B . . 109.49(13) ?
    O3B S1B C4B . . 108.60(12) ?
    C3B S1B C4B . . 102.12(12) ?
    C12B O1B C13B . . 116.5(2) ?
    C15B O5B C16B . . 115.3(2) ?
    C2B N1B C5B . . 113.9(2) ?
    C2B N1B H1B . . 111.6(15) ?
    C5B N1B H1B . . 106.7(15) ?
    N1B C2B C6B . . 110.0(2) ?
    N1B C2B C3B . . 114.1(2) ?
    C6B C2B C3B . . 109.1(2) ?
    N1B C2B H2B . . 107.8 ?
    C6B C2B H2B . . 107.8 ?
    C3B C2B H2B . . 107.8 ?
    C12B C3B C2B . . 112.1(2) ?
    C12B C3B S1B . . 110.50(18) ?
    C2B C3B S1B . . 111.6(2) ?
    C12B C3B H3B . . 107.5 ?
    C2B C3B H3B . . 107.5 ?
    S1B C3B H3B . . 107.5 ?
    C15B C4B C5B . . 108.9(2) ?
    C15B C4B S1B . . 110.20(18) ?
    C5B C4B S1B . . 109.61(17) ?
    C15B C4B H4B . . 109.4 ?
    C5B C4B H4B . . 109.4 ?
    S1B C4B H4B . . 109.4 ?
    N1B C5B C18B . . 109.4(2) ?
    N1B C5B C4B . . 113.9(2) ?
    C18B C5B C4B . . 108.9(2) ?
    N1B C5B H5B . . 108.1 ?
    C18B C5B H5B . . 108.1 ?
    C4B C5B H5B . . 108.1 ?
    N7B C6B C11B . . 122.6(3) ?
    N7B C6B C2B . . 115.6(2) ?
    C11B C6B C2B . . 121.7(2) ?
    C6B N7B C8B . . 117.4(3) ?
    N7B C8B C9B . . 123.0(4) ?
    N7B C8B H8B . . 118.5 ?
    C9B C8B H8B . . 118.5 ?
    C8B C9B C10B . . 118.9(4) ?
    C8B C9B H9B . . 120.5 ?
    C10B C9B H9B . . 120.5 ?
    C11B C10B C9B . . 118.9(3) ?
    C11B C10B H10B . . 120.6 ?
    C9B C10B H10B . . 120.6 ?
    C10B C11B C6B . . 119.2(3) ?
    C10B C11B H11B . . 120.4 ?
    C6B C11B H11B . . 120.4 ?
    O2B C12B O1B . . 126.4(3) ?
    O2B C12B C3B . . 123.9(3) ?
    O1B C12B C3B . . 109.7(2) ?
    O1B C13B C14B . . 107.0(3) ?
    O1B C13B H13C . . 110.3 ?
    C14B C13B H13C . . 110.3 ?
    O1B C13B H13D . . 110.3 ?
    C14B C13B H13D . . 110.3 ?
    H13C C13B H13D . . 108.6 ?
    C13B C14B H14D . . 109.5 ?
    C13B C14B H14E . . 109.5 ?
    H14D C14B H14E . . 109.5 ?
    C13B C14B H14F . . 109.5 ?
    H14D C14B H14F . . 109.5 ?
    H14E C14B H14F . . 109.5 ?
    O6B C15B O5B . . 125.0(3) ?
    O6B C15B C4B . . 123.6(2) ?
    O5B C15B C4B . . 111.3(2) ?
    O5B C16B C17B . . 108.9(3) ?
    O5B C16B H16C . . 109.9 ?
    C17B C16B H16C . . 109.9 ?
    O5B C16B H16D . . 109.9 ?
    C17B C16B H16D . . 109.9 ?
    H16C C16B H16D . . 108.3 ?
    C16B C17B H17D . . 109.5 ?
    C16B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C16B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    N23B C18B C19B . . 122.6(3) ?
    N23B C18B C5B . . 116.4(2) ?
    C19B C18B C5B . . 121.0(3) ?
    C18B N23B C22B . . 117.1(3) ?
    N23B C22B C21B . . 124.4(4) ?
    N23B C22B H22B . . 117.8 ?
    C21B C22B H22B . . 117.8 ?
    C22B C21B C20B . . 117.8(4) ?
    C22B C21B H21B . . 121.1 ?
    C20B C21B H21B . . 121.1 ?
    C21B C20B C19B . . 119.6(3) ?
    C21B C20B H20B . . 120.2 ?
    C19B C20B H20B . . 120.2 ?
    C18B C19B C20B . . 118.5(4) ?
    C18B C19B H19B . . 120.7 ?
    C20B C19B H19B . . 120.7 ?
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
    C5A N1A C2A C6A . . . . 173.6(2) ?
    C5A N1A C2A C3A . . . . -63.9(3) ?
    N1A C2A C3A C12A . . . . -179.6(2) ?
    C6A C2A C3A C12A . . . . -56.7(3) ?
    N1A C2A C3A S1A . . . . 59.1(3) ?
    C6A C2A C3A S1A . . . . -178.03(17) ?
    O3A S1A C3A C12A . . . . 74.7(2) ?
    O4A S1A C3A C12A . . . . -56.1(2) ?
    C4A S1A C3A C12A . . . . -169.94(18) ?
    O3A S1A C3A C2A . . . . -164.99(17) ?
    O4A S1A C3A C2A . . . . 64.2(2) ?
    C4A S1A C3A C2A . . . . -49.63(19) ?
    O3A S1A C4A C15A . . . . 37.0(2) ?
    O4A S1A C4A C15A . . . . 166.8(2) ?
    C3A S1A C4A C15A . . . . -78.3(2) ?
    O3A S1A C4A C5A . . . . 163.07(17) ?
    O4A S1A C4A C5A . . . . -67.2(2) ?
    C3A S1A C4A C5A . . . . 47.8(2) ?
    C2A N1A C5A C18A . . . . -174.9(2) ?
    C2A N1A C5A C4A . . . . 62.0(3) ?
    C15A C4A C5A N1A . . . . 68.8(3) ?
    S1A C4A C5A N1A . . . . -55.5(3) ?
    C15A C4A C5A C18A . . . . -55.4(3) ?
    S1A C4A C5A C18A . . . . -179.67(17) ?
    N1A C2A C6A N7A . . . . 71.3(3) ?
    C3A C2A C6A N7A . . . . -53.7(3) ?
    N1A C2A C6A C11A . . . . -108.8(3) ?
    C3A C2A C6A C11A . . . . 126.3(3) ?
    C11A C10A C9A C8A . . . . -2.2(7) ?
    C10A C9A C8A N7A . . . . 1.7(7) ?
    C11A C6A N7A C8A . . . . 0.5(5) ?
    C2A C6A N7A C8A . . . . -179.5(3) ?
    C9A C8A N7A C6A . . . . -0.8(5) ?
    C13A O1A C12A O2A . . . . 10.4(5) ?
    C13A O1A C12A C3A . . . . -166.5(3) ?
    C2A C3A C12A O2A . . . . -48.3(4) ?
    S1A C3A C12A O2A . . . . 73.0(3) ?
    C2A C3A C12A O1A . . . . 128.7(2) ?
    S1A C3A C12A O1A . . . . -109.9(2) ?
    C12A O1A C13A C14A . . . . 88.6(3) ?
    C16A O5A C15A O6A . . . . -1.1(5) ?
    C16A O5A C15A C4A . . . . -179.2(3) ?
    C5A C4A C15A O6A . . . . -68.7(4) ?
    S1A C4A C15A O6A . . . . 55.8(4) ?
    C5A C4A C15A O5A . . . . 109.4(3) ?
    S1A C4A C15A O5A . . . . -126.1(2) ?
    C15A O5A C16A C17A . . . . 158.4(4) ?
    N1A C5A C18A N23A . . . . -41.2(3) ?
    C4A C5A C18A N23A . . . . 84.9(3) ?
    N1A C5A C18A C19A . . . . 140.5(3) ?
    C4A C5A C18A C19A . . . . -93.4(3) ?
    N23A C18A C19A C20A . . . . -0.4(4) ?
    C5A C18A C19A C20A . . . . 177.8(3) ?
    C18A C19A C20A C21A . . . . 1.1(5) ?
    C19A C20A C21A C22A . . . . -0.5(6) ?
    C20A C21A C22A N23A . . . . -0.8(7) ?
    C9A C10A C11A C6A . . . . 1.9(6) ?
    N7A C6A C11A C10A . . . . -1.1(6) ?
    C2A C6A C11A C10A . . . . 179.0(3) ?
    C19A C18A N23A C22A . . . . -0.9(5) ?
    C5A C18A N23A C22A . . . . -179.2(3) ?
    C21A C22A N23A C18A . . . . 1.5(7) ?
    C5B N1B C2B C6B . . . . 176.0(2) ?
    C5B N1B C2B C3B . . . . -61.0(3) ?
    N1B C2B C3B C12B . . . . -69.3(3) ?
    C6B C2B C3B C12B . . . . 54.2(3) ?
    N1B C2B C3B S1B . . . . 55.2(3) ?
    C6B C2B C3B S1B . . . . 178.71(17) ?
    O4B S1B C3B C12B . . . . -167.6(2) ?
    O3B S1B C3B C12B . . . . -37.5(2) ?
    C4B S1B C3B C12B . . . . 77.5(2) ?
    O4B S1B C3B C2B . . . . 67.0(2) ?
    O3B S1B C3B C2B . . . . -162.92(17) ?
    C4B S1B C3B C2B . . . . -47.94(19) ?
    O4B S1B C4B C15B . . . . 56.6(2) ?
    O3B S1B C4B C15B . . . . -74.7(2) ?
    C3B S1B C4B C15B . . . . 169.59(18) ?
    O4B S1B C4B C5B . . . . -63.2(2) ?
    O3B S1B C4B C5B . . . . 165.46(16) ?
    C3B S1B C4B C5B . . . . 49.78(19) ?
    C2B N1B C5B C18B . . . . -173.5(2) ?
    C2B N1B C5B C4B . . . . 64.3(3) ?
    C15B C4B C5B N1B . . . . 179.4(2) ?
    S1B C4B C5B N1B . . . . -60.0(2) ?
    C15B C4B C5B C18B . . . . 57.0(3) ?
    S1B C4B C5B C18B . . . . 177.62(17) ?
    N1B C2B C6B N7B . . . . 43.8(3) ?
    C3B C2B C6B N7B . . . . -82.1(3) ?
    N1B C2B C6B C11B . . . . -138.7(3) ?
    C3B C2B C6B C11B . . . . 95.4(3) ?
    C11B C6B N7B C8B . . . . -0.2(5) ?
    C2B C6B N7B C8B . . . . 177.2(3) ?
    C6B N7B C8B C9B . . . . -1.1(5) ?
    N7B C8B C9B C10B . . . . 1.3(6) ?
    C8B C9B C10B C11B . . . . -0.1(5) ?
    C9B C10B C11B C6B . . . . -1.1(5) ?
    N7B C6B C11B C10B . . . . 1.3(4) ?
    C2B C6B C11B C10B . . . . -176.0(3) ?
    C13B O1B C12B O2B . . . . -3.9(5) ?
    C13B O1B C12B C3B . . . . 174.9(3) ?
    C2B C3B C12B O2B . . . . 72.3(4) ?
    S1B C3B C12B O2B . . . . -52.8(4) ?
    C2B C3B C12B O1B . . . . -106.4(3) ?
    S1B C3B C12B O1B . . . . 128.4(2) ?
    C12B O1B C13B C14B . . . . -165.0(4) ?
    C16B O5B C15B O6B . . . . -10.6(4) ?
    C16B O5B C15B C4B . . . . 166.0(3) ?
    C5B C4B C15B O6B . . . . 46.4(3) ?
    S1B C4B C15B O6B . . . . -73.8(3) ?
    C5B C4B C15B O5B . . . . -130.3(2) ?
    S1B C4B C15B O5B . . . . 109.5(2) ?
    C15B O5B C16B C17B . . . . -86.6(3) ?
    N1B C5B C18B N23B . . . . -75.4(3) ?
    C4B C5B C18B N23B . . . . 49.7(3) ?
    N1B C5B C18B C19B . . . . 105.2(4) ?
    C4B C5B C18B C19B . . . . -129.7(3) ?
    C19B C18B N23B C22B . . . . 0.0(5) ?
    C5B C18B N23B C22B . . . . -179.3(3) ?
    C18B N23B C22B C21B . . . . -2.3(6) ?
    N23B C22B C21B C20B . . . . 3.0(8) ?
    C22B C21B C20B C19B . . . . -1.3(7) ?
    N23B C18B C19B C20B . . . . 1.5(6) ?
    C5B C18B C19B C20B . . . . -179.3(3) ?
    C21B C20B C19B C18B . . . . -0.7(7) ?
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
    C4B H4B O2B 1 0.98 2.59 3.167(3) 118
    C2A H2A O4B 1_545 0.98 2.34 3.273(3) 158
    C19A H19A O6B 1_545 0.93 2.49 3.360(4) 155
    C5B H5B O4A 1_565 0.98 2.34 3.269(3) 157
    C11B H11B O2A 1_565 0.93 2.53 3.404(4) 156
    C17B H17E O3A 3_565 0.96 2.52 3.402(4) 153
    C14A H14B O3B 3_455 0.96 2.52 3.402(4) 153
