# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_wo025
_database_code_depnum_ccdc_archive 'CCDC 1869283'

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_chemical_name_common            KH-86
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.264 #?# in millimeters
_exptl_crystal_size_mid          0.247 #?# in millimeters
_exptl_crystal_size_min          0.068 #?# in millimeters
_exptl_crystal_density_method    ?
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
 ?
;
_audit_creation_date             2018-06-04 #?# style: 18-Aug-1998

_diffrn_ambient_temperature      143(2) #?# in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             2.00_kW #?# in kW
_diffrn_source_voltage           50_kV #?# in kV
_diffrn_source_current           40_mA #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  48.00   1.00    7.50    --  -20.29  77.00-150.00  101
  2  ω    -11.00  94.00   1.00    7.50    --   21.54  77.00  90.00  105
  3  ω    -12.00  94.00   1.00    7.50    --   21.54  77.00 -30.00  106
;
_diffrn_detector_area_resol_mean 15.9809

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      0.0276449000
_diffrn_orient_matrix_UB_12      0.0759566000
_diffrn_orient_matrix_UB_13      -0.0281338000
_diffrn_orient_matrix_UB_21      -0.0095493000
_diffrn_orient_matrix_UB_22      0.0457606000
_diffrn_orient_matrix_UB_23      0.0497170000
_diffrn_orient_matrix_UB_31      0.1459228000
_diffrn_orient_matrix_UB_32      -0.0322811000
_diffrn_orient_matrix_UB_33      0.0006904000

_cell_length_a                   4.9268(4)
_cell_length_b                   7.7000(7)
_cell_length_c                   12.5316(10)
_cell_angle_alpha                89.531(7)
_cell_angle_beta                 82.298(7)
_cell_angle_gamma                77.518(7)
_cell_volume                     459.87(7)
_cell_measurement_temperature    143(2) #?# in K
_cell_measurement_reflns_used    894
_cell_measurement_theta_min      4.5360
_cell_measurement_theta_max      27.7630
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94560
_exptl_absorpt_correction_T_max  1.00000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_reflns_number            2551 #xl
_diffrn_reflns_av_R_equivalents  0.0205 #xl
_diffrn_reflns_av_unetI/netI     0.0493 #xl
_diffrn_reflns_limit_h_min       -6 #xl
_diffrn_reflns_limit_h_max       6 #xl
_diffrn_reflns_limit_k_min       -8 #xl
_diffrn_reflns_limit_k_max       9 #xl
_diffrn_reflns_limit_l_min       -15 #xl
_diffrn_reflns_limit_l_max       15 #xl
_diffrn_reflns_theta_min         4.212 #xl
_diffrn_reflns_theta_max         26.356 #xl
_diffrn_measured_fraction_theta_max 0.987 #xl
_diffrn_reflns_theta_full        25.240 #xl
_diffrn_measured_fraction_theta_full 0.992 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.987 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.992 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.987 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.992 #xl

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1' #?# style: 'P 21/c' 'R -3 m'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_reflns_number_total             1853 #xl
_reflns_number_gt                1555 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.0147P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed #?# mixed --> _refine_special_details
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         1853 #xl
_refine_ls_number_parameters     122 #xl
_refine_ls_number_restraints     1 #xl
_refine_ls_R_factor_all          0.0457 #xl
_refine_ls_R_factor_gt           0.0361 #xl
_refine_ls_wR_factor_ref         0.0828 #xl
_refine_ls_wR_factor_gt          0.0763 #xl
_refine_ls_goodness_of_fit_ref   1.069 #xl
_refine_ls_restrained_S_all      1.069 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.326 #xl
_refine_diff_density_min         -0.288 #xl
_refine_diff_density_rms         0.073 #xl

_refine_special_details          
;
 H(C) constr
 H(O) restr
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;

_computing_structure_refinement  
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;

_computing_molecular_graphics    ?

_computing_publication_material  ?

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
C1 C 0.0793(5) -0.2997(3) 0.42147(19) 0.0185(5) Uani 1 1 d . . . . .
C2 C 0.1585(5) -0.1520(3) 0.3554(2) 0.0198(5) Uani 1 1 d . . . . .
H2A H 0.2110 -0.1934 0.2794 0.024 Uiso 1 1 calc R U . . .
H2B H 0.3253 -0.1215 0.3802 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0315(5) 0.1817(3) 0.26905(18) 0.0168(5) Uani 1 1 d . . . . .
C4 C -0.1237(5) 0.3558(3) 0.26154(19) 0.0188(5) Uani 1 1 d . . . . .
H4 H -0.2932 0.3980 0.3084 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0253(5) 0.4639(3) 0.18500(19) 0.0183(5) Uani 1 1 d . . . . .
C6 C 0.2242(5) 0.4101(3) 0.11563(19) 0.0196(5) Uani 1 1 d . . . . .
H6 H 0.2881 0.4877 0.0635 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3753(5) 0.2381(3) 0.12614(19) 0.0172(5) Uani 1 1 d . . . . .
C8 C 0.2846(5) 0.1237(3) 0.20103(18) 0.0165(5) Uani 1 1 d . . . . .
H8 H 0.3927 0.0066 0.2065 0.020 Uiso 1 1 calc R U . . .
O2 O 0.2730(4) -0.4323(2) 0.43283(15) 0.0288(5) Uani 1 1 d . . . . .
O1 O -0.1778(4) -0.2863(2) 0.46032(16) 0.0271(4) Uani 1 1 d D . . . .
H1 H -0.207(9) -0.377(4) 0.495(3) 0.114(17) Uiso 1 1 d D . . . .
S1 S -0.11852(13) 0.04500(8) 0.36279(5) 0.02060(17) Uani 1 1 d . . . . .
Cl1 Cl -0.21868(14) 0.67875(8) 0.17071(5) 0.02784(19) Uani 1 1 d . . . . .
Cl2 Cl 0.68498(12) 0.16317(8) 0.03997(5) 0.02228(17) Uani 1 1 d . . . . .


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
C1 O2 1.259(3) . ?
C1 O1 1.277(3) . ?
C1 C2 1.490(3) . ?
C2 S1 1.802(2) . ?
C3 C8 1.401(3) . ?
C3 C4 1.401(3) . ?
C3 S1 1.766(2) . ?
C4 C5 1.373(3) . ?
C5 C6 1.392(3) . ?
C5 Cl1 1.743(2) . ?
C6 C7 1.387(3) . ?
C7 C8 1.378(3) . ?
C7 Cl2 1.736(2) . ?

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
O2 C1 O1 124.4(2) . . ?
O2 C1 C2 116.9(2) . . ?
O1 C1 C2 118.7(2) . . ?
C1 C2 S1 113.15(16) . . ?
C8 C3 C4 119.8(2) . . ?
C8 C3 S1 123.94(18) . . ?
C4 C3 S1 116.24(18) . . ?
C5 C4 C3 118.5(2) . . ?
C4 C5 C6 123.2(2) . . ?
C4 C5 Cl1 119.71(19) . . ?
C6 C5 Cl1 117.11(19) . . ?
C7 C6 C5 116.9(2) . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 Cl2 119.06(18) . . ?
C6 C7 Cl2 118.74(18) . . ?
C7 C8 C3 119.4(2) . . ?
C3 S1 C2 101.28(11) . . ?

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
O2 C1 C2 S1 -170.23(18) . . . . ?
O1 C1 C2 S1 11.4(3) . . . . ?
C8 C3 C4 C5 1.6(4) . . . . ?
S1 C3 C4 C5 -175.83(18) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C3 C4 C5 Cl1 178.00(18) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
Cl1 C5 C6 C7 -179.01(17) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C5 C6 C7 Cl2 178.90(18) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
Cl2 C7 C8 C3 -178.45(18) . . . . ?
C4 C3 C8 C7 -1.1(4) . . . . ?
S1 C3 C8 C7 176.15(18) . . . . ?
C8 C3 S1 C2 8.0(2) . . . . ?
C4 C3 S1 C2 -174.61(19) . . . . ?
C1 C2 S1 C3 -175.29(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.851(10) 1.782(10) 2.633(2) 179(4) 2_546

_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.
;

_audit_block_code                C8H6Cl2O2S_wo025_dube
_audit_creation_method           SHELXL-2014
_shelxl_version_number           2014-3
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H6 Cl2 O2 S'
_chemical_formula_sum            'C8 H6 Cl2 O2 S'
_chemical_formula_weight         237.09 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            2 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             240 #?# check!

####################################################################### 
# 
# 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_wv064
_database_code_depnum_ccdc_archive 'CCDC 1869286'

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_chemical_name_common            KH-116-Z
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.020 #?# in millimeters
_exptl_crystal_size_min          0.020 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      293.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   9.3294(2)
_cell_length_b                   21.9444(6)
_cell_length_c                   10.2119(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.3420(10)
_cell_angle_gamma                90
_cell_volume                     2025.51(9)
_cell_measurement_temperature    293.(2) #?# in K
_cell_measurement_reflns_used    7408
_cell_measurement_theta_min      2.8072
_cell_measurement_theta_max      25.3495
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            19899 #xl
_diffrn_reflns_av_R_equivalents  0.0378 #xl
_diffrn_reflns_av_unetI/netI     0.0270 #xl
_diffrn_reflns_limit_h_min       -11 #xl
_diffrn_reflns_limit_h_max       11 #xl
_diffrn_reflns_limit_k_min       -26 #xl
_diffrn_reflns_limit_k_max       26 #xl
_diffrn_reflns_limit_l_min       -12 #xl
_diffrn_reflns_limit_l_max       12 #xl
_diffrn_reflns_theta_min         3.235 #xl
_diffrn_reflns_theta_max         25.350 #xl
_diffrn_measured_fraction_theta_max 0.994 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.995 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.995 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.995 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14

_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.
;

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'

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'
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'

_reflns_number_total             3697 #xl
_reflns_number_gt                2832 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+1.2983P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         3697 #xl
_refine_ls_number_parameters     257 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0603 #xl
_refine_ls_R_factor_gt           0.0429 #xl
_refine_ls_wR_factor_ref         0.1068 #xl
_refine_ls_wR_factor_gt          0.0972 #xl
_refine_ls_goodness_of_fit_ref   1.037 #xl
_refine_ls_restrained_S_all      1.037 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.478 #xl
_refine_diff_density_min         -0.451 #xl
_refine_diff_density_rms         0.041 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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
Cl1 Cl 0.91880(9) 0.58954(4) 0.58321(8) 0.0731(3) Uani 1 1 d . . . . .
Cl2 Cl 0.54856(11) 0.49455(4) 0.85303(8) 0.0835(3) Uani 1 1 d . . . . .
S1 S 0.60534(7) 0.38260(3) 0.39964(6) 0.04763(19) Uani 1 1 d . . . . .
O1 O 0.7386(2) 0.34823(9) 0.38815(19) 0.0584(5) Uani 1 1 d . . . . .
O2 O 0.4050(2) 0.38561(9) 0.68706(19) 0.0642(5) Uani 1 1 d . . . . .
O3 O 0.42671(19) 0.30801(10) 0.21907(16) 0.0600(5) Uani 1 1 d . . . . .
O4 O 0.5657(3) 0.07894(11) 0.4436(2) 0.0915(8) Uani 1 1 d . . . . .
C1 C 0.6643(3) 0.44326(12) 0.5188(2) 0.0461(6) Uani 1 1 d . . . . .
C2 C 0.7610(3) 0.48802(13) 0.5013(2) 0.0505(6) Uani 1 1 d . . . . .
H2 H 0.803418 0.487395 0.427996 0.061 Uiso 1 1 calc R U . . .
C3 C 0.7926(3) 0.53369(13) 0.5961(3) 0.0528(7) Uani 1 1 d . . . . .
C4 C 0.7275(3) 0.53598(14) 0.7047(3) 0.0568(7) Uani 1 1 d . . . . .
H4 H 0.749790 0.567489 0.767325 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6292(3) 0.49081(13) 0.7179(3) 0.0543(7) Uani 1 1 d . . . . .
C6 C 0.5961(3) 0.44306(12) 0.6255(2) 0.0465(6) Uani 1 1 d . . . . .
C7 C 0.4973(3) 0.39016(13) 0.6219(2) 0.0489(6) Uani 1 1 d . . . . .
C8 C 0.5200(3) 0.34575(13) 0.5192(2) 0.0448(6) Uani 1 1 d . . . . .
C9 C 0.4938(2) 0.28500(13) 0.5165(2) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.4945(2) 0.24195(13) 0.4065(2) 0.0457(6) Uani 1 1 d . . . . .
C11 C 0.4648(3) 0.25071(14) 0.2659(2) 0.0508(7) Uani 1 1 d . . . . .
C12 C 0.4678(3) 0.20046(17) 0.1852(3) 0.0669(9) Uani 1 1 d . . . . .
H12 H 0.446279 0.205241 0.091858 0.080 Uiso 1 1 calc R U . . .
C13 C 0.5023(4) 0.14328(17) 0.2403(3) 0.0763(10) Uani 1 1 d . . . . .
H13 H 0.506910 0.110555 0.183679 0.092 Uiso 1 1 calc R U . . .
C14 C 0.5301(4) 0.13366(15) 0.3785(3) 0.0663(8) Uani 1 1 d . . . . .
C15 C 0.5202(3) 0.18340(14) 0.4594(3) 0.0519(7) Uani 1 1 d . . . . .
C16 C 0.5341(3) 0.18340(13) 0.6083(2) 0.0529(7) Uani 1 1 d . . . . .
H16A H 0.636524 0.178386 0.657793 0.063 Uiso 1 1 calc R U . . .
H16B H 0.475766 0.150861 0.633402 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4746(3) 0.24642(12) 0.6375(2) 0.0449(6) Uani 1 1 d . . . . .
C18 C 0.4186(3) 0.32054(19) 0.0799(3) 0.0778(10) Uani 1 1 d . . . . .
H18A H 0.394746 0.362733 0.061368 0.117 Uiso 1 1 calc R U . . .
H18B H 0.343296 0.295583 0.023819 0.117 Uiso 1 1 calc R U . . .
H18C H 0.512257 0.311708 0.061016 0.117 Uiso 1 1 calc R U . . .
C19 C 0.6071(5) 0.03092(18) 0.3702(4) 0.1006(13) Uani 1 1 d . . . . .
H19A H 0.630989 -0.004283 0.427213 0.151 Uiso 1 1 calc R U . . .
H19B H 0.691982 0.042778 0.338913 0.151 Uiso 1 1 calc R U . . .
H19C H 0.526710 0.021392 0.294053 0.151 Uiso 1 1 calc R U . . .
C20 C 0.3093(3) 0.24156(16) 0.6311(3) 0.0650(8) Uani 1 1 d . . . . .
H20A H 0.295451 0.215965 0.703225 0.098 Uiso 1 1 calc R U . . .
H20B H 0.258324 0.224247 0.545927 0.098 Uiso 1 1 calc R U . . .
H20C H 0.270342 0.281405 0.640118 0.098 Uiso 1 1 calc R U . . .
C21 C 0.5610(3) 0.26775(14) 0.7772(2) 0.0578(7) Uani 1 1 d . . . . .
H21A H 0.565424 0.235351 0.841292 0.087 Uiso 1 1 calc R U . . .
H21B H 0.512302 0.302356 0.804289 0.087 Uiso 1 1 calc R U . . .
H21C H 0.659504 0.278929 0.773907 0.087 Uiso 1 1 calc R U . . .


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
Cl1 C3 1.727(3) . ?
Cl2 C5 1.729(2) . ?
S1 O1 1.4838(18) . ?
S1 C1 1.795(3) . ?
S1 C8 1.806(2) . ?
O2 C7 1.215(3) . ?
O3 C11 1.361(4) . ?
O3 C18 1.431(3) . ?
O4 C14 1.373(4) . ?
O4 C19 1.402(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.392(3) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C6 C7 1.477(4) . ?
C7 C8 1.485(3) . ?
C8 C9 1.354(4) . ?
C9 C10 1.469(3) . ?
C9 C17 1.545(3) . ?
C10 C15 1.391(4) . ?
C10 C11 1.407(3) . ?
C11 C12 1.381(4) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C15 C16 1.494(3) . ?
C16 C17 1.546(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C21 1.529(3) . ?
C17 C20 1.531(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 107.97(11) . . ?
O1 S1 C8 110.14(12) . . ?
C1 S1 C8 89.19(12) . . ?
C11 O3 C18 118.1(2) . . ?
C14 O4 C19 117.6(3) . . ?
C2 C1 C6 123.1(2) . . ?
C2 C1 S1 122.85(18) . . ?
C6 C1 S1 113.9(2) . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 Cl1 119.8(2) . . ?
C4 C3 Cl1 118.4(2) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 Cl2 118.4(2) . . ?
C6 C5 Cl2 120.6(2) . . ?
C1 C6 C5 117.4(2) . . ?
C1 C6 C7 112.7(2) . . ?
C5 C6 C7 129.9(2) . . ?
O2 C7 C6 125.0(2) . . ?
O2 C7 C8 125.3(3) . . ?
C6 C7 C8 109.6(2) . . ?
C9 C8 C7 127.2(2) . . ?
C9 C8 S1 122.29(18) . . ?
C7 C8 S1 110.35(19) . . ?
C8 C9 C10 127.9(2) . . ?
C8 C9 C17 125.4(2) . . ?
C10 C9 C17 106.4(2) . . ?
C15 C10 C11 119.6(2) . . ?
C15 C10 C9 109.3(2) . . ?
C11 C10 C9 131.0(3) . . ?
O3 C11 C12 124.8(2) . . ?
O3 C11 C10 116.9(2) . . ?
C12 C11 C10 118.2(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
O4 C14 C15 116.4(3) . . ?
O4 C14 C13 126.0(3) . . ?
C15 C14 C13 117.6(3) . . ?
C14 C15 C10 121.8(3) . . ?
C14 C15 C16 127.2(3) . . ?
C10 C15 C16 111.0(2) . . ?
C15 C16 C17 104.5(2) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C21 C17 C20 110.7(2) . . ?
C21 C17 C9 116.1(2) . . ?
C20 C17 C9 108.65(19) . . ?
C21 C17 C16 108.8(2) . . ?
C20 C17 C16 109.6(2) . . ?
C9 C17 C16 102.59(19) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 S1 C1 C2 59.6(2) . . . . ?
C8 S1 C1 C2 170.6(2) . . . . ?
O1 S1 C1 C6 -124.29(19) . . . . ?
C8 S1 C1 C6 -13.4(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
S1 C1 C2 C3 177.0(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C1 C2 C3 Cl1 177.5(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
Cl1 C3 C4 C5 -178.4(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 Cl2 -179.7(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
S1 C1 C6 C5 -176.20(19) . . . . ?
C2 C1 C6 C7 -180.0(2) . . . . ?
S1 C1 C6 C7 3.9(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
Cl2 C5 C6 C1 179.5(2) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
Cl2 C5 C6 C7 -0.6(4) . . . . ?
C1 C6 C7 O2 -165.2(3) . . . . ?
C5 C6 C7 O2 15.0(4) . . . . ?
C1 C6 C7 C8 10.5(3) . . . . ?
C5 C6 C7 C8 -169.3(3) . . . . ?
O2 C7 C8 C9 -29.4(4) . . . . ?
C6 C7 C8 C9 154.8(2) . . . . ?
O2 C7 C8 S1 155.5(2) . . . . ?
C6 C7 C8 S1 -20.2(2) . . . . ?
O1 S1 C8 C9 -47.6(2) . . . . ?
C1 S1 C8 C9 -156.4(2) . . . . ?
O1 S1 C8 C7 127.76(17) . . . . ?
C1 S1 C8 C7 18.88(18) . . . . ?
C7 C8 C9 C10 170.1(2) . . . . ?
S1 C8 C9 C10 -15.4(3) . . . . ?
C7 C8 C9 C17 -17.3(4) . . . . ?
S1 C8 C9 C17 157.19(18) . . . . ?
C8 C9 C10 C15 156.9(2) . . . . ?
C17 C9 C10 C15 -16.8(2) . . . . ?
C8 C9 C10 C11 -27.8(4) . . . . ?
C17 C9 C10 C11 158.5(2) . . . . ?
C18 O3 C11 C12 -13.5(4) . . . . ?
C18 O3 C11 C10 170.4(2) . . . . ?
C15 C10 C11 O3 174.0(2) . . . . ?
C9 C10 C11 O3 -0.9(4) . . . . ?
C15 C10 C11 C12 -2.4(3) . . . . ?
C9 C10 C11 C12 -177.3(2) . . . . ?
O3 C11 C12 C13 -177.5(3) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C14 2.3(5) . . . . ?
C19 O4 C14 C15 -166.8(3) . . . . ?
C19 O4 C14 C13 13.7(5) . . . . ?
C12 C13 C14 O4 -179.7(3) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
O4 C14 C15 C10 175.7(3) . . . . ?
C13 C14 C15 C10 -4.7(4) . . . . ?
O4 C14 C15 C16 -4.4(4) . . . . ?
C13 C14 C15 C16 175.1(3) . . . . ?
C11 C10 C15 C14 5.6(4) . . . . ?
C9 C10 C15 C14 -178.5(2) . . . . ?
C11 C10 C15 C16 -174.2(2) . . . . ?
C9 C10 C15 C16 1.7(3) . . . . ?
C14 C15 C16 C17 -165.8(3) . . . . ?
C10 C15 C16 C17 14.0(3) . . . . ?
C8 C9 C17 C21 -31.2(3) . . . . ?
C10 C9 C17 C21 142.8(2) . . . . ?
C8 C9 C17 C20 94.4(3) . . . . ?
C10 C9 C17 C20 -91.7(2) . . . . ?
C8 C9 C17 C16 -149.6(2) . . . . ?
C10 C9 C17 C16 24.3(2) . . . . ?
C15 C16 C17 C21 -146.3(2) . . . . ?
C15 C16 C17 C20 92.5(2) . . . . ?
C15 C16 C17 C9 -22.8(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.
;

_audit_block_code                C21H18Cl2O4S_wv064_dube
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl2 O4 S'
_chemical_formula_sum            'C21 H18 Cl2 O4 S'
_chemical_formula_weight         437.31 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             904 #?# check!

####################################################################### 
# 
# 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_vv510
_database_code_depnum_ccdc_archive 'CCDC 1869284'

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_chemical_name_common            KH-85-Ic
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.060 #?# in millimeters
_exptl_crystal_size_min          0.010 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      123.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.4074

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   12.7042(13)
_cell_length_b                   7.6415(7)
_cell_length_c                   19.807(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.369(4)
_cell_angle_gamma                90
_cell_volume                     1878.2(3)
_cell_measurement_temperature    123.(2) #?# in K
_cell_measurement_reflns_used    2630
_cell_measurement_theta_min      2.8662
_cell_measurement_theta_max      25.3036
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8585
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'

_diffrn_reflns_number            3318 #xl
_diffrn_reflns_av_R_equivalents  0.0593 #xl
_diffrn_reflns_av_unetI/netI     0.0542 #xl
_diffrn_reflns_limit_h_min       -15 #xl
_diffrn_reflns_limit_h_max       14 #xl
_diffrn_reflns_limit_k_min       0 #xl
_diffrn_reflns_limit_k_max       9 #xl
_diffrn_reflns_limit_l_min       0 #xl
_diffrn_reflns_limit_l_max       23 #xl
_diffrn_reflns_theta_min         3.189 #xl
_diffrn_reflns_theta_max         25.339 #xl
_diffrn_measured_fraction_theta_max 0.985 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.985 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.985 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.985 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.985 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.985 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14

_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.
;

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'

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'
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'

_reflns_number_total             3318 #xl
_reflns_number_gt                2804 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 _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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.0426P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         3318 #xl
_refine_ls_number_parameters     249 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0586 #xl
_refine_ls_R_factor_gt           0.0417 #xl
_refine_ls_wR_factor_ref         0.0928 #xl
_refine_ls_wR_factor_gt          0.0859 #xl
_refine_ls_goodness_of_fit_ref   1.152 #xl
_refine_ls_restrained_S_all      1.152 #xl
_refine_ls_shift/su_max          0.001 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.320 #xl
_refine_diff_density_min         -0.345 #xl
_refine_diff_density_rms         0.079 #xl

_refine_special_details          
;

Refined as a 2-component twin. Twin axis (10-1), BASF 0.38
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'

_computing_publication_material  ?

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
Cl1 Cl 1.20370(7) 0.91005(11) 0.46751(5) 0.0240(2) Uani 1 1 d . . . . .
Cl2 Cl 1.10038(8) 0.26523(11) 0.37170(6) 0.0265(2) Uani 1 1 d . . . . .
S1 S 0.78769(7) 0.67577(11) 0.42611(5) 0.0172(2) Uani 1 1 d . . . . .
O1 O 0.86947(19) 0.2080(3) 0.38896(13) 0.0183(5) Uani 1 1 d . . . . .
O2 O 0.59985(19) 0.6188(3) 0.47021(12) 0.0215(6) Uani 1 1 d . . . . .
O3 O 0.31372(18) 0.4953(3) 0.22109(13) 0.0190(6) Uani 1 1 d . . . . .
C1 C 0.9239(3) 0.6574(4) 0.42455(17) 0.0149(7) Uani 1 1 d . . . . .
C2 C 0.9999(3) 0.7910(4) 0.44205(17) 0.0153(8) Uani 1 1 d . . . . .
H2 H 0.9795 0.9049 0.4536 0.018 Uiso 1 1 calc R U . . .
C3 C 1.1055(3) 0.7517(4) 0.44193(18) 0.0168(8) Uani 1 1 d . . . . .
C4 C 1.1380(3) 0.5896(5) 0.42217(19) 0.0205(8) Uani 1 1 d . . . . .
H4 H 1.2117 0.5674 0.4224 0.025 Uiso 1 1 calc R U . . .
C5 C 1.0608(3) 0.4610(4) 0.40206(17) 0.0161(8) Uani 1 1 d . . . . .
C6 C 0.9542(3) 0.4904(4) 0.40485(17) 0.0138(7) Uani 1 1 d . . . . .
C7 C 0.8621(3) 0.3672(4) 0.39173(17) 0.0148(7) Uani 1 1 d . . . . .
C8 C 0.7590(3) 0.4643(4) 0.38876(18) 0.0155(7) Uani 1 1 d . . . . .
C9 C 0.6596(3) 0.4118(4) 0.35651(17) 0.0136(7) Uani 1 1 d . . . . .
C10 C 0.5586(3) 0.5031(4) 0.35656(18) 0.0148(7) Uani 1 1 d . . . . .
C11 C 0.5281(3) 0.6069(4) 0.40823(18) 0.0162(8) Uani 1 1 d . . . . .
C12 C 0.4263(3) 0.6801(5) 0.3948(2) 0.0207(8) Uani 1 1 d . . . . .
H12 H 0.4057 0.7531 0.4286 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3530(3) 0.6489(4) 0.33245(19) 0.0187(8) Uani 1 1 d . . . . .
H13 H 0.2842 0.7033 0.3237 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3808(3) 0.5389(4) 0.28353(19) 0.0174(8) Uani 1 1 d . . . . .
C15 C 0.4829(3) 0.4655(4) 0.29636(19) 0.0164(8) Uani 1 1 d . . . . .
C16 C 0.5305(3) 0.3415(4) 0.25256(18) 0.0178(8) Uani 1 1 d . . . . .
H16A H 0.5518 0.4042 0.2138 0.021 Uiso 1 1 calc R U . . .
H16B H 0.4783 0.2486 0.2335 0.021 Uiso 1 1 calc R U . . .
C17 C 0.6305(3) 0.2629(4) 0.30211(19) 0.0173(8) Uani 1 1 d . . . . .
C18 C 0.5807(3) 0.7472(5) 0.5182(2) 0.0267(9) Uani 1 1 d . . . . .
H18A H 0.6401 0.7459 0.5590 0.040 Uiso 1 1 calc R U . . .
H18B H 0.5129 0.7210 0.5321 0.040 Uiso 1 1 calc R U . . .
H18C H 0.5761 0.8630 0.4965 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2091(3) 0.5714(5) 0.2077(2) 0.0252(9) Uani 1 1 d . . . . .
H19A H 0.1689 0.5338 0.1621 0.038 Uiso 1 1 calc R U . . .
H19B H 0.2155 0.6992 0.2085 0.038 Uiso 1 1 calc R U . . .
H19C H 0.1708 0.5337 0.2432 0.038 Uiso 1 1 calc R U . . .
C20 C 0.5979(3) 0.0985(4) 0.33822(19) 0.0214(8) Uani 1 1 d . . . . .
H20A H 0.5736 0.0070 0.3037 0.032 Uiso 1 1 calc R U . . .
H20B H 0.5393 0.1282 0.3613 0.032 Uiso 1 1 calc R U . . .
H20C H 0.6601 0.0560 0.3725 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7139(3) 0.2141(5) 0.2600(2) 0.0222(8) Uani 1 1 d . . . . .
H21A H 0.6796 0.1427 0.2203 0.033 Uiso 1 1 calc R U . . .
H21B H 0.7724 0.1474 0.2891 0.033 Uiso 1 1 calc R U . . .
H21C H 0.7432 0.3208 0.2437 0.033 Uiso 1 1 calc R U . . .


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
Cl1 C3 1.734(3) . ?
Cl2 C5 1.727(3) . ?
S1 C1 1.743(3) . ?
S1 C8 1.782(3) . ?
O1 C7 1.222(4) . ?
O2 C11 1.366(4) . ?
O2 C18 1.422(4) . ?
O3 C14 1.384(4) . ?
O3 C19 1.423(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.412(5) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(5) . ?
C6 C7 1.480(5) . ?
C7 C8 1.495(4) . ?
C8 C9 1.349(5) . ?
C9 C10 1.461(4) . ?
C9 C17 1.556(5) . ?
C10 C15 1.392(5) . ?
C10 C11 1.413(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.398(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(5) . ?
C15 C16 1.497(5) . ?
C16 C17 1.551(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.528(5) . ?
C17 C20 1.546(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 S1 C8 92.01(16) . . ?
C11 O2 C18 118.0(3) . . ?
C14 O3 C19 116.1(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 S1 125.0(3) . . ?
C6 C1 S1 114.0(3) . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 Cl1 119.2(3) . . ?
C4 C3 Cl1 117.8(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 Cl2 121.0(3) . . ?
C4 C5 Cl2 118.2(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 129.2(3) . . ?
C1 C6 C7 111.8(3) . . ?
O1 C7 C6 125.1(3) . . ?
O1 C7 C8 124.6(3) . . ?
C6 C7 C8 110.1(3) . . ?
C9 C8 C7 126.5(3) . . ?
C9 C8 S1 123.6(3) . . ?
C7 C8 S1 109.5(2) . . ?
C8 C9 C10 126.3(3) . . ?
C8 C9 C17 127.2(3) . . ?
C10 C9 C17 105.8(3) . . ?
C15 C10 C11 119.4(3) . . ?
C15 C10 C9 110.3(3) . . ?
C11 C10 C9 130.2(3) . . ?
O2 C11 C12 124.2(3) . . ?
O2 C11 C10 117.1(3) . . ?
C12 C11 C10 118.6(3) . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O3 C14 C13 124.8(3) . . ?
O3 C14 C15 116.1(3) . . ?
C13 C14 C15 119.1(3) . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 C16 128.9(3) . . ?
C10 C15 C16 109.6(3) . . ?
C15 C16 C17 104.9(3) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C21 C17 C20 109.9(3) . . ?
C21 C17 C16 108.6(3) . . ?
C20 C17 C16 110.1(3) . . ?
C21 C17 C9 117.8(3) . . ?
C20 C17 C9 108.7(3) . . ?
C16 C17 C9 101.3(3) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C8 S1 C1 C2 173.9(3) . . . . ?
C8 S1 C1 C6 -7.3(3) . . . . ?
C6 C1 C2 C3 -2.5(5) . . . . ?
S1 C1 C2 C3 176.3(3) . . . . ?
C1 C2 C3 C4 3.2(5) . . . . ?
C1 C2 C3 Cl1 -176.8(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
Cl1 C3 C4 C5 179.5(3) . . . . ?
C3 C4 C5 C6 -3.2(5) . . . . ?
C3 C4 C5 Cl2 175.4(3) . . . . ?
C4 C5 C6 C1 3.8(5) . . . . ?
Cl2 C5 C6 C1 -174.7(3) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
Cl2 C5 C6 C7 7.3(5) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
S1 C1 C6 C5 -179.8(3) . . . . ?
C2 C1 C6 C7 177.4(3) . . . . ?
S1 C1 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 O1 15.0(6) . . . . ?
C1 C6 C7 O1 -163.1(3) . . . . ?
C5 C6 C7 C8 -170.1(3) . . . . ?
C1 C6 C7 C8 11.8(4) . . . . ?
O1 C7 C8 C9 -28.6(6) . . . . ?
C6 C7 C8 C9 156.6(3) . . . . ?
O1 C7 C8 S1 158.2(3) . . . . ?
C6 C7 C8 S1 -16.7(3) . . . . ?
C1 S1 C8 C9 -159.8(3) . . . . ?
C1 S1 C8 C7 13.6(3) . . . . ?
C7 C8 C9 C10 176.8(3) . . . . ?
S1 C8 C9 C10 -10.9(5) . . . . ?
C7 C8 C9 C17 -14.8(6) . . . . ?
S1 C8 C9 C17 157.5(3) . . . . ?
C8 C9 C10 C15 151.8(3) . . . . ?
C17 C9 C10 C15 -18.5(4) . . . . ?
C8 C9 C10 C11 -32.8(6) . . . . ?
C17 C9 C10 C11 156.8(3) . . . . ?
C18 O2 C11 C12 -15.9(5) . . . . ?
C18 O2 C11 C10 168.3(3) . . . . ?
C15 C10 C11 O2 170.7(3) . . . . ?
C9 C10 C11 O2 -4.4(5) . . . . ?
C15 C10 C11 C12 -5.3(5) . . . . ?
C9 C10 C11 C12 179.7(3) . . . . ?
O2 C11 C12 C13 -173.8(3) . . . . ?
C10 C11 C12 C13 1.9(5) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C19 O3 C14 C13 0.1(5) . . . . ?
C19 O3 C14 C15 -179.6(3) . . . . ?
C12 C13 C14 O3 178.2(3) . . . . ?
C12 C13 C14 C15 -2.1(5) . . . . ?
O3 C14 C15 C10 178.3(3) . . . . ?
C13 C14 C15 C10 -1.4(5) . . . . ?
O3 C14 C15 C16 -1.5(5) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C11 C10 C15 C14 5.1(5) . . . . ?
C9 C10 C15 C14 -178.9(3) . . . . ?
C11 C10 C15 C16 -175.0(3) . . . . ?
C9 C10 C15 C16 1.0(4) . . . . ?
C14 C15 C16 C17 -163.2(3) . . . . ?
C10 C15 C16 C17 17.0(4) . . . . ?
C15 C16 C17 C21 -151.2(3) . . . . ?
C15 C16 C17 C20 88.5(3) . . . . ?
C15 C16 C17 C9 -26.4(3) . . . . ?
C8 C9 C17 C21 -24.7(5) . . . . ?
C10 C9 C17 C21 145.6(3) . . . . ?
C8 C9 C17 C20 101.1(4) . . . . ?
C10 C9 C17 C20 -88.6(3) . . . . ?
C8 C9 C17 C16 -142.9(3) . . . . ?
C10 C9 C17 C16 27.3(3) . . . . ?

_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.
;

_audit_block_code                C21H18Cl2O3S_vv510_dube
_audit_creation_method           'APEX3 v2016.9-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl2 O3 S'
_chemical_formula_sum            'C21 H18 Cl2 O3 S'
_chemical_formula_weight         421.31 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             872 #?# check!

####################################################################### 
# 
# 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_vv595
_database_code_depnum_ccdc_archive 'CCDC 1869288'

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_chemical_name_common            KH-106
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.090 #?# in millimeters
_exptl_crystal_size_mid          0.070 #?# in millimeters
_exptl_crystal_size_min          0.050 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      103.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.4074

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   19.3829(7)
_cell_length_b                   11.6584(4)
_cell_length_c                   12.0827(4)
_cell_angle_alpha                90
_cell_angle_beta                 127.8800(10)
_cell_angle_gamma                90
_cell_volume                     2155.08(13)
_cell_measurement_temperature    103.(2) #?# in K
_cell_measurement_reflns_used    9698
_cell_measurement_theta_min      2.6627
_cell_measurement_theta_max      27.0774
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            14630 #xl
_diffrn_reflns_av_R_equivalents  0.0307 #xl
_diffrn_reflns_av_unetI/netI     0.0204 #xl
_diffrn_reflns_limit_h_min       -24 #xl
_diffrn_reflns_limit_h_max       24 #xl
_diffrn_reflns_limit_k_min       -14 #xl
_diffrn_reflns_limit_k_max       14 #xl
_diffrn_reflns_limit_l_min       -15 #xl
_diffrn_reflns_limit_l_max       15 #xl
_diffrn_reflns_theta_min         3.495 #xl
_diffrn_reflns_theta_max         27.103 #xl
_diffrn_measured_fraction_theta_max 0.991 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.991 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.991 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.994 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

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'
B B 0.0013 0.0007 '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'

_reflns_number_total             2368 #xl
_reflns_number_gt                2110 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+2.2115P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2368 #xl
_refine_ls_number_parameters     120 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0342 #xl
_refine_ls_R_factor_gt           0.0282 #xl
_refine_ls_wR_factor_ref         0.0719 #xl
_refine_ls_wR_factor_gt          0.0668 #xl
_refine_ls_goodness_of_fit_ref   1.079 #xl
_refine_ls_restrained_S_all      1.079 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.317 #xl
_refine_diff_density_min         -0.223 #xl
_refine_diff_density_rms         0.043 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'

_computing_publication_material  ?

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 0.32154(2) 0.07774(2) 0.09487(3) 0.01512(9) Uani 1 1 d . . . . .
O1 O 0.42960(5) 0.53514(7) 0.21338(9) 0.01789(19) Uani 1 1 d . . . . .
C1 C 0.5000 0.33744(14) 0.2500 0.0158(3) Uani 1 2 d S T P . .
C2 C 0.42138(8) 0.27617(10) 0.18193(12) 0.0159(2) Uani 1 1 d . . . . .
H2 H 0.3677 0.3167 0.1349 0.019 Uiso 1 1 calc R U . . .
C3 C 0.42097(8) 0.15630(10) 0.18238(12) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.5000 0.09716(14) 0.2500 0.0154(3) Uani 1 2 d S T P . .
H4 H 0.5000 0.0157 0.2500 0.019 Uiso 1 2 calc R U P . .
C5 C 0.30243(8) 0.07391(10) 0.22768(13) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.28289(9) 0.19392(11) 0.25162(14) 0.0232(3) Uani 1 1 d . . . . .
H6A H 0.2681 0.1898 0.3159 0.035 Uiso 1 1 calc R U . . .
H6B H 0.2335 0.2265 0.1619 0.035 Uiso 1 1 calc R U . . .
H6C H 0.3345 0.2427 0.2924 0.035 Uiso 1 1 calc R U . . .
C7 C 0.22248(9) -0.00323(12) 0.16184(15) 0.0247(3) Uani 1 1 d . . . . .
H7A H 0.2063 -0.0079 0.2243 0.037 Uiso 1 1 calc R U . . .
H7B H 0.2361 -0.0802 0.1476 0.037 Uiso 1 1 calc R U . . .
H7C H 0.1736 0.0288 0.0714 0.037 Uiso 1 1 calc R U . . .
C8 C 0.38120(9) 0.02247(13) 0.36448(14) 0.0255(3) Uani 1 1 d . . . . .
H8A H 0.3702 0.0210 0.4335 0.038 Uiso 1 1 calc R U . . .
H8B H 0.4331 0.0692 0.4004 0.038 Uiso 1 1 calc R U . . .
H8C H 0.3910 -0.0559 0.3475 0.038 Uiso 1 1 calc R U . . .
C9 C 0.45994(8) 0.65403(10) 0.25090(13) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.48532(9) 0.67376(12) 0.39650(14) 0.0250(3) Uani 1 1 d . . . . .
H10A H 0.5045 0.7533 0.4251 0.038 Uiso 1 1 calc R U . . .
H10B H 0.5330 0.6217 0.4636 0.038 Uiso 1 1 calc R U . . .
H10C H 0.4347 0.6589 0.3943 0.038 Uiso 1 1 calc R U . . .
C11 C 0.38598(9) 0.73333(11) 0.14448(15) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.4073 0.8126 0.1634 0.037 Uiso 1 1 calc R U . . .
H11B H 0.3383 0.7271 0.1513 0.037 Uiso 1 1 calc R U . . .
H11C H 0.3646 0.7115 0.0499 0.037 Uiso 1 1 calc R U . . .
B1 B 0.5000 0.47108(16) 0.2500 0.0160(4) Uani 1 2 d S T P . .


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 C3 1.7800(12) . ?
S1 C5 1.8560(12) . ?
O1 B1 1.3689(13) . ?
O1 C9 1.4646(14) . ?
C1 C2 1.4034(14) 2_655 ?
C1 C2 1.4035(14) . ?
C1 B1 1.558(2) . ?
C2 C3 1.3975(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3974(14) . ?
C4 C3 1.3974(14) 2_655 ?
C4 H4 0.9500 . ?
C5 C6 1.5228(17) . ?
C5 C8 1.5244(17) . ?
C5 C7 1.5262(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.5164(17) . ?
C9 C10 1.5254(18) . ?
C9 C9 1.567(2) 2_655 ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
B1 O1 1.3689(13) 2_655 ?

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
C3 S1 C5 102.52(5) . . ?
B1 O1 C9 106.57(10) . . ?
C2 C1 C2 118.80(15) 2_655 . ?
C2 C1 B1 120.60(7) 2_655 . ?
C2 C1 B1 120.60(7) . . ?
C3 C2 C1 120.90(11) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.26(11) . . ?
C4 C3 S1 119.46(9) . . ?
C2 C3 S1 121.26(9) . . ?
C3 C4 C3 120.87(15) . 2_655 ?
C3 C4 H4 119.6 . . ?
C3 C4 H4 119.6 2_655 . ?
C6 C5 C8 110.85(11) . . ?
C6 C5 C7 110.44(10) . . ?
C8 C5 C7 110.72(11) . . ?
C6 C5 S1 110.30(8) . . ?
C8 C5 S1 110.38(8) . . ?
C7 C5 S1 103.96(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C11 108.89(10) . . ?
O1 C9 C10 106.48(10) . . ?
C11 C9 C10 110.70(11) . . ?
O1 C9 C9 102.04(6) . 2_655 ?
C11 C9 C9 114.67(11) . 2_655 ?
C10 C9 C9 113.30(13) . 2_655 ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 B1 O1 113.88(15) . 2_655 ?
O1 B1 C1 123.06(8) . . ?
O1 B1 C1 123.06(8) 2_655 . ?

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
C2 C1 C2 C3 0.46(8) 2_655 . . . ?
B1 C1 C2 C3 -179.53(8) . . . . ?
C1 C2 C3 C4 -0.92(16) . . . . ?
C1 C2 C3 S1 -179.35(7) . . . . ?
C5 S1 C3 C4 97.10(8) . . . . ?
C5 S1 C3 C2 -84.47(11) . . . . ?
C2 C3 C4 C3 0.46(8) . . . 2_655 ?
S1 C3 C4 C3 178.91(9) . . . 2_655 ?
C3 S1 C5 C6 67.12(9) . . . . ?
C3 S1 C5 C8 -55.71(10) . . . . ?
C3 S1 C5 C7 -174.49(8) . . . . ?
B1 O1 C9 C11 145.80(9) . . . . ?
B1 O1 C9 C10 -94.80(10) . . . . ?
B1 O1 C9 C9 24.20(13) . . . 2_655 ?
C9 O1 B1 O1 -10.12(6) . . . 2_655 ?
C9 O1 B1 C1 169.88(6) . . . . ?
C2 C1 B1 O1 -165.22(7) 2_655 . . . ?
C2 C1 B1 O1 14.78(7) . . . . ?
C2 C1 B1 O1 14.78(7) 2_655 . . 2_655 ?
C2 C1 B1 O1 -165.22(7) . . . 2_655 ?

_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.
;

_audit_block_code                C20H33BO2S2_vv595_dube
_audit_creation_method           'APEX3 v2016.9-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H33 B O2 S2'
_chemical_formula_sum            'C20 H33 B O2 S2'
_chemical_formula_weight         380.39 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             824 #?# check!

####################################################################### 
# 
# 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_vv512
_database_code_depnum_ccdc_archive 'CCDC 1869287'
# end Validation Reply Form

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_vv512               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: These reflections have not been measured at all or were (partly)
affected by the beamstop and hence have been omitted during the structure
refinement in order to improve the final R and S values.
;

_chemical_name_common            KH-111
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.050 #?# in millimeters
_exptl_crystal_size_min          0.040 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      103.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.4074

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   12.7347(14)
_cell_length_b                   14.3201(15)
_cell_length_c                   22.210(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.007(3)
_cell_angle_gamma                90
_cell_volume                     3893.2(7)
_cell_measurement_temperature    103.(2) #?# in K
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      2.3798
_cell_measurement_theta_max      25.3601
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8927
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            22336 #xl
_diffrn_reflns_av_R_equivalents  0.0442 #xl
_diffrn_reflns_av_unetI/netI     0.0468 #xl
_diffrn_reflns_limit_h_min       -15 #xl
_diffrn_reflns_limit_h_max       15 #xl
_diffrn_reflns_limit_k_min       -17 #xl
_diffrn_reflns_limit_k_max       14 #xl
_diffrn_reflns_limit_l_min       -26 #xl
_diffrn_reflns_limit_l_max       24 #xl
_diffrn_reflns_theta_min         3.192 #xl
_diffrn_reflns_theta_max         24.999 #xl
_diffrn_measured_fraction_theta_max 0.991 #xl
_diffrn_reflns_theta_full        24.999 #xl
_diffrn_measured_fraction_theta_full 0.991 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.991 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.991 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.991 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.991 #xl

_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

_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.
;

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'

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'
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'

_reflns_number_total             6798 #xl
_reflns_number_gt                5757 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+2.0380P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         6798 #xl
_refine_ls_number_parameters     513 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0438 #xl
_refine_ls_R_factor_gt           0.0339 #xl
_refine_ls_wR_factor_ref         0.0932 #xl
_refine_ls_wR_factor_gt          0.0869 #xl
_refine_ls_goodness_of_fit_ref   1.076 #xl
_refine_ls_restrained_S_all      1.076 #xl
_refine_ls_shift/su_max          0.001 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.243 #xl
_refine_diff_density_min         -0.402 #xl
_refine_diff_density_rms         0.063 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'

_computing_publication_material  ?

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
Cl1 Cl 0.02558(5) 0.52594(4) 0.39630(3) 0.03853(16) Uani 1 1 d . . . . .
Cl2 Cl 0.16308(5) 0.22439(4) 0.29569(3) 0.03747(16) Uani 1 1 d . . . . .
Cl3 Cl 0.30542(4) 0.27320(3) 0.50346(2) 0.02151(13) Uani 1 1 d . . . . .
Cl4 Cl 0.43993(4) -0.01787(3) 0.39022(2) 0.02191(13) Uani 1 1 d . . . . .
S1 S 0.45997(4) 0.47861(3) 0.41230(2) 0.01858(12) Uani 1 1 d . . . . .
S2 S 0.74223(4) 0.20373(3) 0.53864(2) 0.01800(12) Uani 1 1 d . . . . .
O1 O 0.46691(12) 0.57691(9) 0.39150(7) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.41222(12) 0.24329(9) 0.32830(7) 0.0236(3) Uani 1 1 d . . . . .
O3 O 0.39579(11) 0.34121(10) 0.21998(6) 0.0190(3) Uani 1 1 d . . . . .
O4 O 0.83637(11) 0.27195(10) 0.24875(7) 0.0214(3) Uani 1 1 d . . . . .
O5 O 0.76834(12) 0.30349(10) 0.53087(7) 0.0252(3) Uani 1 1 d . . . . .
O6 O 0.69237(11) -0.01661(9) 0.44281(7) 0.0221(3) Uani 1 1 d . . . . .
O7 O 0.68333(11) 0.10465(10) 0.34295(6) 0.0214(3) Uani 1 1 d . . . . .
O8 O 1.11650(11) 0.02362(10) 0.36060(7) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.31826(16) 0.44554(14) 0.38822(9) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.23745(17) 0.49743(14) 0.40276(9) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.2532 0.5540 0.4259 0.026 Uiso 1 1 calc R U . . .
C3 C 0.13203(18) 0.46282(15) 0.38193(10) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.10808(18) 0.37895(15) 0.34906(10) 0.0246(5) Uani 1 1 d . . . . .
H4 H 0.0350 0.3567 0.3356 0.030 Uiso 1 1 calc R U . . .
C5 C 0.19247(17) 0.32842(14) 0.33635(10) 0.0225(5) Uani 1 1 d . . . . .
C6 C 0.29912(17) 0.36202(14) 0.35524(9) 0.0191(4) Uani 1 1 d . . . . .
C7 C 0.39925(17) 0.32321(14) 0.34258(9) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.48532(16) 0.39723(13) 0.35644(9) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.57162(16) 0.40122(13) 0.33224(9) 0.0171(4) Uani 1 1 d . . . . .
C10 C 0.58172(16) 0.34770(13) 0.27783(9) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.50123(15) 0.31836(13) 0.22389(9) 0.0161(4) Uani 1 1 d . . . . .
C12 C 0.53539(17) 0.27201(13) 0.17778(9) 0.0187(4) Uani 1 1 d . . . . .
H12 H 0.4827 0.2518 0.1409 0.022 Uiso 1 1 calc R U . . .
C13 C 0.64636(17) 0.25456(14) 0.18484(9) 0.0191(4) Uani 1 1 d . . . . .
H13 H 0.6677 0.2209 0.1533 0.023 Uiso 1 1 calc R U . . .
C14 C 0.72558(16) 0.28579(13) 0.23735(10) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.69227(16) 0.33517(13) 0.28255(9) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.75991(16) 0.38254(14) 0.34037(10) 0.0222(4) Uani 1 1 d . . . . .
H16A H 0.8235 0.4146 0.3322 0.027 Uiso 1 1 calc R U . . .
H16B H 0.7864 0.3371 0.3748 0.027 Uiso 1 1 calc R U . . .
C17 C 0.67953(16) 0.45435(14) 0.35662(9) 0.0199(4) Uani 1 1 d . . . . .
C18 C 0.31398(17) 0.31836(14) 0.16336(10) 0.0228(5) Uani 1 1 d . . . . .
H18A H 0.2429 0.3418 0.1658 0.034 Uiso 1 1 calc R U . . .
H18B H 0.3103 0.2504 0.1579 0.034 Uiso 1 1 calc R U . . .
H18C H 0.3327 0.3473 0.1277 0.034 Uiso 1 1 calc R U . . .
C19 C 0.86996(18) 0.21911(16) 0.20277(10) 0.0275(5) Uani 1 1 d . . . . .
H19A H 0.9492 0.2098 0.2166 0.041 Uiso 1 1 calc R U . . .
H19B H 0.8504 0.2529 0.1629 0.041 Uiso 1 1 calc R U . . .
H19C H 0.8333 0.1583 0.1973 0.041 Uiso 1 1 calc R U . . .
C20 C 0.67669(17) 0.54379(14) 0.31783(10) 0.0240(5) Uani 1 1 d . . . . .
H20A H 0.7479 0.5750 0.3311 0.036 Uiso 1 1 calc R U . . .
H20B H 0.6200 0.5858 0.3243 0.036 Uiso 1 1 calc R U . . .
H20C H 0.6603 0.5276 0.2733 0.036 Uiso 1 1 calc R U . . .
C21 C 0.71348(18) 0.47714(15) 0.42645(10) 0.0267(5) Uani 1 1 d . . . . .
H21A H 0.7902 0.4966 0.4391 0.040 Uiso 1 1 calc R U . . .
H21B H 0.7043 0.4216 0.4503 0.040 Uiso 1 1 calc R U . . .
H21C H 0.6677 0.5279 0.4348 0.040 Uiso 1 1 calc R U . . .
C22 C 0.59928(16) 0.18501(14) 0.50228(9) 0.0170(4) Uani 1 1 d . . . . .
C23 C 0.51774(16) 0.23890(13) 0.51541(9) 0.0171(4) Uani 1 1 d . . . . .
H23 H 0.5337 0.2928 0.5412 0.021 Uiso 1 1 calc R U . . .
C24 C 0.41144(16) 0.20919(14) 0.48850(9) 0.0179(4) Uani 1 1 d . . . . .
C25 C 0.38559(16) 0.13062(14) 0.45034(9) 0.0185(4) Uani 1 1 d . . . . .
H25 H 0.3117 0.1126 0.4328 0.022 Uiso 1 1 calc R U . . .
C26 C 0.47029(16) 0.07909(13) 0.43847(9) 0.0180(4) Uani 1 1 d . . . . .
C27 C 0.57850(16) 0.10611(13) 0.46428(9) 0.0167(4) Uani 1 1 d . . . . .
C28 C 0.68038(16) 0.06329(14) 0.45722(9) 0.0175(4) Uani 1 1 d . . . . .
C29 C 0.77165(16) 0.13166(13) 0.47925(9) 0.0175(4) Uani 1 1 d . . . . .
C30 C 0.86177(15) 0.13691(13) 0.45852(9) 0.0164(4) Uani 1 1 d . . . . .
C31 C 0.86883(16) 0.09413(13) 0.39995(9) 0.0169(4) Uani 1 1 d . . . . .
C32 C 0.78557(16) 0.07557(14) 0.34468(9) 0.0184(4) Uani 1 1 d . . . . .
C33 C 0.81486(17) 0.03290(14) 0.29578(9) 0.0209(4) Uani 1 1 d . . . . .
H33 H 0.7600 0.0166 0.2587 0.025 Uiso 1 1 calc R U . . .
C34 C 0.92425(17) 0.01355(14) 0.30033(10) 0.0217(4) Uani 1 1 d . . . . .
H34 H 0.9425 -0.0172 0.2667 0.026 Uiso 1 1 calc R U . . .
C35 C 1.00669(16) 0.03847(14) 0.35306(10) 0.0197(4) Uani 1 1 d . . . . .
C36 C 0.97835(16) 0.07950(13) 0.40293(9) 0.0180(4) Uani 1 1 d . . . . .
C37 C 1.05020(16) 0.11465(14) 0.46441(9) 0.0202(4) Uani 1 1 d . . . . .
H37A H 1.1134 0.1497 0.4582 0.024 Uiso 1 1 calc R U . . .
H37B H 1.0774 0.0623 0.4937 0.024 Uiso 1 1 calc R U . . .
C38 C 0.97384(16) 0.18016(14) 0.48984(9) 0.0184(4) Uani 1 1 d . . . . .
C39 C 0.59541(16) 0.08235(14) 0.28881(9) 0.0200(4) Uani 1 1 d . . . . .
H39A H 0.5280 0.1120 0.2924 0.030 Uiso 1 1 calc R U . . .
H39B H 0.5853 0.0145 0.2859 0.030 Uiso 1 1 calc R U . . .
H39C H 0.6128 0.1053 0.2511 0.030 Uiso 1 1 calc R U . . .
C40 C 1.14464(19) -0.01597(18) 0.30803(12) 0.0378(6) Uani 1 1 d . . . . .
H40A H 1.2243 -0.0211 0.3174 0.057 Uiso 1 1 calc R U . . .
H40B H 1.1171 0.0242 0.2713 0.057 Uiso 1 1 calc R U . . .
H40C H 1.1119 -0.0782 0.2993 0.057 Uiso 1 1 calc R U . . .
C41 C 1.00564(17) 0.18082(15) 0.56132(9) 0.0230(5) Uani 1 1 d . . . . .
H41A H 1.0836 0.1952 0.5775 0.035 Uiso 1 1 calc R U . . .
H41B H 0.9909 0.1194 0.5766 0.035 Uiso 1 1 calc R U . . .
H41C H 0.9629 0.2284 0.5758 0.035 Uiso 1 1 calc R U . . .
C42 C 0.98081(16) 0.27955(14) 0.46524(10) 0.0211(4) Uani 1 1 d . . . . .
H42A H 1.0545 0.3044 0.4833 0.032 Uiso 1 1 calc R U . . .
H42B H 0.9275 0.3196 0.4772 0.032 Uiso 1 1 calc R U . . .
H42C H 0.9648 0.2781 0.4195 0.032 Uiso 1 1 calc R U . . .


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
Cl1 C3 1.731(2) . ?
Cl2 C5 1.729(2) . ?
Cl3 C24 1.7381(19) . ?
Cl4 C26 1.731(2) . ?
S1 O1 1.4917(14) . ?
S1 C8 1.7950(19) . ?
S1 C1 1.799(2) . ?
S2 O5 1.4876(15) . ?
S2 C29 1.7938(19) . ?
S2 C22 1.796(2) . ?
O2 C7 1.211(2) . ?
O3 C11 1.361(2) . ?
O3 C18 1.432(2) . ?
O4 C14 1.377(2) . ?
O4 C19 1.428(2) . ?
O6 C28 1.209(2) . ?
O7 C32 1.357(2) . ?
O7 C39 1.435(2) . ?
O8 C35 1.378(2) . ?
O8 C40 1.430(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.487(3) . ?
C7 C8 1.495(3) . ?
C8 C9 1.351(3) . ?
C9 C10 1.466(3) . ?
C9 C17 1.533(3) . ?
C10 C15 1.394(3) . ?
C10 C11 1.409(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.401(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C15 C16 1.497(3) . ?
C16 C17 1.562(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.526(3) . ?
C17 C20 1.539(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.388(3) . ?
C22 C27 1.391(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(3) . ?
C25 C26 1.391(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(3) . ?
C27 C28 1.482(3) . ?
C28 C29 1.495(3) . ?
C29 C30 1.351(3) . ?
C30 C31 1.463(3) . ?
C30 C38 1.535(3) . ?
C31 C36 1.394(3) . ?
C31 C32 1.409(3) . ?
C32 C33 1.384(3) . ?
C33 C34 1.396(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(3) . ?
C36 C37 1.505(3) . ?
C37 C38 1.564(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C41 1.526(3) . ?
C38 C42 1.536(3) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
O1 S1 C8 111.18(9) . . ?
O1 S1 C1 107.26(9) . . ?
C8 S1 C1 88.89(9) . . ?
O5 S2 C29 111.62(9) . . ?
O5 S2 C22 108.80(9) . . ?
C29 S2 C22 88.56(9) . . ?
C11 O3 C18 117.84(15) . . ?
C14 O4 C19 116.00(16) . . ?
C32 O7 C39 118.43(15) . . ?
C35 O8 C40 115.88(17) . . ?
C2 C1 C6 123.67(19) . . ?
C2 C1 S1 122.78(16) . . ?
C6 C1 S1 113.54(15) . . ?
C1 C2 C3 116.51(19) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 Cl1 119.19(17) . . ?
C4 C3 Cl1 118.48(17) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.30(19) . . ?
C4 C5 Cl2 119.16(16) . . ?
C6 C5 Cl2 120.53(16) . . ?
C1 C6 C5 118.13(19) . . ?
C1 C6 C7 112.75(18) . . ?
C5 C6 C7 129.05(19) . . ?
O2 C7 C6 126.06(19) . . ?
O2 C7 C8 125.38(19) . . ?
C6 C7 C8 108.32(17) . . ?
C9 C8 C7 125.36(18) . . ?
C9 C8 S1 124.65(16) . . ?
C7 C8 S1 109.96(14) . . ?
C8 C9 C10 124.86(18) . . ?
C8 C9 C17 128.95(18) . . ?
C10 C9 C17 106.07(16) . . ?
C15 C10 C11 120.55(18) . . ?
C15 C10 C9 108.75(17) . . ?
C11 C10 C9 130.40(18) . . ?
O3 C11 C12 124.93(18) . . ?
O3 C11 C10 117.14(17) . . ?
C12 C11 C10 117.88(18) . . ?
C11 C12 C13 120.99(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.89(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O4 C14 C15 116.28(18) . . ?
O4 C14 C13 125.32(18) . . ?
C15 C14 C13 118.40(18) . . ?
C14 C15 C10 121.02(18) . . ?
C14 C15 C16 129.31(18) . . ?
C10 C15 C16 109.66(17) . . ?
C15 C16 C17 103.75(16) . . ?
C15 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C21 C17 C9 116.12(17) . . ?
C21 C17 C20 110.33(17) . . ?
C9 C17 C20 109.57(16) . . ?
C21 C17 C16 110.82(16) . . ?
C9 C17 C16 99.93(16) . . ?
C20 C17 C16 109.54(17) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 123.43(18) . . ?
C23 C22 S2 123.15(15) . . ?
C27 C22 S2 113.18(14) . . ?
C24 C23 C22 115.90(18) . . ?
C24 C23 H23 122.1 . . ?
C22 C23 H23 122.1 . . ?
C23 C24 C25 123.29(18) . . ?
C23 C24 Cl3 118.23(15) . . ?
C25 C24 Cl3 118.48(15) . . ?
C26 C25 C24 118.59(18) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C25 C26 C27 120.36(18) . . ?
C25 C26 Cl4 119.36(15) . . ?
C27 C26 Cl4 120.27(15) . . ?
C22 C27 C26 118.43(18) . . ?
C22 C27 C28 112.00(17) . . ?
C26 C27 C28 129.57(18) . . ?
O6 C28 C27 126.71(18) . . ?
O6 C28 C29 124.24(18) . . ?
C27 C28 C29 108.59(16) . . ?
C30 C29 C28 125.56(18) . . ?
C30 C29 S2 126.00(16) . . ?
C28 C29 S2 108.44(13) . . ?
C29 C30 C31 123.09(18) . . ?
C29 C30 C38 129.70(18) . . ?
C31 C30 C38 107.12(16) . . ?
C36 C31 C32 121.06(18) . . ?
C36 C31 C30 109.07(17) . . ?
C32 C31 C30 129.63(18) . . ?
O7 C32 C33 125.26(18) . . ?
O7 C32 C31 116.90(17) . . ?
C33 C32 C31 117.79(18) . . ?
C32 C33 C34 120.68(19) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 121.19(19) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
O8 C35 C36 116.57(18) . . ?
O8 C35 C34 124.70(18) . . ?
C36 C35 C34 118.71(18) . . ?
C35 C36 C31 120.22(19) . . ?
C35 C36 C37 129.73(18) . . ?
C31 C36 C37 110.05(17) . . ?
C36 C37 C38 104.19(15) . . ?
C36 C37 H37A 110.9 . . ?
C38 C37 H37A 110.9 . . ?
C36 C37 H37B 110.9 . . ?
C38 C37 H37B 110.9 . . ?
H37A C37 H37B 108.9 . . ?
C41 C38 C30 114.87(16) . . ?
C41 C38 C42 109.85(17) . . ?
C30 C38 C42 110.51(16) . . ?
C41 C38 C37 111.48(16) . . ?
C30 C38 C37 100.79(15) . . ?
C42 C38 C37 108.94(16) . . ?
O7 C39 H39A 109.5 . . ?
O7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O8 C40 H40A 109.5 . . ?
O8 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O8 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
O1 S1 C1 C2 -52.84(19) . . . . ?
C8 S1 C1 C2 -164.70(18) . . . . ?
O1 S1 C1 C6 128.73(14) . . . . ?
C8 S1 C1 C6 16.87(15) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
S1 C1 C2 C3 -179.06(15) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 Cl1 -178.03(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
Cl1 C3 C4 C5 178.96(16) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 Cl2 179.93(16) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
S1 C1 C6 C5 177.78(15) . . . . ?
C2 C1 C6 C7 176.57(18) . . . . ?
S1 C1 C6 C7 -5.0(2) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
Cl2 C5 C6 C1 -179.47(15) . . . . ?
C4 C5 C6 C7 -175.07(19) . . . . ?
Cl2 C5 C6 C7 3.9(3) . . . . ?
C1 C6 C7 O2 161.69(19) . . . . ?
C5 C6 C7 O2 -21.5(3) . . . . ?
C1 C6 C7 C8 -12.9(2) . . . . ?
C5 C6 C7 C8 163.9(2) . . . . ?
O2 C7 C8 C9 28.6(3) . . . . ?
C6 C7 C8 C9 -156.77(19) . . . . ?
O2 C7 C8 S1 -149.50(17) . . . . ?
C6 C7 C8 S1 25.16(19) . . . . ?
O1 S1 C8 C9 50.1(2) . . . . ?
C1 S1 C8 C9 158.15(18) . . . . ?
O1 S1 C8 C7 -131.87(13) . . . . ?
C1 S1 C8 C7 -23.77(14) . . . . ?
C7 C8 C9 C10 15.4(3) . . . . ?
S1 C8 C9 C10 -166.85(15) . . . . ?
C7 C8 C9 C17 -160.00(19) . . . . ?
S1 C8 C9 C17 17.8(3) . . . . ?
C8 C9 C10 C15 -153.63(19) . . . . ?
C17 C9 C10 C15 22.6(2) . . . . ?
C8 C9 C10 C11 32.8(3) . . . . ?
C17 C9 C10 C11 -151.0(2) . . . . ?
C18 O3 C11 C12 -2.0(3) . . . . ?
C18 O3 C11 C10 175.23(17) . . . . ?
C15 C10 C11 O3 -173.63(17) . . . . ?
C9 C10 C11 O3 -0.7(3) . . . . ?
C15 C10 C11 C12 3.8(3) . . . . ?
C9 C10 C11 C12 176.75(19) . . . . ?
O3 C11 C12 C13 177.50(17) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -2.0(3) . . . . ?
C19 O4 C14 C15 178.54(17) . . . . ?
C19 O4 C14 C13 -1.5(3) . . . . ?
C12 C13 C14 O4 179.73(17) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
O4 C14 C15 C10 -175.60(17) . . . . ?
C13 C14 C15 C10 4.5(3) . . . . ?
O4 C14 C15 C16 5.2(3) . . . . ?
C13 C14 C15 C16 -174.8(2) . . . . ?
C11 C10 C15 C14 -6.3(3) . . . . ?
C9 C10 C15 C14 179.36(17) . . . . ?
C11 C10 C15 C16 173.09(17) . . . . ?
C9 C10 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C17 159.4(2) . . . . ?
C10 C15 C16 C17 -19.9(2) . . . . ?
C8 C9 C17 C21 23.9(3) . . . . ?
C10 C9 C17 C21 -152.15(17) . . . . ?
C8 C9 C17 C20 -101.9(2) . . . . ?
C10 C9 C17 C20 82.05(19) . . . . ?
C8 C9 C17 C16 143.1(2) . . . . ?
C10 C9 C17 C16 -32.95(19) . . . . ?
C15 C16 C17 C21 154.42(17) . . . . ?
C15 C16 C17 C9 31.41(19) . . . . ?
C15 C16 C17 C20 -83.61(19) . . . . ?
O5 S2 C22 C23 -52.57(18) . . . . ?
C29 S2 C22 C23 -164.95(17) . . . . ?
O5 S2 C22 C27 133.04(14) . . . . ?
C29 S2 C22 C27 20.65(15) . . . . ?
C27 C22 C23 C24 0.5(3) . . . . ?
S2 C22 C23 C24 -173.34(14) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C22 C23 C24 Cl3 179.62(14) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
Cl3 C24 C25 C26 -179.78(14) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C24 C25 C26 Cl4 -179.06(14) . . . . ?
C23 C22 C27 C26 -0.6(3) . . . . ?
S2 C22 C27 C26 173.75(14) . . . . ?
C23 C22 C27 C28 178.79(17) . . . . ?
S2 C22 C27 C28 -6.8(2) . . . . ?
C25 C26 C27 C22 0.4(3) . . . . ?
Cl4 C26 C27 C22 179.34(14) . . . . ?
C25 C26 C27 C28 -178.86(18) . . . . ?
Cl4 C26 C27 C28 0.0(3) . . . . ?
C22 C27 C28 O6 157.8(2) . . . . ?
C26 C27 C28 O6 -22.8(3) . . . . ?
C22 C27 C28 C29 -14.6(2) . . . . ?
C26 C27 C28 C29 164.72(19) . . . . ?
O6 C28 C29 C30 35.7(3) . . . . ?
C27 C28 C29 C30 -151.60(19) . . . . ?
O6 C28 C29 S2 -143.25(17) . . . . ?
C27 C28 C29 S2 29.43(19) . . . . ?
O5 S2 C29 C30 43.3(2) . . . . ?
C22 S2 C29 C30 152.97(19) . . . . ?
O5 S2 C29 C28 -137.75(13) . . . . ?
C22 S2 C29 C28 -28.07(14) . . . . ?
C28 C29 C30 C31 17.6(3) . . . . ?
S2 C29 C30 C31 -163.64(15) . . . . ?
C28 C29 C30 C38 -158.59(19) . . . . ?
S2 C29 C30 C38 20.2(3) . . . . ?
C29 C30 C31 C36 -157.17(19) . . . . ?
C38 C30 C31 C36 19.7(2) . . . . ?
C29 C30 C31 C32 28.4(3) . . . . ?
C38 C30 C31 C32 -154.7(2) . . . . ?
C39 O7 C32 C33 6.2(3) . . . . ?
C39 O7 C32 C31 -176.57(17) . . . . ?
C36 C31 C32 O7 -170.52(17) . . . . ?
C30 C31 C32 O7 3.4(3) . . . . ?
C36 C31 C32 C33 6.9(3) . . . . ?
C30 C31 C32 C33 -179.21(19) . . . . ?
O7 C32 C33 C34 173.94(18) . . . . ?
C31 C32 C33 C34 -3.2(3) . . . . ?
C32 C33 C34 C35 -1.6(3) . . . . ?
C40 O8 C35 C36 -178.07(19) . . . . ?
C40 O8 C35 C34 3.4(3) . . . . ?
C33 C34 C35 O8 -178.60(18) . . . . ?
C33 C34 C35 C36 2.9(3) . . . . ?
O8 C35 C36 C31 -177.88(17) . . . . ?
C34 C35 C36 C31 0.7(3) . . . . ?
O8 C35 C36 C37 2.7(3) . . . . ?
C34 C35 C36 C37 -178.65(19) . . . . ?
C32 C31 C36 C35 -5.7(3) . . . . ?
C30 C31 C36 C35 179.25(18) . . . . ?
C32 C31 C36 C37 173.78(18) . . . . ?
C30 C31 C36 C37 -1.3(2) . . . . ?
C35 C36 C37 C38 162.3(2) . . . . ?
C31 C36 C37 C38 -17.1(2) . . . . ?
C29 C30 C38 C41 28.0(3) . . . . ?
C31 C30 C38 C41 -148.58(17) . . . . ?
C29 C30 C38 C42 -96.9(2) . . . . ?
C31 C30 C38 C42 86.45(19) . . . . ?
C29 C30 C38 C37 148.0(2) . . . . ?
C31 C30 C38 C37 -28.64(19) . . . . ?
C36 C37 C38 C41 149.38(17) . . . . ?
C36 C37 C38 C30 27.02(19) . . . . ?
C36 C37 C38 C42 -89.24(19) . . . . ?

_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.
;

_audit_block_code                C21H18Cl2O4S_vv512_dube
_audit_creation_method           'APEX3 v2016.9-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl2 O4 S'
_chemical_formula_sum            'C21 H18 Cl2 O4 S'
_chemical_formula_weight         437.31 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            8 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             1808 #?# check!

####################################################################### 
# 
# 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_wv319
_database_code_depnum_ccdc_archive 'CCDC 1869285'

_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_chemical_name_common            KH-114
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.090 #?# in millimeters
_exptl_crystal_size_mid          0.080 #?# in millimeters
_exptl_crystal_size_min          0.020 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      106.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   16.0174(11)
_cell_length_b                   15.9817(10)
_cell_length_c                   7.3482(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1881.0(2)
_cell_measurement_temperature    106.(2) #?# in K
_cell_measurement_reflns_used    8123
_cell_measurement_theta_min      2.5432
_cell_measurement_theta_max      26.4908
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            8980 #xl
_diffrn_reflns_av_R_equivalents  0.0328 #xl
_diffrn_reflns_av_unetI/netI     0.0377 #xl
_diffrn_reflns_limit_h_min       -20 #xl
_diffrn_reflns_limit_h_max       19 #xl
_diffrn_reflns_limit_k_min       -18 #xl
_diffrn_reflns_limit_k_max       19 #xl
_diffrn_reflns_limit_l_min       -9 #xl
_diffrn_reflns_limit_l_max       5 #xl
_diffrn_reflns_theta_min         3.306 #xl
_diffrn_reflns_theta_max         26.372 #xl
_diffrn_measured_fraction_theta_max 0.994 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.791 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.809 #xl

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

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'
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'

_reflns_number_total             3025 #xl
_reflns_number_gt                2871 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.468 #xl
_reflns_Friedel_fraction_max     0.551 #xl
_reflns_Friedel_fraction_full    0.590 #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0160P)²+2.1696P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details 
;

Flack x determined using 870 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4) #xl
_refine_ls_number_reflns         3025 #xl
_refine_ls_number_parameters     248 #xl
_refine_ls_number_restraints     1 #xl
_refine_ls_R_factor_all          0.0410 #xl
_refine_ls_R_factor_gt           0.0374 #xl
_refine_ls_wR_factor_ref         0.0829 #xl
_refine_ls_wR_factor_gt          0.0814 #xl
_refine_ls_goodness_of_fit_ref   1.156 #xl
_refine_ls_restrained_S_all      1.156 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.340 #xl
_refine_diff_density_min         -0.270 #xl
_refine_diff_density_rms         0.063 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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
Cl1 Cl 0.94224(6) 0.16105(6) 0.49196(17) 0.0231(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74009(6) 0.41325(6) 0.31214(16) 0.0212(2) Uani 1 1 d . . . . .
S1 S 0.60383(6) 0.11919(6) 0.49220(18) 0.0189(2) Uani 1 1 d . . . . .
O1 O 0.56379(16) 0.34119(16) 0.3122(5) 0.0213(6) Uani 1 1 d . . . . .
O2 O 0.50209(19) 0.37930(18) 0.6355(4) 0.0226(7) Uani 1 1 d . . . . .
O3 O 0.17647(15) 0.28489(16) 0.4911(5) 0.0218(6) Uani 1 1 d . . . . .
C1 C 0.6954(2) 0.1765(2) 0.4609(5) 0.0167(9) Uani 1 1 d . . . . .
C2 C 0.7752(2) 0.1441(2) 0.4867(7) 0.0178(8) Uani 1 1 d . . . . .
H2 H 0.783646 0.087747 0.523405 0.021 Uiso 1 1 calc R U . . .
C3 C 0.8415(2) 0.1974(2) 0.4566(5) 0.0171(9) Uani 1 1 d . . . . .
C4 C 0.8316(3) 0.2796(3) 0.3999(6) 0.0180(9) Uani 1 1 d . . . . .
H4 H 0.878721 0.314322 0.378524 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7519(3) 0.3094(2) 0.3755(5) 0.0164(8) Uani 1 1 d . . . . .
C6 C 0.6820(3) 0.2590(3) 0.4061(5) 0.0156(9) Uani 1 1 d . . . . .
C7 C 0.5922(3) 0.2800(3) 0.3880(6) 0.0169(9) Uani 1 1 d . . . . .
C8 C 0.5405(2) 0.2088(2) 0.4605(6) 0.0170(9) Uani 1 1 d . . . . .
C9 C 0.4567(2) 0.2091(2) 0.4891(7) 0.0159(8) Uani 1 1 d . . . . .
C10 C 0.4037(2) 0.2832(2) 0.5164(6) 0.0160(9) Uani 1 1 d . . . . .
C11 C 0.4223(3) 0.3637(3) 0.5808(6) 0.0185(9) Uani 1 1 d . . . . .
C12 C 0.3577(3) 0.4210(2) 0.5942(6) 0.0184(9) Uani 1 1 d . . . . .
H12 H 0.369861 0.477445 0.624972 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2750(3) 0.3972(2) 0.5632(6) 0.0189(9) Uani 1 1 d . . . . .
H13 H 0.231734 0.437440 0.574970 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2553(2) 0.3160(2) 0.5156(6) 0.0169(9) Uani 1 1 d . . . . .
C15 C 0.3204(2) 0.2599(2) 0.4897(7) 0.0167(8) Uani 1 1 d . . . . .
C16 C 0.3140(3) 0.1698(2) 0.4387(6) 0.0199(10) Uani 1 1 d . . . . .
H16A H 0.304284 0.163465 0.306361 0.024 Uiso 1 1 calc R U . . .
H16B H 0.267891 0.142219 0.505481 0.024 Uiso 1 1 calc R U . . .
C17 C 0.3993(2) 0.1323(2) 0.4939(8) 0.0176(8) Uani 1 1 d . . . . .
C18 C 0.5243(3) 0.4635(3) 0.6763(7) 0.0318(11) Uani 1 1 d . . . . .
H18A H 0.583948 0.466366 0.705191 0.048 Uiso 1 1 calc R U . . .
H18B H 0.491775 0.483001 0.781050 0.048 Uiso 1 1 calc R U . . .
H18C H 0.512403 0.499074 0.570843 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1090(3) 0.3385(3) 0.5435(6) 0.0246(11) Uani 1 1 d . . . . .
H19A H 0.115178 0.353982 0.671874 0.037 Uiso 1 1 calc R U . . .
H19B H 0.055877 0.309130 0.526251 0.037 Uiso 1 1 calc R U . . .
H19C H 0.109729 0.389157 0.468313 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3941(3) 0.0986(3) 0.6901(7) 0.0256(10) Uani 1 1 d . . . . .
H20A H 0.356062 0.050625 0.693702 0.038 Uiso 1 1 calc R U . . .
H20B H 0.373100 0.142719 0.770725 0.038 Uiso 1 1 calc R U . . .
H20C H 0.449708 0.081161 0.730467 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4230(3) 0.0624(3) 0.3628(7) 0.0286(11) Uani 1 1 d . . . . .
H21A H 0.376499 0.022876 0.352386 0.043 Uiso 1 1 calc R U . . .
H21B H 0.472470 0.033183 0.408648 0.043 Uiso 1 1 calc R U . . .
H21C H 0.435241 0.086310 0.242834 0.043 Uiso 1 1 calc R U . . .


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
Cl1 C3 1.734(4) . ?
Cl2 C5 1.733(4) . ?
S1 C1 1.744(4) . ?
S1 C8 1.770(4) . ?
O1 C7 1.213(5) . ?
O2 C11 1.363(5) . ?
O2 C18 1.424(5) . ?
O3 C14 1.370(5) . ?
O3 C19 1.432(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.396(6) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(6) . ?
C4 C5 1.376(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(6) . ?
C6 C7 1.484(6) . ?
C7 C8 1.505(6) . ?
C8 C9 1.358(5) . ?
C9 C10 1.471(5) . ?
C9 C17 1.533(5) . ?
C10 C15 1.399(5) . ?
C10 C11 1.403(6) . ?
C11 C12 1.385(6) . ?
C12 C13 1.397(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C15 C16 1.492(5) . ?
C16 C17 1.547(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.523(6) . ?
C17 C20 1.541(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 S1 C8 92.31(19) . . ?
C11 O2 C18 118.0(4) . . ?
C14 O3 C19 116.3(3) . . ?
C2 C1 C6 122.1(4) . . ?
C2 C1 S1 124.0(3) . . ?
C6 C1 S1 113.9(3) . . ?
C3 C2 C1 117.1(4) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 123.0(4) . . ?
C2 C3 Cl1 119.0(3) . . ?
C4 C3 Cl1 117.9(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 Cl2 117.9(3) . . ?
C6 C5 Cl2 120.6(3) . . ?
C1 C6 C5 118.0(4) . . ?
C1 C6 C7 112.9(4) . . ?
C5 C6 C7 129.2(4) . . ?
O1 C7 C6 125.9(4) . . ?
O1 C7 C8 124.5(4) . . ?
C6 C7 C8 109.3(3) . . ?
C9 C8 C7 126.5(4) . . ?
C9 C8 S1 123.3(3) . . ?
C7 C8 S1 110.1(3) . . ?
C8 C9 C10 126.5(4) . . ?
C8 C9 C17 126.3(3) . . ?
C10 C9 C17 107.2(3) . . ?
C15 C10 C11 119.6(4) . . ?
C15 C10 C9 108.5(3) . . ?
C11 C10 C9 131.4(4) . . ?
O2 C11 C12 124.0(4) . . ?
O2 C11 C10 117.8(4) . . ?
C12 C11 C10 118.1(4) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O3 C14 C13 125.8(4) . . ?
O3 C14 C15 116.1(3) . . ?
C13 C14 C15 118.0(4) . . ?
C14 C15 C10 121.7(4) . . ?
C14 C15 C16 127.3(3) . . ?
C10 C15 C16 110.9(3) . . ?
C15 C16 C17 104.3(3) . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C21 C17 C9 115.0(4) . . ?
C21 C17 C20 110.4(4) . . ?
C9 C17 C20 109.5(4) . . ?
C21 C17 C16 109.7(4) . . ?
C9 C17 C16 102.3(3) . . ?
C20 C17 C16 109.4(4) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C8 S1 C1 C2 173.1(4) . . . . ?
C8 S1 C1 C6 -7.1(3) . . . . ?
C6 C1 C2 C3 0.3(7) . . . . ?
S1 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C1 C2 C3 Cl1 178.5(3) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
Cl1 C3 C4 C5 -178.6(3) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 Cl2 177.9(3) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
S1 C1 C6 C5 -179.2(3) . . . . ?
C2 C1 C6 C7 -179.7(4) . . . . ?
S1 C1 C6 C7 0.5(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
Cl2 C5 C6 C1 -178.5(3) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
Cl2 C5 C6 C7 1.8(6) . . . . ?
C1 C6 C7 O1 -165.8(4) . . . . ?
C5 C6 C7 O1 13.9(7) . . . . ?
C1 C6 C7 C8 8.0(5) . . . . ?
C5 C6 C7 C8 -172.3(4) . . . . ?
O1 C7 C8 C9 -15.3(7) . . . . ?
C6 C7 C8 C9 170.8(4) . . . . ?
O1 C7 C8 S1 161.0(4) . . . . ?
C6 C7 C8 S1 -12.9(4) . . . . ?
C1 S1 C8 C9 -172.1(4) . . . . ?
C1 S1 C8 C7 11.4(3) . . . . ?
C7 C8 C9 C10 -22.5(8) . . . . ?
S1 C8 C9 C10 161.6(4) . . . . ?
C7 C8 C9 C17 155.8(5) . . . . ?
S1 C8 C9 C17 -20.1(7) . . . . ?
C8 C9 C10 C15 163.5(5) . . . . ?
C17 C9 C10 C15 -15.1(5) . . . . ?
C8 C9 C10 C11 -24.7(8) . . . . ?
C17 C9 C10 C11 156.7(5) . . . . ?
C18 O2 C11 C12 -12.4(6) . . . . ?
C18 O2 C11 C10 171.2(4) . . . . ?
C15 C10 C11 O2 168.6(4) . . . . ?
C9 C10 C11 O2 -2.4(7) . . . . ?
C15 C10 C11 C12 -8.0(6) . . . . ?
C9 C10 C11 C12 -179.0(4) . . . . ?
O2 C11 C12 C13 -169.7(4) . . . . ?
C10 C11 C12 C13 6.7(6) . . . . ?
C11 C12 C13 C14 -1.0(7) . . . . ?
C19 O3 C14 C13 -8.9(6) . . . . ?
C19 O3 C14 C15 171.0(4) . . . . ?
C12 C13 C14 O3 176.5(4) . . . . ?
C12 C13 C14 C15 -3.5(7) . . . . ?
O3 C14 C15 C10 -177.9(4) . . . . ?
C13 C14 C15 C10 2.1(7) . . . . ?
O3 C14 C15 C16 -0.1(7) . . . . ?
C13 C14 C15 C16 179.9(5) . . . . ?
C11 C10 C15 C14 3.7(7) . . . . ?
C9 C10 C15 C14 176.6(4) . . . . ?
C11 C10 C15 C16 -174.4(4) . . . . ?
C9 C10 C15 C16 -1.5(5) . . . . ?
C14 C15 C16 C17 -160.9(5) . . . . ?
C10 C15 C16 C17 17.1(5) . . . . ?
C8 C9 C17 C21 -35.1(7) . . . . ?
C10 C9 C17 C21 143.4(4) . . . . ?
C8 C9 C17 C20 89.9(5) . . . . ?
C10 C9 C17 C20 -91.5(4) . . . . ?
C8 C9 C17 C16 -154.1(5) . . . . ?
C10 C9 C17 C16 24.5(5) . . . . ?
C15 C16 C17 C21 -147.2(4) . . . . ?
C15 C16 C17 C9 -24.6(5) . . . . ?
C15 C16 C17 C20 91.5(4) . . . . ?

_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.
;

_audit_block_code                C21H18Cl2O3S_wv319_dube
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl2 O3 S'
_chemical_formula_sum            'C21 H18 Cl2 O3 S'
_chemical_formula_weight         421.31 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             872 #?# check!

####################################################################### 
# 
# 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_wv470
_database_code_depnum_ccdc_archive 'CCDC 1873825'
# end Validation Reply Form

_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_wv470               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01106 Ang.  
RESPONSE: This could be caused by twinning combined with poor data quality at 
high angles (therefore data have been considered only up to a resolution of
0.84 A).
;

_chemical_name_common            KH-87
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.010 #?# in millimeters
_exptl_crystal_size_min          0.010 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      107.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   26.058(2)
_cell_length_b                   3.9096(4)
_cell_length_c                   16.8317(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.831(6)
_cell_angle_gamma                90
_cell_volume                     1623.0(3)
_cell_measurement_temperature    107.(2) #?# in K
_cell_measurement_reflns_used    111
_cell_measurement_theta_min      2.9654
_cell_measurement_theta_max      9.1946
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            9503 #xl
_diffrn_reflns_av_R_equivalents  0.0773 #xl
_diffrn_reflns_av_unetI/netI     0.0949 #xl
_diffrn_reflns_limit_h_min       -31 #xl
_diffrn_reflns_limit_h_max       30 #xl
_diffrn_reflns_limit_k_min       -4 #xl
_diffrn_reflns_limit_k_max       4 #xl
_diffrn_reflns_limit_l_min       -20 #xl
_diffrn_reflns_limit_l_max       19 #xl
_diffrn_reflns_theta_min         2.393 #xl
_diffrn_reflns_theta_max         25.026 #xl
_diffrn_measured_fraction_theta_max 0.994 #xl
_diffrn_reflns_theta_full        25.026 #xl
_diffrn_measured_fraction_theta_full 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.994 #xl

_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

_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.
;

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'

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'
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'

_reflns_number_total             2831 #xl
_reflns_number_gt                2136 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2831 #xl
_refine_ls_number_parameters     218 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0836 #xl
_refine_ls_R_factor_gt           0.0550 #xl
_refine_ls_wR_factor_ref         0.1099 #xl
_refine_ls_wR_factor_gt          0.1010 #xl
_refine_ls_goodness_of_fit_ref   1.029 #xl
_refine_ls_restrained_S_all      1.029 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.528 #xl
_refine_diff_density_min         -0.602 #xl
_refine_diff_density_rms         0.130 #xl

_refine_special_details          
;
pseudo-merohedral twin
TWIN 1 0 1 0 -1 0 0 0 -1
BASF 0.5

Refined as a 2-component twin.
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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
Cl1 Cl 0.52690(7) 0.8946(4) 0.62550(12) 0.0245(5) Uani 1 1 d . . . . .
Cl2 Cl 0.34445(7) 0.3007(4) 0.43628(12) 0.0246(5) Uani 1 1 d . . . . .
Cl3 Cl -0.02810(7) 0.9209(4) 0.09603(12) 0.0241(5) Uani 1 1 d . . . . .
Cl4 Cl 0.16004(7) 0.3580(4) 0.09656(12) 0.0225(5) Uani 1 1 d . . . . .
S1 S 0.35140(8) 0.8044(4) 0.73627(13) 0.0227(5) Uani 1 1 d . . . . .
S2 S 0.14596(8) 0.9263(4) 0.37988(13) 0.0252(5) Uani 1 1 d . . . . .
O1 O 0.2692(2) 0.2696(11) 0.5445(3) 0.0267(13) Uani 1 1 d . . . . .
O2 O 0.2349(2) 0.4084(12) 0.2755(3) 0.0300(14) Uani 1 1 d . . . . .
C1 C 0.3853(3) 0.7276(16) 0.6626(5) 0.0143(17) Uani 1 1 d . . . . .
C2 C 0.4384(3) 0.8332(14) 0.6748(4) 0.0160(17) Uani 1 1 d . . . . .
H2 H 0.458630 0.948197 0.724821 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4609(3) 0.7659(15) 0.6118(5) 0.0165(18) Uani 1 1 d . . . . .
C4 C 0.4322(3) 0.6001(15) 0.5396(5) 0.0179(17) Uani 1 1 d . . . . .
H4 H 0.448248 0.556400 0.497259 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3791(3) 0.4957(15) 0.5286(4) 0.0167(16) Uani 1 1 d . . . . .
C6 C 0.3561(3) 0.5521(15) 0.5917(5) 0.0167(16) Uani 1 1 d . . . . .
C7 C 0.3016(3) 0.4561(16) 0.5946(5) 0.0223(17) Uani 1 1 d . . . . .
C8 C 0.2901(3) 0.6097(17) 0.6688(5) 0.0230(18) Uani 1 1 d . . . . .
H8A H 0.277700 0.429843 0.699845 0.028 Uiso 1 1 calc R U . . .
H8B H 0.261133 0.783875 0.649775 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1123(3) 0.8182(16) 0.2743(5) 0.0225(19) Uani 1 1 d . . . . .
C10 C 0.0593(3) 0.9054(15) 0.2340(5) 0.0167(17) Uani 1 1 d . . . . .
H10 H 0.038068 1.021008 0.262112 0.020 Uiso 1 1 calc R U . . .
C11 C 0.0388(3) 0.8167(14) 0.1513(5) 0.0194(19) Uani 1 1 d . . . . .
C12 C 0.0694(3) 0.6411(14) 0.1086(5) 0.0182(17) Uani 1 1 d . . . . .
H12 H 0.053377 0.575656 0.051551 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1220(3) 0.5677(15) 0.1503(5) 0.0179(17) Uani 1 1 d . . . . .
C14 C 0.1457(3) 0.6504(15) 0.2353(5) 0.0206(17) Uani 1 1 d . . . . .
C15 C 0.1998(3) 0.5800(16) 0.2916(5) 0.0233(17) Uani 1 1 d . . . . .
C16 C 0.2089(3) 0.7396(17) 0.3774(5) 0.0231(18) Uani 1 1 d . . . . .
H16A H 0.237233 0.918047 0.388175 0.028 Uiso 1 1 calc R U . . .
H16B H 0.221117 0.562624 0.421584 0.028 Uiso 1 1 calc R U . . .


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
Cl1 C3 1.734(7) . ?
Cl2 C5 1.705(7) . ?
Cl3 C11 1.738(7) . ?
Cl4 C13 1.746(7) . ?
S1 C1 1.764(7) . ?
S1 C8 1.802(7) . ?
S2 C9 1.760(8) . ?
S2 C16 1.807(7) . ?
O1 C7 1.223(8) . ?
O2 C15 1.232(7) . ?
C1 C6 1.374(10) . ?
C1 C2 1.394(9) . ?
C2 C3 1.394(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(10) . ?
C4 C5 1.396(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(10) . ?
C6 C7 1.485(10) . ?
C7 C8 1.502(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.372(9) . ?
C9 C14 1.409(10) . ?
C10 C11 1.365(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(10) . ?
C12 C13 1.354(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(10) . ?
C14 C15 1.450(9) . ?
C15 C16 1.520(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C1 S1 C8 91.6(4) . . ?
C9 S2 C16 92.2(4) . . ?
C6 C1 C2 121.3(6) . . ?
C6 C1 S1 115.8(5) . . ?
C2 C1 S1 122.9(6) . . ?
C3 C2 C1 118.3(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 Cl1 119.3(6) . . ?
C2 C3 Cl1 119.2(5) . . ?
C3 C4 C5 119.4(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 Cl2 122.2(5) . . ?
C4 C5 Cl2 117.5(5) . . ?
C1 C6 C5 119.2(6) . . ?
C1 C6 C7 111.3(6) . . ?
C5 C6 C7 129.4(6) . . ?
O1 C7 C6 125.7(7) . . ?
O1 C7 C8 122.2(6) . . ?
C6 C7 C8 112.1(6) . . ?
C7 C8 S1 108.5(5) . . ?
C7 C8 H8A 110.0 . . ?
S1 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
S1 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C14 124.1(7) . . ?
C10 C9 S2 122.2(6) . . ?
C14 C9 S2 113.7(6) . . ?
C11 C10 C9 116.2(7) . . ?
C11 C10 H10 121.9 . . ?
C9 C10 H10 121.9 . . ?
C10 C11 C12 122.9(7) . . ?
C10 C11 Cl3 118.8(6) . . ?
C12 C11 Cl3 118.4(6) . . ?
C13 C12 C11 118.9(7) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.3(6) . . ?
C12 C13 Cl4 118.7(6) . . ?
C14 C13 Cl4 120.1(5) . . ?
C13 C14 C9 116.7(6) . . ?
C13 C14 C15 129.7(6) . . ?
C9 C14 C15 113.6(7) . . ?
O2 C15 C14 126.4(7) . . ?
O2 C15 C16 122.3(6) . . ?
C14 C15 C16 111.3(6) . . ?
C15 C16 S2 108.9(5) . . ?
C15 C16 H16A 109.9 . . ?
S2 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
S2 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?

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
C8 S1 C1 C6 -3.0(5) . . . . ?
C8 S1 C1 C2 177.7(6) . . . . ?
C6 C1 C2 C3 2.0(9) . . . . ?
S1 C1 C2 C3 -178.7(5) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
C1 C2 C3 Cl1 180.0(4) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
Cl1 C3 C4 C5 179.9(4) . . . . ?
C3 C4 C5 C6 -1.7(9) . . . . ?
C3 C4 C5 Cl2 178.2(5) . . . . ?
C2 C1 C6 C5 -3.7(9) . . . . ?
S1 C1 C6 C5 176.9(5) . . . . ?
C2 C1 C6 C7 177.8(5) . . . . ?
S1 C1 C6 C7 -1.6(7) . . . . ?
C4 C5 C6 C1 3.5(9) . . . . ?
Cl2 C5 C6 C1 -176.4(5) . . . . ?
C4 C5 C6 C7 -178.3(6) . . . . ?
Cl2 C5 C6 C7 1.8(10) . . . . ?
C1 C6 C7 O1 -172.1(6) . . . . ?
C5 C6 C7 O1 9.5(11) . . . . ?
C1 C6 C7 C8 6.6(8) . . . . ?
C5 C6 C7 C8 -171.7(6) . . . . ?
O1 C7 C8 S1 170.3(5) . . . . ?
C6 C7 C8 S1 -8.5(7) . . . . ?
C1 S1 C8 C7 6.4(5) . . . . ?
C16 S2 C9 C10 -177.9(6) . . . . ?
C16 S2 C9 C14 -0.7(6) . . . . ?
C14 C9 C10 C11 0.7(10) . . . . ?
S2 C9 C10 C11 177.7(5) . . . . ?
C9 C10 C11 C12 0.8(9) . . . . ?
C9 C10 C11 Cl3 -179.7(5) . . . . ?
C10 C11 C12 C13 -2.4(9) . . . . ?
Cl3 C11 C12 C13 178.0(5) . . . . ?
C11 C12 C13 C14 2.5(9) . . . . ?
C11 C12 C13 Cl4 -178.8(5) . . . . ?
C12 C13 C14 C9 -1.1(9) . . . . ?
Cl4 C13 C14 C9 -179.8(5) . . . . ?
C12 C13 C14 C15 176.7(6) . . . . ?
Cl4 C13 C14 C15 -1.9(10) . . . . ?
C10 C9 C14 C13 -0.6(10) . . . . ?
S2 C9 C14 C13 -177.8(5) . . . . ?
C10 C9 C14 C15 -178.8(6) . . . . ?
S2 C9 C14 C15 4.0(8) . . . . ?
C13 C14 C15 O2 -5.4(12) . . . . ?
C9 C14 C15 O2 172.5(7) . . . . ?
C13 C14 C15 C16 176.2(6) . . . . ?
C9 C14 C15 C16 -5.9(8) . . . . ?
O2 C15 C16 S2 -173.3(5) . . . . ?
C14 C15 C16 S2 5.2(7) . . . . ?
C9 S2 C16 C15 -2.6(5) . . . . ?

_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.
;

_audit_block_code                C8H4Cl2OS_wv470_dube
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 Cl2 O S'
_chemical_formula_sum            'C8 H4 Cl2 O S'
_chemical_formula_weight         219.07 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            8 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.793
_exptl_crystal_F_000             880 #?# check!

