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

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

data_V210919e
_database_code_depnum_ccdc_archive 'CCDC 2141218'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Nishimoto'
;University of Hyogo
Japan
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H8 O S2'
_chemical_formula_moiety         'C12 H8 O S2'
_chemical_formula_weight         232.31
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.9198(16)
_cell_length_b                   7.670(2)
_cell_length_c                   22.977(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.417(6)
_cell_angle_gamma                90.0000
_cell_volume                     1036.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3131
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.17
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480.00
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            17838
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2376
_reflns_number_gt                2126
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1985
_refine_ls_wR_factor_gt          0.1933
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1115P)²+1.0852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.44
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.97597(13) 0.03689(11) 0.75598(4) 0.0477(3) Uani 1 1 d . . . . .
S2 S 0.57139(13) 0.22727(12) 0.78702(4) 0.0515(3) Uani 1 1 d . . . . .
O13 O 0.4585(6) 0.1635(5) 0.55431(12) 0.0774(9) Uani 1 1 d . . . . .
C1 C 0.7177(5) 0.1383(4) 0.73211(13) 0.0418(6) Uani 1 1 d . . . . .
C2 C 0.7710(6) 0.2332(5) 0.90229(16) 0.0530(8) Uani 1 1 d . . . . .
H2 H 0.6423 0.2918 0.9116 0.064 Uiso 1 1 calc R U . . .
C3 C 0.7488(6) 0.0658(4) 0.62769(15) 0.0486(7) Uani 1 1 d . . . . .
H3 H 0.8861 0.0073 0.6362 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6332(5) 0.1436(4) 0.67534(13) 0.0447(7) Uani 1 1 d . . . . .
C5 C 0.4140(5) 0.2239(4) 0.65411(15) 0.0467(7) Uani 1 1 d . . . . .
H5 H 0.3229 0.2705 0.6807 0.056 Uiso 1 1 calc R U . . .
C6 C 0.9763(5) 0.0980(4) 0.83082(14) 0.0435(7) Uani 1 1 d . . . . .
C7 C 1.1507(6) 0.0576(4) 0.87303(14) 0.0473(7) Uani 1 1 d . . . . .
H7 H 1.2769 -0.0024 0.8628 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7884(6) 0.1853(4) 0.84495(14) 0.0458(7) Uani 1 1 d . . . . .
C9 C 0.3461(7) 0.2300(5) 0.59760(17) 0.0617(9) Uani 1 1 d . . . . .
H9 H 0.2082 0.2851 0.5863 0.074 Uiso 1 1 calc R U . . .
C10 C 0.9442(7) 0.1944(5) 0.94585(16) 0.0620(9) Uani 1 1 d . . . . .
H10 H 0.9321 0.2259 0.9845 0.074 Uiso 1 1 calc R U . . .
C11 C 1.1402(6) 0.1060(5) 0.93114(16) 0.0592(9) Uani 1 1 d . . . . .
H11 H 1.2596 0.0807 0.9597 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6556(7) 0.0802(5) 0.57288(16) 0.0609(9) Uani 1 1 d . . . . .
H12 H 0.7325 0.0281 0.5443 0.073 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.748(3) . ?
S1 C6 1.782(3) . ?
S2 C1 1.747(3) . ?
S2 C8 1.773(3) . ?
O13 C12 1.357(5) . ?
O13 C9 1.357(5) . ?
C1 C4 1.344(4) . ?
C2 C8 1.383(5) . ?
C2 C10 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C12 1.322(5) . ?
C3 C4 1.480(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.470(5) . ?
C5 C9 1.316(5) . ?
C5 H5 0.9300 . ?
C6 C8 1.368(5) . ?
C6 C7 1.370(4) . ?
C7 C11 1.394(5) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.417(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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 C6 95.29(14) . . ?
C1 S2 C8 95.45(14) . . ?
C12 O13 C9 114.9(3) . . ?
C4 C1 S2 121.9(2) . . ?
C4 C1 S1 122.4(2) . . ?
S2 C1 S1 115.73(17) . . ?
C8 C2 C10 120.3(3) . . ?
C8 C2 H2 119.9 . . ?
C10 C2 H2 119.9 . . ?
C12 C3 C4 119.5(3) . . ?
C12 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C1 C4 C5 123.6(3) . . ?
C1 C4 C3 123.6(3) . . ?
C5 C4 C3 112.8(3) . . ?
C9 C5 C4 120.2(3) . . ?
C9 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C8 C6 C7 120.7(3) . . ?
C8 C6 S1 116.4(2) . . ?
C7 C6 S1 122.9(3) . . ?
C6 C7 C11 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C11 C7 H7 119.8 . . ?
C6 C8 C2 120.4(3) . . ?
C6 C8 S2 116.8(2) . . ?
C2 C8 S2 122.8(3) . . ?
C5 C9 O13 126.1(4) . . ?
C5 C9 H9 117.0 . . ?
O13 C9 H9 117.0 . . ?
C2 C10 C11 119.4(3) . . ?
C2 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C7 C11 C10 118.8(3) . . ?
C7 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C3 C12 O13 126.3(4) . . ?
C3 C12 H12 116.9 . . ?
O13 C12 H12 116.9 . . ?

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
C8 S2 C1 C4 -176.2(3) . . . . ?
C8 S2 C1 S1 5.6(2) . . . . ?
C6 S1 C1 C4 176.1(3) . . . . ?
C6 S1 C1 S2 -5.79(19) . . . . ?
S2 C1 C4 C5 0.3(4) . . . . ?
S1 C1 C4 C5 178.4(2) . . . . ?
S2 C1 C4 C3 -178.3(2) . . . . ?
S1 C1 C4 C3 -0.3(4) . . . . ?
C12 C3 C4 C1 -178.6(3) . . . . ?
C12 C3 C4 C5 2.6(4) . . . . ?
C1 C4 C5 C9 177.4(3) . . . . ?
C3 C4 C5 C9 -3.8(4) . . . . ?
C1 S1 C6 C8 3.7(3) . . . . ?
C1 S1 C6 C7 -177.8(3) . . . . ?
C8 C6 C7 C11 -0.4(5) . . . . ?
S1 C6 C7 C11 -178.8(3) . . . . ?
C7 C6 C8 C2 -0.5(5) . . . . ?
S1 C6 C8 C2 178.1(3) . . . . ?
C7 C6 C8 S2 -179.0(2) . . . . ?
S1 C6 C8 S2 -0.4(3) . . . . ?
C10 C2 C8 C6 0.4(5) . . . . ?
C10 C2 C8 S2 178.9(3) . . . . ?
C1 S2 C8 C6 -3.1(3) . . . . ?
C1 S2 C8 C2 178.5(3) . . . . ?
C4 C5 C9 O13 1.8(6) . . . . ?
C12 O13 C9 C5 1.7(6) . . . . ?
C8 C2 C10 C11 0.4(6) . . . . ?
C6 C7 C11 C10 1.3(5) . . . . ?
C2 C10 C11 C7 -1.2(6) . . . . ?
C4 C3 C12 O13 0.9(6) . . . . ?
C9 O13 C12 C3 -3.1(6) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_V211001a
_database_code_depnum_ccdc_archive 'CCDC 2141219'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Nishimoto'
;University of Hyogo
Japan
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H8 S3'
_chemical_formula_moiety         'C12 H8 S3'
_chemical_formula_weight         248.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.9049(11)
_cell_length_b                   7.6579(14)
_cell_length_c                   23.865(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.872(3)
_cell_angle_gamma                90.0000
_cell_volume                     1073.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3466
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.18
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.913

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            15098
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.795
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2450
_reflns_number_gt                2340
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0950
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2450
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0490P)²+0.4735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.51684(7) 0.03714(6) 0.73920(2) 0.03742(13) Uani 1 1 d . . . . .
S2 S 0.92734(7) 0.22392(7) 0.71074(2) 0.04212(14) Uani 1 1 d . . . . .
S3 S 1.03093(9) 0.17337(8) 0.95022(2) 0.05258(16) Uani 1 1 d . . . . .
C1 C 0.7770(2) 0.1355(2) 0.76382(7) 0.0313(3) Uani 1 1 d . . . . .
C2 C 0.8569(3) 0.1408(2) 0.81939(7) 0.0319(3) Uani 1 1 d . . . . .
C3 C 1.0769(3) 0.2196(2) 0.83798(7) 0.0378(4) Uani 1 1 d . . . . .
H3 H 1.1645 0.2593 0.8103 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3524(3) 0.0508(2) 0.62627(8) 0.0389(4) Uani 1 1 d . . . . .
H4 H 0.2224 -0.0074 0.6351 0.047 Uiso 1 1 calc R U . . .
C5 C 0.7284(3) 0.0648(2) 0.86220(7) 0.0383(4) Uani 1 1 d . . . . .
H5 H 0.5944 0.0062 0.8500 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7197(3) 0.1806(2) 0.65495(7) 0.0350(3) Uani 1 1 d . . . . .
C7 C 0.7886(3) 0.0728(3) 0.91772(8) 0.0440(4) Uani 1 1 d . . . . .
H7 H 0.6919 0.0198 0.9410 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5245(3) 0.0929(2) 0.66826(6) 0.0323(3) Uani 1 1 d . . . . .
C9 C 0.7433(3) 0.2264(3) 0.59934(8) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.8727 0.2848 0.5903 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5707(4) 0.1835(3) 0.55769(8) 0.0493(4) Uani 1 1 d . . . . .
H10 H 0.5850 0.2134 0.5205 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1621(3) 0.2392(2) 0.89167(8) 0.0426(4) Uani 1 1 d . . . . .
H11 H 1.3038 0.2926 0.8983 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3775(3) 0.0967(3) 0.57096(8) 0.0460(4) Uani 1 1 d . . . . .
H12 H 0.2634 0.0690 0.5426 0.055 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C8 1.7510(16) . ?
S1 C1 1.7573(15) . ?
S2 C6 1.7471(17) . ?
S2 C1 1.7552(16) . ?
S3 C7 1.7362(19) . ?
S3 C11 1.740(2) . ?
C1 C2 1.362(2) . ?
C2 C5 1.455(2) . ?
C2 C3 1.460(2) . ?
C3 C11 1.336(2) . ?
C3 H3 0.9300 . ?
C4 C12 1.389(3) . ?
C4 C8 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C7 1.338(3) . ?
C5 H5 0.9300 . ?
C6 C9 1.393(2) . ?
C6 C8 1.399(2) . ?
C7 H7 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C12 1.385(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C1 96.35(7) . . ?
C6 S2 C1 96.28(8) . . ?
C7 S3 C11 100.61(9) . . ?
C2 C1 S2 122.75(12) . . ?
C2 C1 S1 122.82(12) . . ?
S2 C1 S1 114.42(9) . . ?
C1 C2 C5 121.24(15) . . ?
C1 C2 C3 121.12(15) . . ?
C5 C2 C3 117.62(15) . . ?
C11 C3 C2 125.02(17) . . ?
C11 C3 H3 117.5 . . ?
C2 C3 H3 117.5 . . ?
C12 C4 C8 119.02(17) . . ?
C12 C4 H4 120.5 . . ?
C8 C4 H4 120.5 . . ?
C7 C5 C2 124.93(16) . . ?
C7 C5 H5 117.5 . . ?
C2 C5 H5 117.5 . . ?
C9 C6 C8 120.14(16) . . ?
C9 C6 S2 123.20(14) . . ?
C8 C6 S2 116.64(12) . . ?
C5 C7 S3 125.88(15) . . ?
C5 C7 H7 117.1 . . ?
S3 C7 H7 117.1 . . ?
C4 C8 C6 120.43(15) . . ?
C4 C8 S1 123.44(13) . . ?
C6 C8 S1 116.12(12) . . ?
C10 C9 C6 119.01(18) . . ?
C10 C9 H9 120.5 . . ?
C6 C9 H9 120.5 . . ?
C12 C10 C9 120.77(17) . . ?
C12 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C3 C11 S3 125.63(14) . . ?
C3 C11 H11 117.2 . . ?
S3 C11 H11 117.2 . . ?
C10 C12 C4 120.64(17) . . ?
C10 C12 H12 119.7 . . ?
C4 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 S2 C1 C2 -176.78(14) . . . . ?
C6 S2 C1 S1 4.05(10) . . . . ?
C8 S1 C1 C2 176.57(14) . . . . ?
C8 S1 C1 S2 -4.25(10) . . . . ?
S2 C1 C2 C5 -179.47(12) . . . . ?
S1 C1 C2 C5 -0.4(2) . . . . ?
S2 C1 C2 C3 -0.8(2) . . . . ?
S1 C1 C2 C3 178.31(12) . . . . ?
C1 C2 C3 C11 176.00(17) . . . . ?
C5 C2 C3 C11 -5.3(3) . . . . ?
C1 C2 C5 C7 -176.13(17) . . . . ?
C3 C2 C5 C7 5.1(3) . . . . ?
C1 S2 C6 C9 178.98(16) . . . . ?
C1 S2 C6 C8 -2.17(14) . . . . ?
C2 C5 C7 S3 -0.4(3) . . . . ?
C11 S3 C7 C5 -3.5(2) . . . . ?
C12 C4 C8 C6 0.1(3) . . . . ?
C12 C4 C8 S1 -178.24(13) . . . . ?
C9 C6 C8 C4 -0.1(3) . . . . ?
S2 C6 C8 C4 -178.97(13) . . . . ?
C9 C6 C8 S1 178.42(14) . . . . ?
S2 C6 C8 S1 -0.47(17) . . . . ?
C1 S1 C8 C4 -178.70(14) . . . . ?
C1 S1 C8 C6 2.84(13) . . . . ?
C8 C6 C9 C10 0.0(3) . . . . ?
S2 C6 C9 C10 178.79(15) . . . . ?
C6 C9 C10 C12 0.1(3) . . . . ?
C2 C3 C11 S3 0.6(3) . . . . ?
C7 S3 C11 C3 3.3(2) . . . . ?
C9 C10 C12 C4 0.0(3) . . . . ?
C8 C4 C12 C10 -0.1(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


