#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158967.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158967
loop_
_publ_author_name
'Liu, Baolin'
'Deng, Qingsong'
'Zhang, Lei'
'Meng, Xiangtai'
_publ_section_title
;
 Switchable C2/C3 positional selectivity of thioisatins in a
 three-component domino reaction: combined computational and experimental
 studies
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01764D
_journal_year                    2022
_chemical_absolute_configuration ab
_chemical_formula_moiety         'C19 H16 N2 O S'
_chemical_formula_sum            'C19 H16 N2 O S'
_chemical_formula_weight         320.39
_chemical_name_systematic        1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.94330(10)
_cell_length_b                   17.21630(10)
_cell_length_c                   18.86940(10)
_cell_measurement_reflns_used    19162
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9730
_cell_measurement_theta_min      2.3280
_cell_volume                     3230.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  66.00   0.50    0.52    --   42.30 -65.00  90.00  150
  2  ω     38.00 132.00   0.50    0.52    --   42.30  77.00-150.00  188
  3  ω     -3.00  27.00   0.50    0.52    --   42.30 -77.00  90.00   60
  4  ω     -4.00  69.00   0.50    0.52    --   42.30 -82.00-180.00  146
  5  ω     44.00  69.00   0.50    0.52    --   42.30 -82.00-120.00   50
  6  ω     14.00  41.00   0.50    0.52    --   42.30 -54.00 -60.00   54
  7  ω     47.00  73.00   0.50    0.52    --   42.30  65.00 -30.00   52
  8  ω     39.00  67.00   0.50    0.52    --   42.30  65.00-180.00   56
  9  ω     36.00  82.00   0.50    0.52    --   42.30  65.00 -90.00   92
 10  ω    -42.00 -12.00   0.50    0.52    --   42.30 -54.00 -60.00   60
 11  ω    -42.00 -13.00   0.50    0.52    --   42.30 -82.00-180.00   58
 12  ω    -24.00   1.00   0.50    0.52    --   42.30 -82.00-120.00   50
 13  ω    -37.00 -12.00   0.50    0.52    --   42.30 -65.00  90.00   50
 14  ω    -43.00  70.00   0.50    0.52    --   42.30 -82.00   0.00  226
 15  ω     17.00 132.00   0.50    0.52    --   42.30  54.00 -30.00  230
 16  ω     30.00  61.00   0.50    0.52    --   42.30 -77.00 -60.00   62
 17  ω     41.00  68.00   0.50    0.52    --   42.30 -77.00  90.00   54
 18  ω     78.00 128.00   0.50    0.52    --   42.30  65.00-180.00  100
 19  ω    -39.00 -14.00   0.50    0.52    --   42.30 -77.00  90.00   50
 20  ω      4.00  69.00   0.50    0.52    --   42.30 -82.00  60.00  130
 21  ω     59.00 182.00   0.50    1.00    --   93.70  33.00  60.00  246
 22  ω     38.00 114.00   0.50    1.00    --   93.70 -50.00-120.00  152
 23  ω     59.00 119.00   0.50    1.00    --   93.70 -42.00   0.00  120
 24  ω     73.00 101.00   0.50    1.00    --   93.70 -82.00 150.00   56
 25  ω      8.00  68.00   0.50    1.00    --   93.70 -82.00 150.00  120
 26  ω      4.00  34.00   0.50    1.00    --   93.70 -50.00-120.00   60
 27  ω     34.00 110.00   0.50    1.00    --   93.70 -82.00  30.00  152
 28  ω     45.00  96.00   0.50    1.00    --   93.70 -82.00  90.00  102
 29  ω     22.00  48.00   0.50    1.00    --   93.70 -42.00   0.00   52
 30  ω    145.00 170.00   0.50    1.00    --   93.70  33.00-120.00   50
 31  ω     25.00  97.00   0.50    1.00    --   93.70 -82.00-150.00  144
 32  ω     21.00  68.00   0.50    1.00    --   93.70 -82.00-180.00   94
 33  ω      6.00  34.00   0.50    1.00    --   93.70 -82.00  90.00   56
 34  ω      4.00  95.00   0.50    1.00    --   93.70 -82.00  60.00  182
 35  ω     40.00  96.00   0.50    1.00    --   93.70 -82.00   0.00  112
 36  ω    105.00 173.00   0.50    1.00    --   93.70  42.00 -60.00  136
 37  ω     99.00 162.00   0.50    1.00    --   93.70  68.00  90.00  126
 38  ω     44.00  92.00   0.50    1.00    --   93.70 -82.00 120.00   96
 39  ω     69.00  95.00   0.50    1.00    --   93.70 -82.00 -60.00   52
 40  ω     31.00 111.00   0.50    1.00    --   93.70 -82.00 -90.00  160
 41  ω    112.00 166.00   0.50    1.00    --   93.70  50.00 -30.00  108
 42  ω     64.00 165.00   0.50    1.00    --   93.70  33.00   0.00  202
 43  ω     68.00  98.00   0.50    1.00    --   93.70 -82.00 -30.00   60
 44  ω     73.00  98.00   0.50    1.00    --   93.70 -82.00-180.00   50
 45  ω      4.00  98.00   0.50    1.00    --   93.70 -82.00-120.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1293372000
_diffrn_orient_matrix_UB_12      -0.0360505000
_diffrn_orient_matrix_UB_13      -0.0306174000
_diffrn_orient_matrix_UB_21      0.0483703000
_diffrn_orient_matrix_UB_22      0.0812395000
_diffrn_orient_matrix_UB_23      -0.0228128000
_diffrn_orient_matrix_UB_31      0.0702655000
_diffrn_orient_matrix_UB_32      0.0104234000
_diffrn_orient_matrix_UB_33      0.0721588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear blackish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.015(16)
_refine_ls_extinction_coef       0.0050(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0313
_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)+(0.0537P)²+0.1524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5593
_reflns_number_total             5865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01764d2.cif
_cod_data_source_block           zj20210426_auto
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H32 N4 O2 S2'
_cod_original_formula_weight         640.79
_cod_original_formula_moiety         '2(C19 H16 N2 O S)'
_cod_original_formula_units_Z            4
_cod_database_code               7158967
_shelx_shelxl_version_number     2018/3
_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_max   0.915
_shelx_estimated_absorpt_t_min   0.899
_diffrn_oxdiff_digest_frames
;
01306a6a4f7d41633db7d1dafb3efbb0da00028ff4a
;
_diffrn_oxdiff_digest_hkl
;
0142b8cb57d44e4a9609a76cb15ce2b6b331e3
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.015(16)
 -0.015(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 N44(H44), N21(H21), C27(H27), C4(H4), C39(H39), C6(H6), C7(H7), C42(H42),
 C16(H16), C17(H17), C40(H40), C19(H19), C29(H29), C41(H41), C30(H30), C18(H18)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C46(H46A,H46B,H46C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.582
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S9 S 0.82063(7) 0.44401(4) 0.39052(4) 0.0601(2) Uani 1 1 d . . . . .
S32 S 0.29577(8) 0.18350(5) 0.43492(4) 0.0653(2) Uani 1 1 d . . . . .
N44 N 0.2523(2) 0.36135(10) 0.28837(10) 0.0424(4) Uani 1 1 d . . . . .
H44 H 0.287543 0.371052 0.329029 0.051 Uiso 1 1 calc R . . . .
O22 O 0.6665(2) 0.48408(14) 0.49810(10) 0.0735(6) Uani 1 1 d . . . . .
N21 N 0.50783(19) 0.62020(11) 0.38577(11) 0.0450(4) Uani 1 1 d . . . . .
H21 H 0.581703 0.633325 0.365321 0.054 Uiso 1 1 calc R . . . .
O45 O 0.0787(2) 0.19103(15) 0.35559(11) 0.0742(6) Uani 1 1 d . . . . .
N10 N 0.4605(2) 0.40587(12) 0.39578(10) 0.0474(5) Uani 1 1 d . . . . .
N33 N 0.2797(2) 0.15374(12) 0.23600(12) 0.0471(5) Uani 1 1 d . . . . .
C14 C 0.4656(2) 0.54517(13) 0.39963(11) 0.0412(5) Uani 1 1 d . . . . .
C37 C 0.2427(2) 0.28942(12) 0.25651(11) 0.0389(5) Uani 1 1 d . . . . .
C36 C 0.1767(2) 0.29438(13) 0.19377(12) 0.0433(5) Uani 1 1 d . . . . .
C38 C 0.1949(2) 0.41476(13) 0.24321(13) 0.0442(5) Uani 1 1 d . . . . .
C43 C 0.1474(2) 0.37494(14) 0.18327(12) 0.0445(5) Uani 1 1 d . . . . .
C25 C 0.2902(2) 0.21524(12) 0.29056(11) 0.0401(5) Uani 1 1 d . . . . .
C27 C 0.5445(2) 0.23465(14) 0.27836(14) 0.0481(5) Uani 1 1 d . . . . .
H27 H 0.534039 0.245370 0.230368 0.058 Uiso 1 1 calc R . . . .
C4 C 0.5339(2) 0.48258(13) 0.24889(13) 0.0443(5) Uani 1 1 d . . . . .
H4 H 0.442637 0.493981 0.251535 0.053 Uiso 1 1 calc R . . . .
C26 C 0.4322(2) 0.21885(12) 0.31871(12) 0.0419(5) Uani 1 1 d . . . . .
C15 C 0.4098(3) 0.67042(14) 0.41075(12) 0.0462(5) Uani 1 1 d . . . . .
C5 C 0.5953(3) 0.47724(14) 0.18267(12) 0.0469(5) Uani 1 1 d . . . . .
C2 C 0.5476(2) 0.47486(13) 0.38447(12) 0.0417(5) Uani 1 1 d . . . . .
C3 C 0.6056(2) 0.47133(12) 0.31050(12) 0.0409(5) Uani 1 1 d . . . . .
C13 C 0.3450(2) 0.54568(14) 0.43407(12) 0.0461(5) Uani 1 1 d . . . . .
C39 C 0.1815(2) 0.49525(14) 0.25046(16) 0.0554(6) Uani 1 1 d . . . . .
H39 H 0.212060 0.521036 0.290661 0.067 Uiso 1 1 calc R . . . .
C28 C 0.6736(3) 0.23501(14) 0.30755(16) 0.0551(6) Uani 1 1 d . . . . .
C1 C 0.6709(3) 0.47169(14) 0.43558(13) 0.0502(6) Uani 1 1 d . . . . .
C6 C 0.7335(3) 0.46275(15) 0.18089(14) 0.0539(6) Uani 1 1 d . . . . .
H6 H 0.777185 0.460731 0.137349 0.065 Uiso 1 1 calc R . . . .
C34 C 0.1518(3) 0.15322(15) 0.19612(16) 0.0565(6) Uani 1 1 d . . . . .
H34A H 0.076768 0.151894 0.228954 0.068 Uiso 1 1 calc R . . . .
H34B H 0.147309 0.107138 0.166634 0.068 Uiso 1 1 calc R . . . .
C24 C 0.1993(3) 0.19711(14) 0.35623(13) 0.0500(6) Uani 1 1 d . . . . .
C35 C 0.1421(3) 0.22500(16) 0.15016(14) 0.0568(6) Uani 1 1 d . . . . .
H35A H 0.203751 0.220756 0.110509 0.068 Uiso 1 1 calc R . . . .
H35B H 0.051591 0.230117 0.131578 0.068 Uiso 1 1 calc R . . . .
C20 C 0.3062(3) 0.62552(15) 0.44059(12) 0.0486(5) Uani 1 1 d . . . . .
C7 C 0.8071(3) 0.45131(15) 0.24232(14) 0.0543(6) Uani 1 1 d . . . . .
H7 H 0.898872 0.441300 0.240063 0.065 Uiso 1 1 calc R . . . .
C8 C 0.7422(2) 0.45496(14) 0.30703(13) 0.0458(5) Uani 1 1 d . . . . .
C42 C 0.0841(3) 0.41690(18) 0.12877(14) 0.0584(7) Uani 1 1 d . . . . .
H42 H 0.051089 0.391799 0.088751 0.070 Uiso 1 1 calc R . . . .
C16 C 0.4068(3) 0.75130(16) 0.41082(14) 0.0581(6) Uani 1 1 d . . . . .
H16 H 0.477111 0.780204 0.391830 0.070 Uiso 1 1 calc R . . . .
C31 C 0.4472(3) 0.20431(14) 0.39074(14) 0.0525(6) Uani 1 1 d . . . . .
C17 C 0.2957(4) 0.78691(18) 0.44007(14) 0.0687(8) Uani 1 1 d . . . . .
H17 H 0.290769 0.840851 0.440853 0.082 Uiso 1 1 calc R . . . .
C40 C 0.1212(3) 0.53456(17) 0.19572(19) 0.0654(8) Uani 1 1 d . . . . .
H40 H 0.112639 0.588272 0.198413 0.079 Uiso 1 1 calc R . . . .
C19 C 0.1938(3) 0.66365(18) 0.46942(14) 0.0619(7) Uani 1 1 d . . . . .
H19 H 0.122911 0.635519 0.488760 0.074 Uiso 1 1 calc R . . . .
C11 C 0.3820(3) 0.40699(16) 0.46228(13) 0.0578(7) Uani 1 1 d . . . . .
H11A H 0.441848 0.414605 0.502258 0.069 Uiso 1 1 calc R . . . .
H11B H 0.336339 0.357641 0.468444 0.069 Uiso 1 1 calc R . . . .
C29 C 0.6850(3) 0.22082(17) 0.37962(17) 0.0663(8) Uani 1 1 d . . . . .
H29 H 0.769760 0.221364 0.400401 0.080 Uiso 1 1 calc R . . . .
C41 C 0.0724(3) 0.49576(19) 0.13618(17) 0.0695(9) Uani 1 1 d . . . . .
H41 H 0.030833 0.524210 0.100478 0.083 Uiso 1 1 calc R . . . .
C30 C 0.5749(3) 0.20601(18) 0.42112(16) 0.0676(8) Uani 1 1 d . . . . .
H30 H 0.585323 0.197123 0.469423 0.081 Uiso 1 1 calc R . . . .
C18 C 0.1911(3) 0.7434(2) 0.46839(15) 0.0713(8) Uani 1 1 d . . . . .
H18 H 0.116963 0.769073 0.487223 0.086 Uiso 1 1 calc R . . . .
C12 C 0.2792(3) 0.47228(16) 0.45972(15) 0.0583(7) Uani 1 1 d . . . . .
H12A H 0.206326 0.458209 0.428063 0.070 Uiso 1 1 calc R . . . .
H12B H 0.241852 0.480553 0.506604 0.070 Uiso 1 1 calc R . . . .
C23 C 0.5154(3) 0.48762(19) 0.11579(15) 0.0635(7) Uani 1 1 d . . . . .
H23A H 0.467821 0.440490 0.105308 0.095 Uiso 1 1 calc GR . . . .
H23B H 0.575161 0.499748 0.077384 0.095 Uiso 1 1 calc GR . . . .
H23C H 0.452275 0.529254 0.121930 0.095 Uiso 1 1 calc GR . . . .
C46 C 0.7943(3) 0.24887(19) 0.2614(2) 0.0756(9) Uani 1 1 d . . . . .
H46A H 0.811856 0.203362 0.233504 0.113 Uiso 1 1 calc GR . . . .
H46B H 0.871015 0.259948 0.290644 0.113 Uiso 1 1 calc GR . . . .
H46C H 0.777333 0.292154 0.230629 0.113 Uiso 1 1 calc GR . . . .
H33 H 0.284(3) 0.1100(18) 0.2579(15) 0.058(8) Uiso 1 1 d . . . . .
H10 H 0.518(3) 0.3646(18) 0.3966(16) 0.056(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S9 C1 91.63(11) . . ?
C31 S32 C24 92.24(12) . . ?
C37 N44 H44 126.2 . . ?
C38 N44 H44 126.2 . . ?
C38 N44 C37 107.53(18) . . ?
C14 N21 H21 126.1 . . ?
C14 N21 C15 107.74(19) . . ?
C15 N21 H21 126.1 . . ?
C2 N10 H10 105.2(19) . . ?
C11 N10 C2 114.81(19) . . ?
C11 N10 H10 109.0(19) . . ?
C25 N33 H33 106.7(19) . . ?
C34 N33 C25 114.78(18) . . ?
C34 N33 H33 106(2) . . ?
N21 C14 C2 123.9(2) . . ?
C13 C14 N21 110.6(2) . . ?
C13 C14 C2 125.4(2) . . ?
N44 C37 C25 123.64(18) . . ?
C36 C37 N44 110.92(19) . . ?
C36 C37 C25 125.3(2) . . ?
C37 C36 C43 106.28(19) . . ?
C37 C36 C35 122.9(2) . . ?
C43 C36 C35 130.8(2) . . ?
N44 C38 C43 108.15(19) . . ?
N44 C38 C39 129.8(2) . . ?
C39 C38 C43 122.0(2) . . ?
C38 C43 C36 107.05(19) . . ?
C38 C43 C42 119.3(2) . . ?
C42 C43 C36 133.7(2) . . ?
N33 C25 C37 106.73(17) . . ?
N33 C25 C26 109.87(17) . . ?
N33 C25 C24 111.55(18) . . ?
C37 C25 C26 114.08(18) . . ?
C37 C25 C24 109.05(18) . . ?
C26 C25 C24 105.64(18) . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.8(2) . . ?
C28 C27 H27 119.1 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C27 C26 C25 124.8(2) . . ?
C27 C26 C31 119.3(2) . . ?
C31 C26 C25 115.9(2) . . ?
N21 C15 C20 108.0(2) . . ?
N21 C15 C16 129.7(2) . . ?
C16 C15 C20 122.3(2) . . ?
C4 C5 C6 117.6(2) . . ?
C4 C5 C23 121.0(2) . . ?
C6 C5 C23 121.4(2) . . ?
N10 C2 C14 107.68(19) . . ?
N10 C2 C3 108.83(18) . . ?
N10 C2 C1 109.94(18) . . ?
C14 C2 C3 114.80(19) . . ?
C14 C2 C1 109.89(18) . . ?
C3 C2 C1 105.65(19) . . ?
C4 C3 C2 125.2(2) . . ?
C4 C3 C8 119.7(2) . . ?
C8 C3 C2 115.1(2) . . ?
C14 C13 C20 106.5(2) . . ?
C14 C13 C12 122.1(2) . . ?
C20 C13 C12 131.4(2) . . ?
C38 C39 H39 121.4 . . ?
C40 C39 C38 117.2(3) . . ?
C40 C39 H39 121.4 . . ?
C27 C28 C46 120.4(3) . . ?
C29 C28 C27 117.4(3) . . ?
C29 C28 C46 122.1(3) . . ?
O22 C1 S9 123.2(2) . . ?
O22 C1 C2 124.9(3) . . ?
C2 C1 S9 111.79(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
N33 C34 H34A 109.7 . . ?
N33 C34 H34B 109.7 . . ?
N33 C34 C35 110.0(2) . . ?
H34A C34 H34B 108.2 . . ?
C35 C34 H34A 109.7 . . ?
C35 C34 H34B 109.7 . . ?
O45 C24 S32 122.2(2) . . ?
O45 C24 C25 125.8(2) . . ?
C25 C24 S32 112.02(18) . . ?
C36 C35 C34 108.9(2) . . ?
C36 C35 H35A 109.9 . . ?
C36 C35 H35B 109.9 . . ?
C34 C35 H35A 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C15 C20 C13 107.2(2) . . ?
C15 C20 C19 118.7(2) . . ?
C19 C20 C13 134.1(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.4 . . ?
C3 C8 S9 114.27(19) . . ?
C7 C8 S9 125.23(19) . . ?
C7 C8 C3 120.4(2) . . ?
C43 C42 H42 120.9 . . ?
C41 C42 C43 118.2(3) . . ?
C41 C42 H42 120.9 . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.5(3) . . ?
C17 C16 H16 121.2 . . ?
C26 C31 S32 114.1(2) . . ?
C26 C31 C30 119.8(3) . . ?
C30 C31 S32 126.1(2) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C39 C40 H40 119.3 . . ?
C39 C40 C41 121.5(3) . . ?
C41 C40 H40 119.3 . . ?
C20 C19 H19 120.8 . . ?
C18 C19 C20 118.5(3) . . ?
C18 C19 H19 120.8 . . ?
N10 C11 H11A 109.7 . . ?
N10 C11 H11B 109.7 . . ?
N10 C11 C12 109.7(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C28 C29 H29 119.0 . . ?
C30 C29 C28 121.9(3) . . ?
C30 C29 H29 119.0 . . ?
C42 C41 C40 121.9(2) . . ?
C42 C41 H41 119.1 . . ?
C40 C41 H41 119.1 . . ?
C31 C30 H30 120.1 . . ?
C29 C30 C31 119.8(2) . . ?
C29 C30 H30 120.1 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.0(3) . . ?
C19 C18 H18 119.0 . . ?
C13 C12 C11 109.8(2) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C5 C23 H23A 109.5 . . ?
C5 C23 H23B 109.5 . . ?
C5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C28 C46 H46A 109.5 . . ?
C28 C46 H46B 109.5 . . ?
C28 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S9 C1 1.780(3) . ?
S9 C8 1.768(3) . ?
S32 C24 1.783(3) . ?
S32 C31 1.758(3) . ?
N44 H44 0.8600 . ?
N44 C37 1.380(3) . ?
N44 C38 1.377(3) . ?
O22 C1 1.200(3) . ?
N21 H21 0.8600 . ?
N21 C14 1.383(3) . ?
N21 C15 1.386(3) . ?
O45 C24 1.203(3) . ?
N10 C2 1.485(3) . ?
N10 C11 1.478(3) . ?
N10 H10 0.91(3) . ?
N33 C25 1.480(3) . ?
N33 C34 1.478(3) . ?
N33 H33 0.86(3) . ?
C14 C2 1.487(3) . ?
C14 C13 1.364(3) . ?
C37 C36 1.357(3) . ?
C37 C25 1.505(3) . ?
C36 C43 1.431(3) . ?
C36 C35 1.491(3) . ?
C38 C43 1.405(3) . ?
C38 C39 1.399(3) . ?
C43 C42 1.405(3) . ?
C25 C26 1.510(3) . ?
C25 C24 1.565(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.379(4) . ?
C27 C28 1.397(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(3) . ?
C4 C3 1.377(3) . ?
C26 C31 1.390(3) . ?
C15 C20 1.405(4) . ?
C15 C16 1.393(4) . ?
C5 C6 1.397(4) . ?
C5 C23 1.502(4) . ?
C2 C3 1.511(3) . ?
C2 C1 1.561(3) . ?
C3 C8 1.390(3) . ?
C13 C20 1.433(3) . ?
C13 C12 1.503(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.373(4) . ?
C28 C29 1.386(4) . ?
C28 C46 1.502(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.513(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C20 C19 1.406(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C42 H42 0.9300 . ?
C42 C41 1.370(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C31 C30 1.393(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.394(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.374(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.520(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.370(5) . ?
C41 H41 0.9300 . ?
C30 H30 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S32 C31 C30 C29 178.0(2) . . . . ?
N44 C37 C36 C43 2.7(3) . . . . ?
N44 C37 C36 C35 -175.2(2) . . . . ?
N44 C37 C25 N33 -172.4(2) . . . . ?
N44 C37 C25 C26 -50.8(3) . . . . ?
N44 C37 C25 C24 67.0(3) . . . . ?
N44 C38 C43 C36 0.6(3) . . . . ?
N44 C38 C43 C42 -180.0(2) . . . . ?
N44 C38 C39 C40 178.9(2) . . . . ?
N21 C14 C2 N10 -171.2(2) . . . . ?
N21 C14 C2 C3 -49.8(3) . . . . ?
N21 C14 C2 C1 69.1(3) . . . . ?
N21 C14 C13 C20 1.9(3) . . . . ?
N21 C14 C13 C12 -176.2(2) . . . . ?
N21 C15 C20 C13 0.9(3) . . . . ?
N21 C15 C20 C19 -179.6(2) . . . . ?
N21 C15 C16 C17 -179.4(2) . . . . ?
N10 C2 C3 C4 70.8(3) . . . . ?
N10 C2 C3 C8 -108.9(2) . . . . ?
N10 C2 C1 S9 104.3(2) . . . . ?
N10 C2 C1 O22 -73.7(3) . . . . ?
N10 C11 C12 C13 -46.7(3) . . . . ?
N33 C25 C26 C27 60.5(3) . . . . ?
N33 C25 C26 C31 -119.0(2) . . . . ?
N33 C25 C24 S32 116.54(18) . . . . ?
N33 C25 C24 O45 -62.0(3) . . . . ?
N33 C34 C35 C36 -48.0(3) . . . . ?
C14 N21 C15 C20 0.2(2) . . . . ?
C14 N21 C15 C16 178.3(3) . . . . ?
C14 C2 C3 C4 -49.9(3) . . . . ?
C14 C2 C3 C8 130.4(2) . . . . ?
C14 C2 C1 S9 -137.35(17) . . . . ?
C14 C2 C1 O22 44.6(3) . . . . ?
C14 C13 C20 C15 -1.7(3) . . . . ?
C14 C13 C20 C19 179.0(3) . . . . ?
C14 C13 C12 C11 17.4(3) . . . . ?
C37 N44 C38 C43 1.0(3) . . . . ?
C37 N44 C38 C39 -178.8(2) . . . . ?
C37 C36 C43 C38 -2.0(3) . . . . ?
C37 C36 C43 C42 178.7(3) . . . . ?
C37 C36 C35 C34 17.5(4) . . . . ?
C37 C25 C26 C27 -59.3(3) . . . . ?
C37 C25 C26 C31 121.2(2) . . . . ?
C37 C25 C24 S32 -125.83(17) . . . . ?
C37 C25 C24 O45 55.6(3) . . . . ?
C36 C37 C25 N33 12.9(3) . . . . ?
C36 C37 C25 C26 134.4(2) . . . . ?
C36 C37 C25 C24 -107.8(3) . . . . ?
C36 C43 C42 C41 179.8(3) . . . . ?
C38 N44 C37 C36 -2.4(3) . . . . ?
C38 N44 C37 C25 -177.8(2) . . . . ?
C38 C43 C42 C41 0.6(4) . . . . ?
C38 C39 C40 C41 1.5(4) . . . . ?
C43 C36 C35 C34 -159.9(2) . . . . ?
C43 C38 C39 C40 -1.0(4) . . . . ?
C43 C42 C41 C40 0.0(4) . . . . ?
C25 N33 C34 C35 67.7(3) . . . . ?
C25 C37 C36 C43 178.1(2) . . . . ?
C25 C37 C36 C35 0.1(4) . . . . ?
C25 C26 C31 S32 0.6(3) . . . . ?
C25 C26 C31 C30 179.6(2) . . . . ?
C27 C26 C31 S32 -178.98(18) . . . . ?
C27 C26 C31 C30 0.1(4) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C4 C5 C6 C7 2.2(4) . . . . ?
C4 C3 C8 S9 178.78(17) . . . . ?
C4 C3 C8 C7 1.2(4) . . . . ?
C26 C25 C24 S32 -2.8(2) . . . . ?
C26 C25 C24 O45 178.6(3) . . . . ?
C26 C27 C28 C29 -1.7(4) . . . . ?
C26 C27 C28 C46 177.2(3) . . . . ?
C26 C31 C30 C29 -1.0(4) . . . . ?
C15 N21 C14 C2 -176.2(2) . . . . ?
C15 N21 C14 C13 -1.3(3) . . . . ?
C15 C20 C19 C18 -1.2(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C5 C4 C3 C2 -179.1(2) . . . . ?
C5 C4 C3 C8 0.6(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C2 N10 C11 C12 66.1(3) . . . . ?
C2 C14 C13 C20 176.7(2) . . . . ?
C2 C14 C13 C12 -1.4(4) . . . . ?
C2 C3 C8 S9 -1.5(3) . . . . ?
C2 C3 C8 C7 -179.1(2) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C3 C4 C5 C23 178.4(2) . . . . ?
C3 C2 C1 S9 -13.0(2) . . . . ?
C3 C2 C1 O22 169.0(3) . . . . ?
C13 C14 C2 N10 14.7(3) . . . . ?
C13 C14 C2 C3 136.0(2) . . . . ?
C13 C14 C2 C1 -105.1(3) . . . . ?
C13 C20 C19 C18 178.1(3) . . . . ?
C39 C38 C43 C36 -179.5(2) . . . . ?
C39 C38 C43 C42 -0.1(4) . . . . ?
C39 C40 C41 C42 -1.1(4) . . . . ?
C28 C27 C26 C25 -178.2(2) . . . . ?
C28 C27 C26 C31 1.3(3) . . . . ?
C28 C29 C30 C31 0.6(5) . . . . ?
C1 S9 C8 C3 -5.7(2) . . . . ?
C1 S9 C8 C7 171.8(2) . . . . ?
C1 C2 C3 C4 -171.2(2) . . . . ?
C1 C2 C3 C8 9.1(3) . . . . ?
C6 C7 C8 S9 -178.5(2) . . . . ?
C6 C7 C8 C3 -1.2(4) . . . . ?
C34 N33 C25 C37 -46.1(3) . . . . ?
C34 N33 C25 C26 -170.3(2) . . . . ?
C34 N33 C25 C24 72.9(3) . . . . ?
C24 S32 C31 C26 -2.0(2) . . . . ?
C24 S32 C31 C30 179.0(3) . . . . ?
C24 C25 C26 C27 -179.0(2) . . . . ?
C24 C25 C26 C31 1.4(3) . . . . ?
C35 C36 C43 C38 175.7(3) . . . . ?
C35 C36 C43 C42 -3.6(5) . . . . ?
C20 C15 C16 C17 -1.5(4) . . . . ?
C20 C13 C12 C11 -160.1(2) . . . . ?
C20 C19 C18 C17 -0.2(4) . . . . ?
C8 S9 C1 O22 -171.0(3) . . . . ?
C8 S9 C1 C2 10.94(18) . . . . ?
C16 C15 C20 C13 -177.4(2) . . . . ?
C16 C15 C20 C19 2.1(4) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C31 S32 C24 O45 -178.6(3) . . . . ?
C31 S32 C24 C25 2.78(18) . . . . ?
C11 N10 C2 C14 -46.9(3) . . . . ?
C11 N10 C2 C3 -171.9(2) . . . . ?
C11 N10 C2 C1 72.8(3) . . . . ?
C12 C13 C20 C15 176.1(3) . . . . ?
C12 C13 C20 C19 -3.2(5) . . . . ?
C23 C5 C6 C7 -178.5(3) . . . . ?
C46 C28 C29 C30 -178.1(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.015(16)
2 -0.015(16)
