# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zj20210426_auto
_database_code_depnum_ccdc_archive 'CCDC 2205447'
loop_
_audit_author_name
_audit_author_address
'xiangtai meng'
;tjut
China
;
_audit_update_record             
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         '2(C19 H16 N2 O S)'
_chemical_formula_sum            'C38 H32 N4 O2 S2'
_chemical_formula_weight         640.79
_chemical_absolute_configuration ab
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   9.94330(10)
_cell_length_b                   17.21630(10)
_cell_length_c                   18.86940(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3230.19(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19162
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9730
_cell_measurement_theta_min      2.3280
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.899
_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_absorpt_special_details   ?
_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_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_oxdiff_digest_frames     
;
01306a6a4f7d41633db7d1dafb3efbb0da00028ff4a
;
_diffrn_oxdiff_digest_hkl        
;
0142b8cb57d44e4a9609a76cb15ce2b6b331e3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_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_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.043
_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
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.015(16)
2 -0.015(16)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1162_auto
_database_code_depnum_ccdc_archive 'CCDC 2205449'
loop_
_audit_author_name
_audit_author_address
'xiangtai meng'
;tjut
China
;
_audit_update_record             
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2021-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O S'
_chemical_formula_sum            'C20 H18 N2 O S'
_chemical_formula_weight         334.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5789(2)
_cell_length_b                   7.19470(10)
_cell_length_c                   18.2456(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.301(2)
_cell_angle_gamma                90
_cell_volume                     1710.87(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0770
_cell_measurement_theta_min      3.4000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74528
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14768
_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         68.307
_diffrn_reflns_theta_min         3.391
_diffrn_ambient_temperature      293(2)
_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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  18.00   0.50    0.56    --   42.30 -82.00-120.00  124
  2  ω     26.00  66.00   0.50    0.56    --   42.30 -77.00  60.00   80
  3  ω     45.00  70.00   0.50    0.56    --   42.30 -82.00 150.00   50
  4  ω     23.00  55.00   0.50    0.56    --   42.30  77.00 150.00   64
  5  ω     40.00  70.00   0.50    0.56    --   42.30 -82.00  30.00   60
  6  ω     19.00  74.00   0.50    0.56    --   42.30  82.00-150.00  110
  7  ω     42.00  69.00   0.50    0.56    --   42.30 -82.00 120.00   54
  8  ω     -6.00  67.00   0.50    0.56    --   42.30 -82.00   0.00  146
  9  ω    -47.00  15.00   0.50    0.56    --   42.30 -82.00 150.00  124
 10  ω     59.00  96.00   0.50    0.56    --   42.30  77.00 150.00   74
 11  ω     18.00  97.00   0.50    0.56    --   42.30  54.00 -30.00  158
 12  ω     24.00  68.00   0.50    0.56    --   42.30 -82.00-120.00   88
 13  ω    -12.00  58.00   0.50    0.56    --   42.30 -82.00 -60.00  140
 14  ω     87.00 130.00   0.50    0.56    --   42.30  82.00-150.00   86
 15  ω     46.00  71.00   0.50    0.56    --   42.30 -54.00 -90.00   50
 16  ω    -31.00  -3.00   0.50    0.56    --   42.30 -54.00 -90.00   56
 17  ω     -4.00  21.00   0.50    0.56    --   42.30 -82.00 120.00   50
 18  ω    -47.00  -1.00   0.50    0.56    --   42.30 -77.00  60.00   92
 19  ω     64.00 100.00   0.50    0.80    --   93.70 -82.00  30.00   72
 20  ω      6.00 109.00   0.50    0.80    --   93.70 -82.00-150.00  206
 21  ω      5.00  35.00   0.50    0.80    --   93.70 -50.00  90.00   60
 22  ω     91.00 137.00   0.50    0.80    --   93.70  82.00   0.00   92
 23  ω    122.00 170.00   0.50    0.80    --   93.70  33.00 -90.00   96
 24  ω     74.00 105.00   0.50    0.80    --   93.70 -82.00 120.00   62
 25  ω      6.00 182.00   0.50    0.80    --   93.70  17.00  90.00  352
 26  ω     62.00  88.00   0.50    0.80    --   93.70 -82.00 150.00   52
 27  ω     55.00  94.00   0.50    0.80    --   93.70 -82.00 -30.00   78
 28  ω      5.00  41.00   0.50    0.80    --   93.70 -82.00-180.00   72
 29  ω     61.00  90.00   0.50    0.80    --   93.70 -82.00-180.00   58
 30  ω     25.00  71.00   0.50    0.80    --   93.70 -82.00-120.00   92
 31  ω      4.00 120.00   0.50    0.80    --   93.70 -82.00 -60.00  232
 32  ω     83.00 109.00   0.50    0.80    --   93.70 -82.00   0.00   52
 33  ω      4.00  82.00   0.50    0.80    --   93.70 -82.00 -90.00  156
 34  ω      5.00  31.00   0.50    0.80    --   93.70 -42.00-150.00   52
 35  ω     27.00  55.00   0.50    0.80    --   93.70 -77.00  60.00   56
 36  ω    158.00 183.00   0.50    0.80    --   93.70  68.00 120.00   50
 37  ω    103.00 129.00   0.50    0.80    --   93.70  68.00 120.00   52
 38  ω     70.00  97.00   0.50    0.80    --   93.70  68.00 120.00   54
 39  ω     41.00 103.00   0.50    0.80    --   93.70 -50.00  90.00  124
 40  ω     65.00 152.00   0.50    0.80    --   93.70  33.00-180.00  174
 41  ω     10.00 123.00   0.50    0.80    --   93.70 -50.00 -60.00  226
 42  ω     15.00  95.00   0.50    0.80    --   93.70 -82.00  87.55  160
;
_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      -0.0875643000
_diffrn_orient_matrix_UB_12      0.0459982000
_diffrn_orient_matrix_UB_13      -0.0719374000
_diffrn_orient_matrix_UB_21      0.0716606000
_diffrn_orient_matrix_UB_22      -0.0409019000
_diffrn_orient_matrix_UB_23      -0.0501552000
_diffrn_orient_matrix_UB_31      -0.0340349000
_diffrn_orient_matrix_UB_32      -0.2053204000
_diffrn_orient_matrix_UB_33      -0.0061473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2791
_reflns_number_total             3121
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0031(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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.089
_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)+(0.0512P)²+0.3628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N21(H21), C19(H19), C16(H16), C4(H4), C17(H17), C6(H6), C7(H7), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.11077(4) 1.04839(6) 0.59510(3) 0.05993(18) Uani 1 1 d . . . . .
N21 N 0.36474(9) 0.76922(18) 0.72752(7) 0.0440(3) Uani 1 1 d . . . . .
H21 H 0.372265 0.865154 0.701489 0.053 Uiso 1 1 calc R U . . .
O23 O 0.11294(11) 0.9187(2) 0.73081(8) 0.0688(4) Uani 1 1 d . . . . .
N14 N 0.10970(10) 0.54220(18) 0.64948(8) 0.0455(3) Uani 1 1 d . . . . .
C20 C 0.39447(11) 0.5416(2) 0.81563(8) 0.0387(3) Uani 1 1 d . . . . .
C10 C 0.27718(11) 0.6615(2) 0.71473(8) 0.0371(3) Uani 1 1 d . . . . .
C11 C 0.29176(11) 0.5232(2) 0.76692(8) 0.0391(3) Uani 1 1 d . . . . .
C15 C 0.43793(11) 0.6962(2) 0.78924(8) 0.0409(3) Uani 1 1 d . . . . .
C3 C 0.19825(11) 0.7300(2) 0.57588(8) 0.0384(3) Uani 1 1 d . . . . .
C2 C 0.18054(11) 0.6999(2) 0.65304(8) 0.0389(3) Uani 1 1 d . . . . .
C8 C 0.16462(11) 0.8977(2) 0.54065(9) 0.0443(4) Uani 1 1 d . . . . .
C12 C 0.20990(12) 0.3856(2) 0.76711(9) 0.0488(4) Uani 1 1 d . . . . .
H12A H 0.210172 0.358149 0.819219 0.059 Uiso 1 1 calc R U . . .
H12B H 0.222380 0.270866 0.743241 0.059 Uiso 1 1 calc R U . . .
C19 C 0.45303(13) 0.4426(2) 0.87868(9) 0.0487(4) Uani 1 1 d . . . . .
H19 H 0.425469 0.340617 0.897297 0.058 Uiso 1 1 calc R U . . .
C1 C 0.13370(12) 0.8871(2) 0.67230(10) 0.0481(4) Uani 1 1 d . . . . .
C16 C 0.53866(13) 0.7521(2) 0.82338(10) 0.0515(4) Uani 1 1 d . . . . .
H16 H 0.567159 0.853642 0.805262 0.062 Uiso 1 1 calc R U . . .
C5 C 0.25593(13) 0.6393(3) 0.46760(9) 0.0517(4) Uani 1 1 d . . . . .
C4 C 0.24387(12) 0.6022(2) 0.53947(9) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.266906 0.489720 0.563251 0.055 Uiso 1 1 calc R U . . .
C13 C 0.10694(13) 0.4656(3) 0.72360(10) 0.0527(4) Uani 1 1 d . . . . .
H13A H 0.055156 0.369004 0.715386 0.063 Uiso 1 1 calc R U . . .
H13B H 0.087914 0.563036 0.753776 0.063 Uiso 1 1 calc R U . . .
C17 C 0.59422(13) 0.6501(3) 0.88522(10) 0.0531(4) Uani 1 1 d . . . . .
H17 H 0.661697 0.684074 0.909103 0.064 Uiso 1 1 calc R U . . .
C6 C 0.21978(13) 0.8066(3) 0.43323(9) 0.0546(4) Uani 1 1 d . . . . .
H6 H 0.226207 0.832051 0.384811 0.065 Uiso 1 1 calc R U . . .
C7 C 0.17455(14) 0.9363(3) 0.46870(10) 0.0556(4) Uani 1 1 d . . . . .
H7 H 0.150984 1.048363 0.444735 0.067 Uiso 1 1 calc R U . . .
C18 C 0.55258(14) 0.4986(3) 0.91289(10) 0.0532(4) Uani 1 1 d . . . . .
H18 H 0.592213 0.434002 0.955036 0.064 Uiso 1 1 calc R U . . .
C22 C 0.00593(14) 0.5793(3) 0.60147(12) 0.0645(5) Uani 1 1 d . . . . .
H22A H -0.027604 0.664232 0.627218 0.097 Uiso 1 1 calc R U . . .
H22B H -0.032045 0.465055 0.591597 0.097 Uiso 1 1 calc R U . . .
H22C H 0.009195 0.632943 0.554040 0.097 Uiso 1 1 calc R U . . .
C24 C 0.3081(2) 0.5022(4) 0.42824(13) 0.0870(7) Uani 1 1 d . . . . .
H24A H 0.379711 0.531783 0.439739 0.131 Uiso 1 1 calc R U . . .
H24B H 0.277459 0.508686 0.374055 0.131 Uiso 1 1 calc R U . . .
H24C H 0.300160 0.378872 0.445873 0.131 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 1.7621(17) . ?
S9 C1 1.7838(18) . ?
N21 H21 0.8600 . ?
N21 C10 1.3831(18) . ?
N21 C15 1.3797(19) . ?
O23 C1 1.200(2) . ?
N14 C2 1.4773(19) . ?
N14 C13 1.470(2) . ?
N14 C22 1.460(2) . ?
C20 C11 1.434(2) . ?
C20 C15 1.406(2) . ?
C20 C19 1.396(2) . ?
C10 C11 1.353(2) . ?
C10 C2 1.495(2) . ?
C11 C12 1.489(2) . ?
C15 C16 1.394(2) . ?
C3 C2 1.509(2) . ?
C3 C8 1.383(2) . ?
C3 C4 1.379(2) . ?
C2 C1 1.570(2) . ?
C8 C7 1.385(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.515(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.381(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(2) . ?
C5 C4 1.392(2) . ?
C5 C6 1.382(3) . ?
C5 C24 1.508(3) . ?
C4 H4 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 92.11(7) . . ?
C10 N21 H21 125.9 . . ?
C15 N21 H21 125.9 . . ?
C15 N21 C10 108.21(12) . . ?
C13 N14 C2 115.58(12) . . ?
C22 N14 C2 113.13(13) . . ?
C22 N14 C13 110.53(13) . . ?
C15 C20 C11 106.81(13) . . ?
C19 C20 C11 133.92(14) . . ?
C19 C20 C15 119.28(14) . . ?
N21 C10 C2 123.68(13) . . ?
C11 C10 N21 110.14(13) . . ?
C11 C10 C2 126.15(13) . . ?
C20 C11 C12 131.02(14) . . ?
C10 C11 C20 107.06(13) . . ?
C10 C11 C12 121.92(14) . . ?
N21 C15 C20 107.78(13) . . ?
N21 C15 C16 130.30(14) . . ?
C16 C15 C20 121.92(14) . . ?
C8 C3 C2 116.13(13) . . ?
C4 C3 C2 124.40(13) . . ?
C4 C3 C8 119.47(14) . . ?
N14 C2 C10 108.30(12) . . ?
N14 C2 C3 109.96(12) . . ?
N14 C2 C1 111.66(12) . . ?
C10 C2 C3 113.12(12) . . ?
C10 C2 C1 108.37(12) . . ?
C3 C2 C1 105.46(12) . . ?
C3 C8 S9 114.19(12) . . ?
C3 C8 C7 120.55(15) . . ?
C7 C8 S9 125.25(13) . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 109.01(13) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.84(15) . . ?
C18 C19 H19 120.6 . . ?
O23 C1 S9 123.15(14) . . ?
O23 C1 C2 124.93(16) . . ?
C2 C1 S9 111.90(11) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 C15 117.08(16) . . ?
C17 C16 H16 121.5 . . ?
C4 C5 C24 121.22(17) . . ?
C6 C5 C4 118.26(16) . . ?
C6 C5 C24 120.52(17) . . ?
C3 C4 C5 120.91(15) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N14 C13 C12 111.49(13) . . ?
N14 C13 H13A 109.3 . . ?
N14 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 122.04(16) . . ?
C18 C17 H17 119.0 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.76(16) . . ?
C7 C6 H6 119.1 . . ?
C8 C7 H7 120.5 . . ?
C6 C7 C8 119.02(16) . . ?
C6 C7 H7 120.5 . . ?
C19 C18 C17 120.84(15) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N14 C22 H22A 109.5 . . ?
N14 C22 H22B 109.5 . . ?
N14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C24 H24A 109.5 . . ?
C5 C24 H24B 109.5 . . ?
C5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
S9 C8 C7 C6 178.94(13) . . . . ?
N21 C10 C11 C20 -0.50(17) . . . . ?
N21 C10 C11 C12 179.81(14) . . . . ?
N21 C10 C2 N14 171.83(13) . . . . ?
N21 C10 C2 C3 49.68(19) . . . . ?
N21 C10 C2 C1 -66.88(17) . . . . ?
N21 C15 C16 C17 -179.92(17) . . . . ?
N14 C2 C1 S9 -114.69(12) . . . . ?
N14 C2 C1 O23 63.6(2) . . . . ?
C20 C11 C12 C13 159.97(15) . . . . ?
C20 C15 C16 C17 -0.7(2) . . . . ?
C20 C19 C18 C17 -0.2(3) . . . . ?
C10 N21 C15 C20 -0.63(17) . . . . ?
C10 N21 C15 C16 178.64(16) . . . . ?
C10 C11 C12 C13 -20.4(2) . . . . ?
C10 C2 C1 S9 126.11(11) . . . . ?
C10 C2 C1 O23 -55.6(2) . . . . ?
C11 C20 C15 N21 0.32(16) . . . . ?
C11 C20 C15 C16 -179.02(15) . . . . ?
C11 C20 C19 C18 179.58(16) . . . . ?
C11 C10 C2 N14 -10.2(2) . . . . ?
C11 C10 C2 C3 -132.36(15) . . . . ?
C11 C10 C2 C1 111.07(17) . . . . ?
C11 C12 C13 N14 48.55(19) . . . . ?
C15 N21 C10 C11 0.71(17) . . . . ?
C15 N21 C10 C2 178.95(13) . . . . ?
C15 C20 C11 C10 0.11(16) . . . . ?
C15 C20 C11 C12 179.76(16) . . . . ?
C15 C20 C19 C18 -0.6(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C3 C2 C1 S9 4.70(14) . . . . ?
C3 C2 C1 O23 -177.04(15) . . . . ?
C3 C8 C7 C6 -1.0(2) . . . . ?
C2 N14 C13 C12 -62.85(19) . . . . ?
C2 C10 C11 C20 -178.69(13) . . . . ?
C2 C10 C11 C12 1.6(2) . . . . ?
C2 C3 C8 S9 2.02(17) . . . . ?
C2 C3 C8 C7 -178.07(14) . . . . ?
C2 C3 C4 C5 178.92(15) . . . . ?
C8 S9 C1 O23 178.36(15) . . . . ?
C8 S9 C1 C2 -3.35(11) . . . . ?
C8 C3 C2 N14 116.27(14) . . . . ?
C8 C3 C2 C10 -122.51(14) . . . . ?
C8 C3 C2 C1 -4.24(17) . . . . ?
C8 C3 C4 C5 -0.4(2) . . . . ?
C19 C20 C11 C10 179.94(17) . . . . ?
C19 C20 C11 C12 -0.4(3) . . . . ?
C19 C20 C15 N21 -179.54(14) . . . . ?
C19 C20 C15 C16 1.1(2) . . . . ?
C1 S9 C8 C3 0.88(12) . . . . ?
C1 S9 C8 C7 -179.03(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 C3 C2 N14 -63.07(18) . . . . ?
C4 C3 C2 C10 58.14(19) . . . . ?
C4 C3 C2 C1 176.41(14) . . . . ?
C4 C3 C8 S9 -178.60(12) . . . . ?
C4 C3 C8 C7 1.3(2) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C13 N14 C2 C10 40.27(17) . . . . ?
C13 N14 C2 C3 164.33(13) . . . . ?
C13 N14 C2 C1 -78.97(17) . . . . ?
C6 C5 C4 C3 -0.8(2) . . . . ?
C22 N14 C2 C10 169.12(14) . . . . ?
C22 N14 C2 C3 -66.82(17) . . . . ?
C22 N14 C2 C1 49.88(18) . . . . ?
C22 N14 C13 C12 167.03(14) . . . . ?
C24 C5 C4 C3 178.50(19) . . . . ?
C24 C5 C6 C7 -178.14(19) . . . . ?

_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 1.499
_oxdiff_exptl_absorpt_empirical_full_min 0.655
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mxtlbl2022051903_auto
_database_code_depnum_ccdc_archive 'CCDC 2205450'
loop_
_audit_author_name
_audit_author_address
'xiangtai meng'
;tjut
China
;
_audit_update_record             
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2022-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O S, C H Cl3'
_chemical_formula_sum            'C21 H21 Cl3 N2 O S'
_chemical_formula_weight         455.81
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.4056(3)
_cell_length_b                   7.68510(10)
_cell_length_c                   13.5446(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.632(3)
_cell_angle_gamma                90
_cell_volume                     1095.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.3440
_cell_measurement_theta_min      3.5280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73285
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9613
_diffrn_reflns_point_group_measured_fraction_full 0.703
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         3.535
_diffrn_ambient_temperature      293(2)
_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 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  15.00   0.50    0.50    --   42.30 -65.00 -60.00  108
  2  ω     45.00  70.00   0.50    0.50    --   42.30 -82.00  30.00   50
  3  ω    -33.00   4.00   0.50    0.50    --   42.30 -77.00  30.00   74
  4  ω     74.00 130.00   0.50    0.50    --   42.30  11.00  90.00  112
  5  ω      0.00  77.00   0.50    0.50    --   42.30 -32.00 -60.00  154
  6  ω     18.00  66.00   0.50    0.50    --   42.30 -77.00 -90.00   96
  7  ω    -34.00  68.00   0.50    0.50    --   42.30 -82.00 150.00  204
  8  ω     13.00  45.00   0.50    0.50    --   42.30 -77.00  30.00   64
  9  ω    -31.00  -6.00   0.50    0.50    --   42.30 -32.00 -60.00   50
 10  ω    -31.00  68.00   0.50    0.50    --   42.30 -77.00-180.00  198
 11  ω    -19.00   6.00   0.50    0.50    --   42.30 -82.00-150.00   50
 12  ω     16.00  59.00   0.50    0.50    --   42.30 -77.00  90.00   86
 13  ω     35.00  67.00   0.50    0.50    --   42.30 -82.00-150.00   64
 14  ω    -40.00  -8.00   0.50    0.50    --   42.30 -77.00 -90.00   64
 15  ω     -6.00  20.00   0.50    0.50    --   42.30  11.00  90.00   52
 16  ω     74.00  99.00   0.50    0.50    --   93.70 -82.00-150.00   50
 17  ω      4.00 183.00   0.50    0.50    --   93.70   0.00-120.00  358
 18  ω    145.00 183.00   0.50    0.50    --   93.70  50.00-180.00   76
 19  ω      4.00 128.00   0.50    0.50    --   93.70 -33.00-150.00  248
 20  ω     60.00  86.00   0.50    0.50    --   93.70 -82.00 -60.00   52
 21  ω     89.00 121.00   0.50    0.50    --   93.70 -33.00 -30.00   64
 22  ω     18.00  92.00   0.50    0.50    --   93.70 -82.00 -90.00  148
 23  ω     24.00  59.00   0.50    0.50    --   93.70 -82.00 -60.00   70
 24  ω     28.00  97.00   0.50    0.50    --   93.70 -82.00  30.00  138
 25  ω     55.00 111.00   0.50    0.50    --   93.70 -59.00 150.00  112
 26  ω      6.00  93.00   0.50    0.50    --   93.70 -82.00  90.00  174
 27  ω     18.00  43.00   0.50    0.50    --   93.70 -33.00 -30.00   50
 28  ω     11.00  37.00   0.50    0.50    --   93.70 -59.00 150.00   52
 29  ω     73.00  99.00   0.50    0.50    --   93.70 -82.00   0.00   52
 30  ω      9.00  63.00   0.50    0.50    --   93.70 -82.00 120.00  108
 31  ω     86.00 111.00   0.50    0.50    --   93.70 -82.00-180.00   50
 32  ω     19.00  62.00   0.50    0.50    --   93.70 -82.00   0.00   86
 33  ω     71.00  97.00   0.50    0.50    --   93.70 -82.00 120.00   52
 34  ω      6.00  82.00   0.50    0.50    --   93.70 -82.00-180.00  152
 35  ω    107.00 133.00   0.50    0.50    --   93.70  59.00 -60.00   52
 36  ω     19.00  86.00   0.50    0.50    --   93.70 -33.00 150.00  134
 37  ω     73.00  98.00   0.50    0.50    --   93.70 -82.00-120.00   50
 38  ω     31.00  91.00   0.50    0.50    --   93.70 -82.00 -30.00  120
 39  ω     38.00  80.00   0.50    0.50    --   93.70 -82.00  60.00   84
 40  ω      4.00 103.00   0.50    0.50    --   93.70 -82.00 145.35  198
;
_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      0.1430854000
_diffrn_orient_matrix_UB_12      0.0414664000
_diffrn_orient_matrix_UB_13      0.0436983000
_diffrn_orient_matrix_UB_21      0.0039282000
_diffrn_orient_matrix_UB_22      -0.0023139000
_diffrn_orient_matrix_UB_23      0.1149367000
_diffrn_orient_matrix_UB_31      0.0302089000
_diffrn_orient_matrix_UB_32      -0.1962305000
_diffrn_orient_matrix_UB_33      0.0078837000
_diffrn_oxdiff_digest_frames     
;
01dbcc61eaca1997555d2c738db835097900029c593
;
_diffrn_oxdiff_digest_hkl        
;
01bb2aa49779aa56268de66440aadac907c39c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.307
_reflns_Friedel_fraction_full    0.360
_reflns_Friedel_fraction_max     0.357
_reflns_number_gt                2605
_reflns_number_total             2795
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+0.3026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1561
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00P(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00K(H00K),
 C00M(H00M), C00N(H00N)
2.d Idealised Me refined as rotating group:
 C00Q(H00I,H00L,H00O), C00R(H00P,H00Q,H00R)
2.e Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S001 S 0.73013(12) 0.74125(19) 0.92659(9) 0.0705(4) Uani 1 1 d . . . . .
Cl00 Cl 0.1438(2) 0.8222(5) 0.7048(2) 0.1355(10) Uani 1 1 d . . . . .
Cl1 Cl 0.2496(4) 0.7447(4) 0.5512(3) 0.1694(14) Uani 1 1 d . . . . .
Cl2 Cl 0.0842(3) 0.5012(5) 0.5919(4) 0.1871(17) Uani 1 1 d . . . . .
N005 N 0.5338(3) 0.4702(6) 0.6131(3) 0.0493(8) Uani 1 1 d . . . . .
H005 H 0.590196 0.543826 0.612183 0.059 Uiso 1 1 calc R . . . .
C006 C 0.5262(3) 0.3952(6) 0.7031(3) 0.0457(9) Uani 1 1 d . . . . .
O007 O 0.4832(4) 0.6440(8) 0.8693(3) 0.0918(15) Uani 1 1 d . . . . .
H007 H 0.489594 0.730781 0.906251 0.138 Uiso 1 1 calc GR . . . .
C008 C 0.7522(4) 0.4473(6) 0.8312(3) 0.0466(9) Uani 1 1 d . . . . .
N009 N 0.5809(4) 0.3381(8) 0.8919(3) 0.0683(13) Uani 1 1 d . . . . .
C00A C 0.4348(4) 0.4060(6) 0.5249(3) 0.0457(9) Uani 1 1 d . . . . .
C00B C 0.3654(4) 0.2896(6) 0.5608(3) 0.0508(10) Uani 1 1 d . . . . .
C00C C 0.3997(5) 0.4455(7) 0.4168(3) 0.0562(11) Uani 1 1 d . . . . .
H00C H 0.445966 0.523900 0.393801 0.067 Uiso 1 1 calc R . . . .
C00D C 0.6132(4) 0.4463(7) 0.8146(3) 0.0511(10) Uani 1 1 d . . . . .
C00E C 0.8127(4) 0.3200(7) 0.7965(3) 0.0505(10) Uani 1 1 d . . . . .
H00E H 0.766130 0.226035 0.757651 0.061 Uiso 1 1 calc R . . . .
C00F C 0.8205(4) 0.5902(7) 0.8885(3) 0.0531(11) Uani 1 1 d . . . . .
C00G C 0.2940(5) 0.3636(7) 0.3458(3) 0.0605(12) Uani 1 1 d . . . . .
H00G H 0.269409 0.385657 0.273046 0.073 Uiso 1 1 calc R . . . .
C00H C 1.0080(4) 0.4747(8) 0.8757(3) 0.0595(12) Uani 1 1 d . . . . .
H00H H 1.094470 0.484398 0.890627 0.071 Uiso 1 1 calc R . . . .
C00I C 0.4259(4) 0.2837(7) 0.6754(3) 0.0516(10) Uani 1 1 d . . . . .
C00J C 0.5808(5) 0.6414(8) 0.8332(4) 0.0638(13) Uani 1 1 d . . . . .
H00J H 0.553234 0.703578 0.764832 0.077 Uiso 1 1 calc R . . . .
C00K C 0.9498(4) 0.6030(8) 0.9103(3) 0.0592(12) Uani 1 1 d . . . . .
H00K H 0.996157 0.697944 0.948037 0.071 Uiso 1 1 calc R . . . .
C00L C 0.9426(4) 0.3299(8) 0.8189(3) 0.0565(11) Uani 1 1 d . . . . .
C00M C 0.2223(4) 0.2484(8) 0.3792(4) 0.0635(12) Uani 1 1 d . . . . .
H00M H 0.149717 0.198354 0.328725 0.076 Uiso 1 1 calc R . . . .
C00N C 0.2571(4) 0.2073(7) 0.4859(4) 0.0596(11) Uani 1 1 d . . . . .
H00N H 0.210490 0.127762 0.507748 0.072 Uiso 1 1 calc R . . . .
C00O C 0.5264(6) 0.1678(10) 0.8547(4) 0.0794(17) Uani 1 1 d . . . . .
H00A H 0.511871 0.108271 0.912171 0.095 Uiso 1 1 calc R . . . .
H00B H 0.586259 0.099208 0.836066 0.095 Uiso 1 1 calc R . . . .
C00P C 0.4014(5) 0.1803(10) 0.7578(4) 0.0768(17) Uani 1 1 d . . . . .
H00D H 0.371287 0.065074 0.730696 0.092 Uiso 1 1 calc R . . . .
H00F H 0.337390 0.236785 0.777411 0.092 Uiso 1 1 calc R . . . .
C00Q C 0.6855(6) 0.3233(14) 0.9980(4) 0.096(3) Uani 1 1 d . . . . .
H00I H 0.746273 0.239478 0.994615 0.144 Uiso 1 1 calc GR . . . .
H00L H 0.652063 0.286454 1.049668 0.144 Uiso 1 1 calc GR . . . .
H00O H 0.726169 0.434338 1.018563 0.144 Uiso 1 1 calc GR . . . .
C00R C 1.0066(5) 0.1873(11) 0.7824(5) 0.0847(19) Uani 1 1 d . . . . .
H00P H 1.001573 0.080468 0.817256 0.127 Uiso 1 1 calc GR . . . .
H00Q H 1.094129 0.217117 0.800243 0.127 Uiso 1 1 calc GR . . . .
H00R H 0.965056 0.173258 0.706334 0.127 Uiso 1 1 calc GR . . . .
C00S C 0.1992(6) 0.6576(12) 0.6438(7) 0.098(2) Uani 1 1 d . . . . .
H00S H 0.272556 0.602629 0.699425 0.118 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S001 C00F 1.757(5) . ?
S001 C00J 1.853(5) . ?
Cl00 C00S 1.756(9) . ?
Cl1 C00S 1.704(8) . ?
Cl2 C00S 1.717(9) . ?
N005 H005 0.8600 . ?
N005 C006 1.381(5) . ?
N005 C00A 1.381(5) . ?
C006 C00D 1.505(6) . ?
C006 C00I 1.362(6) . ?
O007 H007 0.8200 . ?
O007 C00J 1.378(6) . ?
C008 C00D 1.513(6) . ?
C008 C00E 1.380(6) . ?
C008 C00F 1.396(7) . ?
N009 C00D 1.490(6) . ?
N009 C00O 1.453(9) . ?
N009 C00Q 1.477(6) . ?
C00A C00B 1.400(6) . ?
C00A C00C 1.394(6) . ?
C00B C00I 1.437(6) . ?
C00B C00N 1.411(6) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.372(7) . ?
C00D C00J 1.588(8) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.395(6) . ?
C00F C00K 1.391(7) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.394(8) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.369(8) . ?
C00H C00L 1.395(8) . ?
C00I C00P 1.482(7) . ?
C00J H00J 0.9800 . ?
C00K H00K 0.9300 . ?
C00L C00R 1.502(8) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.379(7) . ?
C00N H00N 0.9300 . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00O C00P 1.524(8) . ?
C00P H00D 0.9700 . ?
C00P H00F 0.9700 . ?
C00Q H00I 0.9600 . ?
C00Q H00L 0.9600 . ?
C00Q H00O 0.9600 . ?
C00R H00P 0.9600 . ?
C00R H00Q 0.9600 . ?
C00R H00R 0.9600 . ?
C00S H00S 0.9800 . ?

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
C00F S001 C00J 90.9(2) . . ?
C006 N005 H005 126.1 . . ?
C006 N005 C00A 107.9(4) . . ?
C00A N005 H005 126.1 . . ?
N005 C006 C00D 122.4(4) . . ?
C00I C006 N005 110.6(3) . . ?
C00I C006 C00D 126.9(4) . . ?
C00J O007 H007 109.5 . . ?
C00E C008 C00D 125.3(4) . . ?
C00E C008 C00F 120.1(4) . . ?
C00F C008 C00D 114.6(4) . . ?
C00O N009 C00D 116.6(4) . . ?
C00O N009 C00Q 110.2(6) . . ?
C00Q N009 C00D 113.6(4) . . ?
N005 C00A C00B 108.1(4) . . ?
N005 C00A C00C 129.8(4) . . ?
C00C C00A C00B 122.1(4) . . ?
C00A C00B C00I 107.2(4) . . ?
C00A C00B C00N 119.5(4) . . ?
C00N C00B C00I 133.3(4) . . ?
C00A C00C H00C 121.4 . . ?
C00G C00C C00A 117.2(5) . . ?
C00G C00C H00C 121.4 . . ?
C006 C00D C008 113.5(3) . . ?
C006 C00D C00J 107.6(4) . . ?
C008 C00D C00J 105.4(4) . . ?
N009 C00D C006 108.3(4) . . ?
N009 C00D C008 115.2(4) . . ?
N009 C00D C00J 106.2(4) . . ?
C008 C00E H00E 119.5 . . ?
C008 C00E C00L 121.0(4) . . ?
C00L C00E H00E 119.5 . . ?
C008 C00F S001 114.7(3) . . ?
C00K C00F S001 125.8(4) . . ?
C00K C00F C008 119.5(4) . . ?
C00C C00G H00G 119.0 . . ?
C00C C00G C00M 122.1(4) . . ?
C00M C00G H00G 119.0 . . ?
C00K C00H H00H 118.8 . . ?
C00K C00H C00L 122.4(4) . . ?
C00L C00H H00H 118.8 . . ?
C006 C00I C00B 106.3(4) . . ?
C006 C00I C00P 120.8(4) . . ?
C00B C00I C00P 132.8(4) . . ?
S001 C00J H00J 108.6 . . ?
O007 C00J S001 114.1(3) . . ?
O007 C00J C00D 109.8(5) . . ?
O007 C00J H00J 108.6 . . ?
C00D C00J S001 106.9(3) . . ?
C00D C00J H00J 108.6 . . ?
C00F C00K H00K 120.3 . . ?
C00H C00K C00F 119.4(5) . . ?
C00H C00K H00K 120.3 . . ?
C00E C00L C00R 119.9(5) . . ?
C00H C00L C00E 117.5(4) . . ?
C00H C00L C00R 122.6(4) . . ?
C00G C00M H00M 119.4 . . ?
C00N C00M C00G 121.2(4) . . ?
C00N C00M H00M 119.4 . . ?
C00B C00N H00N 121.0 . . ?
C00M C00N C00B 118.0(5) . . ?
C00M C00N H00N 121.0 . . ?
N009 C00O H00A 109.2 . . ?
N009 C00O H00B 109.2 . . ?
N009 C00O C00P 112.0(6) . . ?
H00A C00O H00B 107.9 . . ?
C00P C00O H00A 109.2 . . ?
C00P C00O H00B 109.2 . . ?
C00I C00P C00O 107.3(4) . . ?
C00I C00P H00D 110.2 . . ?
C00I C00P H00F 110.2 . . ?
C00O C00P H00D 110.2 . . ?
C00O C00P H00F 110.2 . . ?
H00D C00P H00F 108.5 . . ?
N009 C00Q H00I 109.5 . . ?
N009 C00Q H00L 109.5 . . ?
N009 C00Q H00O 109.5 . . ?
H00I C00Q H00L 109.5 . . ?
H00I C00Q H00O 109.5 . . ?
H00L C00Q H00O 109.5 . . ?
C00L C00R H00P 109.5 . . ?
C00L C00R H00Q 109.5 . . ?
C00L C00R H00R 109.5 . . ?
H00P C00R H00Q 109.5 . . ?
H00P C00R H00R 109.5 . . ?
H00Q C00R H00R 109.5 . . ?
Cl00 C00S H00S 107.7 . . ?
Cl1 C00S Cl00 110.3(5) . . ?
Cl1 C00S Cl2 113.2(5) . . ?
Cl1 C00S H00S 107.7 . . ?
Cl2 C00S Cl00 109.9(4) . . ?
Cl2 C00S H00S 107.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 C00F C00K C00H 179.9(4) . . . . ?
N005 C006 C00D C008 -49.5(6) . . . . ?
N005 C006 C00D N009 -178.9(4) . . . . ?
N005 C006 C00D C00J 66.7(5) . . . . ?
N005 C006 C00I C00B -0.5(5) . . . . ?
N005 C006 C00I C00P 177.0(5) . . . . ?
N005 C00A C00B C00I -0.2(5) . . . . ?
N005 C00A C00B C00N 179.0(4) . . . . ?
N005 C00A C00C C00G -178.5(5) . . . . ?
C006 N005 C00A C00B -0.2(5) . . . . ?
C006 N005 C00A C00C 178.0(5) . . . . ?
C006 C00D C00J S001 -149.2(3) . . . . ?
C006 C00D C00J O007 86.6(4) . . . . ?
C006 C00I C00P C00O -22.4(8) . . . . ?
C008 C00D C00J S001 -27.7(4) . . . . ?
C008 C00D C00J O007 -151.9(4) . . . . ?
C008 C00E C00L C00H -1.2(6) . . . . ?
C008 C00E C00L C00R 178.6(5) . . . . ?
C008 C00F C00K C00H -0.4(7) . . . . ?
N009 C00D C00J S001 95.1(4) . . . . ?
N009 C00D C00J O007 -29.2(5) . . . . ?
N009 C00O C00P C00I 54.6(7) . . . . ?
C00A N005 C006 C00D -175.0(4) . . . . ?
C00A N005 C006 C00I 0.4(5) . . . . ?
C00A C00B C00I C006 0.4(5) . . . . ?
C00A C00B C00I C00P -176.6(6) . . . . ?
C00A C00B C00N C00M -1.3(7) . . . . ?
C00A C00C C00G C00M 1.3(8) . . . . ?
C00B C00A C00C C00G -0.7(7) . . . . ?
C00B C00I C00P C00O 154.3(6) . . . . ?
C00C C00A C00B C00I -178.4(4) . . . . ?
C00C C00A C00B C00N 0.7(7) . . . . ?
C00C C00G C00M C00N -2.0(8) . . . . ?
C00D C006 C00I C00B 174.6(4) . . . . ?
C00D C006 C00I C00P -7.9(8) . . . . ?
C00D C008 C00E C00L -177.9(4) . . . . ?
C00D C008 C00F S001 -1.4(5) . . . . ?
C00D C008 C00F C00K 178.8(4) . . . . ?
C00D N009 C00O C00P -60.7(6) . . . . ?
C00E C008 C00D C006 -44.4(6) . . . . ?
C00E C008 C00D N009 81.3(5) . . . . ?
C00E C008 C00D C00J -161.9(4) . . . . ?
C00E C008 C00F S001 179.8(3) . . . . ?
C00E C008 C00F C00K 0.0(6) . . . . ?
C00F S001 C00J O007 145.6(5) . . . . ?
C00F S001 C00J C00D 24.0(4) . . . . ?
C00F C008 C00D C006 136.8(4) . . . . ?
C00F C008 C00D N009 -97.5(5) . . . . ?
C00F C008 C00D C00J 19.3(5) . . . . ?
C00F C008 C00E C00L 0.8(6) . . . . ?
C00G C00M C00N C00B 1.9(8) . . . . ?
C00I C006 C00D C008 135.8(5) . . . . ?
C00I C006 C00D N009 6.5(6) . . . . ?
C00I C006 C00D C00J -107.9(5) . . . . ?
C00I C00B C00N C00M 177.6(5) . . . . ?
C00J S001 C00F C008 -14.0(4) . . . . ?
C00J S001 C00F C00K 165.7(5) . . . . ?
C00K C00H C00L C00E 0.8(7) . . . . ?
C00K C00H C00L C00R -178.9(5) . . . . ?
C00L C00H C00K C00F 0.0(7) . . . . ?
C00N C00B C00I C006 -178.5(5) . . . . ?
C00N C00B C00I C00P 4.4(10) . . . . ?
C00O N009 C00D C006 27.7(6) . . . . ?
C00O N009 C00D C008 -100.6(5) . . . . ?
C00O N009 C00D C00J 143.0(5) . . . . ?
C00Q N009 C00D C006 157.5(6) . . . . ?
C00Q N009 C00D C008 29.2(7) . . . . ?
C00Q N009 C00D C00J -87.2(6) . . . . ?
C00Q N009 C00O C00P 167.9(5) . . . . ?

_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.755
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m1_auto
_database_code_depnum_ccdc_archive 'CCDC 2216328'
loop_
_audit_author_name
_audit_author_address
'xiangtai meng'
;tjut edu
China
;
_audit_update_record             
;
2022-10-30 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2022-10-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H28 N2 O5 S'
_chemical_formula_sum            'C31 H28 N2 O5 S'
_chemical_formula_weight         540.61
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3292(10)
_cell_length_b                   9.8454(6)
_cell_length_c                   18.1637(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.633(6)
_cell_angle_gamma                90
_cell_volume                     2750.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.5770
_cell_measurement_theta_min      2.8680
_shelx_estimated_absorpt_T_max   0.767
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    1.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57799
_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_absorpt_special_details   ?
_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    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26697
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.623
_diffrn_reflns_theta_min         2.873
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00  87.00   0.50    0.50    --   42.30  32.00 -90.00   54
  2  ω     19.00  69.00   0.50    0.50    --   42.30 -82.00  60.00  100
  3  ω     34.00  65.00   0.50    0.50    --   42.30 -82.00-150.00   62
  4  ω     91.00 121.00   0.50    0.50    --   42.30  32.00 -90.00   60
  5  ω    -45.00  12.00   0.50    0.50    --   42.30 -65.00 -30.00  114
  6  ω     21.00  89.00   0.50    0.50    --   42.30  77.00 120.00  136
  7  ω     15.00  41.00   0.50    0.50    --   42.30 -65.00-180.00   52
  8  ω     18.00 123.00   0.50    0.50    --   42.30  65.00  60.00  210
  9  ω    -47.00  13.00   0.50    0.50    --   42.30 -82.00 120.00  120
 10  ω     11.00  69.00   0.50    0.50    --   42.30 -82.00 -90.00  116
 11  ω    -47.00  51.00   0.50    0.50    --   42.30 -82.00-120.00  196
 12  ω     95.00 132.00   0.50    0.50    --   42.30  82.00 150.00   74
 13  ω    100.00 132.00   0.50    0.50    --   42.30  77.00 120.00   64
 14  ω     17.00  43.00   0.50    0.50    --   42.30 -65.00 -30.00   52
 15  ω    -36.00 -10.00   0.50    0.50    --   42.30 -82.00 -90.00   52
 16  ω     36.00  61.00   0.50    0.50    --   42.30 -77.00 -90.00   50
 17  ω     36.00  67.00   0.50    0.50    --   42.30 -82.00 120.00   62
 18  ω    -40.00 -15.00   0.50    0.50    --   42.30 -65.00-180.00   50
 19  ω     18.00  87.00   0.50    0.50    --   42.30  82.00 150.00  138
 20  ω     -5.00  21.00   0.50    0.50    --   42.30 -82.00-150.00   52
 21  ω     42.00  69.00   0.50    0.50    --   42.30 -82.00   0.00   54
 22  ω    -34.00  10.00   0.50    0.50    --   42.30 -82.00   0.00   88
 23  ω    -46.00   3.00   0.50    0.50    --   42.30 -82.00  60.00   98
 24  ω      6.00  98.00   0.50    0.50    --   93.70 -82.00 -30.00  184
 25  ω     28.00  96.00   0.50    0.50    --   93.70 -82.00 150.00  136
 26  ω    103.00 183.00   0.50    0.50    --   93.70  68.00-120.00  160
 27  ω     69.00 162.00   0.50    0.50    --   93.70  59.00   0.00  186
 28  ω     22.00 103.00   0.50    0.50    --   93.70 -82.00-180.00  162
 29  ω     86.00 171.00   0.50    0.50    --   93.70  59.00  30.00  170
 30  ω     50.00  81.00   0.50    0.50    --   93.70 -82.00 120.00   62
 31  ω     37.00  97.00   0.50    0.50    --   93.70 -82.00   0.00  120
 32  ω     65.00  91.00   0.50    0.50    --   93.70 -82.00 -60.00   52
 33  ω     10.00 104.00   0.50    0.50    --   93.70 -82.00-120.00  188
 34  ω      5.00  30.00   0.50    0.50    --   93.70 -82.00   0.00   50
 35  ω     59.00 110.00   0.50    0.50    --   93.70 -59.00 120.00  102
 36  ω     13.00  92.00   0.50    0.50    --   93.70 -82.00  60.00  158
 37  ω     65.00 174.00   0.50    0.50    --   93.70  50.00 -60.00  218
 38  ω    112.00 180.00   0.50    0.50    --   93.70  42.00 -90.00  136
 39  ω      5.00  97.00   0.50    0.50    --   93.70 -82.00  30.00  184
 40  ω      4.00 107.00   0.50    0.50    --   93.70 -82.00  90.00  206
 41  ω     67.00 181.00   0.50    0.50    --   93.70  59.00 -30.00  228
 42  ω    102.00 129.00   0.50    0.50    --   93.70  42.00  60.00   54
 43  ω     87.00 112.00   0.50    0.50    --   93.70 -82.00 -73.16   50
 44  ω     33.00  74.00   0.50    0.50    --   93.70 -82.00 -73.16   82
;
_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      -0.0308425000
_diffrn_orient_matrix_UB_12      -0.1465956000
_diffrn_orient_matrix_UB_13      0.0042214000
_diffrn_orient_matrix_UB_21      0.0926086000
_diffrn_orient_matrix_UB_22      -0.0529027000
_diffrn_orient_matrix_UB_23      0.0127980000
_diffrn_orient_matrix_UB_31      0.0221984000
_diffrn_orient_matrix_UB_32      0.0145065000
_diffrn_orient_matrix_UB_33      0.0890786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3023
_reflns_number_total             4919
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1857
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C00S(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010)
2.c Idealised Me refined as rotating group:
 C00W(H00F,H00G,H00H), C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,
 H01H,H01I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S01 S 0.12976(6) 0.37833(10) 0.13320(5) 0.0761(3) Uani 1 1 d . . . . .
O002 O 0.18032(15) 0.4962(3) 0.37898(12) 0.0763(7) Uani 1 1 d . . . . .
O003 O 0.25488(16) 0.6248(3) 0.48288(12) 0.0846(7) Uani 1 1 d . . . . .
N004 N 0.31236(16) 0.5872(3) 0.38966(13) 0.0611(7) Uani 1 1 d . . . . .
O005 O 0.30702(16) 0.2202(3) 0.16080(14) 0.0912(8) Uani 1 1 d . . . . .
O006 O 0.08000(17) 0.2653(3) 0.14499(17) 0.1055(9) Uani 1 1 d . . . . .
O007 O 0.14382(18) 0.3893(3) 0.05974(13) 0.1059(9) Uani 1 1 d . . . . .
C008 C 0.15625(19) 0.5916(3) 0.22178(16) 0.0585(8) Uani 1 1 d . . . . .
C009 C 0.23431(19) 0.5029(3) 0.25265(16) 0.0584(8) Uani 1 1 d . . . . .
C00A C 0.2420(2) 0.5630(3) 0.41551(16) 0.0630(8) Uani 1 1 d . . . . .
N00B N 0.3774(2) 0.2999(3) 0.22065(18) 0.0841(8) Uani 1 1 d . . . . .
C00C C 0.3141(2) 0.5425(3) 0.31641(16) 0.0597(8) Uani 1 1 d . . . . .
C00D C 0.2295(2) 0.3875(3) 0.21238(17) 0.0631(8) Uani 1 1 d . . . . .
C00E C 0.1422(2) 0.7191(3) 0.24636(17) 0.0647(8) Uani 1 1 d . . . . .
H00E H 0.184282 0.758816 0.288895 0.078 Uiso 1 1 calc R U . . .
C00F C 0.09383(19) 0.5343(3) 0.15711(16) 0.0632(8) Uani 1 1 d . . . . .
C00G C 0.3969(2) 0.6314(3) 0.43343(19) 0.0702(9) Uani 1 1 d . . . . .
C00H C 0.3963(2) 0.5562(3) 0.31420(19) 0.0693(9) Uani 1 1 d . . . . .
C00I C 0.0173(2) 0.6020(4) 0.11754(19) 0.0764(10) Uani 1 1 d . . . . .
H00I H -0.023847 0.563234 0.074023 0.092 Uiso 1 1 calc R U . . .
C00J C 0.2930(2) 0.2731(4) 0.22844(18) 0.0702(9) Uani 1 1 d . . . . .
C00K C 0.4488(2) 0.6128(3) 0.3877(2) 0.0757(10) Uani 1 1 d . . . . .
C00L C 0.0653(2) 0.7893(4) 0.20787(19) 0.0727(9) Uani 1 1 d . . . . .
C00M C 0.2923(2) 0.1717(4) 0.2892(2) 0.0735(9) Uani 1 1 d . . . . .
C00N C 0.0036(2) 0.7277(4) 0.1441(2) 0.0764(10) Uani 1 1 d . . . . .
H00N H -0.048228 0.772859 0.118818 0.092 Uiso 1 1 calc R U . . .
C00O C 0.2400(2) 0.1875(4) 0.3352(2) 0.0801(10) Uani 1 1 d . . . . .
H00O H 0.202945 0.261808 0.327397 0.096 Uiso 1 1 calc R U . . .
C00P C 0.1874(3) 0.6249(5) 0.5215(2) 0.0883(12) Uani 1 1 d . . . . .
C00Q C 0.4306(3) 0.6846(4) 0.5089(2) 0.0933(12) Uani 1 1 d . . . . .
H00Q H 0.396253 0.696326 0.540255 0.112 Uiso 1 1 calc R U . . .
C00R C 0.3864(3) 0.4325(4) 0.1861(2) 0.0918(12) Uani 1 1 d . . . . .
H00A H 0.329471 0.468509 0.156899 0.110 Uiso 1 1 calc R U . . .
H00B H 0.418981 0.421782 0.150589 0.110 Uiso 1 1 calc R U . . .
C00S C 0.4334(3) 0.5288(4) 0.2511(2) 0.0919(12) Uani 1 1 d . . . . .
H00C H 0.491876 0.494124 0.275591 0.110 Uiso 1 1 calc R U . . .
H00D H 0.438615 0.615196 0.227358 0.110 Uiso 1 1 calc R U . . .
C00T C 0.5364(2) 0.6493(4) 0.4160(3) 0.0976(13) Uani 1 1 d . . . . .
H00T H 0.571573 0.637132 0.385437 0.117 Uiso 1 1 calc R U . . .
C00U C 0.2427(3) 0.0937(4) 0.3923(2) 0.0952(12) Uani 1 1 d . . . . .
H00U H 0.208248 0.106114 0.423450 0.114 Uiso 1 1 calc R U . . .
C00V C 0.3453(3) 0.0579(4) 0.3008(3) 0.0965(12) Uani 1 1 d . . . . .
H00V H 0.379711 0.044352 0.269745 0.116 Uiso 1 1 calc R U . . .
C00W C 0.0510(3) 0.9300(4) 0.2344(3) 0.1059(14) Uani 1 1 d . . . . .
H00F H 0.078184 0.936800 0.290013 0.159 Uiso 1 1 calc R U . . .
H00G H -0.010251 0.946637 0.220716 0.159 Uiso 1 1 calc R U . . .
H00H H 0.075940 0.995975 0.209231 0.159 Uiso 1 1 calc R U . . .
C00X C 0.5696(3) 0.7031(5) 0.4893(3) 0.1193(18) Uani 1 1 d . . . . .
H00X H 0.627669 0.729345 0.508654 0.143 Uiso 1 1 calc R U . . .
C00Y C 0.5181(4) 0.7189(5) 0.5346(3) 0.1190(18) Uani 1 1 d . . . . .
H00Y H 0.542873 0.754058 0.584724 0.143 Uiso 1 1 calc R U . . .
C00Z C 0.2959(3) -0.0177(5) 0.4035(3) 0.1119(15) Uani 1 1 d . . . . .
H00Z H 0.297196 -0.081456 0.441649 0.134 Uiso 1 1 calc R U . . .
C010 C 0.3474(3) -0.0342(5) 0.3576(3) 0.1164(16) Uani 1 1 d . . . . .
H010 H 0.383991 -0.109174 0.365429 0.140 Uiso 1 1 calc R U . . .
C011 C 0.1639(4) 0.4847(6) 0.5358(3) 0.138(2) Uani 1 1 d . . . . .
H01A H 0.126598 0.446000 0.487649 0.208 Uiso 1 1 calc R U . . .
H01B H 0.134058 0.486080 0.573192 0.208 Uiso 1 1 calc R U . . .
H01C H 0.215681 0.430873 0.555693 0.208 Uiso 1 1 calc R U . . .
C012 C 0.1121(4) 0.7071(7) 0.4720(3) 0.149(2) Uani 1 1 d . . . . .
H01D H 0.132364 0.794428 0.462036 0.224 Uiso 1 1 calc R U . . .
H01E H 0.070939 0.718630 0.498763 0.224 Uiso 1 1 calc R U . . .
H01F H 0.084719 0.661012 0.423317 0.224 Uiso 1 1 calc R U . . .
C013 C 0.2366(4) 0.6963(7) 0.5980(3) 0.169(3) Uani 1 1 d . . . . .
H01G H 0.292296 0.654063 0.621345 0.253 Uiso 1 1 calc R U . . .
H01H H 0.203929 0.689707 0.633087 0.253 Uiso 1 1 calc R U . . .
H01I H 0.244483 0.790241 0.587887 0.253 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S01 O006 1.436(3) . ?
S01 O007 1.432(3) . ?
S01 C00D 1.776(3) . ?
S01 C00F 1.750(3) . ?
O002 C00A 1.200(4) . ?
O003 C00A 1.318(4) . ?
O003 C00P 1.493(4) . ?
N004 C00A 1.400(4) . ?
N004 C00C 1.411(4) . ?
N004 C00G 1.411(4) . ?
O005 N00B 1.510(4) . ?
O005 C00J 1.422(4) . ?
C008 C009 1.491(4) . ?
C008 C00E 1.377(4) . ?
C008 C00F 1.390(4) . ?
C009 C00C 1.476(4) . ?
C009 C00D 1.339(4) . ?
N00B C00J 1.456(4) . ?
N00B C00R 1.478(5) . ?
C00C C00H 1.363(4) . ?
C00D C00J 1.492(4) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.399(4) . ?
C00F C00I 1.385(4) . ?
C00G C00K 1.384(5) . ?
C00G C00Q 1.397(5) . ?
C00H C00K 1.435(5) . ?
C00H C00S 1.490(5) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.373(5) . ?
C00J C00M 1.491(5) . ?
C00K C00T 1.395(5) . ?
C00L C00N 1.393(5) . ?
C00L C00W 1.510(5) . ?
C00M C00O 1.389(5) . ?
C00M C00V 1.388(5) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00U 1.378(5) . ?
C00P C011 1.479(6) . ?
C00P C012 1.494(6) . ?
C00P C013 1.524(6) . ?
C00Q H00Q 0.9300 . ?
C00Q C00Y 1.389(6) . ?
C00R H00A 0.9700 . ?
C00R H00B 0.9700 . ?
C00R C00S 1.506(5) . ?
C00S H00C 0.9700 . ?
C00S H00D 0.9700 . ?
C00T H00T 0.9300 . ?
C00T C00X 1.366(6) . ?
C00U H00U 0.9300 . ?
C00U C00Z 1.371(6) . ?
C00V H00V 0.9300 . ?
C00V C010 1.366(6) . ?
C00W H00F 0.9600 . ?
C00W H00G 0.9600 . ?
C00W H00H 0.9600 . ?
C00X H00X 0.9300 . ?
C00X C00Y 1.368(7) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C00Z C010 1.378(6) . ?
C010 H010 0.9300 . ?
C011 H01A 0.9600 . ?
C011 H01B 0.9600 . ?
C011 H01C 0.9600 . ?
C012 H01D 0.9600 . ?
C012 H01E 0.9600 . ?
C012 H01F 0.9600 . ?
C013 H01G 0.9600 . ?
C013 H01H 0.9600 . ?
C013 H01I 0.9600 . ?

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
O006 S01 C00D 109.25(16) . . ?
O006 S01 C00F 112.94(17) . . ?
O007 S01 O006 118.23(17) . . ?
O007 S01 C00D 111.12(16) . . ?
O007 S01 C00F 109.71(16) . . ?
C00F S01 C00D 92.69(15) . . ?
C00A O003 C00P 121.6(3) . . ?
C00A N004 C00C 122.8(3) . . ?
C00A N004 C00G 128.4(3) . . ?
C00C N004 C00G 107.6(3) . . ?
C00J O005 N00B 59.46(19) . . ?
C00E C008 C009 128.8(3) . . ?
C00E C008 C00F 119.3(3) . . ?
C00F C008 C009 111.8(3) . . ?
C00C C009 C008 123.9(3) . . ?
C00D C009 C008 113.9(3) . . ?
C00D C009 C00C 121.8(3) . . ?
O002 C00A O003 127.5(3) . . ?
O002 C00A N004 122.6(3) . . ?
O003 C00A N004 109.9(3) . . ?
C00J N00B O005 57.28(18) . . ?
C00J N00B C00R 115.7(3) . . ?
C00R N00B O005 108.3(3) . . ?
N004 C00C C009 122.0(3) . . ?
C00H C00C N004 109.2(3) . . ?
C00H C00C C009 128.4(3) . . ?
C009 C00D S01 110.8(2) . . ?
C009 C00D C00J 128.6(3) . . ?
C00J C00D S01 120.5(2) . . ?
C008 C00E H00E 119.7 . . ?
C008 C00E C00L 120.5(3) . . ?
C00L C00E H00E 119.7 . . ?
C008 C00F S01 110.7(2) . . ?
C00I C00F S01 127.8(3) . . ?
C00I C00F C008 121.4(3) . . ?
C00K C00G N004 107.5(3) . . ?
C00K C00G C00Q 121.4(3) . . ?
C00Q C00G N004 131.0(4) . . ?
C00C C00H C00K 107.3(3) . . ?
C00C C00H C00S 131.6(3) . . ?
C00K C00H C00S 121.1(3) . . ?
C00F C00I H00I 120.8 . . ?
C00N C00I C00F 118.4(3) . . ?
C00N C00I H00I 120.8 . . ?
O005 C00J N00B 63.3(2) . . ?
O005 C00J C00D 114.3(3) . . ?
O005 C00J C00M 116.0(3) . . ?
N00B C00J C00D 117.6(3) . . ?
N00B C00J C00M 115.9(3) . . ?
C00M C00J C00D 118.2(3) . . ?
C00G C00K C00H 108.4(3) . . ?
C00G C00K C00T 120.3(4) . . ?
C00T C00K C00H 131.3(4) . . ?
C00E C00L C00W 120.2(3) . . ?
C00N C00L C00E 118.5(3) . . ?
C00N C00L C00W 121.3(3) . . ?
C00O C00M C00J 122.0(3) . . ?
C00V C00M C00J 119.5(4) . . ?
C00V C00M C00O 118.5(4) . . ?
C00I C00N C00L 121.8(3) . . ?
C00I C00N H00N 119.1 . . ?
C00L C00N H00N 119.1 . . ?
C00M C00O H00O 119.7 . . ?
C00U C00O C00M 120.5(4) . . ?
C00U C00O H00O 119.7 . . ?
O003 C00P C012 107.8(3) . . ?
O003 C00P C013 100.5(4) . . ?
C011 C00P O003 111.0(3) . . ?
C011 C00P C012 113.7(5) . . ?
C011 C00P C013 111.1(4) . . ?
C012 C00P C013 112.0(5) . . ?
C00G C00Q H00Q 121.9 . . ?
C00Y C00Q C00G 116.2(4) . . ?
C00Y C00Q H00Q 121.9 . . ?
N00B C00R H00A 109.9 . . ?
N00B C00R H00B 109.9 . . ?
N00B C00R C00S 108.7(3) . . ?
H00A C00R H00B 108.3 . . ?
C00S C00R H00A 109.9 . . ?
C00S C00R H00B 109.9 . . ?
C00H C00S C00R 119.0(3) . . ?
C00H C00S H00C 107.6 . . ?
C00H C00S H00D 107.6 . . ?
C00R C00S H00C 107.6 . . ?
C00R C00S H00D 107.6 . . ?
H00C C00S H00D 107.0 . . ?
C00K C00T H00T 120.6 . . ?
C00X C00T C00K 118.7(5) . . ?
C00X C00T H00T 120.6 . . ?
C00O C00U H00U 119.8 . . ?
C00Z C00U C00O 120.4(5) . . ?
C00Z C00U H00U 119.8 . . ?
C00M C00V H00V 119.8 . . ?
C010 C00V C00M 120.4(4) . . ?
C010 C00V H00V 119.8 . . ?
C00L C00W H00F 109.5 . . ?
C00L C00W H00G 109.5 . . ?
C00L C00W H00H 109.5 . . ?
H00F C00W H00G 109.5 . . ?
H00F C00W H00H 109.5 . . ?
H00G C00W H00H 109.5 . . ?
C00T C00X H00X 119.7 . . ?
C00T C00X C00Y 120.5(5) . . ?
C00Y C00X H00X 119.7 . . ?
C00Q C00Y H00Y 118.6 . . ?
C00X C00Y C00Q 122.8(5) . . ?
C00X C00Y H00Y 118.6 . . ?
C00U C00Z H00Z 120.3 . . ?
C00U C00Z C010 119.3(4) . . ?
C010 C00Z H00Z 120.3 . . ?
C00V C010 C00Z 120.9(4) . . ?
C00V C010 H010 119.6 . . ?
C00Z C010 H010 119.6 . . ?
C00P C011 H01A 109.5 . . ?
C00P C011 H01B 109.5 . . ?
C00P C011 H01C 109.5 . . ?
H01A C011 H01B 109.5 . . ?
H01A C011 H01C 109.5 . . ?
H01B C011 H01C 109.5 . . ?
C00P C012 H01D 109.5 . . ?
C00P C012 H01E 109.5 . . ?
C00P C012 H01F 109.5 . . ?
H01D C012 H01E 109.5 . . ?
H01D C012 H01F 109.5 . . ?
H01E C012 H01F 109.5 . . ?
C00P C013 H01G 109.5 . . ?
C00P C013 H01H 109.5 . . ?
C00P C013 H01I 109.5 . . ?
H01G C013 H01H 109.5 . . ?
H01G C013 H01I 109.5 . . ?
H01H C013 H01I 109.5 . . ?

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
S01 C00D C00J O005 44.8(4) . . . . ?
S01 C00D C00J N00B 116.1(3) . . . . ?
S01 C00D C00J C00M -97.0(3) . . . . ?
S01 C00F C00I C00N -176.6(3) . . . . ?
N004 C00C C00H C00K -0.7(4) . . . . ?
N004 C00C C00H C00S -177.8(3) . . . . ?
N004 C00G C00K C00H 0.0(4) . . . . ?
N004 C00G C00K C00T 179.4(3) . . . . ?
N004 C00G C00Q C00Y -179.8(4) . . . . ?
O005 N00B C00J C00D -104.8(3) . . . . ?
O005 N00B C00J C00M 107.5(3) . . . . ?
O005 N00B C00R C00S 161.8(3) . . . . ?
O005 C00J C00M C00O -146.8(3) . . . . ?
O005 C00J C00M C00V 33.3(4) . . . . ?
O006 S01 C00D C009 -116.3(3) . . . . ?
O006 S01 C00D C00J 61.3(3) . . . . ?
O006 S01 C00F C008 113.4(2) . . . . ?
O006 S01 C00F C00I -70.3(3) . . . . ?
O007 S01 C00D C009 111.5(3) . . . . ?
O007 S01 C00D C00J -70.9(3) . . . . ?
O007 S01 C00F C008 -112.4(2) . . . . ?
O007 S01 C00F C00I 63.9(3) . . . . ?
C008 C009 C00C N004 54.4(4) . . . . ?
C008 C009 C00C C00H -118.5(4) . . . . ?
C008 C009 C00D S01 0.4(3) . . . . ?
C008 C009 C00D C00J -177.0(3) . . . . ?
C008 C00E C00L C00N -0.3(5) . . . . ?
C008 C00E C00L C00W -179.0(3) . . . . ?
C008 C00F C00I C00N -0.6(5) . . . . ?
C009 C008 C00E C00L 177.6(3) . . . . ?
C009 C008 C00F S01 -1.1(3) . . . . ?
C009 C008 C00F C00I -177.7(3) . . . . ?
C009 C00C C00H C00K 172.9(3) . . . . ?
C009 C00C C00H C00S -4.2(6) . . . . ?
C009 C00D C00J O005 -138.0(3) . . . . ?
C009 C00D C00J N00B -66.8(4) . . . . ?
C009 C00D C00J C00M 80.2(4) . . . . ?
C00A O003 C00P C011 57.7(4) . . . . ?
C00A O003 C00P C012 -67.4(5) . . . . ?
C00A O003 C00P C013 175.3(4) . . . . ?
C00A N004 C00C C009 18.1(4) . . . . ?
C00A N004 C00C C00H -167.8(3) . . . . ?
C00A N004 C00G C00K 167.3(3) . . . . ?
C00A N004 C00G C00Q -12.2(6) . . . . ?
N00B O005 C00J C00D 110.0(3) . . . . ?
N00B O005 C00J C00M -107.3(3) . . . . ?
N00B C00J C00M C00O 141.9(3) . . . . ?
N00B C00J C00M C00V -38.0(4) . . . . ?
N00B C00R C00S C00H -57.4(5) . . . . ?
C00C N004 C00A O002 4.2(5) . . . . ?
C00C N004 C00A O003 -175.2(3) . . . . ?
C00C N004 C00G C00K -0.4(3) . . . . ?
C00C N004 C00G C00Q -179.9(3) . . . . ?
C00C C009 C00D S01 -173.6(2) . . . . ?
C00C C009 C00D C00J 9.0(5) . . . . ?
C00C C00H C00K C00G 0.5(4) . . . . ?
C00C C00H C00K C00T -178.8(4) . . . . ?
C00C C00H C00S C00R -21.7(6) . . . . ?
C00D S01 C00F C008 1.1(2) . . . . ?
C00D S01 C00F C00I 177.5(3) . . . . ?
C00D C009 C00C N004 -132.2(3) . . . . ?
C00D C009 C00C C00H 54.9(5) . . . . ?
C00D C00J C00M C00O -5.6(5) . . . . ?
C00D C00J C00M C00V 174.5(3) . . . . ?
C00E C008 C009 C00C -2.1(5) . . . . ?
C00E C008 C009 C00D -176.0(3) . . . . ?
C00E C008 C00F S01 175.7(2) . . . . ?
C00E C008 C00F C00I -0.9(5) . . . . ?
C00E C00L C00N C00I -1.3(5) . . . . ?
C00F S01 C00D C009 -0.9(3) . . . . ?
C00F S01 C00D C00J 176.7(3) . . . . ?
C00F C008 C009 C00C 174.3(3) . . . . ?
C00F C008 C009 C00D 0.5(4) . . . . ?
C00F C008 C00E C00L 1.4(4) . . . . ?
C00F C00I C00N C00L 1.7(5) . . . . ?
C00G N004 C00A O002 -161.8(3) . . . . ?
C00G N004 C00A O003 18.8(4) . . . . ?
C00G N004 C00C C009 -173.4(3) . . . . ?
C00G N004 C00C C00H 0.7(3) . . . . ?
C00G C00K C00T C00X 0.1(5) . . . . ?
C00G C00Q C00Y C00X 0.4(7) . . . . ?
C00H C00K C00T C00X 179.3(4) . . . . ?
C00J O005 N00B C00R -109.3(3) . . . . ?
C00J N00B C00R C00S 100.0(4) . . . . ?
C00J C00M C00O C00U -178.2(3) . . . . ?
C00J C00M C00V C010 178.2(4) . . . . ?
C00K C00G C00Q C00Y 0.8(5) . . . . ?
C00K C00H C00S C00R 161.5(3) . . . . ?
C00K C00T C00X C00Y 1.1(7) . . . . ?
C00M C00O C00U C00Z -1.2(6) . . . . ?
C00M C00V C010 C00Z 1.2(7) . . . . ?
C00O C00M C00V C010 -1.6(6) . . . . ?
C00O C00U C00Z C010 0.7(7) . . . . ?
C00P O003 C00A O002 -3.8(5) . . . . ?
C00P O003 C00A N004 175.5(3) . . . . ?
C00Q C00G C00K C00H 179.5(3) . . . . ?
C00Q C00G C00K C00T -1.1(5) . . . . ?
C00R N00B C00J O005 96.1(3) . . . . ?
C00R N00B C00J C00D -8.8(4) . . . . ?
C00R N00B C00J C00M -156.5(3) . . . . ?
C00S C00H C00K C00G 177.9(3) . . . . ?
C00S C00H C00K C00T -1.4(6) . . . . ?
C00T C00X C00Y C00Q -1.3(8) . . . . ?
C00U C00Z C010 C00V -0.7(7) . . . . ?
C00V C00M C00O C00U 1.6(5) . . . . ?
C00W C00L C00N C00I 177.4(4) . . . . ?

_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 1.838
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mxtlbl2022060901_auto
_database_code_depnum_ccdc_archive 'CCDC 2205448'
loop_
_audit_author_name
_audit_author_address
'xiangtai meng'
;tjut
China
;
_audit_update_record             
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H26 N2 S, C H2 Cl2, C H Cl2'
_chemical_formula_sum            'C31 H29 Cl4 N2 S'
_chemical_formula_weight         603.42
_chemical_melting_point          ?
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.57330(10)
_cell_length_b                   25.8833(3)
_cell_length_c                   11.55000(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.1760(10)
_cell_angle_gamma                90
_cell_volume                     3100.97(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0580
_cell_measurement_theta_min      1.7370
_shelx_estimated_absorpt_T_max   0.361
_shelx_estimated_absorpt_T_min   0.280
_exptl_absorpt_coefficient_mu    4.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48333
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29665
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.079
_diffrn_reflns_theta_max         65.079
_diffrn_reflns_theta_min         3.415
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  69.00   0.50    1.00    --   42.30 -82.00  90.00  122
  2  ω    -46.00  13.00   0.50    1.00    --   42.30 -82.00 -60.00  118
  3  ω     72.00  98.00   0.50    1.00    --   42.30  82.00-180.00   52
  4  ω     38.00  70.00   0.50    1.00    --   42.30 -82.00 -30.00   64
  5  ω    -46.00  24.00   0.50    1.00    --   42.30 -82.00  60.00  140
  6  ω     74.00 128.00   0.50    1.00    --   42.30  54.00 -60.00  108
  7  ω     18.00  54.00   0.50    1.00    --   42.30  43.00  30.00   72
  8  ω    -46.00 -20.00   0.50    1.00    --   42.30 -43.00  90.00   52
  9  ω     28.00  70.00   0.50    1.00    --   42.30 -82.00 -90.00   84
 10  ω    -46.00  10.00   0.50    1.00    --   42.30 -54.00-150.00  112
 11  ω    -39.00 -14.00   0.50    1.00    --   42.30 -82.00 150.00   50
 12  ω     36.00  66.00   0.50    1.00    --   42.30 -82.00  60.00   60
 13  ω    -47.00   2.00   0.50    1.00    --   42.30 -54.00   0.00   98
 14  ω     12.00  69.00   0.50    1.00    --   42.30 -54.00   0.00  114
 15  ω    -18.00  65.00   0.50    1.00    --   42.30 -82.00-111.33  166
 16  ω     85.00 131.00   0.50    1.00    --   42.30  43.00  30.00   92
 17  ω     35.00  69.00   0.50    1.00    --   42.30 -82.00 150.00   68
 18  ω     32.00  61.00   0.50    1.00    --   42.30 -43.00  90.00   58
 19  ω    -10.00  21.00   0.50    1.00    --   42.30 -82.00 150.00   62
 20  ω     21.00  71.00   0.50    1.00    --   42.30  82.00-180.00  100
 21  ω     -7.00  20.00   0.50    1.00    --   42.30 -82.00 -90.00   54
 22  ω     47.00  72.00   0.50    1.00    --   42.30 -54.00-150.00   50
 23  ω    -20.00   5.00   0.50    1.00    --   42.30 -82.00  90.00   50
 24  ω     44.00  69.00   0.50    1.00    --   42.30 -82.00 -60.00   50
 25  ω      4.00 121.00   0.50    3.00    --   93.70 -82.00 120.00  234
 26  ω     13.00 121.00   0.50    3.00    --   93.70 -59.00 -30.00  216
 27  ω     35.00  80.00   0.50    3.00    --   93.70 -82.00 -60.00   90
 28  ω     87.00 113.00   0.50    3.00    --   93.70 -82.00 150.00   52
 29  ω     15.00 108.00   0.50    3.00    --   93.70 -82.00 -30.00  186
 30  ω     50.00  92.00   0.50    3.00    --   93.70 -82.00-180.00   84
 31  ω     99.00 175.00   0.50    3.00    --   93.70  68.00 -90.00  152
 32  ω      9.00 106.00   0.50    3.00    --   93.70 -82.00-120.00  194
 33  ω     41.00  85.00   0.50    3.00    --   93.70 -82.00  60.00   88
 34  ω      4.00  95.00   0.50    3.00    --   93.70 -82.00-157.95  182
 35  ω     26.00  52.00   0.50    3.00    --   93.70 -82.00  30.00   52
 36  ω     55.00  99.00   0.50    3.00    --   93.70 -82.00 -90.00   88
 37  ω     66.00 124.00   0.50    3.00    --   93.70 -42.00-180.00  116
 38  ω     53.00  92.00   0.50    3.00    --   93.70 -82.00  90.00   78
 39  ω     83.00 122.00   0.50    3.00    --   93.70 -50.00  60.00   78
 40  ω     26.00  53.00   0.50    3.00    --   93.70 -50.00  60.00   54
 41  ω     10.00  47.00   0.50    3.00    --   93.70 -42.00-180.00   74
 42  ω    141.00 181.00   0.50    3.00    --   93.70  50.00  30.00   80
 43  ω     59.00 127.00   0.50    3.00    --   93.70  33.00  90.00  136
 44  ω     77.00 103.00   0.50    3.00    --   93.70  50.00  30.00   52
 45  ω    149.00 183.00   0.50    3.00    --   93.70   8.00  60.00   68
 46  ω     75.00 101.00   0.50    3.00    --   93.70 -82.00  30.00   52
 47  ω     69.00 101.00   0.50    3.00    --   93.70 -82.00   0.00   64
 48  ω     25.00  51.00   0.50    3.00    --   93.70 -82.00   0.00   52
 49  ω    109.00 173.00   0.50    3.00    --   93.70  59.00 -60.00  128
 50  ω     67.00  93.00   0.50    3.00    --   93.70 -82.00-150.00   52
 51  ω     38.00 142.00   0.50    3.00    --   93.70   8.00  60.00  208
 52  ω     64.00  91.00   0.50    3.00    --   93.70 -82.00 145.52   54
;
_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      -0.1338537000
_diffrn_orient_matrix_UB_12      0.0120511000
_diffrn_orient_matrix_UB_13      0.0272309000
_diffrn_orient_matrix_UB_21      -0.0455694000
_diffrn_orient_matrix_UB_22      -0.0549069000
_diffrn_orient_matrix_UB_23      -0.0392666000
_diffrn_orient_matrix_UB_31      0.0453372000
_diffrn_orient_matrix_UB_32      -0.0195370000
_diffrn_orient_matrix_UB_33      0.1273398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4851
_reflns_number_total             5233
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0036(5)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     216
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1455P)²+1.8051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2124
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Uiso/Uaniso restraints and constraints
C20 \\sim C12 \\sim C32 \\sim C19 \\sim C21 \\sim C6: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.03 within 3.8A
C6 \\sim C35 \\sim C21 \\sim C19 \\sim C32 \\sim C37 \\sim C12 \\sim C20 \\sim
C34: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.03 within
3.8A
3. Others
 Fixed Sof: C6(0.33333) H6A(0.33333) H6B(0.33333) H6C(0.33333) C12(0.33333)
 H12A(0.33333) H12B(0.33333) H12C(0.33333) C19(0.33333) H19A(0.33333)
 H19B(0.33333) H19C(0.33333) C32(0.33333) H32A(0.33333) H32B(0.33333)
 H32C(0.33333) C21(0.33333) H21A(0.33333) H21B(0.33333) H21C(0.33333)
 C20(0.33333) H20A(0.33333) H20B(0.33333) H20C(0.33333) C37(0.33333)
 H37A(0.33333) H37B(0.33333) H37C(0.33333) C35(0.33333) H35A(0.33333)
 H35B(0.33333) H35C(0.33333) C34(0.33333) H34A(0.33333) H34B(0.33333)
 H34C(0.33333) Cl3(0.5) Cl4(0.5) Cl5(0.5) H33A(0.5) H33B(0.5) Cl6(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C36(H36A,H36B), C33(H33A,H33B)
4.b Aromatic/amide H refined with riding coordinates:
 N12(H12), C18(H18), C31(H31), C25(H25), C22(H22), C27(H27), C16(H16),
 C15(H15), C23(H23), C24(H24), C30(H30), C28(H28), C29(H29)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C32(H32A,H32B,
 H32C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C), C35(H35A,
 H35B,H35C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S3 S 0.26150(6) 0.32310(3) 0.44153(6) 0.0467(3) Uani 1 1 d . . . . .
N12 N 0.69219(19) 0.31791(8) 0.70606(17) 0.0387(5) Uani 1 1 d . . . . .
H12 H 0.652098 0.323642 0.762841 0.046 Uiso 1 1 calc R U . . .
N6 N 0.5331(2) 0.24746(9) 0.35236(17) 0.0440(5) Uani 1 1 d . . . . .
C14 C 0.5001(2) 0.33026(9) 0.5481(2) 0.0350(5) Uani 1 1 d . . . . .
C1 C 0.4380(2) 0.37597(9) 0.58119(19) 0.0364(5) Uani 1 1 d . . . . .
C11 C 0.8214(2) 0.30656(10) 0.7182(2) 0.0397(5) Uani 1 1 d . . . . .
C13 C 0.6377(2) 0.31853(9) 0.5867(2) 0.0353(5) Uani 1 1 d . . . . .
C5 C 0.4517(2) 0.24991(9) 0.4220(2) 0.0382(5) Uani 1 1 d . . . . .
C4 C 0.4171(2) 0.29920(9) 0.4744(2) 0.0377(5) Uani 1 1 d . . . . .
C9 C 0.7302(2) 0.30904(10) 0.5212(2) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.8492(2) 0.30180(10) 0.6046(2) 0.0406(6) Uani 1 1 d . . . . .
C18 C 0.4921(3) 0.41784(10) 0.6501(2) 0.0419(6) Uani 1 1 d . . . . .
H18 H 0.579192 0.417243 0.684706 0.050 Uiso 1 1 calc R U . . .
C26 C 0.3886(2) 0.20243(10) 0.4544(2) 0.0404(6) Uani 1 1 d . . . . .
C2 C 0.3066(2) 0.37715(10) 0.5287(2) 0.0424(6) Uani 1 1 d . . . . .
C17 C 0.4179(3) 0.46005(10) 0.6673(2) 0.0504(7) Uani 1 1 d . . . . .
C31 C 0.3420(3) 0.20015(11) 0.5593(2) 0.0473(6) Uani 1 1 d . . . . .
H31 H 0.353014 0.228344 0.610158 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5870(3) 0.29544(11) 0.3169(2) 0.0470(6) Uani 1 1 d . . . . .
H7A H 0.528868 0.323666 0.324749 0.056 Uiso 1 1 calc R U . . .
H7B H 0.593325 0.293031 0.234421 0.056 Uiso 1 1 calc R U . . .
C25 C 0.9157(3) 0.30082(12) 0.8192(2) 0.0505(6) Uani 1 1 d . . . . .
H25 H 0.895942 0.303431 0.894054 0.061 Uiso 1 1 calc R U . . .
C22 C 0.9761(2) 0.29276(12) 0.5917(3) 0.0516(7) Uani 1 1 d . . . . .
H22 H 0.996619 0.290179 0.517159 0.062 Uiso 1 1 calc R U . . .
C8 C 0.7198(2) 0.30750(12) 0.3901(2) 0.0480(6) Uani 1 1 d . . . . .
H8A H 0.779918 0.281782 0.372159 0.058 Uiso 1 1 calc R U . . .
H8B H 0.747264 0.340726 0.364952 0.058 Uiso 1 1 calc R U . . .
C27 C 0.3707(3) 0.15985(12) 0.3800(3) 0.0549(7) Uani 1 1 d . . . . .
H27 H 0.401237 0.160487 0.309694 0.066 Uiso 1 1 calc R U . . .
C16 C 0.2861(3) 0.45942(12) 0.6143(3) 0.0602(8) Uani 1 1 d . . . . .
H16 H 0.235101 0.487458 0.626100 0.072 Uiso 1 1 calc R U . . .
C15 C 0.2302(3) 0.41923(12) 0.5460(3) 0.0581(8) Uani 1 1 d . . . . .
H15 H 0.143012 0.419993 0.511860 0.070 Uiso 1 1 calc R U . . .
C23 C 1.0706(3) 0.28774(13) 0.6924(3) 0.0612(8) Uani 1 1 d . . . . .
H23 H 1.155578 0.282077 0.685253 0.073 Uiso 1 1 calc R U . . .
C24 C 1.0401(3) 0.29106(13) 0.8044(3) 0.0594(8) Uani 1 1 d . . . . .
H24 H 1.104995 0.286600 0.870575 0.071 Uiso 1 1 calc R U . . .
C30 C 0.2797(3) 0.15647(13) 0.5886(3) 0.0618(8) Uani 1 1 d . . . . .
H30 H 0.249622 0.155296 0.659080 0.074 Uiso 1 1 calc R U . . .
C28 C 0.3079(3) 0.11662(12) 0.4098(4) 0.0691(9) Uani 1 1 d . . . . .
H28 H 0.296122 0.088268 0.359400 0.083 Uiso 1 1 calc R U . . .
C29 C 0.2624(3) 0.11511(13) 0.5140(4) 0.0696(9) Uani 1 1 d . . . . .
H29 H 0.219797 0.085852 0.533321 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4791(4) 0.50702(12) 0.7380(3) 0.0657(9) Uani 1 1 d . . . . .
C6 C 0.551(3) 0.4892(13) 0.857(3) 0.095(5) Uani 0.3333 1 d . U P A 1
H6A H 0.603390 0.459911 0.847279 0.142 Uiso 0.3333 1 calc R U P A 1
H6B H 0.489827 0.479511 0.905178 0.142 Uiso 0.3333 1 calc R U P A 1
H6C H 0.604203 0.516664 0.894822 0.142 Uiso 0.3333 1 calc R U P A 1
C12 C 0.389(3) 0.5481(8) 0.752(2) 0.115(5) Uani 0.3333 1 d . U P A 1
H12A H 0.354959 0.563041 0.676143 0.172 Uiso 0.3333 1 calc R U P A 1
H12B H 0.433208 0.574213 0.803416 0.172 Uiso 0.3333 1 calc R U P A 1
H12C H 0.319935 0.534124 0.784966 0.172 Uiso 0.3333 1 calc R U P A 1
C19 C 0.591(2) 0.5274(7) 0.6818(19) 0.085(4) Uani 0.3333 1 d . U P A 1
H19A H 0.631364 0.556055 0.727188 0.128 Uiso 0.3333 1 calc R U P A 1
H19B H 0.557102 0.538541 0.602503 0.128 Uiso 0.3333 1 calc R U P A 1
H19C H 0.652525 0.500403 0.680866 0.128 Uiso 0.3333 1 calc R U P A 1
C32 C 0.537(2) 0.5416(7) 0.6622(18) 0.085(4) Uani 0.3333 1 d . U P A 2
H32A H 0.474428 0.549795 0.592676 0.127 Uiso 0.3333 1 calc R U P A 2
H32B H 0.609773 0.524910 0.639886 0.127 Uiso 0.3333 1 calc R U P A 2
H32C H 0.564891 0.572861 0.704383 0.127 Uiso 0.3333 1 calc R U P A 2
C21 C 0.588(2) 0.4859(12) 0.846(3) 0.080(5) Uani 0.3333 1 d . U P A 2
H21A H 0.621658 0.514260 0.896203 0.120 Uiso 0.3333 1 calc R U P A 2
H21B H 0.656278 0.469941 0.815216 0.120 Uiso 0.3333 1 calc R U P A 2
H21C H 0.549970 0.461039 0.890743 0.120 Uiso 0.3333 1 calc R U P A 2
C20 C 0.383(2) 0.5362(6) 0.7984(14) 0.075(4) Uani 0.3333 1 d . U P A 2
H20A H 0.426906 0.563544 0.846253 0.113 Uiso 0.3333 1 calc R U P A 2
H20B H 0.346278 0.512776 0.847297 0.113 Uiso 0.3333 1 calc R U P A 2
H20C H 0.315519 0.550587 0.739469 0.113 Uiso 0.3333 1 calc R U P A 2
C37 C 0.458(3) 0.5536(7) 0.6561(18) 0.114(5) Uani 0.3333 1 d . U P A 3
H37A H 0.368515 0.563302 0.642105 0.172 Uiso 0.3333 1 calc R U P A 3
H37B H 0.482017 0.545026 0.582529 0.172 Uiso 0.3333 1 calc R U P A 3
H37C H 0.509579 0.581973 0.692082 0.172 Uiso 0.3333 1 calc R U P A 3
C35 C 0.616(2) 0.4995(7) 0.787(2) 0.123(5) Uani 0.3333 1 d . U P A 3
H35A H 0.626087 0.470900 0.841140 0.184 Uiso 0.3333 1 calc R U P A 3
H35B H 0.650362 0.530177 0.828109 0.184 Uiso 0.3333 1 calc R U P A 3
H35C H 0.661156 0.492375 0.724422 0.184 Uiso 0.3333 1 calc R U P A 3
C34 C 0.401(3) 0.5189(8) 0.8352(17) 0.103(5) Uani 0.3333 1 d . U P A 3
H34A H 0.404978 0.489846 0.887321 0.155 Uiso 0.3333 1 calc R U P A 3
H34B H 0.312802 0.525656 0.799345 0.155 Uiso 0.3333 1 calc R U P A 3
H34C H 0.436770 0.548740 0.879233 0.155 Uiso 0.3333 1 calc R U P A 3
Cl1 Cl 0.7581(2) 0.34769(11) 1.0730(2) 0.1706(9) Uani 1 1 d . . . . .
Cl2 Cl 0.9725(3) 0.39075(12) 1.2433(3) 0.1987(11) Uani 1 1 d . . . . .
Cl3 Cl -0.1230(7) 0.4420(2) 0.5998(9) 0.170(3) Uani 0.5 1 d . . P B 1
Cl4 Cl 0.0109(7) 0.4756(2) 0.8301(9) 0.204(3) Uani 0.5 1 d . . P B 1
Cl5 Cl -0.0559(8) 0.4521(4) 0.8687(6) 0.202(3) Uani 0.5 1 d . . P B 2
C36 C 0.9262(7) 0.3440(3) 1.1574(7) 0.139(2) Uani 1 1 d . . . . .
H36A H 0.935137 0.312477 1.203677 0.167 Uiso 1 1 calc R U . . .
H36B H 0.983634 0.341341 1.101645 0.167 Uiso 1 1 calc R U . . .
C33 C -0.0356(9) 0.4292(3) 0.7306(7) 0.148(3) Uani 1 1 d . . . . .
H33A H 0.042005 0.412026 0.717513 0.178 Uiso 0.5 1 calc R U P B 1
H33B H -0.083202 0.403973 0.767332 0.178 Uiso 0.5 1 calc R U P B 1
Cl6 Cl -0.0894(8) 0.4672(3) 0.6153(7) 0.164(2) Uani 0.5 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S3 C4 1.729(2) . ?
S3 C2 1.735(3) . ?
N12 H12 0.8600 . ?
N12 C11 1.378(3) . ?
N12 C13 1.388(3) . ?
N6 C5 1.289(3) . ?
N6 C7 1.458(4) . ?
C14 C1 1.441(3) . ?
C14 C13 1.468(3) . ?
C14 C4 1.361(3) . ?
C1 C18 1.400(3) . ?
C1 C2 1.404(3) . ?
C11 C10 1.405(4) . ?
C11 C25 1.388(4) . ?
C13 C9 1.370(3) . ?
C5 C4 1.488(3) . ?
C5 C26 1.481(4) . ?
C9 C10 1.441(3) . ?
C9 C8 1.497(3) . ?
C10 C22 1.399(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(4) . ?
C26 C31 1.394(4) . ?
C26 C27 1.388(4) . ?
C2 C15 1.393(4) . ?
C17 C16 1.410(5) . ?
C17 C3 1.536(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.384(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.525(4) . ?
C25 H25 0.9300 . ?
C25 C24 1.383(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C27 H27 0.9300 . ?
C27 C28 1.379(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(5) . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.395(5) . ?
C24 H24 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.364(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.380(5) . ?
C29 H29 0.9300 . ?
C3 C6 1.51(4) . ?
C3 C12 1.46(2) . ?
C3 C19 1.54(2) . ?
C3 C32 1.467(17) . ?
C3 C21 1.62(3) . ?
C3 C20 1.539(16) . ?
C3 C37 1.523(19) . ?
C3 C35 1.46(2) . ?
C3 C34 1.55(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
Cl1 C36 1.856(8) . ?
Cl2 C36 1.580(8) . ?
Cl3 C33 1.644(12) . ?
Cl4 C33 1.670(11) . ?
Cl5 C33 1.753(11) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 Cl6 1.664(9) . ?

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
C4 S3 C2 91.07(11) . . ?
C11 N12 H12 125.8 . . ?
C11 N12 C13 108.45(19) . . ?
C13 N12 H12 125.8 . . ?
C5 N6 C7 118.6(2) . . ?
C1 C14 C13 124.4(2) . . ?
C4 C14 C1 112.3(2) . . ?
C4 C14 C13 123.3(2) . . ?
C18 C1 C14 129.0(2) . . ?
C18 C1 C2 119.4(2) . . ?
C2 C1 C14 111.5(2) . . ?
N12 C11 C10 107.8(2) . . ?
N12 C11 C25 130.2(2) . . ?
C25 C11 C10 122.0(2) . . ?
N12 C13 C14 120.0(2) . . ?
C9 C13 N12 110.1(2) . . ?
C9 C13 C14 129.8(2) . . ?
N6 C5 C4 122.9(2) . . ?
N6 C5 C26 120.4(2) . . ?
C26 C5 C4 116.8(2) . . ?
C14 C4 S3 113.37(18) . . ?
C14 C4 C5 125.5(2) . . ?
C5 C4 S3 121.08(17) . . ?
C13 C9 C10 106.1(2) . . ?
C13 C9 C8 130.0(2) . . ?
C10 C9 C8 123.8(2) . . ?
C11 C10 C9 107.4(2) . . ?
C22 C10 C11 119.5(2) . . ?
C22 C10 C9 133.0(2) . . ?
C1 C18 H18 119.6 . . ?
C17 C18 C1 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C31 C26 C5 120.5(2) . . ?
C27 C26 C5 121.1(2) . . ?
C27 C26 C31 118.4(3) . . ?
C1 C2 S3 111.75(18) . . ?
C15 C2 S3 127.7(2) . . ?
C15 C2 C1 120.5(2) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C3 120.7(3) . . ?
C16 C17 C3 121.3(3) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.8(3) . . ?
C30 C31 H31 119.6 . . ?
N6 C7 H7A 109.0 . . ?
N6 C7 H7B 109.0 . . ?
N6 C7 C8 112.8(2) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C11 C25 H25 121.3 . . ?
C24 C25 C11 117.5(3) . . ?
C24 C25 H25 121.3 . . ?
C10 C22 H22 120.7 . . ?
C23 C22 C10 118.5(3) . . ?
C23 C22 H22 120.7 . . ?
C9 C8 C7 116.4(2) . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C17 C16 H16 118.7 . . ?
C15 C16 C17 122.7(3) . . ?
C15 C16 H16 118.7 . . ?
C2 C15 H15 120.7 . . ?
C16 C15 C2 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.5(3) . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C17 C3 C19 108.9(7) . . ?
C17 C3 C21 107.8(11) . . ?
C17 C3 C20 112.5(8) . . ?
C17 C3 C34 108.3(7) . . ?
C6 C3 C17 109.1(12) . . ?
C6 C3 C19 101.5(14) . . ?
C12 C3 C17 114.8(10) . . ?
C12 C3 C6 110.3(15) . . ?
C12 C3 C19 111.4(13) . . ?
C32 C3 C17 110.4(8) . . ?
C32 C3 C21 110.5(15) . . ?
C32 C3 C20 111.1(11) . . ?
C20 C3 C21 104.4(12) . . ?
C37 C3 C17 107.5(7) . . ?
C37 C3 C34 104.9(13) . . ?
C35 C3 C17 112.6(7) . . ?
C35 C3 C37 111.3(13) . . ?
C35 C3 C34 111.9(13) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C37 H37A 109.5 . . ?
C3 C37 H37B 109.5 . . ?
C3 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C3 C35 H35A 109.5 . . ?
C3 C35 H35B 109.5 . . ?
C3 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C3 C34 H34A 109.5 . . ?
C3 C34 H34B 109.5 . . ?
C3 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Cl1 C36 H36A 108.3 . . ?
Cl1 C36 H36B 108.3 . . ?
Cl2 C36 Cl1 116.1(4) . . ?
Cl2 C36 H36A 108.3 . . ?
Cl2 C36 H36B 108.3 . . ?
H36A C36 H36B 107.4 . . ?
Cl3 C33 Cl4 121.7(5) . . ?
Cl3 C33 H33A 106.9 . . ?
Cl3 C33 H33B 106.9 . . ?
Cl4 C33 H33A 106.9 . . ?
Cl4 C33 H33B 106.9 . . ?
H33A C33 H33B 106.7 . . ?
Cl6 C33 Cl5 116.4(5) . . ?

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
S3 C2 C15 C16 -176.9(2) . . . . ?
N12 C11 C10 C9 -1.9(3) . . . . ?
N12 C11 C10 C22 176.9(2) . . . . ?
N12 C11 C25 C24 -177.8(3) . . . . ?
N12 C13 C9 C10 0.3(3) . . . . ?
N12 C13 C9 C8 -177.8(3) . . . . ?
N6 C5 C4 S3 116.6(2) . . . . ?
N6 C5 C4 C14 -61.7(3) . . . . ?
N6 C5 C26 C31 155.2(2) . . . . ?
N6 C5 C26 C27 -26.8(3) . . . . ?
N6 C7 C8 C9 -54.7(3) . . . . ?
C14 C1 C18 C17 176.4(2) . . . . ?
C14 C1 C2 S3 0.3(3) . . . . ?
C14 C1 C2 C15 -177.5(2) . . . . ?
C14 C13 C9 C10 177.9(2) . . . . ?
C14 C13 C9 C8 -0.2(4) . . . . ?
C1 C14 C13 N12 54.6(3) . . . . ?
C1 C14 C13 C9 -122.8(3) . . . . ?
C1 C14 C4 S3 -0.1(3) . . . . ?
C1 C14 C4 C5 178.4(2) . . . . ?
C1 C18 C17 C16 0.5(4) . . . . ?
C1 C18 C17 C3 -177.0(2) . . . . ?
C1 C2 C15 C16 0.5(4) . . . . ?
C11 N12 C13 C14 -179.3(2) . . . . ?
C11 N12 C13 C9 -1.5(3) . . . . ?
C11 C10 C22 C23 1.3(4) . . . . ?
C11 C25 C24 C23 0.8(5) . . . . ?
C13 N12 C11 C10 2.1(3) . . . . ?
C13 N12 C11 C25 -178.9(3) . . . . ?
C13 C14 C1 C18 2.3(4) . . . . ?
C13 C14 C1 C2 178.6(2) . . . . ?
C13 C14 C4 S3 -178.86(18) . . . . ?
C13 C14 C4 C5 -0.4(4) . . . . ?
C13 C9 C10 C11 0.9(3) . . . . ?
C13 C9 C10 C22 -177.6(3) . . . . ?
C13 C9 C8 C7 -24.7(4) . . . . ?
C5 N6 C7 C8 98.1(3) . . . . ?
C5 C26 C31 C30 178.2(2) . . . . ?
C5 C26 C27 C28 -177.8(3) . . . . ?
C4 S3 C2 C1 -0.26(19) . . . . ?
C4 S3 C2 C15 177.4(3) . . . . ?
C4 C14 C1 C18 -176.5(2) . . . . ?
C4 C14 C1 C2 -0.1(3) . . . . ?
C4 C14 C13 N12 -126.8(2) . . . . ?
C4 C14 C13 C9 55.9(4) . . . . ?
C4 C5 C26 C31 -24.3(3) . . . . ?
C4 C5 C26 C27 153.7(2) . . . . ?
C9 C10 C22 C23 179.7(3) . . . . ?
C10 C11 C25 C24 1.2(4) . . . . ?
C10 C9 C8 C7 157.5(3) . . . . ?
C10 C22 C23 C24 0.7(5) . . . . ?
C18 C1 C2 S3 177.00(18) . . . . ?
C18 C1 C2 C15 -0.8(4) . . . . ?
C18 C17 C16 C15 -0.8(4) . . . . ?
C18 C17 C3 C6 -54.2(12) . . . . ?
C18 C17 C3 C12 -178.5(11) . . . . ?
C18 C17 C3 C19 55.9(9) . . . . ?
C18 C17 C3 C32 83.2(12) . . . . ?
C18 C17 C3 C21 -37.5(12) . . . . ?
C18 C17 C3 C20 -152.1(7) . . . . ?
C18 C17 C3 C37 119.4(12) . . . . ?
C18 C17 C3 C35 -3.5(12) . . . . ?
C18 C17 C3 C34 -127.7(10) . . . . ?
C26 C5 C4 S3 -63.9(3) . . . . ?
C26 C5 C4 C14 117.7(3) . . . . ?
C26 C31 C30 C29 -0.5(5) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C2 S3 C4 C14 0.2(2) . . . . ?
C2 S3 C4 C5 -178.4(2) . . . . ?
C2 C1 C18 C17 0.3(4) . . . . ?
C17 C16 C15 C2 0.3(5) . . . . ?
C31 C26 C27 C28 0.2(4) . . . . ?
C31 C30 C29 C28 0.6(5) . . . . ?
C7 N6 C5 C4 -4.3(3) . . . . ?
C7 N6 C5 C26 176.3(2) . . . . ?
C25 C11 C10 C9 179.0(2) . . . . ?
C25 C11 C10 C22 -2.3(4) . . . . ?
C22 C23 C24 C25 -1.8(5) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C8 C9 C10 C22 0.7(5) . . . . ?
C27 C26 C31 C30 0.1(4) . . . . ?
C27 C28 C29 C30 -0.2(5) . . . . ?
C16 C17 C3 C6 128.4(12) . . . . ?
C16 C17 C3 C12 4.1(12) . . . . ?
C16 C17 C3 C19 -121.6(9) . . . . ?
C16 C17 C3 C32 -94.2(12) . . . . ?
C16 C17 C3 C21 145.1(11) . . . . ?
C16 C17 C3 C20 30.5(8) . . . . ?
C16 C17 C3 C37 -58.0(12) . . . . ?
C16 C17 C3 C35 179.1(12) . . . . ?
C16 C17 C3 C34 54.9(10) . . . . ?
C3 C17 C16 C15 176.7(3) . . . . ?

_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.646
