#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:42:55 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270509 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158309.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_7158309
loop_
_publ_author_name
'Zeng, Wenlei'
'Yu, Aimin'
'Meng, Xiangtai'
_publ_section_title
;
 Catalyst-controlled switchable [4 + 1], [4 + 3] and [3 + 2] domino
 reactions of azadienes and MBH carbonates: diverse synthesis of
 benzothiophene fused derivatives.
;
_journal_issue                   40
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8783
_journal_page_last               8788
_journal_paper_doi               10.1039/d1ob01702k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C36 H31 Cl N2 O5 S2'
_chemical_formula_sum            'C36 H31 Cl N2 O5 S2'
_chemical_formula_weight         671.20
_chemical_name_systematic        221
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.720(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2429(6)
_cell_length_b                   9.7717(2)
_cell_length_c                   28.6043(7)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.2760
_cell_measurement_theta_min      3.0770
_cell_volume                     6474.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  78.00   0.50    0.50    --   40.90 -32.00-120.00  136
  2  ω    -49.00  -2.00   0.50    0.50    --   40.90 -54.00   0.00   94
  3  ω     40.00  73.00   0.50    0.50    --   40.90 -54.00 -60.00   66
  4  ω      7.00  68.00   0.50    0.50    --   40.90 -82.00 -60.00  122
  5  ω    -48.00  -1.00   0.50    0.50    --   40.90 -77.00 120.00   94
  6  ω     43.00  72.00   0.50    0.50    --   40.90 -54.00   0.00   58
  7  ω     37.00  67.00   0.50    0.50    --   40.90 -82.00 -30.00   60
  8  ω    -44.00  -5.00   0.50    0.50    --   40.90 -82.00-180.00   78
  9  ω    -25.00   3.00   0.50    0.50    --   40.90 -82.00-150.00   56
 10  ω    -48.00 -20.00   0.50    0.50    --   40.90 -82.00  60.00   56
 11  ω    -38.00 -13.00   0.50    0.50    --   40.90 -82.00 -60.00   50
 12  ω      3.00  38.00   0.50    0.50    --   40.90 -77.00 120.00   70
 13  ω     26.00  55.00   0.50    0.50    --   40.90 -65.00-120.00   58
 14  ω    -46.00  18.00   0.50    0.50    --   40.90 -65.00-120.00  128
 15  ω      9.00  48.00   0.50    0.50    --   40.90 -77.00 150.00   78
 16  ω     16.00  68.00   0.50    0.50    --   40.90 -82.00-180.00  104
 17  ω     49.00  74.00   0.50    0.50    --   40.90  65.00 -90.00   50
 18  ω    -16.00  67.00   0.50    0.50    --   40.90 -82.00  60.00  166
 19  ω    -30.00  -5.00   0.50    0.50    --   40.90 -54.00 -60.00   50
 20  ω     24.00  68.00   0.50    0.50    --   40.90 -82.00-150.00   88
 21  ω    -24.00   3.00   0.50    0.50    --   40.90 -77.00 150.00   54
 22  ω     35.00  61.00   0.50    0.50    --   40.90  82.00  30.00   52
 23  ω    -47.00 -22.00   0.50    0.50    --   40.90 -32.00-120.00   50
 24  ω      4.00 121.00   0.50    0.50    --   93.40 -59.00 -30.00  234
 25  ω     88.00 114.00   0.50    0.50    --   93.40 -59.00 150.00   52
 26  ω      4.00 183.00   0.50    0.50    --   93.40   0.00-120.00  358
 27  ω      4.00  81.00   0.50    0.50    --   93.40 -59.00 150.00  154
 28  ω     67.00  93.00   0.50    0.50    --   93.40 -82.00 -60.00   52
 29  ω     56.00 102.00   0.50    0.50    --   93.40 -82.00-150.00   92
 30  ω     18.00  61.00   0.50    0.50    --   93.40 -33.00-180.00   86
 31  ω     87.00 133.00   0.50    0.50    --   93.40 -33.00 150.00   92
 32  ω     78.00 103.00   0.50    0.50    --   93.40 -82.00 150.00   50
 33  ω     66.00  92.00   0.50    0.50    --   93.40 -82.00-180.00   52
 34  ω     59.00 101.00   0.50    0.50    --   93.40 -82.00  60.00   84
 35  ω      4.00 121.00   0.50    0.50    --   93.40 -82.00 120.00  234
 36  ω    126.00 152.00   0.50    0.50    --   93.40  59.00-120.00   52
 37  ω     24.00  62.00   0.50    0.50    --   93.40 -77.00 -60.00   76
 38  ω     71.00  96.00   0.50    0.50    --   93.40 -82.00  90.00   50
 39  ω      4.00  72.00   0.50    0.50    --   93.40 -33.00 150.00  136
 40  ω     67.00  93.00   0.50    0.50    --   93.40 -82.00-120.00   52
 41  ω     88.00 124.00   0.50    0.50    --   93.40 -33.00   0.00   72
 42  ω     19.00  65.00   0.50    0.50    --   93.40 -82.00  90.00   92
 43  ω     20.00  48.00   0.50    0.50    --   93.40 -33.00   0.00   56
 44  ω     84.00 114.00   0.50    0.50    --   93.40 -33.00-180.00   60
 45  ω     12.00  94.00   0.50    0.50    --   93.40 -82.00 -90.00  164
 46  ω      9.00 115.00   0.50    0.50    --   93.40 -33.00 -30.00  212
 47  ω     18.00  71.00   0.50    0.50    --   93.40 -82.00 150.00  106
 48  ω     84.00 110.00   0.50    0.50    --   93.40 -82.00   0.00   52
 49  ω     10.00 101.00   0.50    0.50    --   93.40 -82.00 -30.00  182
;
_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      -0.0236413000
_diffrn_orient_matrix_UB_12      -0.0541727000
_diffrn_orient_matrix_UB_13      -0.0484011000
_diffrn_orient_matrix_UB_21      -0.0112113000
_diffrn_orient_matrix_UB_22      -0.1405076000
_diffrn_orient_matrix_UB_23      0.0219162000
_diffrn_orient_matrix_UB_31      -0.0611328000
_diffrn_orient_matrix_UB_32      0.0467427000
_diffrn_orient_matrix_UB_33      0.0098662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.663
_diffrn_reflns_theta_min         3.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0538
_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)+(0.0775P)²+3.9035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4253
_reflns_number_total             5825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           mxt-3
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158309
_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   0.902
_shelx_estimated_absorpt_t_min   0.858
_diffrn_oxdiff_digest_frames
;
01001d5318ef37c7ebe0243efed19b027200030efee
;
_diffrn_oxdiff_digest_hkl
;
01b46c2bb0d7e157abf8ae0434fbad2b83f955
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C17(H17), C20(H20), C7(H7), C45(H45), C31(H31), C6(H6),
 C18(H18), C41(H41), C27(H27), C19(H19), C44(H44), C42(H42), C30(H30), C28(H28),
  C29(H29)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C46(H46A,H46B,H46C), C35(H35A,H35B,H35C)
;
_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 4.265
_oxdiff_exptl_absorpt_empirical_full_min 0.604
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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
S23 S 0.41202(3) 0.64317(7) 0.53581(2) 0.0463(2) Uani 1 1 d . . . . .
S14 S 0.46499(4) 0.96368(8) 0.68627(3) 0.0543(2) Uani 1 1 d . . . . .
Cl37 Cl 0.21586(4) 0.74050(11) 0.56395(3) 0.0756(3) Uani 1 1 d . . . . .
O25 O 0.36559(9) 0.7387(2) 0.53007(7) 0.0546(5) Uani 1 1 d . . . . .
O24 O 0.45317(10) 0.6379(2) 0.50137(7) 0.0642(6) Uani 1 1 d . . . . .
O38 O 0.43520(10) 0.7843(2) 0.77230(8) 0.0645(6) Uani 1 1 d . . . . .
N22 N 0.44518(12) 0.6690(2) 0.58765(8) 0.0474(6) Uani 1 1 d . . . . .
N9 N 0.34490(11) 0.8535(2) 0.74401(8) 0.0509(6) Uani 1 1 d . . . . .
O33 O 0.38673(11) 0.3480(2) 0.70243(10) 0.0760(7) Uani 1 1 d . . . . .
O36 O 0.32796(12) 0.5046(3) 0.72751(11) 0.0887(9) Uani 1 1 d . . . . .
C15 C 0.44325(12) 0.7996(3) 0.61278(9) 0.0413(6) Uani 1 1 d . . . . .
H15 H 0.404746 0.838404 0.605088 0.050 Uiso 1 1 calc R . . . .
C8 C 0.30927(13) 0.8383(3) 0.70248(10) 0.0469(7) Uani 1 1 d . . . . .
C10 C 0.45134(12) 0.7858(3) 0.66728(9) 0.0424(6) Uani 1 1 d . . . . .
C16 C 0.48649(12) 0.9063(3) 0.59977(10) 0.0444(7) Uani 1 1 d . . . . .
C2 C 0.39745(12) 0.7261(3) 0.69133(10) 0.0449(7) Uani 1 1 d . . . . .
C3 C 0.33743(12) 0.7621(3) 0.66991(10) 0.0436(6) Uani 1 1 d . . . . .
C13 C 0.41305(13) 0.5759(3) 0.69609(10) 0.0456(7) Uani 1 1 d . . . . .
C4 C 0.30843(13) 0.7286(3) 0.62814(10) 0.0493(7) Uani 1 1 d . . . . .
H4 H 0.325957 0.674751 0.606576 0.059 Uiso 1 1 calc R . . . .
C40 C 0.38464(13) 0.4761(3) 0.54055(10) 0.0470(7) Uani 1 1 d . . . . .
C1 C 0.39617(14) 0.7894(3) 0.74104(11) 0.0510(7) Uani 1 1 d . . . . .
C26 C 0.55381(12) 0.6722(3) 0.65800(11) 0.0507(7) Uani 1 1 d . . . . .
C21 C 0.49755(13) 1.0042(3) 0.63468(10) 0.0489(7) Uani 1 1 d . . . . .
C32 C 0.37133(14) 0.4753(3) 0.71004(11) 0.0542(8) Uani 1 1 d . . . . .
C11 C 0.50148(12) 0.6846(3) 0.68612(10) 0.0480(7) Uani 1 1 d . . . . .
H11 H 0.515652 0.717771 0.717290 0.058 Uiso 1 1 calc R . . . .
C12 C 0.46923(13) 0.5546(3) 0.69364(11) 0.0526(8) Uani 1 1 d . . . . .
H12 H 0.486549 0.468867 0.696290 0.063 Uiso 1 1 calc R . . . .
C17 C 0.51426(13) 0.9157(3) 0.55904(11) 0.0534(8) Uani 1 1 d . . . . .
H17 H 0.508189 0.849907 0.535655 0.064 Uiso 1 1 calc R . . . .
C20 C 0.53370(14) 1.1145(3) 0.62894(12) 0.0592(8) Uani 1 1 d . . . . .
H20 H 0.539887 1.180535 0.652245 0.071 Uiso 1 1 calc R . . . .
C5 C 0.25226(13) 0.7760(3) 0.61809(11) 0.0532(8) Uani 1 1 d . . . . .
C7 C 0.25298(13) 0.8827(3) 0.69348(12) 0.0561(8) Uani 1 1 d . . . . .
H7 H 0.234522 0.931358 0.715849 0.067 Uiso 1 1 calc R . . . .
C45 C 0.32640(14) 0.4540(3) 0.54057(13) 0.0604(9) Uani 1 1 d . . . . .
H45 H 0.300691 0.527102 0.538103 0.072 Uiso 1 1 calc R . . . .
C31 C 0.56215(14) 0.5603(4) 0.62948(11) 0.0604(8) Uani 1 1 d . . . . .
H31 H 0.535746 0.488631 0.628522 0.073 Uiso 1 1 calc R . . . .
C39 C 0.32871(16) 0.9246(4) 0.78558(12) 0.0665(9) Uani 1 1 d . . . . .
H39A H 0.331380 1.021581 0.780870 0.100 Uiso 1 1 calc GR . . . .
H39B H 0.354277 0.898189 0.812116 0.100 Uiso 1 1 calc GR . . . .
H39C H 0.289789 0.900986 0.791206 0.100 Uiso 1 1 calc GR . . . .
C6 C 0.22488(14) 0.8524(3) 0.65006(12) 0.0578(8) Uani 1 1 d . . . . .
H6 H 0.187492 0.883826 0.642531 0.069 Uiso 1 1 calc R . . . .
C18 C 0.55160(15) 1.0254(4) 0.55349(12) 0.0638(9) Uani 1 1 d . . . . .
H18 H 0.570822 1.031991 0.526316 0.077 Uiso 1 1 calc R . . . .
C41 C 0.42245(14) 0.3671(3) 0.54351(13) 0.0614(9) Uani 1 1 d . . . . .
H41 H 0.461892 0.381725 0.542749 0.074 Uiso 1 1 calc R . . . .
C27 C 0.59556(14) 0.7740(4) 0.66073(14) 0.0661(9) Uani 1 1 d . . . . .
H27 H 0.592305 0.847782 0.680873 0.079 Uiso 1 1 calc R . . . .
C19 C 0.56028(15) 1.1238(4) 0.58767(12) 0.0636(9) Uani 1 1 d . . . . .
H19 H 0.584393 1.197530 0.582928 0.076 Uiso 1 1 calc R . . . .
C44 C 0.30638(16) 0.3210(4) 0.54434(15) 0.0731(10) Uani 1 1 d . . . . .
H44 H 0.266869 0.305876 0.544298 0.088 Uiso 1 1 calc R . . . .
C42 C 0.40129(18) 0.2362(4) 0.54762(15) 0.0749(11) Uani 1 1 d . . . . .
H42 H 0.427003 0.163115 0.550123 0.090 Uiso 1 1 calc R . . . .
C43 C 0.34327(17) 0.2110(4) 0.54811(15) 0.0739(10) Uani 1 1 d . . . . .
C34 C 0.34626(18) 0.2420(4) 0.71240(17) 0.0812(12) Uani 1 1 d . . . . .
H34A H 0.330591 0.261178 0.742108 0.097 Uiso 1 1 calc R . . . .
H34B H 0.366177 0.154781 0.715170 0.097 Uiso 1 1 calc R . . . .
C30 C 0.60870(18) 0.5525(5) 0.60245(14) 0.0833(12) Uani 1 1 d . . . . .
H30 H 0.613152 0.477386 0.583126 0.100 Uiso 1 1 calc R . . . .
C28 C 0.64200(17) 0.7660(5) 0.63358(18) 0.0901(14) Uani 1 1 d . . . . .
H28 H 0.669400 0.835521 0.635109 0.108 Uiso 1 1 calc R . . . .
C29 C 0.6480(2) 0.6565(6) 0.60446(18) 0.1013(16) Uani 1 1 d . . . . .
H29 H 0.679057 0.653003 0.585958 0.122 Uiso 1 1 calc R . . . .
C46 C 0.3202(2) 0.0666(4) 0.5521(2) 0.123(2) Uani 1 1 d . . . . .
H46A H 0.278765 0.069066 0.550877 0.185 Uiso 1 1 calc GR . . . .
H46B H 0.335156 0.027126 0.581350 0.185 Uiso 1 1 calc GR . . . .
H46C H 0.331913 0.012121 0.526631 0.185 Uiso 1 1 calc GR . . . .
C35 C 0.2996(3) 0.2333(7) 0.6758(3) 0.184(4) Uani 1 1 d . . . . .
H35A H 0.314429 0.203103 0.647196 0.276 Uiso 1 1 calc GR . . . .
H35B H 0.282103 0.321793 0.671002 0.276 Uiso 1 1 calc GR . . . .
H35C H 0.271189 0.169326 0.684855 0.276 Uiso 1 1 calc GR . . . .
H22 H 0.4797(15) 0.633(3) 0.5887(11) 0.063(11) 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'
Cl Cl 0.3639 0.7018 '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
O25 S23 O24 119.17(14) . . ?
O25 S23 N22 107.43(13) . . ?
O25 S23 C40 109.91(13) . . ?
O24 S23 N22 109.80(14) . . ?
O24 S23 C40 106.62(14) . . ?
N22 S23 C40 102.69(13) . . ?
C21 S14 C10 92.33(13) . . ?
S23 N22 H22 109(2) . . ?
C15 N22 S23 123.22(19) . . ?
C15 N22 H22 113(2) . . ?
C8 N9 C39 124.8(3) . . ?
C1 N9 C8 111.1(2) . . ?
C1 N9 C39 124.1(3) . . ?
C32 O33 C34 117.0(3) . . ?
N22 C15 H15 106.9 . . ?
N22 C15 C10 114.1(2) . . ?
N22 C15 C16 115.5(2) . . ?
C10 C15 H15 106.9 . . ?
C16 C15 H15 106.9 . . ?
C16 C15 C10 106.1(2) . . ?
C3 C8 N9 110.2(3) . . ?
C7 C8 N9 127.6(3) . . ?
C7 C8 C3 122.1(3) . . ?
C15 C10 S14 102.52(18) . . ?
C15 C10 C2 115.5(2) . . ?
C15 C10 C11 114.7(2) . . ?
C2 C10 S14 110.00(19) . . ?
C11 C10 S14 112.59(19) . . ?
C11 C10 C2 101.9(2) . . ?
C21 C16 C15 112.6(2) . . ?
C17 C16 C15 128.2(3) . . ?
C17 C16 C21 119.2(3) . . ?
C3 C2 C10 118.1(2) . . ?
C3 C2 C1 101.0(2) . . ?
C13 C2 C10 101.7(2) . . ?
C13 C2 C3 117.8(2) . . ?
C13 C2 C1 109.0(2) . . ?
C1 C2 C10 109.0(2) . . ?
C8 C3 C2 108.6(2) . . ?
C4 C3 C8 119.2(3) . . ?
C4 C3 C2 132.1(3) . . ?
C32 C13 C2 121.2(3) . . ?
C12 C13 C2 112.0(3) . . ?
C12 C13 C32 125.9(3) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C45 C40 S23 120.6(2) . . ?
C45 C40 C41 120.2(3) . . ?
C41 C40 S23 119.2(2) . . ?
O38 C1 N9 125.2(3) . . ?
O38 C1 C2 125.8(3) . . ?
N9 C1 C2 109.0(2) . . ?
C31 C26 C11 122.1(3) . . ?
C27 C26 C11 120.1(3) . . ?
C27 C26 C31 117.9(3) . . ?
C16 C21 S14 112.4(2) . . ?
C20 C21 S14 125.6(2) . . ?
C20 C21 C16 121.9(3) . . ?
O33 C32 C13 113.3(3) . . ?
O36 C32 O33 123.0(3) . . ?
O36 C32 C13 123.7(3) . . ?
C10 C11 H11 106.5 . . ?
C26 C11 C10 117.9(2) . . ?
C26 C11 H11 106.5 . . ?
C12 C11 C10 102.4(2) . . ?
C12 C11 C26 116.2(3) . . ?
C12 C11 H11 106.5 . . ?
C13 C12 C11 112.3(3) . . ?
C13 C12 H12 123.8 . . ?
C11 C12 H12 123.8 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C21 C20 H20 121.0 . . ?
C19 C20 C21 118.1(3) . . ?
C19 C20 H20 121.0 . . ?
C4 C5 Cl37 119.8(3) . . ?
C6 C5 Cl37 118.9(2) . . ?
C6 C5 C4 121.3(3) . . ?
C8 C7 H7 121.0 . . ?
C8 C7 C6 117.9(3) . . ?
C6 C7 H7 121.0 . . ?
C40 C45 H45 120.5 . . ?
C40 C45 C44 119.0(3) . . ?
C44 C45 H45 120.5 . . ?
C26 C31 H31 119.1 . . ?
C30 C31 C26 121.7(4) . . ?
C30 C31 H31 119.1 . . ?
N9 C39 H39A 109.5 . . ?
N9 C39 H39B 109.5 . . ?
N9 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.5(3) . . ?
C42 C41 H41 120.3 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.5 . . ?
C45 C44 H44 119.1 . . ?
C43 C44 C45 121.9(3) . . ?
C43 C44 H44 119.1 . . ?
C41 C42 H42 119.2 . . ?
C43 C42 C41 121.7(3) . . ?
C43 C42 H42 119.2 . . ?
C44 C43 C46 120.7(4) . . ?
C42 C43 C44 117.8(3) . . ?
C42 C43 C46 121.5(4) . . ?
O33 C34 H34A 109.4 . . ?
O33 C34 H34B 109.4 . . ?
O33 C34 C35 111.2(4) . . ?
H34A C34 H34B 108.0 . . ?
C35 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C31 C30 H30 120.4 . . ?
C29 C30 C31 119.2(4) . . ?
C29 C30 H30 120.4 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(4) . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
S23 O25 1.426(2) . ?
S23 O24 1.429(2) . ?
S23 N22 1.633(2) . ?
S23 C40 1.761(3) . ?
S14 C10 1.841(3) . ?
S14 C21 1.758(3) . ?
Cl37 C5 1.737(3) . ?
O38 C1 1.221(4) . ?
N22 C15 1.468(4) . ?
N22 H22 0.87(3) . ?
N9 C8 1.399(4) . ?
N9 C1 1.355(4) . ?
N9 C39 1.453(4) . ?
O33 C32 1.317(4) . ?
O33 C34 1.443(4) . ?
O36 C32 1.196(4) . ?
C15 H15 0.9800 . ?
C15 C10 1.561(4) . ?
C15 C16 1.516(4) . ?
C8 C3 1.397(4) . ?
C8 C7 1.383(4) . ?
C10 C2 1.589(4) . ?
C10 C11 1.589(4) . ?
C16 C21 1.392(4) . ?
C16 C17 1.381(4) . ?
C2 C3 1.518(4) . ?
C2 C13 1.515(4) . ?
C2 C1 1.553(4) . ?
C3 C4 1.362(4) . ?
C13 C32 1.459(4) . ?
C13 C12 1.330(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(4) . ?
C40 C45 1.371(4) . ?
C40 C41 1.379(4) . ?
C26 C11 1.517(4) . ?
C26 C31 1.388(5) . ?
C26 C27 1.387(4) . ?
C21 C20 1.385(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.499(4) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.397(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.380(5) . ?
C5 C6 1.377(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.387(5) . ?
C45 H45 0.9300 . ?
C45 C44 1.388(5) . ?
C31 H31 0.9300 . ?
C31 C30 1.383(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.374(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.379(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(6) . ?
C19 H19 0.9300 . ?
C44 H44 0.9300 . ?
C44 C43 1.374(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.372(5) . ?
C43 C46 1.518(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.447(7) . ?
C30 H30 0.9300 . ?
C30 C29 1.364(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.370(7) . ?
C29 H29 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
S23 N22 C15 C10 152.7(2) . . . . ?
S23 N22 C15 C16 -83.9(3) . . . . ?
S23 C40 C45 C44 180.0(3) . . . . ?
S23 C40 C41 C42 179.5(3) . . . . ?
S14 C10 C2 C3 80.9(3) . . . . ?
S14 C10 C2 C13 -148.48(19) . . . . ?
S14 C10 C2 C1 -33.4(3) . . . . ?
S14 C10 C11 C26 -84.8(3) . . . . ?
S14 C10 C11 C12 146.4(2) . . . . ?
S14 C21 C20 C19 173.5(3) . . . . ?
Cl37 C5 C6 C7 -179.8(3) . . . . ?
O25 S23 N22 C15 -23.8(3) . . . . ?
O25 S23 C40 C45 -2.9(3) . . . . ?
O25 S23 C40 C41 176.1(2) . . . . ?
O24 S23 N22 C15 107.2(3) . . . . ?
O24 S23 C40 C45 -133.3(3) . . . . ?
O24 S23 C40 C41 45.7(3) . . . . ?
N22 S23 C40 C45 111.2(3) . . . . ?
N22 S23 C40 C41 -69.8(3) . . . . ?
N22 C15 C10 S14 166.3(2) . . . . ?
N22 C15 C10 C2 -74.1(3) . . . . ?
N22 C15 C10 C11 44.0(3) . . . . ?
N22 C15 C16 C21 -158.1(2) . . . . ?
N22 C15 C16 C17 22.1(4) . . . . ?
N9 C8 C3 C2 -1.3(3) . . . . ?
N9 C8 C3 C4 175.9(3) . . . . ?
N9 C8 C7 C6 -177.9(3) . . . . ?
C15 C10 C2 C3 -34.4(3) . . . . ?
C15 C10 C2 C13 96.1(3) . . . . ?
C15 C10 C2 C1 -148.8(2) . . . . ?
C15 C10 C11 C26 31.9(4) . . . . ?
C15 C10 C11 C12 -96.9(3) . . . . ?
C15 C16 C21 S14 7.3(3) . . . . ?
C15 C16 C21 C20 -176.9(3) . . . . ?
C15 C16 C17 C18 178.1(3) . . . . ?
C8 N9 C1 O38 -179.0(3) . . . . ?
C8 N9 C1 C2 2.0(3) . . . . ?
C8 C3 C4 C5 2.7(4) . . . . ?
C8 C7 C6 C5 2.4(5) . . . . ?
C10 S14 C21 C16 14.7(2) . . . . ?
C10 S14 C21 C20 -160.9(3) . . . . ?
C10 C15 C16 C21 -30.6(3) . . . . ?
C10 C15 C16 C17 149.6(3) . . . . ?
C10 C2 C3 C8 -116.4(3) . . . . ?
C10 C2 C3 C4 66.9(4) . . . . ?
C10 C2 C13 C32 -170.3(3) . . . . ?
C10 C2 C13 C12 19.7(3) . . . . ?
C10 C2 C1 O38 -56.6(4) . . . . ?
C10 C2 C1 N9 122.5(3) . . . . ?
C10 C11 C12 C13 -18.4(3) . . . . ?
C16 C15 C10 S14 38.0(2) . . . . ?
C16 C15 C10 C2 157.6(2) . . . . ?
C16 C15 C10 C11 -84.3(3) . . . . ?
C16 C21 C20 C19 -1.7(5) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C2 C10 C11 C26 157.4(3) . . . . ?
C2 C10 C11 C12 28.6(3) . . . . ?
C2 C3 C4 C5 179.1(3) . . . . ?
C2 C13 C32 O33 165.6(3) . . . . ?
C2 C13 C32 O36 -15.7(5) . . . . ?
C2 C13 C12 C11 -0.9(4) . . . . ?
C3 C8 C7 C6 -1.6(5) . . . . ?
C3 C2 C13 C32 -39.5(4) . . . . ?
C3 C2 C13 C12 150.5(3) . . . . ?
C3 C2 C1 O38 178.4(3) . . . . ?
C3 C2 C1 N9 -2.6(3) . . . . ?
C3 C4 C5 Cl37 177.2(2) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C13 C2 C3 C8 120.8(3) . . . . ?
C13 C2 C3 C4 -55.9(4) . . . . ?
C13 C2 C1 O38 53.7(4) . . . . ?
C13 C2 C1 N9 -127.2(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C40 S23 N22 C15 -139.7(2) . . . . ?
C40 C45 C44 C43 0.1(6) . . . . ?
C40 C41 C42 C43 1.0(6) . . . . ?
C1 N9 C8 C3 -0.5(3) . . . . ?
C1 N9 C8 C7 176.1(3) . . . . ?
C1 C2 C3 C8 2.2(3) . . . . ?
C1 C2 C3 C4 -174.4(3) . . . . ?
C1 C2 C13 C32 74.7(3) . . . . ?
C1 C2 C13 C12 -95.3(3) . . . . ?
C26 C11 C12 C13 -148.3(3) . . . . ?
C26 C31 C30 C29 1.2(6) . . . . ?
C26 C27 C28 C29 -1.3(6) . . . . ?
C21 S14 C10 C15 -30.3(2) . . . . ?
C21 S14 C10 C2 -153.66(19) . . . . ?
C21 S14 C10 C11 93.4(2) . . . . ?
C21 C16 C17 C18 -1.7(5) . . . . ?
C21 C20 C19 C18 -0.7(5) . . . . ?
C32 O33 C34 C35 77.0(6) . . . . ?
C32 C13 C12 C11 -170.3(3) . . . . ?
C11 C10 C2 C3 -159.4(2) . . . . ?
C11 C10 C2 C13 -28.8(3) . . . . ?
C11 C10 C2 C1 86.2(3) . . . . ?
C11 C26 C31 C30 177.2(3) . . . . ?
C11 C26 C27 C28 -177.2(3) . . . . ?
C12 C13 C32 O33 -25.9(5) . . . . ?
C12 C13 C32 O36 152.8(4) . . . . ?
C17 C16 C21 S14 -172.9(2) . . . . ?
C17 C16 C21 C20 3.0(5) . . . . ?
C17 C18 C19 C20 1.9(5) . . . . ?
C7 C8 C3 C2 -178.1(3) . . . . ?
C7 C8 C3 C4 -0.9(5) . . . . ?
C45 C40 C41 C42 -1.5(5) . . . . ?
C45 C44 C43 C42 -0.6(6) . . . . ?
C45 C44 C43 C46 -179.9(4) . . . . ?
C31 C26 C11 C10 -103.7(3) . . . . ?
C31 C26 C11 C12 18.3(4) . . . . ?
C31 C26 C27 C28 3.6(5) . . . . ?
C31 C30 C29 C28 1.2(7) . . . . ?
C39 N9 C8 C3 -178.6(3) . . . . ?
C39 N9 C8 C7 -2.0(5) . . . . ?
C39 N9 C1 O38 -0.8(5) . . . . ?
C39 N9 C1 C2 -179.9(3) . . . . ?
C41 C40 C45 C44 1.0(5) . . . . ?
C41 C42 C43 C44 0.0(6) . . . . ?
C41 C42 C43 C46 179.3(4) . . . . ?
C27 C26 C11 C10 77.1(4) . . . . ?
C27 C26 C11 C12 -160.9(3) . . . . ?
C27 C26 C31 C30 -3.5(5) . . . . ?
C27 C28 C29 C30 -1.1(7) . . . . ?
C34 O33 C32 O36 5.2(5) . . . . ?
C34 O33 C32 C13 -176.1(3) . . . . ?
