#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/47/1574766.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1574766
loop_
_publ_author_name
'Dassonneville, Benjamin'
'Detert, Heiner'
'Schollmeyer, Dieter'
_publ_section_title
;
 (3Z)-4-Methyl-9-(4-methylbenzenesulfonyl)-N-phenyl-3H,9H-thiopyrano[3,4-b]indol-3-imine
;
_journal_coeditor_code           BT4173
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x250475
_journal_paper_doi               10.1107/S2414314625004754
_journal_volume                  10
_journal_year                    2025
_chemical_formula_iupac          'C25 H20 N2 O2 S2'
_chemical_formula_moiety         'C25 H20 N2 O2 S2'
_chemical_formula_sum            'C25 H20 N2 O2 S2'
_chemical_formula_weight         444.55
_chemical_name_systematic
(3Z)-4-Methyl-9-(4-methylbenzenesulfonyl)-N-phenyl-3H,9H-thiopyrano[3,4-b]indol-3-imine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                110.1289(13)
_cell_angle_beta                 100.7495(16)
_cell_angle_gamma                94.2372(15)
_cell_formula_units_Z            4
_cell_length_a                   9.1997(6)
_cell_length_b                   15.1692(8)
_cell_length_c                   16.7138(9)
_cell_measurement_reflns_used    6518
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     2127.3(2)
_computing_cell_refinement
;
SMART and SAINT (Bruker (1997)
;
_computing_data_collection
;
SMART and SAINT (Bruker (1997)
;
_computing_data_reduction
;
SMART and SAINT (Bruker (1997)
;
_computing_molecular_graphics
;
Platon (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR-2004 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29569
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.903
_diffrn_reflns_theta_min         1.568
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         10121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0548P)²+0.7083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                7293
_reflns_number_total             10121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4173.cif
_cod_data_source_block           I
_cod_database_code               1574766
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.976
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.04721(19) 0.48944(11) 0.37672(10) 0.0314(4) Uani d 1 . .
C C2A 0.0590(2) 0.58682(13) 0.43169(12) 0.0308(4) Uani d 1 . .
C C3A -0.0219(2) 0.65539(15) 0.41690(14) 0.0382(5) Uani d 1 . .
H H3A -0.091966 0.642317 0.363233 0.046 Uiso calc 1 . .
C C4A 0.0034(3) 0.74376(15) 0.48341(15) 0.0433(5) Uani d 1 . .
H H4A -0.048670 0.792537 0.474345 0.052 Uiso calc 1 . .
C C5A 0.1021(3) 0.76293(15) 0.56246(15) 0.0452(5) Uani d 1 . .
H H5A 0.114933 0.823746 0.607353 0.054 Uiso calc 1 . .
C C6A 0.1824(2) 0.69408(15) 0.57670(14) 0.0392(5) Uani d 1 . .
H H6A 0.249815 0.707268 0.631311 0.047 Uiso calc 1 . .
C C7A 0.1637(2) 0.60505(14) 0.51021(12) 0.0312(4) Uani d 1 . .
C C8A 0.2275(2) 0.51789(13) 0.50494(12) 0.0304(4) Uani d 1 . .
C C9A 0.3307(2) 0.50056(14) 0.56565(13) 0.0347(4) Uani d 1 . .
C C10A 0.3678(2) 0.40504(15) 0.55271(13) 0.0367(5) Uani d 1 . .
S S11A 0.31344(7) 0.31426(4) 0.44779(4) 0.04232(14) Uani d 1 . .
C C12A 0.1845(2) 0.35787(15) 0.38829(13) 0.0364(5) Uani d 1 . .
H H12A 0.132372 0.317313 0.331114 0.044 Uiso calc 1 . .
C C13A 0.1549(2) 0.44693(14) 0.41971(12) 0.0303(4) Uani d 1 . .
S S14A -0.01665(5) 0.44661(3) 0.26855(3) 0.03142(12) Uani d 1 . .
O O15A -0.12706(16) 0.50250(11) 0.25037(9) 0.0398(3) Uani d 1 . .
O O16A -0.05747(17) 0.34670(10) 0.24397(9) 0.0405(3) Uani d 1 . .
C C17A 0.1364(2) 0.46768(13) 0.22566(11) 0.0292(4) Uani d 1 . .
C C18A 0.1790(2) 0.55859(14) 0.22872(13) 0.0347(4) Uani d 1 . .
H H18A 0.125516 0.608657 0.253205 0.042 Uiso calc 1 . .
C C19A 0.3004(2) 0.57493(15) 0.19551(14) 0.0387(5) Uani d 1 . .
H H19A 0.330427 0.636964 0.197226 0.046 Uiso calc 1 . .
C C20A 0.3799(2) 0.50230(16) 0.15956(13) 0.0370(5) Uani d 1 . .
C C21A 0.3331(2) 0.41169(15) 0.15598(13) 0.0381(5) Uani d 1 . .
H H21A 0.385417 0.361341 0.130556 0.046 Uiso calc 1 . .
C C22A 0.2120(2) 0.39345(14) 0.18873(12) 0.0352(4) Uani d 1 . .
H H22A 0.180881 0.331184 0.186067 0.042 Uiso calc 1 . .
C C23A 0.5161(3) 0.5223(2) 0.12750(17) 0.0544(6) Uani d 1 . .
H H23A 0.606216 0.529419 0.172362 0.082 Uiso calc 1 . .
H H23B 0.513026 0.581057 0.115455 0.082 Uiso calc 1 . .
H H23C 0.517940 0.469536 0.073783 0.082 Uiso calc 1 . .
C C24A 0.4067(3) 0.57533(17) 0.65269(15) 0.0509(6) Uani d 1 . .
H H24A 0.445393 0.632492 0.643979 0.076 Uiso calc 1 . .
H H24B 0.489644 0.551405 0.680865 0.076 Uiso calc 1 . .
H H24C 0.334568 0.590850 0.689978 0.076 Uiso calc 1 . .
N N25A 0.4383(2) 0.38758(14) 0.61811(12) 0.0451(5) Uani d 1 . .
C C26A 0.4692(2) 0.29518(16) 0.60954(14) 0.0418(5) Uani d 1 . .
C C27A 0.5790(3) 0.25582(19) 0.56890(17) 0.0527(6) Uani d 1 . .
H H27A 0.631147 0.289099 0.541413 0.063 Uiso calc 1 . .
C C28A 0.6136(3) 0.1683(2) 0.5678(2) 0.0632(7) Uani d 1 . .
H H28A 0.689697 0.142053 0.539834 0.076 Uiso calc 1 . .
C C29A 0.5390(3) 0.1192(2) 0.6069(2) 0.0626(7) Uani d 1 . .
H H29A 0.562695 0.058947 0.605950 0.075 Uiso calc 1 . .
C C30A 0.4297(3) 0.1580(2) 0.64749(19) 0.0630(7) Uani d 1 . .
H H30A 0.376979 0.124022 0.674158 0.076 Uiso calc 1 . .
C C31A 0.3954(3) 0.24613(19) 0.65005(17) 0.0527(6) Uani d 1 . .
H H31A 0.321206 0.272907 0.679563 0.063 Uiso calc 1 . .
N N1B 0.5849(2) 0.11035(12) -0.03785(12) 0.0389(4) Uani d 1 . .
C C2B 0.5523(2) 0.02961(15) -0.11763(14) 0.0402(5) Uani d 1 . .
C C3B 0.4545(3) 0.01695(18) -0.19568(17) 0.0539(6) Uani d 1 . .
H H3B 0.399483 0.065558 -0.202339 0.065 Uiso calc 1 . .
C C4B 0.4397(3) -0.0698(2) -0.26406(18) 0.0616(7) Uani d 1 . .
H H4B 0.375848 -0.079614 -0.319031 0.074 Uiso calc 1 . .
C C5B 0.5149(3) -0.14121(19) -0.25407(17) 0.0594(7) Uani d 1 . .
H H5B 0.502002 -0.199723 -0.301958 0.071 Uiso calc 1 . .
C C6B 0.6093(3) -0.12937(16) -0.17531(16) 0.0487(6) Uani d 1 . .
H H6B 0.658470 -0.180031 -0.168331 0.058 Uiso calc 1 . .
C C7B 0.6317(2) -0.04174(14) -0.10569(14) 0.0380(5) Uani d 1 . .
C C8B 0.7225(2) -0.00659(13) -0.01636(13) 0.0343(4) Uani d 1 . .
C C9B 0.8153(3) -0.05090(14) 0.02560(14) 0.0390(5) Uani d 1 . .
C C10B 0.8845(3) -0.00796(14) 0.11901(14) 0.0374(5) Uani d 1 . .
S S11B 0.88750(7) 0.11530(4) 0.17585(4) 0.04207(14) Uani d 1 . .
C C12B 0.7609(3) 0.14905(14) 0.10594(14) 0.0378(5) Uani d 1 . .
H H12B 0.737776 0.211879 0.125847 0.045 Uiso calc 1 . .
C C13B 0.6941(2) 0.09021(14) 0.02483(13) 0.0342(4) Uani d 1 . .
S S14B 0.57056(6) 0.22115(4) -0.03227(4) 0.03805(13) Uani d 1 . .
O O15B 0.44857(18) 0.21419(12) -0.10166(12) 0.0539(4) Uani d 1 . .
O O16B 0.56583(18) 0.27399(11) 0.05614(11) 0.0484(4) Uani d 1 . .
C C17B 0.7374(2) 0.26277(14) -0.05261(13) 0.0333(4) Uani d 1 . .
C C18B 0.7710(3) 0.21880(15) -0.13335(16) 0.0455(6) Uani d 1 . .
H H18B 0.704340 0.166844 -0.177597 0.055 Uiso calc 1 . .
C C19B 0.9034(3) 0.25224(17) -0.14790(18) 0.0539(7) Uani d 1 . .
H H19B 0.927828 0.222265 -0.202737 0.065 Uiso calc 1 . .
C C20B 1.0015(3) 0.32839(19) -0.08460(19) 0.0526(6) Uani d 1 . .
C C21B 0.9635(3) 0.3720(2) -0.00578(17) 0.0547(7) Uani d 1 . .
H H21B 1.028335 0.425561 0.037600 0.066 Uiso calc 1 . .
C C22B 0.8327(3) 0.33931(17) 0.01124(15) 0.0443(5) Uani d 1 . .
H H22B 0.808702 0.369169 0.066237 0.053 Uiso calc 1 . .
C C23B 1.1475(3) 0.3622(3) -0.1015(2) 0.0796(10) Uani d 1 . .
H H23D 1.128407 0.370361 -0.157994 0.119 Uiso calc 1 . .
H H23E 1.215342 0.315164 -0.102407 0.119 Uiso calc 1 . .
H H23F 1.193505 0.423016 -0.054939 0.119 Uiso calc 1 . .
C C24B 0.8473(3) -0.15006(16) -0.01953(16) 0.0553(7) Uani d 1 . .
H H24D 0.755078 -0.195395 -0.037102 0.083 Uiso calc 1 . .
H H24E 0.922891 -0.166211 0.020704 0.083 Uiso calc 1 . .
H H24F 0.884531 -0.152861 -0.071463 0.083 Uiso calc 1 . .
N N25B 0.9425(2) -0.06027(13) 0.15837(12) 0.0445(5) Uani d 1 . .
C C26B 1.0101(3) -0.02585(15) 0.24820(15) 0.0414(5) Uani d 1 . .
C C27B 1.1430(3) 0.03578(17) 0.28392(17) 0.0524(6) Uani d 1 . .
H H27B 1.187374 0.062140 0.248629 0.063 Uiso calc 1 . .
C C28B 1.2118(3) 0.05929(18) 0.37085(19) 0.0610(7) Uani d 1 . .
H H28B 1.303256 0.101967 0.394939 0.073 Uiso calc 1 . .
C C29B 1.1502(4) 0.0220(2) 0.42261(18) 0.0634(8) Uani d 1 . .
H H29B 1.197866 0.038921 0.482484 0.076 Uiso calc 1 . .
C C30B 1.0187(4) -0.0402(2) 0.38730(19) 0.0676(8) Uani d 1 . .
H H30B 0.975712 -0.066580 0.423004 0.081 Uiso calc 1 . .
C C31B 0.9483(3) -0.06469(19) 0.30064(16) 0.0535(6) Uani d 1 . .
H H31B 0.857618 -0.108095 0.276788 0.064 Uiso calc 1 . .
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'
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
C2A N1A C13A . . 107.99(15) ?
C2A N1A S14A . . 124.64(13) ?
C13A N1A S14A . . 122.07(13) ?
C3A C2A C7A . . 122.10(18) ?
C3A C2A N1A . . 128.44(18) ?
C7A C2A N1A . . 109.38(17) ?
C4A C3A C2A . . 117.4(2) ?
C4A C3A H3A . . 121.3 ?
C2A C3A H3A . . 121.3 ?
C5A C4A C3A . . 121.9(2) ?
C5A C4A H4A . . 119.1 ?
C3A C4A H4A . . 119.1 ?
C4A C5A C6A . . 120.4(2) ?
C4A C5A H5A . . 119.8 ?
C6A C5A H5A . . 119.8 ?
C5A C6A C7A . . 119.5(2) ?
C5A C6A H6A . . 120.2 ?
C7A C6A H6A . . 120.2 ?
C6A C7A C2A . . 118.70(19) ?
C6A C7A C8A . . 132.95(19) ?
C2A C7A C8A . . 108.25(16) ?
C9A C8A C13A . . 123.94(18) ?
C9A C8A C7A . . 129.66(18) ?
C13A C8A C7A . . 106.37(16) ?
C8A C9A C10A . . 121.81(18) ?
C8A C9A C24A . . 123.15(19) ?
C10A C9A C24A . . 114.91(18) ?
N25A C10A C9A . . 119.54(19) ?
N25A C10A S11A . . 120.38(17) ?
C9A C10A S11A . . 120.08(15) ?
C12A S11A C10A . . 104.78(10) ?
C13A C12A S11A . . 122.37(16) ?
C13A C12A H12A . . 118.8 ?
S11A C12A H12A . . 118.8 ?
C12A C13A N1A . . 126.85(18) ?
C12A C13A C8A . . 125.28(18) ?
N1A C13A C8A . . 107.88(16) ?
O15A S14A O16A . . 119.65(9) ?
O15A S14A N1A . . 106.32(8) ?
O16A S14A N1A . . 106.06(8) ?
O15A S14A C17A . . 109.16(9) ?
O16A S14A C17A . . 109.23(9) ?
N1A S14A C17A . . 105.46(9) ?
C18A C17A C22A . . 121.26(19) ?
C18A C17A S14A . . 118.97(15) ?
C22A C17A S14A . . 119.77(16) ?
C19A C18A C17A . . 118.71(18) ?
C19A C18A H18A . . 120.6 ?
C17A C18A H18A . . 120.6 ?
C18A C19A C20A . . 121.3(2) ?
C18A C19A H19A . . 119.4 ?
C20A C19A H19A . . 119.4 ?
C21A C20A C19A . . 118.8(2) ?
C21A C20A C23A . . 120.7(2) ?
C19A C20A C23A . . 120.5(2) ?
C22A C21A C20A . . 121.13(19) ?
C22A C21A H21A . . 119.4 ?
C20A C21A H21A . . 119.4 ?
C21A C22A C17A . . 118.87(19) ?
C21A C22A H22A . . 120.6 ?
C17A C22A H22A . . 120.6 ?
C20A C23A H23A . . 109.5 ?
C20A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
C20A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C9A C24A H24A . . 109.5 ?
C9A C24A H24B . . 109.5 ?
H24A C24A H24B . . 109.5 ?
C9A C24A H24C . . 109.5 ?
H24A C24A H24C . . 109.5 ?
H24B C24A H24C . . 109.5 ?
C10A N25A C26A . . 121.39(19) ?
C27A C26A C31A . . 118.9(2) ?
C27A C26A N25A . . 122.3(2) ?
C31A C26A N25A . . 118.5(2) ?
C26A C27A C28A . . 120.5(2) ?
C26A C27A H27A . . 119.7 ?
C28A C27A H27A . . 119.7 ?
C29A C28A C27A . . 120.5(3) ?
C29A C28A H28A . . 119.8 ?
C27A C28A H28A . . 119.8 ?
C28A C29A C30A . . 119.2(3) ?
C28A C29A H29A . . 120.4 ?
C30A C29A H29A . . 120.4 ?
C29A C30A C31A . . 120.9(3) ?
C29A C30A H30A . . 119.6 ?
C31A C30A H30A . . 119.6 ?
C30A C31A C26A . . 119.9(2) ?
C30A C31A H31A . . 120.0 ?
C26A C31A H31A . . 120.0 ?
C2B N1B C13B . . 107.83(17) ?
C2B N1B S14B . . 124.10(15) ?
C13B N1B S14B . . 121.76(14) ?
C3B C2B C7B . . 122.3(2) ?
C3B C2B N1B . . 128.3(2) ?
C7B C2B N1B . . 109.39(19) ?
C2B C3B C4B . . 117.4(3) ?
C2B C3B H3B . . 121.3 ?
C4B C3B H3B . . 121.3 ?
C5B C4B C3B . . 121.6(3) ?
C5B C4B H4B . . 119.2 ?
C3B C4B H4B . . 119.2 ?
C4B C5B C6B . . 120.9(2) ?
C4B C5B H5B . . 119.6 ?
C6B C5B H5B . . 119.6 ?
C5B C6B C7B . . 119.3(2) ?
C5B C6B H6B . . 120.3 ?
C7B C6B H6B . . 120.3 ?
C2B C7B C6B . . 118.5(2) ?
C2B C7B C8B . . 108.67(18) ?
C6B C7B C8B . . 132.8(2) ?
C9B C8B C13B . . 123.72(19) ?
C9B C8B C7B . . 129.98(18) ?
C13B C8B C7B . . 106.28(18) ?
C8B C9B C10B . . 122.24(18) ?
C8B C9B C24B . . 122.7(2) ?
C10B C9B C24B . . 114.99(19) ?
N25B C10B C9B . . 119.01(18) ?
N25B C10B S11B . . 121.17(17) ?
C9B C10B S11B . . 119.82(15) ?
C12B S11B C10B . . 104.57(10) ?
C13B C12B S11B . . 122.56(16) ?
C13B C12B H12B . . 118.7 ?
S11B C12B H12B . . 118.7 ?
C12B C13B N1B . . 127.04(18) ?
C12B C13B C8B . . 125.2(2) ?
N1B C13B C8B . . 107.74(17) ?
O15B S14B O16B . . 119.76(10) ?
O15B S14B N1B . . 106.28(10) ?
O16B S14B N1B . . 106.09(9) ?
O15B S14B C17B . . 109.44(10) ?
O16B S14B C17B . . 108.75(10) ?
N1B S14B C17B . . 105.57(9) ?
C22B C17B C18B . . 120.9(2) ?
C22B C17B S14B . . 119.69(17) ?
C18B C17B S14B . . 119.41(17) ?
C19B C18B C17B . . 118.5(2) ?
C19B C18B H18B . . 120.7 ?
C17B C18B H18B . . 120.7 ?
C18B C19B C20B . . 121.7(2) ?
C18B C19B H19B . . 119.2 ?
C20B C19B H19B . . 119.2 ?
C21B C20B C19B . . 118.5(2) ?
C21B C20B C23B . . 120.9(3) ?
C19B C20B C23B . . 120.6(3) ?
C20B C21B C22B . . 121.2(2) ?
C20B C21B H21B . . 119.4 ?
C22B C21B H21B . . 119.4 ?
C17B C22B C21B . . 119.2(2) ?
C17B C22B H22B . . 120.4 ?
C21B C22B H22B . . 120.4 ?
C20B C23B H23D . . 109.5 ?
C20B C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
C20B C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 109.5 ?
C9B C24B H24D . . 109.5 ?
C9B C24B H24E . . 109.5 ?
H24D C24B H24E . . 109.5 ?
C9B C24B H24F . . 109.5 ?
H24D C24B H24F . . 109.5 ?
H24E C24B H24F . . 109.5 ?
C10B N25B C26B . . 123.26(18) ?
C27B C26B C31B . . 119.0(2) ?
C27B C26B N25B . . 122.9(2) ?
C31B C26B N25B . . 117.7(2) ?
C26B C27B C28B . . 120.2(3) ?
C26B C27B H27B . . 119.9 ?
C28B C27B H27B . . 119.9 ?
C29B C28B C27B . . 120.8(3) ?
C29B C28B H28B . . 119.6 ?
C27B C28B H28B . . 119.6 ?
C28B C29B C30B . . 119.3(3) ?
C28B C29B H29B . . 120.3 ?
C30B C29B H29B . . 120.3 ?
C29B C30B C31B . . 120.8(3) ?
C29B C30B H30B . . 119.6 ?
C31B C30B H30B . . 119.6 ?
C30B C31B C26B . . 119.9(3) ?
C30B C31B H31B . . 120.0 ?
C26B C31B H31B . . 120.0 ?
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
N1A C2A . 1.429(2) ?
N1A C13A . 1.436(2) ?
N1A S14A . 1.6659(16) ?
C2A C3A . 1.385(3) ?
C2A C7A . 1.402(3) ?
C3A C4A . 1.385(3) ?
C3A H3A . 0.9500 ?
C4A C5A . 1.380(3) ?
C4A H4A . 0.9500 ?
C5A C6A . 1.383(3) ?
C5A H5A . 0.9500 ?
C6A C7A . 1.396(3) ?
C6A H6A . 0.9500 ?
C7A C8A . 1.468(3) ?
C8A C9A . 1.364(3) ?
C8A C13A . 1.455(3) ?
C9A C10A . 1.465(3) ?
C9A C24A . 1.503(3) ?
C10A N25A . 1.283(3) ?
C10A S11A . 1.769(2) ?
S11A C12A . 1.721(2) ?
C12A C13A . 1.339(3) ?
C12A H12A . 0.9500 ?
S14A O15A . 1.4255(15) ?
S14A O16A . 1.4271(15) ?
S14A C17A . 1.751(2) ?
C17A C18A . 1.386(3) ?
C17A C22A . 1.389(3) ?
C18A C19A . 1.380(3) ?
C18A H18A . 0.9500 ?
C19A C20A . 1.391(3) ?
C19A H19A . 0.9500 ?
C20A C21A . 1.387(3) ?
C20A C23A . 1.502(3) ?
C21A C22A . 1.380(3) ?
C21A H21A . 0.9500 ?
C22A H22A . 0.9500 ?
C23A H23A . 0.9800 ?
C23A H23B . 0.9800 ?
C23A H23C . 0.9800 ?
C24A H24A . 0.9800 ?
C24A H24B . 0.9800 ?
C24A H24C . 0.9800 ?
N25A C26A . 1.415(3) ?
C26A C27A . 1.379(3) ?
C26A C31A . 1.385(3) ?
C27A C28A . 1.383(4) ?
C27A H27A . 0.9500 ?
C28A C29A . 1.371(4) ?
C28A H28A . 0.9500 ?
C29A C30A . 1.373(4) ?
C29A H29A . 0.9500 ?
C30A C31A . 1.384(4) ?
C30A H30A . 0.9500 ?
C31A H31A . 0.9500 ?
N1B C2B . 1.428(3) ?
N1B C13B . 1.440(3) ?
N1B S14B . 1.6674(18) ?
C2B C3B . 1.383(3) ?
C2B C7B . 1.399(3) ?
C3B C4B . 1.391(4) ?
C3B H3B . 0.9500 ?
C4B C5B . 1.369(4) ?
C4B H4B . 0.9500 ?
C5B C6B . 1.381(4) ?
C5B H5B . 0.9500 ?
C6B C7B . 1.403(3) ?
C6B H6B . 0.9500 ?
C7B C8B . 1.460(3) ?
C8B C9B . 1.364(3) ?
C8B C13B . 1.458(3) ?
C9B C10B . 1.461(3) ?
C9B C24B . 1.512(3) ?
C10B N25B . 1.280(3) ?
C10B S11B . 1.777(2) ?
S11B C12B . 1.725(2) ?
C12B C13B . 1.337(3) ?
C12B H12B . 0.9500 ?
S14B O15B . 1.4241(17) ?
S14B O16B . 1.4289(16) ?
S14B C17B . 1.752(2) ?
C17B C22B . 1.379(3) ?
C17B C18B . 1.389(3) ?
C18B C19B . 1.380(3) ?
C18B H18B . 0.9500 ?
C19B C20B . 1.384(4) ?
C19B H19B . 0.9500 ?
C20B C21B . 1.379(4) ?
C20B C23B . 1.512(3) ?
C21B C22B . 1.383(3) ?
C21B H21B . 0.9500 ?
C22B H22B . 0.9500 ?
C23B H23D . 0.9800 ?
C23B H23E . 0.9800 ?
C23B H23F . 0.9800 ?
C24B H24D . 0.9800 ?
C24B H24E . 0.9800 ?
C24B H24F . 0.9800 ?
N25B C26B . 1.406(3) ?
C26B C27B . 1.378(3) ?
C26B C31B . 1.389(3) ?
C27B C28B . 1.380(4) ?
C27B H27B . 0.9500 ?
C28B C29B . 1.364(4) ?
C28B H28B . 0.9500 ?
C29B C30B . 1.372(4) ?
C29B H29B . 0.9500 ?
C30B C31B . 1.378(4) ?
C30B H30B . 0.9500 ?
C31B H31B . 0.9500 ?
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
C3A H3A O15A . 0.95 2.25 2.878(3) 123
C3B H3B O15B . 0.95 2.25 2.871(3) 122
C12A H12A O16A . 0.95 2.23 2.909(2) 127
C12B H12B O16B . 0.95 2.24 2.922(3) 128
C21A H21A O16B . 0.95 2.45 3.366(3) 161
C22A H22A O16A . 0.95 2.55 2.923(2) 104
C22B H22B O16B . 0.95 2.51 2.900(3) 104
C24A H24B N25A . 0.98 2.31 2.754(4) 106
C24B H24E N25B . 0.98 2.27 2.744(3) 108
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
C13A N1A C2A C3A . . . . 179.6(2) ?
S14A N1A C2A C3A . . . . 25.1(3) ?
C13A N1A C2A C7A . . . . -3.8(2) ?
S14A N1A C2A C7A . . . . -158.39(14) ?
C7A C2A C3A C4A . . . . -0.5(3) ?
N1A C2A C3A C4A . . . . 175.62(19) ?
C2A C3A C4A C5A . . . . -1.7(3) ?
C3A C4A C5A C6A . . . . 1.7(4) ?
C4A C5A C6A C7A . . . . 0.4(3) ?
C5A C6A C7A C2A . . . . -2.5(3) ?
C5A C6A C7A C8A . . . . -178.3(2) ?
C3A C2A C7A C6A . . . . 2.6(3) ?
N1A C2A C7A C6A . . . . -174.23(17) ?
C3A C2A C7A C8A . . . . 179.35(18) ?
N1A C2A C7A C8A . . . . 2.6(2) ?
C6A C7A C8A C9A . . . . -2.4(4) ?
C2A C7A C8A C9A . . . . -178.5(2) ?
C6A C7A C8A C13A . . . . 175.8(2) ?
C2A C7A C8A C13A . . . . -0.3(2) ?
C13A C8A C9A C10A . . . . -5.6(3) ?
C7A C8A C9A C10A . . . . 172.34(19) ?
C13A C8A C9A C24A . . . . 178.8(2) ?
C7A C8A C9A C24A . . . . -3.3(3) ?
C8A C9A C10A N25A . . . . -164.4(2) ?
C24A C9A C10A N25A . . . . 11.6(3) ?
C8A C9A C10A S11A . . . . 14.8(3) ?
C24A C9A C10A S11A . . . . -169.15(17) ?
N25A C10A S11A C12A . . . . 164.98(18) ?
C9A C10A S11A C12A . . . . -14.2(2) ?
C10A S11A C12A C13A . . . . 6.6(2) ?
S11A C12A C13A N1A . . . . -178.19(16) ?
S11A C12A C13A C8A . . . . 1.4(3) ?
C2A N1A C13A C12A . . . . -176.75(19) ?
S14A N1A C13A C12A . . . . -21.4(3) ?
C2A N1A C13A C8A . . . . 3.6(2) ?
S14A N1A C13A C8A . . . . 158.90(13) ?
C9A C8A C13A C12A . . . . -3.4(3) ?
C7A C8A C13A C12A . . . . 178.32(19) ?
C9A C8A C13A N1A . . . . 176.31(18) ?
C7A C8A C13A N1A . . . . -2.0(2) ?
C2A N1A S14A O15A . . . . -32.36(18) ?
C13A N1A S14A O15A . . . . 176.49(15) ?
C2A N1A S14A O16A . . . . -160.73(15) ?
C13A N1A S14A O16A . . . . 48.12(17) ?
C2A N1A S14A C17A . . . . 83.47(17) ?
C13A N1A S14A C17A . . . . -67.68(17) ?
O15A S14A C17A C18A . . . . 36.65(18) ?
O16A S14A C17A C18A . . . . 169.17(15) ?
N1A S14A C17A C18A . . . . -77.22(16) ?
O15A S14A C17A C22A . . . . -142.83(15) ?
O16A S14A C17A C22A . . . . -10.31(18) ?
N1A S14A C17A C22A . . . . 103.30(16) ?
C22A C17A C18A C19A . . . . -1.1(3) ?
S14A C17A C18A C19A . . . . 179.45(15) ?
C17A C18A C19A C20A . . . . -0.1(3) ?
C18A C19A C20A C21A . . . . 1.2(3) ?
C18A C19A C20A C23A . . . . -177.1(2) ?
C19A C20A C21A C22A . . . . -1.2(3) ?
C23A C20A C21A C22A . . . . 177.2(2) ?
C20A C21A C22A C17A . . . . 0.1(3) ?
C18A C17A C22A C21A . . . . 1.1(3) ?
S14A C17A C22A C21A . . . . -179.45(15) ?
C9A C10A N25A C26A . . . . 176.5(2) ?
S11A C10A N25A C26A . . . . -2.7(3) ?
C10A N25A C26A C27A . . . . 74.8(3) ?
C10A N25A C26A C31A . . . . -110.9(3) ?
C31A C26A C27A C28A . . . . 0.7(4) ?
N25A C26A C27A C28A . . . . 174.9(2) ?
C26A C27A C28A C29A . . . . 0.2(4) ?
C27A C28A C29A C30A . . . . -0.3(5) ?
C28A C29A C30A C31A . . . . -0.6(5) ?
C29A C30A C31A C26A . . . . 1.5(4) ?
C27A C26A C31A C30A . . . . -1.5(4) ?
N25A C26A C31A C30A . . . . -176.0(2) ?
C13B N1B C2B C3B . . . . -179.8(2) ?
S14B N1B C2B C3B . . . . -27.5(3) ?
C13B N1B C2B C7B . . . . 2.8(2) ?
S14B N1B C2B C7B . . . . 155.11(15) ?
C7B C2B C3B C4B . . . . -1.5(4) ?
N1B C2B C3B C4B . . . . -178.6(2) ?
C2B C3B C4B C5B . . . . 2.1(4) ?
C3B C4B C5B C6B . . . . -0.3(4) ?
C4B C5B C6B C7B . . . . -2.1(4) ?
C3B C2B C7B C6B . . . . -0.8(3) ?
N1B C2B C7B C6B . . . . 176.74(18) ?
C3B C2B C7B C8B . . . . -179.1(2) ?
N1B C2B C7B C8B . . . . -1.5(2) ?
C5B C6B C7B C2B . . . . 2.6(3) ?
C5B C6B C7B C8B . . . . -179.6(2) ?
C2B C7B C8B C9B . . . . 178.5(2) ?
C6B C7B C8B C9B . . . . 0.6(4) ?
C2B C7B C8B C13B . . . . -0.3(2) ?
C6B C7B C8B C13B . . . . -178.2(2) ?
C13B C8B C9B C10B . . . . 6.0(3) ?
C7B C8B C9B C10B . . . . -172.7(2) ?
C13B C8B C9B C24B . . . . -177.7(2) ?
C7B C8B C9B C24B . . . . 3.6(4) ?
C8B C9B C10B N25B . . . . 164.6(2) ?
C24B C9B C10B N25B . . . . -12.0(3) ?
C8B C9B C10B S11B . . . . -15.6(3) ?
C24B C9B C10B S11B . . . . 167.81(17) ?
N25B C10B S11B C12B . . . . -165.89(19) ?
C9B C10B S11B C12B . . . . 14.4(2) ?
C10B S11B C12B C13B . . . . -5.8(2) ?
S11B C12B C13B N1B . . . . 178.52(16) ?
S11B C12B C13B C8B . . . . -2.8(3) ?
C2B N1B C13B C12B . . . . 175.9(2) ?
S14B N1B C13B C12B . . . . 22.9(3) ?
C2B N1B C13B C8B . . . . -3.0(2) ?
S14B N1B C13B C8B . . . . -156.04(14) ?
C9B C8B C13B C12B . . . . 4.1(3) ?
C7B C8B C13B C12B . . . . -176.9(2) ?
C9B C8B C13B N1B . . . . -176.93(19) ?
C7B C8B C13B N1B . . . . 2.0(2) ?
C2B N1B S14B O15B . . . . 33.6(2) ?
C13B N1B S14B O15B . . . . -177.74(16) ?
C2B N1B S14B O16B . . . . 162.11(17) ?
C13B N1B S14B O16B . . . . -49.25(18) ?
C2B N1B S14B C17B . . . . -82.56(19) ?
C13B N1B S14B C17B . . . . 66.08(18) ?
O15B S14B C17B C22B . . . . 128.49(17) ?
O16B S14B C17B C22B . . . . -4.02(19) ?
N1B S14B C17B C22B . . . . -117.50(17) ?
O15B S14B C17B C18B . . . . -50.74(19) ?
O16B S14B C17B C18B . . . . 176.76(16) ?
N1B S14B C17B C18B . . . . 63.27(18) ?
C22B C17B C18B C19B . . . . 1.2(3) ?
S14B C17B C18B C19B . . . . -179.61(17) ?
C17B C18B C19B C20B . . . . -0.6(3) ?
C18B C19B C20B C21B . . . . -0.9(4) ?
C18B C19B C20B C23B . . . . 178.6(2) ?
C19B C20B C21B C22B . . . . 1.9(4) ?
C23B C20B C21B C22B . . . . -177.6(2) ?
C18B C17B C22B C21B . . . . -0.3(3) ?
S14B C17B C22B C21B . . . . -179.47(17) ?
C20B C21B C22B C17B . . . . -1.3(3) ?
C9B C10B N25B C26B . . . . -179.3(2) ?
S11B C10B N25B C26B . . . . 1.0(3) ?
C10B N25B C26B C27B . . . . -68.9(3) ?
C10B N25B C26B C31B . . . . 118.7(2) ?
C31B C26B C27B C28B . . . . -0.9(3) ?
N25B C26B C27B C28B . . . . -173.2(2) ?
C26B C27B C28B C29B . . . . 0.2(4) ?
C27B C28B C29B C30B . . . . 0.5(4) ?
C28B C29B C30B C31B . . . . -0.4(4) ?
C29B C30B C31B C26B . . . . -0.4(4) ?
C27B C26B C31B C30B . . . . 1.0(4) ?
N25B C26B C31B C30B . . . . 173.7(2) ?
