# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_test
_database_code_depnum_ccdc_archive 'CCDC 1889035'
loop_
_audit_author_name
_audit_author_address
lb
;Anhui normal university
China
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O S'
_chemical_formula_weight         356.46

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'

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

_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'

_cell_length_a                   15.8263(7)
_cell_length_b                   7.7607(3)
_cell_length_c                   15.9189(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.393(2)
_cell_angle_gamma                90
_cell_volume                     1875.73(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66223
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4303
_reflns_number_gt                3031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1300P)²+0.3760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4303
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1751
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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 0.0670(2) 1.2196(4) 0.4422(2) 0.0649(9) Uani 1 1 d . . . . .
H1A H 0.057127 1.242825 0.380931 0.097 Uiso 1 1 calc R U . . .
H1B H 0.100567 1.311911 0.475867 0.097 Uiso 1 1 calc R U . . .
H1C H 0.011437 1.210288 0.454987 0.097 Uiso 1 1 calc R U . . .
C2 C 0.11689(17) 1.0537(4) 0.46528(18) 0.0457(6) Uani 1 1 d . . . . .
C3 C 0.09299(19) 0.9097(4) 0.4132(2) 0.0567(8) Uani 1 1 d . . . . .
H3 H 0.045405 0.916687 0.363212 0.068 Uiso 1 1 calc R U . . .
C4 C 0.13791(19) 0.7547(4) 0.43323(19) 0.0532(7) Uani 1 1 d . . . . .
H4 H 0.120547 0.659673 0.396831 0.064 Uiso 1 1 calc R U . . .
C5 C 0.20857(16) 0.7420(3) 0.50749(17) 0.0400(6) Uani 1 1 d . . . . .
C6 C 0.23315(18) 0.8853(4) 0.55991(17) 0.0480(7) Uani 1 1 d . . . . .
H6 H 0.280571 0.878269 0.610028 0.058 Uiso 1 1 calc R U . . .
C7 C 0.18838(19) 1.0389(4) 0.53901(19) 0.0495(7) Uani 1 1 d . . . . .
H7 H 0.206455 1.134168 0.575012 0.059 Uiso 1 1 calc R U . . .
C8 C 0.37103(16) 0.5871(3) 0.56736(17) 0.0392(6) Uani 1 1 d . . . . .
C9 C 0.41305(17) 0.7147(3) 0.51984(16) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.50897(16) 0.7042(3) 0.56423(16) 0.0373(5) Uani 1 1 d . . . . .
C11 C 0.57781(17) 0.7999(3) 0.55301(17) 0.0422(6) Uani 1 1 d . . . . .
H11 H 0.568281 0.887412 0.511483 0.051 Uiso 1 1 calc R U . . .
C12 C 0.66201(18) 0.7628(4) 0.60517(19) 0.0474(6) Uani 1 1 d . . . . .
H12 H 0.709376 0.825802 0.597760 0.057 Uiso 1 1 calc R U . . .
C13 C 0.67723(17) 0.6346(4) 0.66782(18) 0.0449(6) Uani 1 1 d . . . . .
C14 C 0.60555(16) 0.5396(3) 0.67950(17) 0.0422(6) Uani 1 1 d . . . . .
H14 H 0.614583 0.454575 0.722270 0.051 Uiso 1 1 calc R U . . .
C15 C 0.52256(15) 0.5737(3) 0.62733(16) 0.0354(5) Uani 1 1 d . . . . .
C16 C 0.43526(15) 0.4991(3) 0.62592(16) 0.0366(5) Uani 1 1 d . . . . .
C17 C 0.42641(15) 0.3444(3) 0.67685(15) 0.0354(5) Uani 1 1 d . . . . .
C18 C 0.47949(16) 0.2022(3) 0.67706(16) 0.0384(6) Uani 1 1 d . . . . .
H18 H 0.522898 0.207803 0.648109 0.046 Uiso 1 1 calc R U . . .
C19 C 0.46874(16) 0.0521(3) 0.71975(17) 0.0401(6) Uani 1 1 d . . . . .
H19 H 0.504415 -0.042357 0.718160 0.048 Uiso 1 1 calc R U . . .
C20 C 0.40560(16) 0.0398(3) 0.76498(17) 0.0411(6) Uani 1 1 d . . . . .
C21 C 0.35417(17) 0.1839(4) 0.76616(18) 0.0456(6) Uani 1 1 d . . . . .
H21 H 0.312222 0.179623 0.796916 0.055 Uiso 1 1 calc R U . . .
C22 C 0.36366(16) 0.3332(3) 0.72292(17) 0.0420(6) Uani 1 1 d . . . . .
H22 H 0.327836 0.427420 0.724473 0.050 Uiso 1 1 calc R U . . .
C23 C 0.76913(19) 0.5943(5) 0.7233(2) 0.0686(10) Uani 1 1 d . . . . .
H23A H 0.810529 0.665674 0.705492 0.103 Uiso 1 1 calc R U . . .
H23B H 0.782082 0.475262 0.716078 0.103 Uiso 1 1 calc R U . . .
H23C H 0.773357 0.616153 0.783708 0.103 Uiso 1 1 calc R U . . .
C24 C 0.3945(2) -0.1233(4) 0.8112(2) 0.0652(9) Uani 1 1 d . . . . .
H24A H 0.335272 -0.130035 0.815507 0.098 Uiso 1 1 calc R U . . .
H24B H 0.434998 -0.123854 0.868827 0.098 Uiso 1 1 calc R U . . .
H24C H 0.405996 -0.220498 0.778756 0.098 Uiso 1 1 calc R U . . .
O1 O 0.37621(13) 0.7992(2) 0.45674(13) 0.0517(5) Uani 1 1 d . . . . .
S1 S 0.25933(4) 0.53788(9) 0.53265(5) 0.0514(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.501(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(4) . ?
C2 C7 1.386(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 S1 1.770(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C16 1.354(3) . ?
C8 C9 1.510(3) . ?
C8 S1 1.739(3) . ?
C9 O1 1.204(3) . ?
C9 C10 1.485(3) . ?
C10 C11 1.371(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(4) . ?
C13 C23 1.506(4) . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.492(3) . ?
C16 C17 1.477(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.394(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(4) . ?
C20 C24 1.499(4) . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C1 121.7(3) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 S1 123.53(19) . . ?
C4 C5 S1 117.6(2) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C16 C8 C9 108.9(2) . . ?
C16 C8 S1 127.3(2) . . ?
C9 C8 S1 122.47(19) . . ?
O1 C9 C10 128.1(2) . . ?
O1 C9 C8 126.7(2) . . ?
C10 C9 C8 105.15(19) . . ?
C11 C10 C15 121.2(2) . . ?
C11 C10 C9 130.7(2) . . ?
C15 C10 C9 108.1(2) . . ?
C10 C11 C12 118.3(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 C23 121.1(2) . . ?
C14 C13 C23 119.6(3) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 C16 131.4(2) . . ?
C10 C15 C16 108.4(2) . . ?
C8 C16 C17 128.2(2) . . ?
C8 C16 C15 109.1(2) . . ?
C17 C16 C15 122.5(2) . . ?
C18 C17 C22 118.0(2) . . ?
C18 C17 C16 119.8(2) . . ?
C22 C17 C16 122.1(2) . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 117.5(2) . . ?
C21 C20 C24 121.6(3) . . ?
C19 C20 C24 120.9(3) . . ?
C22 C21 C20 121.6(2) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 S1 C5 103.36(12) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_mo_20180411c_0m
_database_code_depnum_ccdc_archive 'CCDC 1889037'
loop_
_audit_author_name
_audit_author_address
lc
; Anhui Normal University
China
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Cl F O S'
_chemical_formula_weight         380.84

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.3464(2)
_cell_length_b                   8.5371(3)
_cell_length_c                   15.0907(5)
_cell_angle_alpha                95.3370(10)
_cell_angle_beta                 91.5180(10)
_cell_angle_gamma                104.3610(10)
_cell_volume                     911.69(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.341
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36064
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.866
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4161
_reflns_number_gt                3454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.3186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.4441(3) 0.8054(2) 0.84646(11) 0.0489(4) Uani 1 1 d . . . . .
C2 C 0.6104(3) 0.9221(2) 0.84301(12) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.627538 1.024242 0.874236 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7511(3) 0.88563(19) 0.79279(11) 0.0497(4) Uani 1 1 d . . . . .
H3 H 0.863388 0.964155 0.789952 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7273(2) 0.73287(17) 0.74626(10) 0.0401(3) Uani 1 1 d . . . . .
C5 C 0.5580(2) 0.61764(18) 0.75013(11) 0.0444(3) Uani 1 1 d . . . . .
H5 H 0.539691 0.515404 0.718816 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4168(2) 0.65398(19) 0.80016(11) 0.0472(4) Uani 1 1 d . . . . .
H6 H 0.303566 0.576470 0.802648 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8429(2) 0.50992(19) 0.62690(12) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.7593(2) 0.4849(2) 0.53341(12) 0.0474(4) Uani 1 1 d . . . . .
C9 C 0.7416(2) 0.30959(19) 0.50282(10) 0.0428(3) Uani 1 1 d . . . . .
C10 C 0.6686(2) 0.2198(2) 0.42428(11) 0.0507(4) Uani 1 1 d . . . . .
H10 H 0.619576 0.265374 0.378477 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6714(2) 0.0577(2) 0.41661(11) 0.0492(4) Uani 1 1 d . . . . .
C12 C 0.7402(2) -0.0146(2) 0.48300(11) 0.0469(4) Uani 1 1 d . . . . .
H12 H 0.738736 -0.124205 0.474871 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8124(2) 0.07860(19) 0.56275(11) 0.0427(3) Uani 1 1 d . . . . .
H13 H 0.858724 0.031918 0.608856 0.051 Uiso 1 1 calc R U . . .
C14 C 0.8140(2) 0.24137(18) 0.57221(10) 0.0385(3) Uani 1 1 d . . . . .
C15 C 0.8770(2) 0.36800(18) 0.64851(10) 0.0404(3) Uani 1 1 d . . . . .
C16 C 0.9625(2) 0.33728(18) 0.73195(10) 0.0419(3) Uani 1 1 d . . . . .
C17 C 0.8973(3) 0.3815(2) 0.81406(11) 0.0518(4) Uani 1 1 d . . . . .
H17 H 0.797395 0.430409 0.816137 0.062 Uiso 1 1 calc R U . . .
C18 C 0.9791(3) 0.3535(2) 0.89199(12) 0.0597(5) Uani 1 1 d . . . . .
H18 H 0.931144 0.380904 0.946029 0.072 Uiso 1 1 calc R U . . .
C19 C 1.1315(3) 0.2853(2) 0.89173(12) 0.0594(5) Uani 1 1 d . . . . .
C20 C 1.1955(3) 0.2396(2) 0.81000(12) 0.0540(4) Uani 1 1 d . . . . .
H20 H 1.296408 0.191961 0.808342 0.065 Uiso 1 1 calc R U . . .
C21 C 1.1119(2) 0.26383(19) 0.73105(11) 0.0460(4) Uani 1 1 d . . . . .
H21 H 1.155631 0.230818 0.676975 0.055 Uiso 1 1 calc R U . . .
C22 C 1.2265(5) 0.2645(4) 0.97852(16) 0.0989(10) Uani 1 1 d . . . . .
H22A H 1.241574 0.361155 1.018852 0.148 Uiso 1 1 calc R U . . .
H22B H 1.347693 0.245591 0.967282 0.148 Uiso 1 1 calc R U . . .
H22C H 1.150491 0.173484 1.004468 0.148 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26523(9) 0.84874(8) 0.91012(4) 0.0854(2) Uani 1 1 d . . . . .
F1 F 0.60087(18) -0.03495(16) 0.33963(7) 0.0734(3) Uani 1 1 d . . . . .
O1 O 0.7198(2) 0.58581(16) 0.49034(10) 0.0683(4) Uani 1 1 d . . . . .
S1 S 0.92172(6) 0.70171(5) 0.68702(4) 0.05603(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(3) . ?
C1 C6 1.377(2) . ?
C1 Cl1 1.7401(17) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 S1 1.7670(16) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C15 1.363(2) . ?
C7 C8 1.499(2) . ?
C7 S1 1.7507(17) . ?
C8 O1 1.2113(19) . ?
C8 C9 1.497(2) . ?
C9 C10 1.369(2) . ?
C9 C14 1.399(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 F1 1.355(2) . ?
C11 C12 1.372(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.483(2) . ?
C15 C16 1.466(2) . ?
C16 C21 1.392(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(3) . ?
C19 C22 1.513(3) . ?
C20 C21 1.382(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C2 C1 C6 120.88(16) . . ?
C2 C1 Cl1 119.92(13) . . ?
C6 C1 Cl1 119.20(14) . . ?
C1 C2 C3 119.24(15) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.82(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.95(15) . . ?
C5 C4 S1 125.18(12) . . ?
C3 C4 S1 115.86(12) . . ?
C6 C5 C4 120.31(14) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 119.78(15) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C15 C7 C8 108.98(14) . . ?
C15 C7 S1 126.81(14) . . ?
C8 C7 S1 123.18(11) . . ?
O1 C8 C9 126.98(17) . . ?
O1 C8 C7 127.53(17) . . ?
C9 C8 C7 105.45(12) . . ?
C10 C9 C14 122.00(15) . . ?
C10 C9 C8 130.52(14) . . ?
C14 C9 C8 107.47(14) . . ?
C9 C10 C11 116.49(15) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
F1 C11 C12 118.32(16) . . ?
F1 C11 C10 118.16(15) . . ?
C12 C11 C10 123.51(16) . . ?
C11 C12 C13 119.10(15) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 118.89(14) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C9 119.99(15) . . ?
C13 C14 C15 131.01(14) . . ?
C9 C14 C15 108.97(13) . . ?
C7 C15 C16 127.88(15) . . ?
C7 C15 C14 109.10(14) . . ?
C16 C15 C14 123.02(13) . . ?
C21 C16 C17 118.31(15) . . ?
C21 C16 C15 120.71(14) . . ?
C17 C16 C15 120.98(14) . . ?
C18 C17 C16 120.64(17) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.36(17) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 118.07(17) . . ?
C18 C19 C22 120.5(2) . . ?
C20 C19 C22 121.5(2) . . ?
C21 C20 C19 121.15(17) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C16 120.42(16) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 S1 C4 105.45(7) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.038



