# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cxy0576_0m
_database_code_depnum_ccdc_archive 'CCDC 1943599'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_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        ?
_chemical_formula_moiety         'C14 H12 O S, H2 O'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.30
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.1140(12)
_cell_length_b                   5.0373(4)
_cell_length_c                   17.2267(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.575(3)
_cell_angle_gamma                90
_cell_volume                     1211.07(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1758 before and 0.1036 after correction. The Ratio of minimum to maximum transmission is 0.4210. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13053
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.609
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2112
_reflns_number_total             2799
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.010(4)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.046
_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)+(0.0972P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1641
_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 O(H,H) groups
2.a Free rotating group:
 O003(H00A,H00B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.42573(4) 0.71009(12) 0.43610(3) 0.0173(2) Uani 1 1 d . . . . .
O003 O 0.52774(14) 1.1090(4) 0.28115(10) 0.0284(5) Uani 1 1 d . . . . .
H00A H 0.512460 1.268101 0.264055 0.043 Uiso 1 1 d G . . . .
H00B H 0.498364 1.073421 0.320900 0.043 Uiso 1 1 d G . . . .
O1 O 0.43889(12) 0.9847(3) 0.40484(9) 0.0213(4) Uani 1 1 d . . . . .
C1 C 0.12604(19) 0.9297(5) 0.26639(14) 0.0241(6) Uani 1 1 d . . . . .
H1 H 0.109786 1.036342 0.220879 0.029 Uiso 1 1 calc R . . . .
C2 C 0.21654(19) 0.8201(4) 0.28315(14) 0.0207(6) Uani 1 1 d . . . . .
H2 H 0.261933 0.849735 0.248522 0.025 Uiso 1 1 calc R . . . .
C3 C 0.24197(17) 0.6661(4) 0.35051(13) 0.0159(5) Uani 1 1 d . . . . .
C4 C 0.17542(17) 0.6261(4) 0.40222(12) 0.0153(5) Uani 1 1 d . . . . .
C5 C 0.20221(16) 0.4780(4) 0.47737(13) 0.0149(5) Uani 1 1 d . . . . .
C6 C 0.14236(17) 0.2820(4) 0.49995(14) 0.0184(5) Uani 1 1 d . . . . .
H6 H 0.084281 0.240526 0.466779 0.022 Uiso 1 1 calc R . . . .
C7 C 0.16650(18) 0.1459(5) 0.57059(14) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.125242 0.011217 0.584874 0.025 Uiso 1 1 calc R . . . .
C8 C 0.24992(19) 0.2058(4) 0.61976(14) 0.0213(6) Uani 1 1 d . . . . .
H8 H 0.266255 0.113177 0.667935 0.026 Uiso 1 1 calc R . . . .
C9 C 0.33873(17) 0.5400(4) 0.36520(13) 0.0181(5) Uani 1 1 d . . . . .
H9A H 0.364273 0.529629 0.314794 0.022 Uiso 1 1 calc R . . . .
H9B H 0.331526 0.356070 0.383687 0.022 Uiso 1 1 calc R . . . .
C10 C 0.34869(17) 0.7690(4) 0.50964(13) 0.0163(5) Uani 1 1 d . . . . .
H10A H 0.389483 0.823351 0.558866 0.020 Uiso 1 1 calc R . . . .
H10B H 0.306207 0.920532 0.492025 0.020 Uiso 1 1 calc R . . . .
C11 C 0.28714(16) 0.5413(4) 0.52809(12) 0.0150(5) Uani 1 1 d . . . . .
C12 C 0.30976(18) 0.4017(5) 0.59852(13) 0.0186(5) Uani 1 1 d . . . . .
H12 H 0.367348 0.442230 0.632472 0.022 Uiso 1 1 calc R . . . .
C13 C 0.08388(18) 0.7321(5) 0.38329(14) 0.0194(5) Uani 1 1 d . . . . .
H13 H 0.037559 0.700253 0.416948 0.023 Uiso 1 1 calc R . . . .
C14 C 0.05908(18) 0.8839(5) 0.31598(14) 0.0226(6) Uani 1 1 d . . . . .
H14 H -0.003596 0.955958 0.304017 0.027 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
S1 O1 1.5058(16) . ?
S1 C9 1.813(2) . ?
S1 C10 1.813(2) . ?
O003 H00A 0.8701 . ?
O003 H00B 0.8703 . ?
C1 H1 0.9500 . ?
C1 C2 1.382(4) . ?
C1 C14 1.384(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 C4 1.402(3) . ?
C3 C9 1.493(3) . ?
C4 C5 1.493(3) . ?
C4 C13 1.391(3) . ?
C5 C6 1.392(3) . ?
C5 C11 1.411(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9500 . ?
C8 C12 1.383(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.501(3) . ?
C11 C12 1.397(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?

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
O1 S1 C9 107.48(10) . . ?
O1 S1 C10 102.62(10) . . ?
C10 S1 C9 97.56(11) . . ?
H00A O003 H00B 109.4 . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C14 120.0(2) . . ?
C14 C1 H1 120.0 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 C9 119.5(2) . . ?
C4 C3 C9 120.9(2) . . ?
C3 C4 C5 121.0(2) . . ?
C13 C4 C3 118.9(2) . . ?
C13 C4 C5 120.1(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 C11 118.8(2) . . ?
C11 C5 C4 120.4(2) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C12 119.6(2) . . ?
C12 C8 H8 120.2 . . ?
S1 C9 H9A 108.5 . . ?
S1 C9 H9B 108.5 . . ?
C3 C9 S1 115.08(15) . . ?
C3 C9 H9A 108.5 . . ?
C3 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
S1 C10 H10A 108.1 . . ?
S1 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 S1 116.70(16) . . ?
C11 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C5 C11 C10 120.4(2) . . ?
C12 C11 C5 119.2(2) . . ?
C12 C11 C10 120.2(2) . . ?
C8 C12 C11 121.3(2) . . ?
C8 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C4 C13 H13 119.5 . . ?
C14 C13 C4 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C1 C14 C13 119.8(2) . . ?
C1 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?

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
S1 C10 C11 C5 -78.4(2) . . . . ?
S1 C10 C11 C12 106.2(2) . . . . ?
O1 S1 C9 C3 -60.91(19) . . . . ?
O1 S1 C10 C11 154.30(17) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C9 177.2(2) . . . . ?
C2 C1 C14 C13 1.3(4) . . . . ?
C2 C3 C4 C5 -175.90(19) . . . . ?
C2 C3 C4 C13 2.7(3) . . . . ?
C2 C3 C9 S1 101.2(2) . . . . ?
C3 C4 C5 C6 -133.6(2) . . . . ?
C3 C4 C5 C11 48.7(3) . . . . ?
C3 C4 C13 C14 -2.4(3) . . . . ?
C4 C3 C9 S1 -80.6(2) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C11 C10 3.7(3) . . . . ?
C4 C5 C11 C12 179.1(2) . . . . ?
C4 C13 C14 C1 0.4(4) . . . . ?
C5 C4 C13 C14 176.2(2) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C5 C11 C12 C8 -0.9(3) . . . . ?
C6 C5 C11 C10 -174.0(2) . . . . ?
C6 C5 C11 C12 1.4(3) . . . . ?
C6 C7 C8 C12 -0.1(4) . . . . ?
C7 C8 C12 C11 0.2(4) . . . . ?
C9 S1 C10 C11 44.41(19) . . . . ?
C9 C3 C4 C5 5.8(3) . . . . ?
C9 C3 C4 C13 -175.5(2) . . . . ?
C10 S1 C9 C3 44.92(19) . . . . ?
C10 C11 C12 C8 174.6(2) . . . . ?
C11 C5 C6 C7 -1.4(3) . . . . ?
C13 C4 C5 C6 47.8(3) . . . . ?
C13 C4 C5 C11 -129.9(2) . . . . ?
C14 C1 C2 C3 -1.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0682_0m
_database_code_depnum_ccdc_archive 'CCDC 1943601'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H28 Cl Ir O S'
_chemical_formula_sum            'C24 H28 Cl Ir O S'
_chemical_formula_weight         592.17
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.5119(9)
_cell_length_b                   33.049(3)
_cell_length_c                   8.1129(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.969(4)
_cell_angle_gamma                90
_cell_volume                     2194.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.479
_cell_measurement_theta_min      2.469
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.314
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1523 before and 0.0938 after correction. The Ratio of minimum to maximum transmission is 0.2782. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28327
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4692
_reflns_number_total             5001
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.614
_refine_diff_density_min         -2.563
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       0.0028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.198
_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)+23.1309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0989
_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. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C4(H4), C14(H14), C6(H6), C7(H7), C13(H13),
 C5(H5)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C)
;
_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
Ir1 Ir 0.31807(3) 0.15217(2) 0.96741(3) 0.01482(11) Uani 1 1 d . . . . .
Cl1 Cl 0.1749(2) 0.16753(5) 0.6756(2) 0.0210(3) Uani 1 1 d . . . . .
S1 S 0.2821(2) 0.08511(5) 0.9360(2) 0.0196(3) Uani 1 1 d . . . . .
O1 O 0.1987(7) 0.06276(16) 1.0445(7) 0.0327(13) Uani 1 1 d . . . . .
C15 C 0.3581(8) 0.15669(19) 1.2421(8) 0.0162(12) Uani 1 1 d . . . . .
C16 C 0.4628(8) 0.1854(2) 1.1926(8) 0.0187(13) Uani 1 1 d . . . . .
C17 C 0.3573(9) 0.2130(2) 1.0715(9) 0.0219(14) Uani 1 1 d . . . . .
C18 C 0.1887(8) 0.20367(19) 1.0676(8) 0.0175(13) Uani 1 1 d . U . . .
C1 C 0.4886(10) 0.0673(2) 0.9766(10) 0.035(2) Uani 1 1 d . . . . .
H1A H 0.539874 0.064807 1.101468 0.042 Uiso 1 1 calc R . . . .
H1B H 0.490778 0.040480 0.922950 0.042 Uiso 1 1 calc R . . . .
C21 C 0.0463(9) 0.2280(2) 0.9687(10) 0.0264(15) Uani 1 1 d . . . . .
H21A H -0.055296 0.214653 0.973005 0.040 Uiso 1 1 calc GR . . . .
H21B H 0.049464 0.230204 0.849194 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.051264 0.255084 1.018932 0.040 Uiso 1 1 calc GR . . . .
C12 C 0.1771(9) -0.0592(2) 0.6333(10) 0.0261(15) Uani 1 1 d . . . . .
H12 H 0.169879 -0.087558 0.613162 0.031 Uiso 1 1 calc R . . . .
C22 C 0.4068(11) 0.2500(2) 0.9898(10) 0.0307(17) Uani 1 1 d . . . . .
H22A H 0.346081 0.250901 0.868177 0.046 Uiso 1 1 calc GR . . . .
H22B H 0.524222 0.248963 1.000589 0.046 Uiso 1 1 calc GR . . . .
H22C H 0.382176 0.274334 1.047335 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.4105(9) 0.1238(2) 1.3735(9) 0.0226(14) Uani 1 1 d . . . . .
H24A H 0.524461 0.116549 1.384042 0.034 Uiso 1 1 calc GR . . . .
H24B H 0.340728 0.100054 1.337926 0.034 Uiso 1 1 calc GR . . . .
H24C H 0.400618 0.133493 1.484462 0.034 Uiso 1 1 calc GR . . . .
C2 C 0.5779(9) 0.0978(3) 0.9004(10) 0.0295(17) Uani 1 1 d . . . . .
C11 C 0.0808(9) -0.0410(2) 0.7241(10) 0.0286(16) Uani 1 1 d . . . . .
H11 H 0.009127 -0.057005 0.768389 0.034 Uiso 1 1 calc R . . . .
C19 C 0.1884(8) 0.1697(2) 1.1703(8) 0.0166(13) Uani 1 1 d . . . . .
C20 C 0.0451(9) 0.1493(2) 1.2032(9) 0.0229(15) Uani 1 1 d . . . . .
H20A H -0.053528 0.156496 1.112738 0.034 Uiso 1 1 calc GR . . . .
H20B H 0.032945 0.158043 1.314511 0.034 Uiso 1 1 calc GR . . . .
H20C H 0.060902 0.119939 1.204167 0.034 Uiso 1 1 calc GR . . . .
C9 C 0.1953(8) 0.0241(2) 0.6908(8) 0.0190(13) Uani 1 1 d . . . . .
C10 C 0.0875(9) 0.0002(2) 0.7511(9) 0.0231(14) Uani 1 1 d . . . . .
H10 H 0.018514 0.012451 0.811142 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6004(9) 0.1647(3) 0.8132(9) 0.0348(19) Uani 1 1 d . U . . .
H4 H 0.562068 0.191788 0.800222 0.042 Uiso 1 1 calc R . . . .
C3 C 0.5191(8) 0.1381(3) 0.8844(9) 0.0268(16) Uani 1 1 d . . . . .
C8 C 0.2006(9) 0.0694(2) 0.7142(8) 0.0199(14) Uani 1 1 d . . . . .
H8A H 0.088616 0.080344 0.669753 0.024 Uiso 1 1 calc R . . . .
H8B H 0.268660 0.081280 0.645246 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2940(9) 0.0054(2) 0.6020(9) 0.0218(14) Uani 1 1 d . . . . .
H14 H 0.369176 0.021030 0.561322 0.026 Uiso 1 1 calc R . . . .
C23 C 0.6435(9) 0.1864(2) 1.2508(10) 0.0280(16) Uani 1 1 d . . . . .
H23A H 0.685663 0.197924 1.160020 0.042 Uiso 1 1 calc GR . . . .
H23B H 0.685667 0.158909 1.276861 0.042 Uiso 1 1 calc GR . . . .
H23C H 0.678739 0.203235 1.353965 0.042 Uiso 1 1 calc GR . . . .
C6 C 0.7928(11) 0.1171(4) 0.7730(12) 0.051(3) Uani 1 1 d . U . . .
H6 H 0.886010 0.110333 0.735849 0.062 Uiso 1 1 calc R . . . .
C7 C 0.7157(11) 0.0874(3) 0.8439(12) 0.047(2) Uani 1 1 d . U . . .
H7 H 0.755232 0.060380 0.854190 0.057 Uiso 1 1 calc R . . . .
C13 C 0.2830(9) -0.0362(2) 0.5724(10) 0.0281(16) Uani 1 1 d . . . . .
H13 H 0.349227 -0.048705 0.509758 0.034 Uiso 1 1 calc R . . . .
C5 C 0.7371(10) 0.1554(3) 0.7566(10) 0.042(2) Uani 1 1 d . U . . .
H5 H 0.789491 0.175687 0.707656 0.050 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
Ir1 Cl1 2.4000(16) . ?
Ir1 S1 2.2424(16) . ?
Ir1 C15 2.165(6) . ?
Ir1 C16 2.196(6) . ?
Ir1 C17 2.171(7) . ?
Ir1 C18 2.294(6) . ?
Ir1 C19 2.294(6) . ?
Ir1 C3 2.057(7) . ?
S1 O1 1.473(5) . ?
S1 C1 1.796(8) . ?
S1 C8 1.817(7) . ?
C15 C16 1.432(9) . ?
C15 C24 1.501(9) . ?
C15 C19 1.465(9) . ?
C16 C17 1.457(10) . ?
C16 C23 1.480(10) . ?
C17 C18 1.459(10) . ?
C17 C22 1.506(10) . ?
C18 C21 1.491(9) . ?
C18 C19 1.399(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.494(12) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.383(11) . ?
C12 C13 1.371(11) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C2 C3 1.419(11) . ?
C2 C7 1.414(11) . ?
C11 H11 0.9500 . ?
C11 C10 1.377(10) . ?
C19 C20 1.481(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C9 C10 1.397(10) . ?
C9 C8 1.509(9) . ?
C9 C14 1.393(9) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.342(12) . ?
C4 C5 1.397(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C13 1.395(10) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C7 1.391(15) . ?
C6 C5 1.344(15) . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?

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
S1 Ir1 Cl1 94.62(6) . . ?
S1 Ir1 C18 135.21(17) . . ?
S1 Ir1 C19 104.66(17) . . ?
C15 Ir1 Cl1 153.42(17) . . ?
C15 Ir1 S1 99.37(18) . . ?
C15 Ir1 C16 38.3(2) . . ?
C15 Ir1 C17 64.7(2) . . ?
C15 Ir1 C18 62.6(2) . . ?
C15 Ir1 C19 38.2(2) . . ?
C16 Ir1 Cl1 137.03(18) . . ?
C16 Ir1 S1 128.03(18) . . ?
C16 Ir1 C18 63.2(2) . . ?
C16 Ir1 C19 63.1(2) . . ?
C17 Ir1 Cl1 99.78(19) . . ?
C17 Ir1 S1 164.00(19) . . ?
C17 Ir1 C16 39.0(3) . . ?
C17 Ir1 C18 38.0(2) . . ?
C17 Ir1 C19 62.6(2) . . ?
C18 Ir1 Cl1 91.70(17) . . ?
C19 Ir1 Cl1 116.14(17) . . ?
C19 Ir1 C18 35.5(2) . . ?
C3 Ir1 Cl1 88.1(2) . . ?
C3 Ir1 S1 80.8(2) . . ?
C3 Ir1 C15 116.3(3) . . ?
C3 Ir1 C16 93.3(3) . . ?
C3 Ir1 C17 106.5(3) . . ?
C3 Ir1 C18 143.8(3) . . ?
C3 Ir1 C19 154.1(3) . . ?
O1 S1 Ir1 120.1(2) . . ?
O1 S1 C1 109.6(4) . . ?
O1 S1 C8 109.5(3) . . ?
C1 S1 Ir1 101.9(3) . . ?
C1 S1 C8 100.1(3) . . ?
C8 S1 Ir1 113.4(2) . . ?
C16 C15 Ir1 72.0(4) . . ?
C16 C15 C24 126.3(6) . . ?
C16 C15 C19 108.4(6) . . ?
C24 C15 Ir1 127.8(4) . . ?
C19 C15 Ir1 75.6(4) . . ?
C19 C15 C24 124.2(6) . . ?
C15 C16 Ir1 69.7(4) . . ?
C15 C16 C17 106.8(6) . . ?
C15 C16 C23 126.8(6) . . ?
C17 C16 Ir1 69.6(4) . . ?
C17 C16 C23 126.4(6) . . ?
C23 C16 Ir1 125.0(5) . . ?
C16 C17 Ir1 71.4(4) . . ?
C16 C17 C18 107.6(6) . . ?
C16 C17 C22 127.7(7) . . ?
C18 C17 Ir1 75.5(4) . . ?
C18 C17 C22 123.7(6) . . ?
C22 C17 Ir1 127.8(5) . . ?
C17 C18 Ir1 66.4(3) . . ?
C17 C18 C21 123.1(6) . . ?
C21 C18 Ir1 127.4(5) . . ?
C19 C18 Ir1 72.2(4) . . ?
C19 C18 C17 108.7(6) . . ?
C19 C18 C21 128.2(6) . . ?
S1 C1 H1A 110.4 . . ?
S1 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 S1 106.7(5) . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.7(7) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 C2 C1 117.7(6) . . ?
C7 C2 C1 122.2(8) . . ?
C7 C2 C3 120.1(8) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.7(7) . . ?
C10 C11 H11 119.6 . . ?
C15 C19 Ir1 66.1(3) . . ?
C15 C19 C20 124.5(6) . . ?
C18 C19 Ir1 72.2(3) . . ?
C18 C19 C15 108.0(6) . . ?
C18 C19 C20 127.5(6) . . ?
C20 C19 Ir1 126.7(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C9 C8 121.1(6) . . ?
C14 C9 C10 118.5(6) . . ?
C14 C9 C8 120.3(6) . . ?
C11 C10 C9 120.3(7) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C3 C4 H4 117.5 . . ?
C3 C4 C5 125.0(9) . . ?
C5 C4 H4 117.5 . . ?
C2 C3 Ir1 119.1(6) . . ?
C4 C3 Ir1 124.6(6) . . ?
C4 C3 C2 116.3(7) . . ?
S1 C8 H8A 108.9 . . ?
S1 C8 H8B 108.9 . . ?
C9 C8 S1 113.5(5) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C14 H14 119.8 . . ?
C9 C14 C13 120.4(7) . . ?
C13 C14 H14 119.8 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(9) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.4(9) . . ?
C6 C7 H7 120.3 . . ?
C12 C13 C14 120.2(7) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(9) . . ?
C6 C5 H5 120.8 . . ?

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
Ir1 S1 C1 C2 -37.1(5) . . . . ?
Ir1 S1 C8 C9 173.1(4) . . . . ?
Ir1 C15 C16 C17 60.0(4) . . . . ?
Ir1 C15 C16 C23 -119.1(7) . . . . ?
Ir1 C15 C19 C18 -60.4(4) . . . . ?
Ir1 C15 C19 C20 119.3(6) . . . . ?
Ir1 C16 C17 C18 67.5(5) . . . . ?
Ir1 C16 C17 C22 -123.8(7) . . . . ?
Ir1 C17 C18 C21 -120.5(6) . . . . ?
Ir1 C17 C18 C19 60.1(4) . . . . ?
Ir1 C18 C19 C15 56.6(4) . . . . ?
Ir1 C18 C19 C20 -123.1(6) . . . . ?
S1 C1 C2 C3 26.1(8) . . . . ?
S1 C1 C2 C7 -153.3(6) . . . . ?
O1 S1 C1 C2 -165.3(5) . . . . ?
O1 S1 C8 C9 -49.8(6) . . . . ?
C15 C16 C17 Ir1 -60.1(4) . . . . ?
C15 C16 C17 C18 7.4(7) . . . . ?
C15 C16 C17 C22 176.1(7) . . . . ?
C16 C15 C19 Ir1 65.1(4) . . . . ?
C16 C15 C19 C18 4.7(7) . . . . ?
C16 C15 C19 C20 -175.7(6) . . . . ?
C16 C17 C18 Ir1 -64.7(4) . . . . ?
C16 C17 C18 C21 174.8(6) . . . . ?
C16 C17 C18 C19 -4.6(7) . . . . ?
C17 C18 C19 Ir1 -56.6(4) . . . . ?
C17 C18 C19 C15 0.0(7) . . . . ?
C17 C18 C19 C20 -179.6(6) . . . . ?
C1 S1 C8 C9 65.2(6) . . . . ?
C1 C2 C3 Ir1 0.4(9) . . . . ?
C1 C2 C3 C4 -179.0(7) . . . . ?
C1 C2 C7 C6 179.6(8) . . . . ?
C21 C18 C19 Ir1 124.0(7) . . . . ?
C21 C18 C19 C15 -179.4(6) . . . . ?
C21 C18 C19 C20 1.0(11) . . . . ?
C12 C11 C10 C9 -1.7(11) . . . . ?
C22 C17 C18 Ir1 126.0(7) . . . . ?
C22 C17 C18 C21 5.6(10) . . . . ?
C22 C17 C18 C19 -173.9(6) . . . . ?
C24 C15 C16 Ir1 124.2(6) . . . . ?
C24 C15 C16 C17 -175.8(6) . . . . ?
C24 C15 C16 C23 5.0(11) . . . . ?
C24 C15 C19 Ir1 -126.3(6) . . . . ?
C24 C15 C19 C18 173.4(6) . . . . ?
C24 C15 C19 C20 -7.0(10) . . . . ?
C11 C12 C13 C14 0.1(11) . . . . ?
C19 C15 C16 Ir1 -67.5(4) . . . . ?
C19 C15 C16 C17 -7.4(7) . . . . ?
C19 C15 C16 C23 173.4(6) . . . . ?
C9 C14 C13 C12 -1.2(11) . . . . ?
C10 C9 C8 S1 68.9(8) . . . . ?
C10 C9 C14 C13 0.9(10) . . . . ?
C3 C2 C7 C6 0.2(12) . . . . ?
C3 C4 C5 C6 0.3(12) . . . . ?
C8 S1 C1 C2 79.7(5) . . . . ?
C8 C9 C10 C11 178.0(7) . . . . ?
C8 C9 C14 C13 -176.6(6) . . . . ?
C14 C9 C10 C11 0.5(10) . . . . ?
C14 C9 C8 S1 -113.7(6) . . . . ?
C23 C16 C17 Ir1 119.1(7) . . . . ?
C23 C16 C17 C18 -173.4(6) . . . . ?
C23 C16 C17 C22 -4.8(11) . . . . ?
C7 C2 C3 Ir1 179.9(6) . . . . ?
C7 C2 C3 C4 0.4(11) . . . . ?
C7 C6 C5 C4 0.3(13) . . . . ?
C13 C12 C11 C10 1.4(11) . . . . ?
C5 C4 C3 Ir1 179.9(6) . . . . ?
C5 C4 C3 C2 -0.7(11) . . . . ?
C5 C6 C7 C2 -0.5(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0663_0m
_database_code_depnum_ccdc_archive 'CCDC 1943600'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H27 Ir O S'
_chemical_formula_sum            'C24 H27 Ir O S'
_chemical_formula_weight         555.71
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9930(5)
_cell_length_b                   14.5354(7)
_cell_length_c                   12.7588(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.905(2)
_cell_angle_gamma                90
_cell_volume                     2031.23(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.363
_shelx_estimated_absorpt_T_min   0.223
_exptl_absorpt_coefficient_mu    6.687
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1338 before and 0.0939 after correction. The Ratio of minimum to maximum transmission is 0.4776. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4270
_reflns_number_total             4677
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.771
_refine_diff_density_min         -1.888
_refine_diff_density_rms         0.224
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+1.7277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1077
_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:
 C1(H1A,H1B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C6(H6), C4(H4), C5(H5), C13(H13), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C22(H22A,H22B,H22C)
;
_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
Ir1 Ir 0.45692(2) 0.26283(2) 0.70837(2) 0.02207(11) Uani 1 1 d . . . . .
S1 S 0.48264(10) 0.37866(8) 0.60273(9) 0.0254(2) Uani 1 1 d . . . . .
O1 O 0.4322(4) 0.4714(2) 0.6186(3) 0.0362(8) Uani 1 1 d . . . . .
C7 C 0.3914(4) 0.1915(4) 0.3776(4) 0.0303(10) Uani 1 1 d . . . . .
H7 H 0.393814 0.223540 0.312865 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4154(4) 0.1922(3) 0.5700(4) 0.0242(9) Uani 1 1 d . . . . .
C11 C 0.6888(5) 0.1474(4) 0.7024(4) 0.0313(11) Uani 1 1 d . . . . .
H11 H 0.645743 0.102942 0.739360 0.038 Uiso 1 1 calc R . . . .
C2 C 0.4144(5) 0.2384(3) 0.4724(5) 0.0265(10) Uani 1 1 d . . . . .
C10 C 0.6328(5) 0.2323(3) 0.6759(5) 0.0265(11) Uani 1 1 d . . . . .
C24 C 0.2011(5) 0.3721(4) 0.7742(5) 0.0338(11) Uani 1 1 d . . . . .
H24A H 0.235025 0.428482 0.746200 0.051 Uiso 1 1 calc GR . . . .
H24B H 0.157068 0.387228 0.835564 0.051 Uiso 1 1 calc GR . . . .
H24C H 0.144746 0.343637 0.719963 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.3027(4) 0.3064(3) 0.8061(4) 0.0256(9) Uani 1 1 d . . . . .
C9 C 0.7013(4) 0.2969(4) 0.6233(4) 0.0276(10) Uani 1 1 d . . . . .
C6 C 0.3651(5) 0.0984(4) 0.3775(4) 0.0327(11) Uani 1 1 d . . . . .
H6 H 0.347716 0.066767 0.312786 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3911(4) 0.0982(3) 0.5658(4) 0.0286(10) Uani 1 1 d . . . . .
H4 H 0.393123 0.064495 0.629729 0.034 Uiso 1 1 calc R . . . .
C5 C 0.3640(5) 0.0518(4) 0.4710(4) 0.0334(11) Uani 1 1 d . . . . .
H5 H 0.344815 -0.011948 0.471163 0.040 Uiso 1 1 calc R . . . .
C20 C 0.4537(5) 0.4295(4) 0.8906(4) 0.0333(11) Uani 1 1 d . . . . .
H20A H 0.541905 0.432909 0.909271 0.050 Uiso 1 1 calc GR . . . .
H20B H 0.410209 0.448235 0.951013 0.050 Uiso 1 1 calc GR . . . .
H20C H 0.431486 0.470650 0.831144 0.050 Uiso 1 1 calc GR . . . .
C21 C 0.6080(6) 0.2441(4) 0.9488(5) 0.0369(13) Uani 1 1 d . . . . .
H21A H 0.664941 0.208959 0.909429 0.055 Uiso 1 1 calc GR . . . .
H21B H 0.596404 0.212494 1.015081 0.055 Uiso 1 1 calc GR . . . .
H21C H 0.641239 0.305739 0.963918 0.055 Uiso 1 1 calc GR . . . .
C23 C 0.1949(5) 0.1523(4) 0.7550(4) 0.0325(11) Uani 1 1 d . . . . .
H23A H 0.123842 0.192025 0.738422 0.049 Uiso 1 1 calc GR . . . .
H23B H 0.175680 0.106540 0.807571 0.049 Uiso 1 1 calc GR . . . .
H23C H 0.215618 0.120794 0.690958 0.049 Uiso 1 1 calc GR . . . .
C22 C 0.4453(5) 0.0740(4) 0.8656(4) 0.0357(12) Uani 1 1 d . . . . .
H22A H 0.430865 0.037821 0.800953 0.054 Uiso 1 1 calc GR . . . .
H22B H 0.392698 0.051235 0.918248 0.054 Uiso 1 1 calc GR . . . .
H22C H 0.530995 0.068188 0.892871 0.054 Uiso 1 1 calc GR . . . .
C1 C 0.4331(5) 0.3409(4) 0.4711(4) 0.0305(10) Uani 1 1 d . . . . .
H1A H 0.355810 0.371979 0.446261 0.037 Uiso 1 1 calc R . . . .
H1B H 0.495472 0.356841 0.422517 0.037 Uiso 1 1 calc R . . . .
C13 C 0.8702(4) 0.1909(4) 0.6211(4) 0.0351(12) Uani 1 1 d . . . . .
H13 H 0.949717 0.176934 0.601818 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8070(4) 0.1271(4) 0.6754(4) 0.0338(11) Uani 1 1 d . . . . .
H12 H 0.843382 0.069567 0.694380 0.041 Uiso 1 1 calc R . . . .
C14 C 0.8177(5) 0.2756(4) 0.5948(4) 0.0323(11) Uani 1 1 d . . . . .
H14 H 0.861285 0.319338 0.557195 0.039 Uiso 1 1 calc R . . . .
C16 C 0.3007(4) 0.2092(4) 0.7977(4) 0.0263(10) Uani 1 1 d . . . . .
C17 C 0.4162(4) 0.1741(3) 0.8422(4) 0.0272(10) Uani 1 1 d . . . . .
C19 C 0.4189(4) 0.3320(3) 0.8602(4) 0.0267(10) Uani 1 1 d . . . . .
C8 C 0.6455(4) 0.3903(4) 0.5996(4) 0.0319(11) Uani 1 1 d . . . . .
H8A H 0.665389 0.411637 0.529389 0.038 Uiso 1 1 calc R . . . .
H8B H 0.677805 0.435646 0.652791 0.038 Uiso 1 1 calc R . . . .
C18 C 0.4874(5) 0.2521(4) 0.8846(5) 0.0280(11) Uani 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
Ir1 S1 2.1900(12) . ?
Ir1 C3 2.059(5) . ?
Ir1 C10 2.060(5) . ?
Ir1 C15 2.278(5) . ?
Ir1 C16 2.277(5) . ?
Ir1 C17 2.216(5) . ?
Ir1 C19 2.253(5) . ?
Ir1 C18 2.251(6) . ?
S1 O1 1.479(4) . ?
S1 C1 1.806(5) . ?
S1 C8 1.802(5) . ?
C7 H7 0.9500 . ?
C7 C2 1.393(7) . ?
C7 C6 1.384(7) . ?
C3 C2 1.414(7) . ?
C3 C4 1.392(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.408(7) . ?
C11 C12 1.404(7) . ?
C2 C1 1.505(6) . ?
C10 C9 1.408(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C15 1.500(7) . ?
C15 C16 1.416(7) . ?
C15 C19 1.448(7) . ?
C9 C14 1.394(7) . ?
C9 C8 1.510(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.373(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(7) . ?
C5 H5 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.510(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C18 1.502(9) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C16 1.493(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C17 1.514(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.380(8) . ?
C13 C14 1.389(9) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.439(7) . ?
C17 C18 1.456(7) . ?
C19 C18 1.404(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
S1 Ir1 C15 105.33(12) . . ?
S1 Ir1 C16 135.50(14) . . ?
S1 Ir1 C17 165.23(13) . . ?
S1 Ir1 C19 103.25(13) . . ?
S1 Ir1 C18 130.69(14) . . ?
C3 Ir1 S1 83.50(14) . . ?
C3 Ir1 C10 82.13(19) . . ?
C3 Ir1 C15 119.14(17) . . ?
C3 Ir1 C16 97.88(18) . . ?
C3 Ir1 C17 109.00(19) . . ?
C3 Ir1 C19 156.32(17) . . ?
C3 Ir1 C18 145.61(19) . . ?
C10 Ir1 S1 82.46(15) . . ?
C10 Ir1 C15 157.7(2) . . ?
C10 Ir1 C16 142.0(2) . . ?
C10 Ir1 C17 106.5(2) . . ?
C10 Ir1 C19 121.01(19) . . ?
C10 Ir1 C18 97.1(2) . . ?
C16 Ir1 C15 36.22(18) . . ?
C17 Ir1 C15 62.05(18) . . ?
C17 Ir1 C16 37.33(18) . . ?
C17 Ir1 C19 62.15(19) . . ?
C17 Ir1 C18 38.05(18) . . ?
C19 Ir1 C15 37.27(17) . . ?
C19 Ir1 C16 61.27(17) . . ?
C18 Ir1 C15 61.75(19) . . ?
C18 Ir1 C16 62.02(19) . . ?
C18 Ir1 C19 36.33(18) . . ?
O1 S1 Ir1 123.19(15) . . ?
O1 S1 C1 108.5(2) . . ?
O1 S1 C8 107.6(2) . . ?
C1 S1 Ir1 107.12(17) . . ?
C8 S1 Ir1 105.45(17) . . ?
C8 S1 C1 103.2(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.1(5) . . ?
C2 C3 Ir1 120.2(4) . . ?
C4 C3 Ir1 123.4(4) . . ?
C4 C3 C2 116.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C12 C11 C10 121.3(5) . . ?
C7 C2 C3 121.4(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 119.3(5) . . ?
C11 C10 Ir1 122.6(4) . . ?
C11 C10 C9 117.2(5) . . ?
C9 C10 Ir1 120.1(4) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
C24 C15 Ir1 126.9(3) . . ?
C16 C15 Ir1 71.9(2) . . ?
C16 C15 C24 127.5(4) . . ?
C16 C15 C19 107.4(4) . . ?
C19 C15 Ir1 70.4(3) . . ?
C19 C15 C24 124.9(4) . . ?
C10 C9 C8 118.0(4) . . ?
C14 C9 C10 121.2(5) . . ?
C14 C9 C8 120.9(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6 120.0 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.3(5) . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
S1 C1 H1A 109.9 . . ?
S1 C1 H1B 109.9 . . ?
C2 C1 S1 108.7(4) . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C16 Ir1 71.9(2) . . ?
C15 C16 C23 126.0(4) . . ?
C15 C16 C17 108.5(4) . . ?
C23 C16 Ir1 127.2(4) . . ?
C17 C16 Ir1 69.0(3) . . ?
C17 C16 C23 125.5(5) . . ?
C22 C17 Ir1 131.2(4) . . ?
C16 C17 Ir1 73.7(3) . . ?
C16 C17 C22 125.7(5) . . ?
C16 C17 C18 107.3(4) . . ?
C18 C17 Ir1 72.3(3) . . ?
C18 C17 C22 125.3(5) . . ?
C15 C19 Ir1 72.3(3) . . ?
C15 C19 C20 123.9(5) . . ?
C20 C19 Ir1 125.3(3) . . ?
C18 C19 Ir1 71.8(3) . . ?
C18 C19 C15 109.1(4) . . ?
C18 C19 C20 126.9(5) . . ?
S1 C8 H8A 110.2 . . ?
S1 C8 H8B 110.2 . . ?
C9 C8 S1 107.4(3) . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C21 C18 Ir1 126.8(4) . . ?
C17 C18 Ir1 69.7(3) . . ?
C17 C18 C21 124.3(5) . . ?
C19 C18 Ir1 71.9(3) . . ?
C19 C18 C21 128.1(5) . . ?
C19 C18 C17 107.5(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
Ir1 S1 C1 C2 -11.3(4) . . . . ?
Ir1 S1 C8 C9 26.6(4) . . . . ?
Ir1 C3 C2 C7 177.4(4) . . . . ?
Ir1 C3 C2 C1 -5.3(6) . . . . ?
Ir1 C3 C4 C5 -179.6(4) . . . . ?
Ir1 C10 C9 C14 -176.1(4) . . . . ?
Ir1 C10 C9 C8 4.6(6) . . . . ?
Ir1 C15 C16 C23 -123.3(5) . . . . ?
Ir1 C15 C16 C17 59.6(3) . . . . ?
Ir1 C15 C19 C20 121.1(5) . . . . ?
Ir1 C15 C19 C18 -62.7(4) . . . . ?
Ir1 C16 C17 C22 -129.4(5) . . . . ?
Ir1 C16 C17 C18 64.9(4) . . . . ?
Ir1 C17 C18 C21 -121.4(6) . . . . ?
Ir1 C17 C18 C19 62.4(4) . . . . ?
Ir1 C19 C18 C21 123.1(6) . . . . ?
Ir1 C19 C18 C17 -60.9(4) . . . . ?
O1 S1 C1 C2 -146.3(4) . . . . ?
O1 S1 C8 C9 159.7(3) . . . . ?
C7 C2 C1 S1 -171.7(4) . . . . ?
C7 C6 C5 C4 -0.9(8) . . . . ?
C3 C2 C1 S1 10.9(6) . . . . ?
C3 C4 C5 C6 2.4(8) . . . . ?
C11 C10 C9 C14 2.7(7) . . . . ?
C11 C10 C9 C8 -176.7(5) . . . . ?
C2 C7 C6 C5 -1.3(8) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C10 C11 C12 C13 -0.4(8) . . . . ?
C10 C9 C14 C13 -2.2(8) . . . . ?
C10 C9 C8 S1 -21.1(6) . . . . ?
C24 C15 C16 Ir1 123.1(5) . . . . ?
C24 C15 C16 C23 -0.2(7) . . . . ?
C24 C15 C16 C17 -177.4(5) . . . . ?
C24 C15 C19 Ir1 -121.9(5) . . . . ?
C24 C15 C19 C20 -0.8(8) . . . . ?
C24 C15 C19 C18 175.3(5) . . . . ?
C15 C16 C17 Ir1 -61.4(3) . . . . ?
C15 C16 C17 C22 169.2(5) . . . . ?
C15 C16 C17 C18 3.5(5) . . . . ?
C15 C19 C18 Ir1 63.1(3) . . . . ?
C15 C19 C18 C21 -173.9(5) . . . . ?
C15 C19 C18 C17 2.1(6) . . . . ?
C6 C7 C2 C3 2.1(8) . . . . ?
C6 C7 C2 C1 -175.2(5) . . . . ?
C4 C3 C2 C7 -0.6(7) . . . . ?
C4 C3 C2 C1 176.7(5) . . . . ?
C20 C19 C18 Ir1 -120.9(5) . . . . ?
C20 C19 C18 C21 2.1(9) . . . . ?
C20 C19 C18 C17 178.1(4) . . . . ?
C23 C16 C17 Ir1 121.5(5) . . . . ?
C23 C16 C17 C22 -7.9(8) . . . . ?
C23 C16 C17 C18 -173.6(5) . . . . ?
C22 C17 C18 Ir1 128.4(5) . . . . ?
C22 C17 C18 C21 7.0(9) . . . . ?
C22 C17 C18 C19 -169.2(4) . . . . ?
C1 S1 C8 C9 -85.7(4) . . . . ?
C12 C11 C10 Ir1 177.3(4) . . . . ?
C12 C11 C10 C9 -1.4(7) . . . . ?
C12 C13 C14 C9 0.3(8) . . . . ?
C14 C9 C8 S1 159.5(4) . . . . ?
C14 C13 C12 C11 1.0(8) . . . . ?
C16 C15 C19 Ir1 62.8(3) . . . . ?
C16 C15 C19 C20 -176.1(4) . . . . ?
C16 C15 C19 C18 0.0(5) . . . . ?
C16 C17 C18 Ir1 -65.8(3) . . . . ?
C16 C17 C18 C21 172.7(5) . . . . ?
C16 C17 C18 C19 -3.5(6) . . . . ?
C19 C15 C16 Ir1 -61.8(3) . . . . ?
C19 C15 C16 C23 174.9(5) . . . . ?
C19 C15 C16 C17 -2.2(5) . . . . ?
C8 S1 C1 C2 99.8(4) . . . . ?
C8 C9 C14 C13 177.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0708_0m
_database_code_depnum_ccdc_archive 'CCDC 1943602'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O5 S'
_chemical_formula_sum            'C18 H16 O5 S'
_chemical_formula_weight         344.37
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9916(3)
_cell_length_b                   12.1921(6)
_cell_length_c                   13.9226(8)
_cell_angle_alpha                69.159(2)
_cell_angle_beta                 87.173(2)
_cell_angle_gamma                79.345(2)
_cell_volume                     778.09(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7902
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1203 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.8664. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11283
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3077
_reflns_number_total             3585
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.047
_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)+(0.0377P)²+0.5114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0956
_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:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C13(H13), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_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
S1 S 0.17260(8) 0.50687(3) 0.17841(3) 0.01507(12) Uani 1 1 d . . . . .
O1 O -0.2293(2) 0.20266(10) -0.01632(8) 0.0190(3) Uani 1 1 d . . . . .
O2 O 1.0800(2) 0.21160(10) 0.62557(9) 0.0195(3) Uani 1 1 d . . . . .
O3 O -0.2025(3) 0.01204(10) 0.08950(9) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.8141(3) 0.38972(12) 0.58904(12) 0.0380(4) Uani 1 1 d . . . . .
O5 O -0.1110(2) 0.53563(10) 0.13458(9) 0.0212(3) Uani 1 1 d . . . . .
C1 C -0.4140(4) 0.18316(16) -0.08332(13) 0.0212(4) Uani 1 1 d . . . . .
H1A H -0.311859 0.134461 -0.120464 0.032 Uiso 1 1 calc GR . . . .
H1B H -0.500595 0.260143 -0.132678 0.032 Uiso 1 1 calc GR . . . .
H1C H -0.554329 0.141704 -0.042124 0.032 Uiso 1 1 calc GR . . . .
C2 C -0.1383(3) 0.10847(14) 0.06710(12) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.0489(3) 0.13806(13) 0.13100(11) 0.0129(3) Uani 1 1 d . . . . .
C4 C 0.1491(3) 0.05049(13) 0.22345(12) 0.0144(3) Uani 1 1 d . . . . .
H4 H 0.109412 -0.027621 0.242043 0.017 Uiso 1 1 calc R . . . .
C5 C 0.3067(3) 0.07725(13) 0.28830(11) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.375861 0.016877 0.351063 0.016 Uiso 1 1 calc R . . . .
C6 C 0.3656(3) 0.19175(13) 0.26278(11) 0.0115(3) Uani 1 1 d . . . . .
C7 C 0.5022(3) 0.22149(13) 0.34013(11) 0.0114(3) Uani 1 1 d . . . . .
C8 C 0.7257(3) 0.14251(13) 0.39655(11) 0.0134(3) Uani 1 1 d . . . . .
H8 H 0.793366 0.071481 0.382918 0.016 Uiso 1 1 calc R . . . .
C9 C 0.8514(3) 0.16557(13) 0.47234(11) 0.0136(3) Uani 1 1 d . . . . .
H9 H 1.005231 0.111360 0.509504 0.016 Uiso 1 1 calc R . . . .
C10 C 0.7501(3) 0.26882(13) 0.49342(11) 0.0132(3) Uani 1 1 d . . . . .
C11 C 0.8805(3) 0.29856(14) 0.57287(12) 0.0160(3) Uani 1 1 d . . . . .
C12 C 1.2175(4) 0.23562(16) 0.70340(13) 0.0222(4) Uani 1 1 d . . . . .
H12A H 1.308879 0.303946 0.670523 0.033 Uiso 1 1 calc GR . . . .
H12B H 1.352808 0.165401 0.740258 0.033 Uiso 1 1 calc GR . . . .
H12C H 1.083565 0.253730 0.751997 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.1228(3) 0.25026(13) 0.10119(11) 0.0133(3) Uani 1 1 d . . . . .
H13 H 0.063249 0.308596 0.036248 0.016 Uiso 1 1 calc R . . . .
C14 C 0.2828(3) 0.27753(13) 0.16567(11) 0.0121(3) Uani 1 1 d . . . . .
C15 C 0.3707(3) 0.39670(13) 0.12968(11) 0.0143(3) Uani 1 1 d . . . . .
H15A H 0.360245 0.429692 0.053632 0.017 Uiso 1 1 calc R . . . .
H15B H 0.564099 0.384618 0.150247 0.017 Uiso 1 1 calc R . . . .
C16 C 0.1418(3) 0.40646(13) 0.30966(11) 0.0127(3) Uani 1 1 d . . . . .
H16A H 0.065887 0.455198 0.351631 0.015 Uiso 1 1 calc R . . . .
H16B H 0.007718 0.356004 0.309454 0.015 Uiso 1 1 calc R . . . .
C17 C 0.3989(3) 0.32589(13) 0.36182(11) 0.0120(3) Uani 1 1 d . . . . .
C18 C 0.5255(3) 0.34797(13) 0.43854(11) 0.0133(3) Uani 1 1 d . . . . .
H18 H 0.457228 0.418111 0.453482 0.016 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
S1 O5 1.4998(12) . ?
S1 C15 1.8258(16) . ?
S1 C16 1.8197(15) . ?
O1 C1 1.4492(18) . ?
O1 C2 1.3358(19) . ?
O2 C11 1.3348(19) . ?
O2 C12 1.4505(18) . ?
O3 C2 1.2046(19) . ?
O4 C11 1.196(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.493(2) . ?
C3 C4 1.391(2) . ?
C3 C13 1.395(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(2) . ?
C6 C7 1.483(2) . ?
C6 C14 1.408(2) . ?
C7 C8 1.392(2) . ?
C7 C17 1.412(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C10 C11 1.491(2) . ?
C10 C18 1.390(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 C15 1.500(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.502(2) . ?
C17 C18 1.395(2) . ?
C18 H18 0.9500 . ?

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
O5 S1 C15 107.36(7) . . ?
O5 S1 C16 103.68(7) . . ?
C16 S1 C15 97.21(7) . . ?
C2 O1 C1 115.86(12) . . ?
C11 O2 C12 115.48(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 111.60(13) . . ?
O3 C2 O1 124.50(14) . . ?
O3 C2 C3 123.88(14) . . ?
C4 C3 C2 118.29(13) . . ?
C4 C3 C13 119.62(14) . . ?
C13 C3 C2 122.08(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.94(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.92(14) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 119.27(13) . . ?
C5 C6 C14 119.01(13) . . ?
C14 C6 C7 121.66(13) . . ?
C8 C7 C6 119.89(13) . . ?
C8 C7 C17 119.26(13) . . ?
C17 C7 C6 120.75(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.27(14) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.46(14) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 121.50(14) . . ?
C18 C10 C9 120.00(14) . . ?
C18 C10 C11 118.49(14) . . ?
O2 C11 C10 112.76(13) . . ?
O4 C11 O2 123.01(14) . . ?
O4 C11 C10 124.23(15) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13 119.7 . . ?
C14 C13 C3 120.64(14) . . ?
C14 C13 H13 119.7 . . ?
C6 C14 C15 120.92(13) . . ?
C13 C14 C6 119.50(13) . . ?
C13 C14 C15 119.56(13) . . ?
S1 C15 H15A 108.4 . . ?
S1 C15 H15B 108.4 . . ?
C14 C15 S1 115.32(11) . . ?
C14 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
S1 C16 H16A 108.1 . . ?
S1 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C17 C16 S1 116.62(11) . . ?
C17 C16 H16A 108.1 . . ?
C17 C16 H16B 108.1 . . ?
C7 C17 C16 120.41(13) . . ?
C18 C17 C7 119.07(13) . . ?
C18 C17 C16 120.31(13) . . ?
C10 C18 C17 120.94(14) . . ?
C10 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?

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
S1 C16 C17 C7 -78.84(16) . . . . ?
S1 C16 C17 C18 106.57(14) . . . . ?
O1 C2 C3 C4 176.66(13) . . . . ?
O1 C2 C3 C13 -2.7(2) . . . . ?
O3 C2 C3 C4 -2.0(2) . . . . ?
O3 C2 C3 C13 178.63(15) . . . . ?
O5 S1 C15 C14 -65.63(13) . . . . ?
O5 S1 C16 C17 157.69(11) . . . . ?
C1 O1 C2 O3 -1.1(2) . . . . ?
C1 O1 C2 C3 -179.73(13) . . . . ?
C2 C3 C4 C5 -175.23(13) . . . . ?
C2 C3 C13 C14 175.66(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C13 C14 C6 -1.4(2) . . . . ?
C3 C13 C14 C15 177.04(14) . . . . ?
C4 C3 C13 C14 -3.7(2) . . . . ?
C4 C5 C6 C7 171.68(14) . . . . ?
C4 C5 C6 C14 -5.6(2) . . . . ?
C5 C6 C7 C8 45.5(2) . . . . ?
C5 C6 C7 C17 -130.71(15) . . . . ?
C5 C6 C14 C13 6.0(2) . . . . ?
C5 C6 C14 C15 -172.42(14) . . . . ?
C6 C7 C8 C9 -177.44(13) . . . . ?
C6 C7 C17 C16 2.3(2) . . . . ?
C6 C7 C17 C18 177.00(13) . . . . ?
C6 C14 C15 S1 -81.21(16) . . . . ?
C7 C6 C14 C13 -171.22(14) . . . . ?
C7 C6 C14 C15 10.4(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C17 C18 C10 -0.1(2) . . . . ?
C8 C7 C17 C16 -173.90(13) . . . . ?
C8 C7 C17 C18 0.8(2) . . . . ?
C8 C9 C10 C11 -179.01(14) . . . . ?
C8 C9 C10 C18 -0.2(2) . . . . ?
C9 C10 C11 O2 -6.1(2) . . . . ?
C9 C10 C11 O4 174.54(17) . . . . ?
C9 C10 C18 C17 -0.2(2) . . . . ?
C11 C10 C18 C17 178.66(14) . . . . ?
C12 O2 C11 O4 -1.3(2) . . . . ?
C12 O2 C11 C10 179.33(13) . . . . ?
C13 C3 C4 C5 4.2(2) . . . . ?
C13 C14 C15 S1 100.37(15) . . . . ?
C14 C6 C7 C8 -137.27(15) . . . . ?
C14 C6 C7 C17 46.5(2) . . . . ?
C15 S1 C16 C17 47.80(12) . . . . ?
C16 S1 C15 C14 41.18(12) . . . . ?
C16 C17 C18 C10 174.57(14) . . . . ?
C17 C7 C8 C9 -1.2(2) . . . . ?
C18 C10 C11 O2 175.11(13) . . . . ?
C18 C10 C11 O4 -4.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0801
_database_code_depnum_ccdc_archive 'CCDC 1943604'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 Br O S'
_chemical_formula_sum            'C14 H11 Br O S'
_chemical_formula_weight         307.20
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.9587(9)
_cell_length_b                   15.1534(11)
_cell_length_c                   7.3793(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.891(3)
_cell_angle_gamma                90
_cell_volume                     1210.69(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.437
_shelx_estimated_absorpt_T_min   0.338
_exptl_absorpt_coefficient_mu    3.546
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1222 before and 0.0708 after correction. The Ratio of minimum to maximum transmission is 0.5954. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.312
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2481
_reflns_number_total             2774
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0050(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.136
_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)+2.1643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0707
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
3. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14)
;
_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
Br1 Br 0.50303(3) 0.70741(2) -0.08514(4) 0.02262(11) Uani 1 1 d . . . . .
S1 S 0.93659(6) 0.65366(4) 0.59088(9) 0.01893(15) Uani 1 1 d . . . . .
O1 O 0.9221(2) 0.74783(15) 0.5485(3) 0.0218(5) Uani 0.796(3) 1 d . . P A 1
C1 C 0.5773(2) 0.62942(16) 0.1016(3) 0.0142(5) Uani 1 1 d . . . . .
C2 C 0.5072(2) 0.56512(16) 0.1687(3) 0.0152(5) Uani 1 1 d . . . . .
H2 H 0.422273 0.558071 0.120134 0.018 Uiso 1 1 calc R . . . .
C3 C 0.5637(2) 0.51085(16) 0.3090(3) 0.0146(5) Uani 1 1 d . . . . .
H3 H 0.517248 0.465158 0.354161 0.018 Uiso 1 1 calc R . . . .
C4 C 0.6876(2) 0.52226(15) 0.3848(3) 0.0125(5) Uani 1 1 d . . . . .
C5 C 0.7422(2) 0.47217(16) 0.5507(3) 0.0136(5) Uani 1 1 d . . . . .
C6 C 0.7345(2) 0.38005(17) 0.5574(4) 0.0174(5) Uani 1 1 d . . . . .
H6 H 0.695412 0.348526 0.453131 0.021 Uiso 1 1 calc R . . . .
C7 C 0.7836(2) 0.33417(17) 0.7153(4) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.779275 0.271579 0.717535 0.025 Uiso 1 1 calc R . . . .
C8 C 0.8390(2) 0.37972(19) 0.8697(4) 0.0213(6) Uani 1 1 d . . . . .
H8 H 0.872156 0.348514 0.977769 0.026 Uiso 1 1 calc R . . . .
C9 C 0.8456(2) 0.47095(18) 0.8649(3) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.882167 0.502011 0.971435 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7995(2) 0.51803(16) 0.7068(3) 0.0147(5) Uani 1 1 d . . . . .
C11 C 0.8086(2) 0.61716(17) 0.7042(3) 0.0170(5) Uani 1 1 d . . . . .
H11A H 0.820742 0.639672 0.831672 0.020 Uiso 1 1 calc R . . . .
H11B H 0.730420 0.642001 0.639114 0.020 Uiso 1 1 calc R . . . .
C12 C 0.8938(2) 0.59489(16) 0.3749(3) 0.0154(5) Uani 1 1 d . . . . .
H12A H 0.931906 0.625584 0.279257 0.018 Uiso 1 1 calc R . . . .
H12B H 0.929815 0.534909 0.388698 0.018 Uiso 1 1 calc R . . . .
C13 C 0.7579(2) 0.58629(15) 0.3082(3) 0.0116(5) Uani 1 1 d . . . . .
C14 C 0.7018(2) 0.63978(15) 0.1662(3) 0.0144(5) Uani 1 1 d . . . . .
H14 H 0.748617 0.683050 0.113983 0.017 Uiso 1 1 calc R . . . .
O1A O 1.0429(8) 0.6306(6) 0.6930(13) 0.0218(5) Uani 0.204(3) 1 d . . P A 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
Br1 C1 1.901(2) . ?
S1 O1 1.464(2) . ?
S1 C11 1.826(2) . ?
S1 C12 1.823(3) . ?
S1 O1A 1.332(9) . ?
C1 C2 1.379(3) . ?
C1 C14 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C4 C5 1.486(3) . ?
C4 C13 1.410(3) . ?
C5 C6 1.400(3) . ?
C5 C10 1.407(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(4) . ?
C10 C11 1.506(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.500(3) . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?

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
O1 S1 C11 109.12(13) . . ?
O1 S1 C12 106.54(13) . . ?
C12 S1 C11 98.07(11) . . ?
O1A S1 C11 109.1(4) . . ?
O1A S1 C12 116.8(4) . . ?
C2 C1 Br1 119.95(18) . . ?
C2 C1 C14 122.1(2) . . ?
C14 C1 Br1 117.94(18) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C13 118.8(2) . . ?
C13 C4 C5 120.4(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 C10 119.0(2) . . ?
C10 C5 C4 119.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 C11 120.3(2) . . ?
C9 C10 C5 119.4(2) . . ?
C9 C10 C11 120.3(2) . . ?
S1 C11 H11A 109.3 . . ?
S1 C11 H11B 109.3 . . ?
C10 C11 S1 111.42(17) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
S1 C12 H12A 108.3 . . ?
S1 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 S1 115.95(16) . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C4 C13 C12 120.3(2) . . ?
C14 C13 C4 119.8(2) . . ?
C14 C13 C12 119.8(2) . . ?
C1 C14 C13 119.4(2) . . ?
C1 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?

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
Br1 C1 C2 C3 -178.17(17) . . . . ?
Br1 C1 C14 C13 177.28(17) . . . . ?
S1 C12 C13 C4 -78.7(3) . . . . ?
S1 C12 C13 C14 103.4(2) . . . . ?
O1 S1 C11 C10 165.12(18) . . . . ?
O1 S1 C12 C13 -78.0(2) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C2 C1 C14 C13 -2.6(4) . . . . ?
C2 C3 C4 C5 171.7(2) . . . . ?
C2 C3 C4 C13 -4.3(3) . . . . ?
C3 C4 C5 C6 53.8(3) . . . . ?
C3 C4 C5 C10 -124.2(2) . . . . ?
C3 C4 C13 C12 -174.5(2) . . . . ?
C3 C4 C13 C14 3.4(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C4 C5 C10 C9 177.1(2) . . . . ?
C4 C5 C10 C11 -1.7(3) . . . . ?
C4 C13 C14 C1 0.0(3) . . . . ?
C5 C4 C13 C12 9.5(3) . . . . ?
C5 C4 C13 C14 -172.6(2) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C5 C10 C11 S1 -80.5(2) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
C6 C5 C10 C11 -179.7(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C5 1.8(3) . . . . ?
C8 C9 C10 C11 -179.5(2) . . . . ?
C9 C10 C11 S1 100.7(2) . . . . ?
C10 C5 C6 C7 -0.5(4) . . . . ?
C11 S1 C12 C13 34.8(2) . . . . ?
C12 S1 C11 C10 54.4(2) . . . . ?
C12 C13 C14 C1 177.9(2) . . . . ?
C13 C4 C5 C6 -130.3(2) . . . . ?
C13 C4 C5 C10 51.7(3) . . . . ?
C14 C1 C2 C3 1.7(4) . . . . ?
O1A S1 C11 C10 -67.7(4) . . . . ?
O1A S1 C12 C13 151.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0740_0m
_database_code_depnum_ccdc_archive 'CCDC 1943603'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H27 Ag2 F6 Ir O5 S'
_chemical_formula_sum            'C28 H27 Ag2 F6 Ir O5 S'
_chemical_formula_weight         997.49
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9702(5)
_cell_length_b                   12.7689(6)
_cell_length_c                   13.1134(6)
_cell_angle_alpha                89.3620(10)
_cell_angle_beta                 73.4700(10)
_cell_angle_gamma                68.1400(10)
_cell_volume                     1476.92(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.260
_shelx_estimated_absorpt_T_min   0.189
_exptl_absorpt_coefficient_mu    5.953
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1426 before and 0.0905 after correction. The Ratio of minimum to maximum transmission is 0.3498. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25782
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         2.245
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6386
_reflns_number_total             6804
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.833
_refine_diff_density_min         -1.580
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+3.3607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0856
_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 Riding coordinates:
 C18(H18), C17(H17), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C11(H11), C16(H16), C10(H10)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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
Ir1 Ir 0.72910(2) 0.23473(2) 0.27815(2) 0.01449(8) Uani 1 1 d . . . . .
Ag1 Ag 0.81169(4) 0.50423(3) 0.56077(3) 0.02215(10) Uani 1 1 d . . . . .
Ag2 Ag 0.63638(4) 0.42738(3) 0.02895(3) 0.02576(10) Uani 1 1 d . . . . .
S1 S 0.72833(12) 0.38772(9) 0.35094(9) 0.0167(2) Uani 1 1 d . . . . .
F1 F 0.8226(4) 0.8739(2) 0.4531(3) 0.0335(7) Uani 1 1 d . . . . .
F4 F 0.6043(4) 0.7684(3) 0.2038(3) 0.0383(8) Uani 1 1 d . . . . .
F2 F 1.0226(4) 0.7609(3) 0.3374(3) 0.0448(9) Uani 1 1 d . . . . .
F3 F 0.8063(5) 0.8063(3) 0.3116(3) 0.0520(10) Uani 1 1 d . . . . .
F5 F 0.3850(4) 0.8640(3) 0.1915(4) 0.0730(16) Uani 1 1 d . . . . .
F6 F 0.5827(7) 0.8383(4) 0.0582(4) 0.0710(14) Uani 1 1 d . . . . .
O4 O 0.6280(4) 0.5927(3) 0.0831(3) 0.0234(7) Uani 1 1 d . . . . .
O5 O 0.6032(4) 0.3027(3) -0.0681(3) 0.0252(7) Uani 1 1 d . . . . .
O1 O 0.7204(4) 0.4006(3) 0.4647(3) 0.0223(7) Uani 1 1 d . . . . .
O3 O 0.7664(5) 0.6441(3) 0.4262(4) 0.0424(10) Uani 1 1 d . . . . .
O2 O 1.0652(5) 0.3544(3) 0.4932(3) 0.0384(10) Uani 1 1 d . . . . .
C15 C 0.4494(5) 0.3097(4) 0.2004(4) 0.0218(9) Uani 1 1 d . . . . .
H15 H 0.486798 0.232637 0.171821 0.026 Uiso 1 1 calc R . . . .
C19 C 0.8961(5) 0.0534(3) 0.2443(4) 0.0201(9) Uani 1 1 d . . . . .
C2 C 0.8768(6) 0.7806(4) 0.3851(4) 0.0235(10) Uani 1 1 d . . . . .
C9 C 0.9562(5) 0.2742(4) -0.0487(4) 0.0223(9) Uani 1 1 d . . . . .
H9 H 0.965857 0.247013 -0.118586 0.027 Uiso 1 1 calc R . . . .
C24 C 1.0047(7) 0.1018(5) 0.3874(5) 0.0320(12) Uani 1 1 d . . . . .
H24A H 0.962526 0.165135 0.443702 0.048 Uiso 1 1 calc GR . . . .
H24B H 1.081337 0.113665 0.327867 0.048 Uiso 1 1 calc GR . . . .
H24C H 1.051608 0.030724 0.416155 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.7509(5) 0.0592(3) 0.2396(4) 0.0199(9) Uani 1 1 d . . . . .
C3 C 0.8981(5) 0.4022(4) 0.2688(4) 0.0205(9) Uani 1 1 d . . . . .
H3A H 0.885679 0.482842 0.271512 0.025 Uiso 1 1 calc R . . . .
H3B H 0.985776 0.358130 0.293728 0.025 Uiso 1 1 calc R . . . .
C1 C 0.8577(6) 0.6794(4) 0.4434(4) 0.0267(11) Uani 1 1 d . . . . .
C5 C 0.8461(5) 0.2847(4) 0.1456(4) 0.0174(8) Uani 1 1 d . . . . .
C14 C 0.5360(5) 0.3442(4) 0.2492(4) 0.0180(9) Uani 1 1 d . . . . .
C13 C 0.4810(5) 0.4622(4) 0.2829(4) 0.0183(9) Uani 1 1 d . . . . .
C7 C 0.5140(5) 0.6815(4) 0.0920(4) 0.0210(9) Uani 1 1 d . . . . .
C4 C 0.9218(5) 0.3568(4) 0.1564(4) 0.0189(9) Uani 1 1 d . . . . .
C23 C 0.8787(5) 0.0951(4) 0.3477(4) 0.0216(9) Uani 1 1 d . . . . .
C22 C 0.7232(6) 0.1232(4) 0.4120(4) 0.0217(10) Uani 1 1 d . . . . .
C18 C 0.3416(5) 0.5379(4) 0.2750(4) 0.0220(9) Uani 1 1 d . . . . .
H18 H 0.305996 0.616043 0.299521 0.026 Uiso 1 1 d R . . . .
C17 C 0.2544(5) 0.4981(4) 0.2305(4) 0.0241(10) Uani 1 1 d . . . . .
H17 H 0.158418 0.548542 0.226525 0.029 Uiso 1 1 d R . . . .
C21 C 0.6459(6) 0.0997(4) 0.3456(4) 0.0222(10) Uani 1 1 d . . . . .
C12 C 0.5779(5) 0.5069(4) 0.3247(4) 0.0194(9) Uani 1 1 d . . . . .
H12A H 0.515628 0.558403 0.391245 0.023 Uiso 1 1 calc R . . . .
H12B H 0.621273 0.550094 0.271129 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8637(5) 0.2473(4) 0.0400(4) 0.0198(9) Uani 1 1 d . . . . .
H6 H 0.810613 0.202366 0.029027 0.024 Uiso 1 1 d R . . . .
C11 C 1.0149(5) 0.3830(4) 0.0677(4) 0.0227(10) Uani 1 1 d . . . . .
H11 H 1.065885 0.430235 0.077167 0.027 Uiso 1 1 calc R . . . .
C28 C 1.0409(5) 0.0083(4) 0.1538(4) 0.0250(10) Uani 1 1 d . . . . .
H28A H 1.099354 0.055350 0.153601 0.037 Uiso 1 1 calc GR . . . .
H28B H 1.017709 0.009989 0.085867 0.037 Uiso 1 1 calc GR . . . .
H28C H 1.100454 -0.070038 0.162664 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.5210(7) 0.7893(5) 0.1373(5) 0.0333(12) Uani 1 1 d . . . . .
C16 C 0.3105(6) 0.3838(4) 0.1923(4) 0.0261(10) Uani 1 1 d . . . . .
H16 H 0.253627 0.356481 0.160492 0.031 Uiso 1 1 calc R . . . .
C27 C 0.7209(6) 0.0095(4) 0.1495(4) 0.0267(10) Uani 1 1 d . . . . .
H27A H 0.767200 0.033814 0.082020 0.040 Uiso 1 1 calc GR . . . .
H27B H 0.611281 0.035765 0.161991 0.040 Uiso 1 1 calc GR . . . .
H27C H 0.764634 -0.073473 0.145602 0.040 Uiso 1 1 calc GR . . . .
C25 C 0.6602(7) 0.1633(4) 0.5287(4) 0.0304(11) Uani 1 1 d . . . . .
H25A H 0.683005 0.097921 0.570011 0.046 Uiso 1 1 calc GR . . . .
H25B H 0.550107 0.204169 0.547345 0.046 Uiso 1 1 calc GR . . . .
H25C H 0.706111 0.214142 0.545410 0.046 Uiso 1 1 calc GR . . . .
C10 C 1.0337(5) 0.3400(4) -0.0356(4) 0.0239(10) Uani 1 1 d . . . . .
H10 H 1.099430 0.356194 -0.096038 0.029 Uiso 1 1 calc R . . . .
C26 C 0.4854(6) 0.1070(4) 0.3812(4) 0.0304(11) Uani 1 1 d . . . . .
H26A H 0.437257 0.136719 0.325705 0.046 Uiso 1 1 calc GR . . . .
H26B H 0.429297 0.157883 0.447726 0.046 Uiso 1 1 calc GR . . . .
H26C H 0.484837 0.031320 0.393368 0.046 Uiso 1 1 calc GR . . . .


_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
Ir1 S1 2.1802(10) . ?
Ir1 C19 2.250(4) . ?
Ir1 C20 2.219(4) . ?
Ir1 C5 2.040(4) . ?
Ir1 C14 2.050(4) . ?
Ir1 C23 2.235(4) . ?
Ir1 C22 2.250(4) . ?
Ir1 C21 2.249(5) . ?
Ag1 O1 2.398(3) . ?
Ag1 O3 2.508(4) . ?
Ag1 O2 2.528(4) 2_766 ?
Ag1 O2 2.449(4) . ?
Ag1 C18 2.445(5) 2_666 ?
Ag1 C17 2.629(5) 2_666 ?
Ag2 Ag2 2.9664(7) 2_665 ?
Ag2 O4 2.199(3) . ?
Ag2 O5 2.223(3) . ?
Ag2 C6 2.597(4) . ?
S1 O1 1.479(3) . ?
S1 C3 1.803(5) . ?
S1 C12 1.808(4) . ?
F1 C2 1.332(6) . ?
F4 C8 1.328(6) . ?
F2 C2 1.334(6) . ?
F3 C2 1.318(6) . ?
F5 C8 1.325(7) . ?
F6 C8 1.325(8) . ?
O4 C7 1.249(6) . ?
O5 C7 1.239(6) 2_665 ?
O3 C1 1.229(7) . ?
O2 C1 1.256(7) 2_766 ?
C15 H15 0.9500 . ?
C15 C14 1.398(6) . ?
C15 C16 1.389(6) . ?
C19 C20 1.441(7) . ?
C19 C23 1.402(7) . ?
C19 C28 1.499(7) . ?
C2 C1 1.539(7) . ?
C9 H9 0.9500 . ?
C9 C6 1.391(7) . ?
C9 C10 1.377(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C23 1.519(7) . ?
C20 C21 1.442(7) . ?
C20 C27 1.499(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.511(6) . ?
C5 C4 1.421(6) . ?
C5 C6 1.411(6) . ?
C14 C13 1.425(6) . ?
C13 C18 1.398(6) . ?
C13 C12 1.509(6) . ?
C7 C8 1.538(7) . ?
C4 C11 1.391(7) . ?
C23 C22 1.446(7) . ?
C22 C21 1.416(7) . ?
C22 C25 1.494(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.407(7) . ?
C17 H17 0.9498 . ?
C17 C16 1.394(7) . ?
C21 C26 1.500(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.403(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C16 H16 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C10 H10 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
S1 Ir1 C19 132.63(12) . . ?
S1 Ir1 C20 164.93(13) . . ?
S1 Ir1 C23 103.39(13) . . ?
S1 Ir1 C22 103.47(12) . . ?
S1 Ir1 C21 132.99(13) . . ?
C20 Ir1 C19 37.61(17) . . ?
C20 Ir1 C23 62.39(17) . . ?
C20 Ir1 C22 62.46(17) . . ?
C20 Ir1 C21 37.64(17) . . ?
C5 Ir1 S1 80.75(13) . . ?
C5 Ir1 C19 93.78(17) . . ?
C5 Ir1 C20 108.75(17) . . ?
C5 Ir1 C14 86.57(17) . . ?
C5 Ir1 C23 113.21(18) . . ?
C5 Ir1 C22 150.83(17) . . ?
C5 Ir1 C21 146.06(17) . . ?
C14 Ir1 S1 84.05(13) . . ?
C14 Ir1 C19 142.95(17) . . ?
C14 Ir1 C20 107.71(18) . . ?
C14 Ir1 C23 159.59(19) . . ?
C14 Ir1 C22 122.44(18) . . ?
C14 Ir1 C21 98.94(18) . . ?
C23 Ir1 C19 36.44(17) . . ?
C23 Ir1 C22 37.62(18) . . ?
C23 Ir1 C21 61.98(18) . . ?
C22 Ir1 C19 61.82(16) . . ?
C21 Ir1 C19 62.02(17) . . ?
C21 Ir1 C22 36.68(17) . . ?
O1 Ag1 O3 85.13(12) . . ?
O1 Ag1 O2 132.56(12) . 2_766 ?
O1 Ag1 O2 88.90(13) . . ?
O1 Ag1 C18 87.15(14) . 2_666 ?
O1 Ag1 C17 118.28(14) . 2_666 ?
O3 Ag1 O2 52.57(13) . 2_766 ?
O3 Ag1 C17 139.11(14) . 2_666 ?
O2 Ag1 O3 110.25(14) . . ?
O2 Ag1 O2 87.40(13) . 2_766 ?
O2 Ag1 C17 103.63(14) . 2_666 ?
O2 Ag1 C17 108.52(15) 2_766 2_666 ?
C18 Ag1 O3 136.57(15) 2_666 . ?
C18 Ag1 O2 112.26(14) 2_666 . ?
C18 Ag1 O2 137.23(15) 2_666 2_766 ?
C18 Ag1 C17 31.94(16) 2_666 2_666 ?
O4 Ag2 Ag2 82.32(9) . 2_665 ?
O4 Ag2 O5 157.84(12) . . ?
O4 Ag2 C6 117.60(13) . . ?
O5 Ag2 Ag2 78.27(9) . 2_665 ?
O5 Ag2 C6 81.42(13) . . ?
C6 Ag2 Ag2 159.69(10) . 2_665 ?
O1 S1 Ir1 121.78(14) . . ?
O1 S1 C3 109.0(2) . . ?
O1 S1 C12 109.3(2) . . ?
C3 S1 Ir1 104.61(15) . . ?
C3 S1 C12 103.4(2) . . ?
C12 S1 Ir1 107.16(15) . . ?
C7 O4 Ag2 121.2(3) . . ?
C7 O5 Ag2 125.2(3) 2_665 . ?
S1 O1 Ag1 133.12(19) . . ?
C1 O3 Ag1 90.6(3) . . ?
Ag1 O2 Ag1 92.60(13) . 2_766 ?
C1 O2 Ag1 89.1(3) 2_766 2_766 ?
C1 O2 Ag1 118.5(3) 2_766 . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C16 C15 C14 122.4(4) . . ?
C20 C19 Ir1 70.0(2) . . ?
C20 C19 C28 125.2(4) . . ?
C23 C19 Ir1 71.2(3) . . ?
C23 C19 C20 108.4(4) . . ?
C23 C19 C28 126.3(4) . . ?
C28 C19 Ir1 125.4(3) . . ?
F1 C2 F2 106.1(4) . . ?
F1 C2 C1 111.4(4) . . ?
F2 C2 C1 111.5(4) . . ?
F3 C2 F1 106.7(4) . . ?
F3 C2 F2 107.6(4) . . ?
F3 C2 C1 113.1(4) . . ?
C6 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C6 120.3(4) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
C19 C20 Ir1 72.3(2) . . ?
C19 C20 C21 107.0(4) . . ?
C19 C20 C27 126.5(4) . . ?
C21 C20 Ir1 72.3(3) . . ?
C21 C20 C27 125.3(4) . . ?
C27 C20 Ir1 130.4(3) . . ?
S1 C3 H3A 110.5 . . ?
S1 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 S1 106.1(3) . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
O3 C1 O2 127.7(5) . 2_766 ?
O3 C1 C2 117.3(5) . . ?
O2 C1 C2 115.0(5) 2_766 . ?
C4 C5 Ir1 120.2(3) . . ?
C6 C5 Ir1 123.6(3) . . ?
C6 C5 C4 116.1(4) . . ?
C15 C14 Ir1 123.7(3) . . ?
C15 C14 C13 116.5(4) . . ?
C13 C14 Ir1 119.7(3) . . ?
C14 C13 C12 119.1(4) . . ?
C18 C13 C14 121.5(4) . . ?
C18 C13 C12 119.4(4) . . ?
O4 C7 C8 115.2(4) . . ?
O5 C7 O4 130.3(4) 2_665 . ?
O5 C7 C8 114.5(4) 2_665 . ?
C5 C4 C3 116.8(4) . . ?
C11 C4 C3 121.7(4) . . ?
C11 C4 C5 121.5(4) . . ?
C19 C23 Ir1 72.4(2) . . ?
C19 C23 C24 125.6(5) . . ?
C19 C23 C22 108.5(4) . . ?
C24 C23 Ir1 125.0(3) . . ?
C22 C23 Ir1 71.7(2) . . ?
C22 C23 C24 125.8(5) . . ?
C23 C22 Ir1 70.6(2) . . ?
C23 C22 C25 125.4(5) . . ?
C21 C22 Ir1 71.7(3) . . ?
C21 C22 C23 107.6(4) . . ?
C21 C22 C25 126.9(5) . . ?
C25 C22 Ir1 125.7(3) . . ?
Ag1 C18 H18 93.3 2_666 . ?
C13 C18 Ag1 95.5(3) . 2_666 ?
C13 C18 H18 120.1 . . ?
C13 C18 C17 119.8(4) . . ?
C17 C18 Ag1 81.3(3) . 2_666 ?
C17 C18 H18 120.1 . . ?
Ag1 C17 H17 99.1 2_666 . ?
C18 C17 Ag1 66.8(3) . 2_666 ?
C18 C17 H17 120.4 . . ?
C16 C17 Ag1 103.6(3) . 2_666 ?
C16 C17 C18 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C20 C21 Ir1 70.0(3) . . ?
C20 C21 C26 125.7(5) . . ?
C22 C21 Ir1 71.7(3) . . ?
C22 C21 C20 108.4(4) . . ?
C22 C21 C26 125.8(4) . . ?
C26 C21 Ir1 127.5(3) . . ?
S1 C12 H12A 110.0 . . ?
S1 C12 H12B 110.0 . . ?
C13 C12 S1 108.4(3) . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
Ag2 C6 H6 89.0 . . ?
C9 C6 Ag2 89.2(3) . . ?
C9 C6 C5 122.2(4) . . ?
C9 C6 H6 118.9 . . ?
C5 C6 Ag2 91.7(3) . . ?
C5 C6 H6 118.9 . . ?
C4 C11 H11 119.9 . . ?
C4 C11 C10 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
F4 C8 C7 113.0(4) . . ?
F5 C8 F4 106.3(5) . . ?
F5 C8 C7 112.3(5) . . ?
F6 C8 F4 106.9(5) . . ?
F6 C8 F5 108.4(5) . . ?
F6 C8 C7 109.8(5) . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
Ir1 S1 O1 Ag1 151.15(17) . . . . ?
Ir1 S1 C3 C4 33.0(3) . . . . ?
Ir1 S1 C12 C13 12.1(3) . . . . ?
Ir1 C19 C20 C21 -64.5(3) . . . . ?
Ir1 C19 C20 C27 127.6(5) . . . . ?
Ir1 C19 C23 C24 -120.9(5) . . . . ?
Ir1 C19 C23 C22 63.1(3) . . . . ?
Ir1 C20 C21 C22 -61.8(3) . . . . ?
Ir1 C20 C21 C26 122.5(5) . . . . ?
Ir1 C5 C4 C3 -5.8(5) . . . . ?
Ir1 C5 C4 C11 173.4(3) . . . . ?
Ir1 C5 C6 Ag2 96.2(3) . . . . ?
Ir1 C5 C6 C9 -173.7(3) . . . . ?
Ir1 C14 C13 C18 -173.1(3) . . . . ?
Ir1 C14 C13 C12 8.8(6) . . . . ?
Ir1 C23 C22 C21 62.5(3) . . . . ?
Ir1 C23 C22 C25 -120.6(4) . . . . ?
Ir1 C22 C21 C20 60.7(3) . . . . ?
Ir1 C22 C21 C26 -123.5(5) . . . . ?
Ag1 O3 C1 O2 0.8(6) . . . 2_766 ?
Ag1 O3 C1 C2 -176.2(4) . . . . ?
Ag1 C18 C17 C16 -93.0(4) 2_666 . . . ?
Ag1 C17 C16 C15 -69.2(5) 2_666 . . . ?
Ag2 O4 C7 O5 -5.2(7) . . . 2_665 ?
Ag2 O4 C7 C8 176.4(3) . . . . ?
S1 C3 C4 C5 -19.3(5) . . . . ?
S1 C3 C4 C11 161.5(4) . . . . ?
F1 C2 C1 O3 111.2(5) . . . . ?
F1 C2 C1 O2 -66.2(6) . . . 2_766 ?
F2 C2 C1 O3 -130.5(5) . . . . ?
F2 C2 C1 O2 52.1(6) . . . 2_766 ?
F3 C2 C1 O3 -9.0(7) . . . . ?
F3 C2 C1 O2 173.6(5) . . . 2_766 ?
O4 C7 C8 F4 -29.6(7) . . . . ?
O4 C7 C8 F5 -149.8(5) . . . . ?
O4 C7 C8 F6 89.6(6) . . . . ?
O5 C7 C8 F4 151.7(5) 2_665 . . . ?
O5 C7 C8 F5 31.5(7) 2_665 . . . ?
O5 C7 C8 F6 -89.1(6) 2_665 . . . ?
O1 S1 C3 C4 164.7(3) . . . . ?
O1 S1 C12 C13 -121.8(3) . . . . ?
C15 C14 C13 C18 4.8(7) . . . . ?
C15 C14 C13 C12 -173.2(4) . . . . ?
C19 C20 C21 Ir1 64.5(3) . . . . ?
C19 C20 C21 C22 2.7(5) . . . . ?
C19 C20 C21 C26 -173.0(4) . . . . ?
C19 C23 C22 Ir1 -63.5(3) . . . . ?
C19 C23 C22 C21 -1.0(5) . . . . ?
C19 C23 C22 C25 175.9(4) . . . . ?
C24 C23 C22 Ir1 120.5(5) . . . . ?
C24 C23 C22 C21 -177.0(4) . . . . ?
C24 C23 C22 C25 -0.2(7) . . . . ?
C20 C19 C23 Ir1 -60.4(3) . . . . ?
C20 C19 C23 C24 178.7(4) . . . . ?
C20 C19 C23 C22 2.7(5) . . . . ?
C3 S1 O1 Ag1 29.3(3) . . . . ?
C3 S1 C12 C13 122.2(3) . . . . ?
C3 C4 C11 C10 -179.6(4) . . . . ?
C5 C4 C11 C10 1.3(7) . . . . ?
C14 C15 C16 C17 2.0(8) . . . . ?
C14 C13 C18 Ag1 81.4(4) . . . 2_666 ?
C14 C13 C18 C17 -1.6(7) . . . . ?
C14 C13 C12 S1 -13.6(5) . . . . ?
C13 C18 C17 Ag1 91.3(4) . . . 2_666 ?
C13 C18 C17 C16 -1.7(7) . . . . ?
C4 C5 C6 Ag2 -86.8(4) . . . . ?
C4 C5 C6 C9 3.3(6) . . . . ?
C4 C11 C10 C9 1.7(7) . . . . ?
C23 C19 C20 Ir1 61.1(3) . . . . ?
C23 C19 C20 C21 -3.3(5) . . . . ?
C23 C19 C20 C27 -171.3(4) . . . . ?
C23 C22 C21 Ir1 -61.9(3) . . . . ?
C23 C22 C21 C20 -1.1(5) . . . . ?
C23 C22 C21 C26 174.6(4) . . . . ?
C18 C13 C12 S1 168.4(4) . . . . ?
C18 C17 C16 C15 1.5(7) . . . . ?
C12 S1 O1 Ag1 -83.0(3) . . . . ?
C12 S1 C3 C4 -79.0(3) . . . . ?
C12 C13 C18 Ag1 -100.5(4) . . . 2_666 ?
C12 C13 C18 C17 176.4(4) . . . . ?
C6 C9 C10 C11 -2.1(7) . . . . ?
C6 C5 C4 C3 177.1(4) . . . . ?
C6 C5 C4 C11 -3.7(6) . . . . ?
C28 C19 C20 Ir1 -119.8(4) . . . . ?
C28 C19 C20 C21 175.7(4) . . . . ?
C28 C19 C20 C27 7.8(7) . . . . ?
C28 C19 C23 Ir1 120.6(4) . . . . ?
C28 C19 C23 C24 -0.3(7) . . . . ?
C28 C19 C23 C22 -176.3(4) . . . . ?
C16 C15 C14 Ir1 172.9(4) . . . . ?
C16 C15 C14 C13 -5.0(7) . . . . ?
C27 C20 C21 Ir1 -127.4(4) . . . . ?
C27 C20 C21 C22 170.8(4) . . . . ?
C27 C20 C21 C26 -4.9(7) . . . . ?
C25 C22 C21 Ir1 121.4(5) . . . . ?
C25 C22 C21 C20 -177.9(4) . . . . ?
C25 C22 C21 C26 -2.2(7) . . . . ?
C10 C9 C6 Ag2 91.0(4) . . . . ?
C10 C9 C6 C5 -0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy1020_0m
_database_code_depnum_ccdc_archive 'CCDC 1971161'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br2 O2 S3'
_chemical_formula_sum            'C10 H6 Br2 O2 S3'
_chemical_formula_weight         414.15
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8021(3)
_cell_length_b                   10.4926(5)
_cell_length_c                   10.9378(5)
_cell_angle_alpha                73.356(2)
_cell_angle_beta                 87.222(2)
_cell_angle_gamma                79.5970(10)
_cell_volume                     627.49(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      3.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.942
_exptl_absorpt_correction_T_max  0.0999
_exptl_absorpt_correction_T_min  0.0291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1572 before and 0.0862 after correction. The Ratio of minimum to maximum transmission is 0.2913. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.617
_diffrn_reflns_theta_min         2.057
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3399
_reflns_number_total             3865
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.440
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       0.0110(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.060
_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)+(0.0616P)²+0.3780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10)
;
_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
Br1 Br 0.87145(5) 0.93821(3) 0.37133(3) 0.01911(10) Uani 1 1 d . . . . .
Br2 Br 0.67932(5) 0.05473(3) 0.86058(3) 0.02154(11) Uani 1 1 d . . . . .
S1 S 0.73012(12) 0.65809(7) 0.49540(6) 0.01517(15) Uani 1 1 d . . . . .
S2 S 0.19864(11) 0.67085(7) 0.87428(6) 0.01278(14) Uani 1 1 d . . . . .
S3 S 0.75264(12) 0.34039(7) 0.70903(6) 0.01471(14) Uani 1 1 d . . . . .
O1 O 0.0252(4) 0.7915(2) 0.8366(2) 0.0200(4) Uani 1 1 d . . . . .
O2 O 0.2086(3) 0.5948(2) 1.00759(18) 0.0180(4) Uani 1 1 d . . . . .
C1 C 0.1516(4) 0.5625(3) 0.7810(3) 0.0143(5) Uani 1 1 d . . . . .
H1A H 0.015158 0.519284 0.816020 0.017 Uiso 1 1 calc R . . . .
H1B H 0.111847 0.618493 0.692606 0.017 Uiso 1 1 calc R . . . .
C2 C 0.3567(4) 0.4545(3) 0.7771(2) 0.0130(5) Uani 1 1 d . . . . .
C3 C 0.5518(4) 0.4842(3) 0.7063(2) 0.0133(5) Uani 1 1 d . . . . .
C4 C 0.6008(4) 0.6175(3) 0.6438(2) 0.0127(5) Uani 1 1 d . . . . .
C5 C 0.7389(5) 0.8186(3) 0.5043(3) 0.0157(5) Uani 1 1 d . . . . .
C6 C 0.5643(4) 0.7250(3) 0.6956(2) 0.0128(5) Uani 1 1 d . . . . .
C7 C 0.4879(5) 0.7098(3) 0.8320(2) 0.0139(5) Uani 1 1 d . . . . .
H7A H 0.496991 0.794975 0.852048 0.017 Uiso 1 1 calc R . . . .
H7B H 0.602530 0.637679 0.887705 0.017 Uiso 1 1 calc R . . . .
C8 C 0.3696(5) 0.3130(3) 0.8364(2) 0.0145(5) Uani 1 1 d . . . . .
H8 H 0.251012 0.274262 0.889524 0.017 Uiso 1 1 calc R . . . .
C9 C 0.5745(5) 0.2404(3) 0.8070(3) 0.0154(5) Uani 1 1 d . . . . .
C10 C 0.6439(5) 0.8410(3) 0.6144(3) 0.0152(5) Uani 1 1 d . . . . .
H10 H 0.632137 0.924199 0.634489 0.018 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
Br1 C5 1.865(3) . ?
Br2 C9 1.860(3) . ?
S1 C4 1.726(3) . ?
S1 C5 1.724(3) . ?
S2 O1 1.438(2) . ?
S2 O2 1.446(2) . ?
S2 C1 1.792(3) . ?
S2 C7 1.806(3) . ?
S3 C3 1.726(3) . ?
S3 C9 1.720(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.496(4) . ?
C2 C3 1.372(4) . ?
C2 C8 1.430(4) . ?
C3 C4 1.443(4) . ?
C4 C6 1.380(4) . ?
C5 C10 1.364(4) . ?
C6 C7 1.507(4) . ?
C6 C10 1.424(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.369(4) . ?
C10 H10 0.9500 . ?

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
C5 S1 C4 91.11(13) . . ?
O1 S2 O2 117.53(12) . . ?
O1 S2 C1 107.63(13) . . ?
O1 S2 C7 110.25(13) . . ?
O2 S2 C1 108.73(13) . . ?
O2 S2 C7 106.64(12) . . ?
C1 S2 C7 105.43(12) . . ?
C9 S3 C3 91.13(13) . . ?
S2 C1 H1A 108.7 . . ?
S2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C2 C1 S2 114.35(18) . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 C8 112.8(2) . . ?
C8 C2 C1 125.9(2) . . ?
C2 C3 S3 111.8(2) . . ?
C2 C3 C4 126.2(2) . . ?
C4 C3 S3 121.84(19) . . ?
C3 C4 S1 122.8(2) . . ?
C6 C4 S1 111.7(2) . . ?
C6 C4 C3 125.4(2) . . ?
S1 C5 Br1 119.66(15) . . ?
C10 C5 Br1 127.6(2) . . ?
C10 C5 S1 112.7(2) . . ?
C4 C6 C7 122.1(2) . . ?
C4 C6 C10 112.5(2) . . ?
C10 C6 C7 124.7(2) . . ?
S2 C7 H7A 107.9 . . ?
S2 C7 H7B 107.9 . . ?
C6 C7 S2 117.41(18) . . ?
C6 C7 H7A 107.9 . . ?
C6 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
C2 C8 H8 124.3 . . ?
C9 C8 C2 111.4(2) . . ?
C9 C8 H8 124.3 . . ?
S3 C9 Br2 118.35(15) . . ?
C8 C9 Br2 128.7(2) . . ?
C8 C9 S3 112.9(2) . . ?
C5 C10 C6 112.0(3) . . ?
C5 C10 H10 124.0 . . ?
C6 C10 H10 124.0 . . ?

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
Br1 C5 C10 C6 -178.57(19) . . . . ?
S1 C4 C6 C7 -170.59(19) . . . . ?
S1 C4 C6 C10 -0.5(3) . . . . ?
S1 C5 C10 C6 1.0(3) . . . . ?
S2 C1 C2 C3 -73.9(3) . . . . ?
S2 C1 C2 C8 110.2(3) . . . . ?
S3 C3 C4 S1 43.8(3) . . . . ?
S3 C3 C4 C6 -132.4(2) . . . . ?
O1 S2 C1 C2 161.61(19) . . . . ?
O1 S2 C7 C6 -80.7(2) . . . . ?
O2 S2 C1 C2 -70.1(2) . . . . ?
O2 S2 C7 C6 150.7(2) . . . . ?
C1 S2 C7 C6 35.2(2) . . . . ?
C1 C2 C3 S3 -175.57(19) . . . . ?
C1 C2 C3 C4 9.1(4) . . . . ?
C1 C2 C8 C9 175.5(2) . . . . ?
C2 C3 C4 S1 -141.3(2) . . . . ?
C2 C3 C4 C6 42.5(4) . . . . ?
C2 C8 C9 Br2 179.1(2) . . . . ?
C2 C8 C9 S3 0.2(3) . . . . ?
C3 S3 C9 Br2 -178.87(16) . . . . ?
C3 S3 C9 C8 0.2(2) . . . . ?
C3 C2 C8 C9 -0.6(3) . . . . ?
C3 C4 C6 C7 6.0(4) . . . . ?
C3 C4 C6 C10 176.1(2) . . . . ?
C4 S1 C5 Br1 178.52(17) . . . . ?
C4 S1 C5 C10 -1.0(2) . . . . ?
C4 C6 C7 S2 -66.6(3) . . . . ?
C4 C6 C10 C5 -0.3(3) . . . . ?
C5 S1 C4 C3 -175.8(2) . . . . ?
C5 S1 C4 C6 0.8(2) . . . . ?
C7 S2 C1 C2 43.9(2) . . . . ?
C7 C6 C10 C5 169.5(2) . . . . ?
C8 C2 C3 S3 0.8(3) . . . . ?
C8 C2 C3 C4 -174.5(2) . . . . ?
C9 S3 C3 C2 -0.6(2) . . . . ?
C9 S3 C3 C4 175.0(2) . . . . ?
C10 C6 C7 S2 124.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy0815_0m
_database_code_depnum_ccdc_archive 'CCDC 1943605'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_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        ?
_chemical_formula_moiety         'C10 H8 O S3'
_chemical_formula_sum            'C10 H8 O S3'
_chemical_formula_weight         240.34
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1465(5)
_cell_length_b                   14.4371(8)
_cell_length_c                   8.8840(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.673(2)
_cell_angle_gamma                90
_cell_volume                     1026.79(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100
_cell_measurement_theta_max      45.27
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0756 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.8896. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.358
_diffrn_reflns_theta_min         2.727
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6542
_reflns_number_total             8609
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         8609
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.028
_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)+(0.0416P)²+0.4808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Restrained distances
 S3-O1 \\sim S3A-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(S3) = Uanis(S3A)
4. Others
 Sof(H5BC)=Sof(H5BD)=Sof(H9BC)=Sof(H9BD)=Sof(O1A)=Sof(S3A)=1-FVAR(1)
 Sof(S3)=Sof(O1)=Sof(H5AA)=Sof(H5AB)=Sof(H9AA)=Sof(H9AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C9(H9AA,H9AB), C9(H9BC,H9BD)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C10(H10)
;
_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
S1 S 0.34426(3) 0.73416(2) 0.90315(3) 0.01625(4) Uani 1 1 d . . . . .
S2 S 0.73972(3) 0.64784(2) 0.84118(3) 0.01849(5) Uani 1 1 d . . . . .
S3 S 0.27819(5) 0.42912(2) 0.61136(4) 0.01471(6) Uani 0.958(2) 1 d D . P A 1
O1 O 0.11205(10) 0.40115(6) 0.64509(11) 0.02534(18) Uani 0.958(2) 1 d D . P A 1
C1 C 0.14287(11) 0.74220(6) 0.80449(11) 0.01541(13) Uani 1 1 d . . . . .
H1 H 0.063002 0.785596 0.826715 0.018 Uiso 1 1 calc R . . . .
C2 C 0.38936(10) 0.64410(5) 0.79064(9) 0.01139(10) Uani 1 1 d . . . . .
C3 C 0.54757(10) 0.59522(6) 0.81342(9) 0.01179(11) Uani 1 1 d . . . . .
C4 C 0.84215(11) 0.54357(7) 0.85127(11) 0.01808(14) Uani 1 1 d . . . . .
H4 H 0.960118 0.536905 0.867249 0.022 Uiso 1 1 calc R . . . .
C5 C 0.26451(11) 0.55095(6) 0.55854(8) 0.01295(11) Uani 1 1 d . . . . .
H5AA H 0.363779 0.566329 0.513823 0.016 Uiso 0.958(2) 1 calc R . P A 1
H5AB H 0.165305 0.558898 0.476431 0.016 Uiso 0.958(2) 1 calc R . P A 1
H5BC H 0.372601 0.558386 0.524125 0.016 Uiso 0.042(2) 1 calc R . P A 2
H5BD H 0.174123 0.562553 0.469515 0.016 Uiso 0.042(2) 1 calc R . P A 2
C6 C 0.25320(9) 0.62062(5) 0.68055(8) 0.01085(10) Uani 1 1 d . . . . .
C7 C 0.11198(10) 0.67720(6) 0.68830(9) 0.01375(12) Uani 1 1 d . . . . .
H7 H 0.007535 0.670992 0.620815 0.017 Uiso 1 1 calc R . . . .
C8 C 0.56077(10) 0.49978(6) 0.81104(8) 0.01168(11) Uani 1 1 d . . . . .
C9 C 0.41088(10) 0.43874(6) 0.80039(9) 0.01316(11) Uani 1 1 d . . . . .
H9AA H 0.341815 0.462195 0.872868 0.016 Uiso 0.958(2) 1 calc R . P A 1
H9AB H 0.449316 0.375848 0.834728 0.016 Uiso 0.958(2) 1 calc R . P A 1
H9BC H 0.353778 0.457983 0.884454 0.016 Uiso 0.042(2) 1 calc R . P A 2
H9BD H 0.453916 0.375439 0.825939 0.016 Uiso 0.042(2) 1 calc R . P A 2
C10 C 0.73017(11) 0.47027(7) 0.83305(10) 0.01595(13) Uani 1 1 d . . . . .
H10 H 0.763070 0.407090 0.835053 0.019 Uiso 1 1 calc R . . . .
O1A O 0.325(2) 0.3745(13) 0.518(2) 0.02534(18) Uani 0.042(2) 1 d D . P A 2
S3A S 0.2466(12) 0.4273(6) 0.6287(10) 0.01471(6) Uani 0.042(2) 1 d D . P A 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
S1 C1 1.7148(9) . ?
S1 C2 1.7206(8) . ?
S2 C3 1.7161(8) . ?
S2 C4 1.7154(10) . ?
S3 O1 1.4950(10) . ?
S3 C5 1.8185(9) . ?
S3 C9 1.8263(8) . ?
C1 H1 0.9500 . ?
C1 C7 1.3831(13) . ?
C2 C3 1.4503(11) . ?
C2 C6 1.3785(11) . ?
C3 C8 1.3826(11) . ?
C4 H4 0.9500 . ?
C4 C10 1.3869(14) . ?
C5 H5AA 0.9900 . ?
C5 H5AB 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 C6 1.4940(11) . ?
C5 S3A 1.905(9) . ?
C6 C7 1.4230(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.4946(11) . ?
C8 C10 1.4227(12) . ?
C9 H9AA 0.9900 . ?
C9 H9AB 0.9900 . ?
C9 H9BC 0.9900 . ?
C9 H9BD 0.9900 . ?
C9 S3A 1.841(9) . ?
C10 H10 0.9500 . ?
O1A S3A 1.483(16) . ?

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
C1 S1 C2 92.36(4) . . ?
C4 S2 C3 92.35(4) . . ?
O1 S3 C5 107.37(5) . . ?
O1 S3 C9 103.88(5) . . ?
C5 S3 C9 99.28(4) . . ?
S1 C1 H1 124.4 . . ?
C7 C1 S1 111.11(6) . . ?
C7 C1 H1 124.4 . . ?
C3 C2 S1 124.51(6) . . ?
C6 C2 S1 111.57(6) . . ?
C6 C2 C3 123.84(7) . . ?
C2 C3 S2 124.61(6) . . ?
C8 C3 S2 111.83(6) . . ?
C8 C3 C2 123.53(7) . . ?
S2 C4 H4 124.4 . . ?
C10 C4 S2 111.12(6) . . ?
C10 C4 H4 124.4 . . ?
S3 C5 H5AA 107.8 . . ?
S3 C5 H5AB 107.8 . . ?
H5AA C5 H5AB 107.1 . . ?
H5BC C5 H5BD 107.9 . . ?
C6 C5 S3 118.23(5) . . ?
C6 C5 H5AA 107.8 . . ?
C6 C5 H5AB 107.8 . . ?
C6 C5 H5BC 109.2 . . ?
C6 C5 H5BD 109.2 . . ?
C6 C5 S3A 112.0(3) . . ?
S3A C5 H5BC 109.2 . . ?
S3A C5 H5BD 109.2 . . ?
C2 C6 C5 122.05(7) . . ?
C2 C6 C7 112.09(7) . . ?
C7 C6 C5 125.50(7) . . ?
C1 C7 C6 112.87(7) . . ?
C1 C7 H7 123.6 . . ?
C6 C7 H7 123.6 . . ?
C3 C8 C9 121.58(7) . . ?
C3 C8 C10 111.87(7) . . ?
C10 C8 C9 126.33(8) . . ?
S3 C9 H9AA 108.3 . . ?
S3 C9 H9AB 108.3 . . ?
C8 C9 S3 116.14(6) . . ?
C8 C9 H9AA 108.3 . . ?
C8 C9 H9AB 108.3 . . ?
C8 C9 H9BC 106.2 . . ?
C8 C9 H9BD 106.2 . . ?
C8 C9 S3A 124.4(3) . . ?
H9AA C9 H9AB 107.4 . . ?
H9BC C9 H9BD 106.4 . . ?
S3A C9 H9BC 106.2 . . ?
S3A C9 H9BD 106.2 . . ?
C4 C10 C8 112.82(8) . . ?
C4 C10 H10 123.6 . . ?
C8 C10 H10 123.6 . . ?
C9 S3A C5 95.7(4) . . ?
O1A S3A C5 101.3(9) . . ?
O1A S3A C9 105.1(9) . . ?

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
S1 C1 C7 C6 0.22(9) . . . . ?
S1 C2 C3 S2 -48.15(9) . . . . ?
S1 C2 C3 C8 133.71(7) . . . . ?
S1 C2 C6 C5 173.78(6) . . . . ?
S1 C2 C6 C7 0.36(9) . . . . ?
S2 C3 C8 C9 175.25(6) . . . . ?
S2 C3 C8 C10 0.32(9) . . . . ?
S2 C4 C10 C8 -0.06(10) . . . . ?
S3 C5 C6 C2 74.55(9) . . . . ?
S3 C5 C6 C7 -112.94(8) . . . . ?
O1 S3 C5 C6 70.22(8) . . . . ?
O1 S3 C9 C8 -156.67(7) . . . . ?
C1 S1 C2 C3 -176.97(7) . . . . ?
C1 S1 C2 C6 -0.20(6) . . . . ?
C2 S1 C1 C7 -0.01(7) . . . . ?
C2 C3 C8 C9 -6.39(12) . . . . ?
C2 C3 C8 C10 178.67(7) . . . . ?
C2 C6 C7 C1 -0.37(10) . . . . ?
C3 S2 C4 C10 0.21(7) . . . . ?
C3 C2 C6 C5 -9.42(12) . . . . ?
C3 C2 C6 C7 177.16(7) . . . . ?
C3 C8 C9 S3 76.75(9) . . . . ?
C3 C8 C9 S3A 70.0(4) . . . . ?
C3 C8 C10 C4 -0.16(10) . . . . ?
C4 S2 C3 C2 -178.64(7) . . . . ?
C4 S2 C3 C8 -0.30(6) . . . . ?
C5 S3 C9 C8 -46.07(7) . . . . ?
C5 C6 C7 C1 -173.53(8) . . . . ?
C6 C2 C3 S2 135.46(7) . . . . ?
C6 C2 C3 C8 -42.68(12) . . . . ?
C8 C9 S3A C5 -31.6(5) . . . . ?
C8 C9 S3A O1A 71.7(9) . . . . ?
C9 S3 C5 C6 -37.59(7) . . . . ?
C9 C8 C10 C4 -174.81(8) . . . . ?
C10 C8 C9 S3 -109.09(8) . . . . ?
C10 C8 C9 S3A -115.9(4) . . . . ?
S3A C5 C6 C2 82.7(3) . . . . ?
S3A C5 C6 C7 -104.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
