# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_hyang411_0m
_database_code_depnum_ccdc_archive 'CCDC 2117020'
loop_
_audit_author_name
_audit_author_address
'Peng-Ju Xia'
;GuangXi Normal university
China
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2021-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 Cl F3 O2 S2'
_chemical_formula_sum            'C18 H14 Cl F3 O2 S2'
_chemical_formula_weight         418.86
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.2236(4)
_cell_length_b                   21.1767(9)
_cell_length_c                   9.7813(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.690(2)
_cell_angle_gamma                90.00
_cell_volume                     1762.67(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15776
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      1.92
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15776
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.92
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3543
_reflns_number_total             4033
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+1.3982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C12(H12), C13(H13), C3(H3), C2(H2), C1(H1), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S3 S 0.21925(8) 0.41248(3) 0.32275(6) 0.04152(18) Uani 1 d . . .
S2 S 0.14080(9) 0.41973(3) 0.82735(7) 0.0523(2) Uani 1 d . . .
Cl2 Cl -0.15592(9) 0.39058(5) 0.32647(8) 0.0713(3) Uani 1 d . . .
C14 C 0.3778(3) 0.42106(10) 0.4930(3) 0.0373(5) Uani 1 d . . .
C5 C 0.2311(2) 0.33091(10) 0.6929(2) 0.0308(4) Uani 1 d . . .
F3 F 0.0410(2) 0.23159(8) 0.4637(2) 0.0680(5) Uani 1 d . . .
C16 C 0.0124(3) 0.33986(11) 0.4218(2) 0.0391(5) Uani 1 d . . .
C7 C 0.0901(2) 0.35946(10) 0.5839(2) 0.0334(4) Uani 1 d . . .
O1 O 0.2799(3) 0.39803(11) 0.2117(2) 0.0602(5) Uani 1 d . . .
C4 C 0.2702(3) 0.36016(11) 0.8325(2) 0.0370(5) Uani 1 d . . .
C15 C 0.1189(3) 0.34049(11) 0.3341(2) 0.0380(5) Uani 1 d . . .
H15A H 0.0554 0.3275 0.2335 0.046 Uiso 1 calc . . R
H15B H 0.1983 0.3082 0.3761 0.046 Uiso 1 calc . . R
C6 C 0.3302(3) 0.28314(10) 0.6818(3) 0.0367(5) Uani 1 d . . .
H6 H 0.3075 0.2626 0.5919 0.044 Uiso 1 calc . . R
C8 C 0.0352(3) 0.40658(12) 0.6436(3) 0.0453(5) Uani 1 d . . .
H8 H -0.0535 0.4301 0.5888 0.054 Uiso 1 calc . . R
F2 F -0.1598(2) 0.27077(12) 0.4787(2) 0.0860(7) Uani 1 d . . .
F1 F -0.1428(3) 0.25743(11) 0.2688(2) 0.0859(7) Uani 1 d . . .
C12 C 0.6342(3) 0.38964(13) 0.6580(3) 0.0553(7) Uani 1 d . . .
H12 H 0.7235 0.3650 0.6779 0.066 Uiso 1 calc . . R
O2 O 0.1159(3) 0.46504(9) 0.3018(2) 0.0611(5) Uani 1 d . . .
C13 C 0.5123(3) 0.38485(12) 0.5223(3) 0.0475(6) Uani 1 d . . .
H13 H 0.5196 0.3576 0.4506 0.057 Uiso 1 calc . . R
C3 C 0.4023(3) 0.34262(13) 0.9555(3) 0.0463(6) Uani 1 d . . .
H3 H 0.4259 0.3623 1.0465 0.056 Uiso 1 calc . . R
C2 C 0.4969(3) 0.29573(14) 0.9395(3) 0.0494(6) Uani 1 d . . .
H2 H 0.5856 0.2834 1.0205 0.059 Uiso 1 calc . . R
C1 C 0.4615(3) 0.26636(12) 0.8034(3) 0.0456(6) Uani 1 d . . .
H1 H 0.5275 0.2349 0.7943 0.055 Uiso 1 calc . . R
C10 C 0.4946(4) 0.46706(14) 0.7327(3) 0.0564(7) Uani 1 d . . .
H10 H 0.4892 0.4953 0.8034 0.068 Uiso 1 calc . . R
C11 C 0.6269(4) 0.43039(14) 0.7659(3) 0.0543(7) Uani 1 d . . .
C17 C -0.0587(3) 0.27172(18) 0.4103(3) 0.0595(8) Uani 1 d . . .
C9 C 0.3691(3) 0.46331(12) 0.5973(3) 0.0473(6) Uani 1 d . . .
H9 H 0.2809 0.4887 0.5769 0.057 Uiso 1 calc . . R
C18 C 0.7596(5) 0.4335(2) 0.9152(4) 0.0811(11) Uani 1 d . . .
H18A H 0.8101 0.3930 0.9389 0.122 Uiso 1 calc . . GR
H18B H 0.7191 0.4447 0.9888 0.122 Uiso 1 calc . . GR
H18C H 0.8343 0.4647 0.9134 0.122 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 C14 1.751(2) . ?
S3 O1 1.433(2) . ?
S3 C15 1.809(2) . ?
S3 O2 1.428(2) . ?
S2 C4 1.724(2) . ?
S2 C8 1.705(3) . ?
Cl2 C16 1.821(2) . ?
C14 C13 1.391(4) . ?
C14 C9 1.382(3) . ?
C5 C7 1.458(3) . ?
C5 C4 1.414(3) . ?
C5 C6 1.395(3) . ?
F3 C17 1.212(4) . ?
C16 C7 1.524(3) . ?
C16 C15 1.533(3) . ?
C16 C17 1.571(4) . ?
C7 C8 1.350(3) . ?
C4 C3 1.393(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C1 1.378(3) . ?
C8 H8 0.9300 . ?
F2 C17 1.342(4) . ?
F1 C17 1.334(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C12 C11 1.385(4) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.370(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.389(4) . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.376(5) . ?
C10 C9 1.385(4) . ?
C11 C18 1.502(4) . ?
C9 H9 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C14 S3 C15 106.78(10) . . ?
O1 S3 C14 108.41(13) . . ?
O1 S3 C15 103.01(11) . . ?
O2 S3 C14 108.79(12) . . ?
O2 S3 O1 119.46(13) . . ?
O2 S3 C15 109.65(12) . . ?
C8 S2 C4 91.09(11) . . ?
C13 C14 S3 119.34(18) . . ?
C9 C14 S3 120.3(2) . . ?
C9 C14 C13 120.4(2) . . ?
C4 C5 C7 110.36(18) . . ?
C6 C5 C7 132.08(19) . . ?
C6 C5 C4 117.54(19) . . ?
C7 C16 Cl2 109.75(16) . . ?
C7 C16 C15 115.73(18) . . ?
C7 C16 C17 109.92(19) . . ?
C15 C16 Cl2 108.17(16) . . ?
C15 C16 C17 107.9(2) . . ?
C17 C16 Cl2 104.80(18) . . ?
C5 C7 C16 125.24(18) . . ?
C8 C7 C5 111.57(19) . . ?
C8 C7 C16 123.2(2) . . ?
C5 C4 S2 112.14(16) . . ?
C3 C4 S2 125.87(18) . . ?
C3 C4 C5 122.0(2) . . ?
S3 C15 H15A 107.4 . . ?
S3 C15 H15B 107.4 . . ?
C16 C15 S3 119.68(16) . . ?
C16 C15 H15A 107.4 . . ?
C16 C15 H15B 107.4 . . ?
H15A C15 H15B 106.9 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
S2 C8 H8 122.6 . . ?
C7 C8 S2 114.83(18) . . ?
C7 C8 H8 122.6 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C11 C10 H10 118.9 . . ?
C11 C10 C9 122.1(3) . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C18 120.5(3) . . ?
C10 C11 C12 118.1(3) . . ?
C10 C11 C18 121.4(3) . . ?
F3 C17 C16 112.8(2) . . ?
F3 C17 F2 109.4(3) . . ?
F3 C17 F1 109.2(3) . . ?
F2 C17 C16 109.2(3) . . ?
F1 C17 C16 110.0(2) . . ?
F1 C17 F2 106.0(2) . . ?
C14 C9 C10 118.6(3) . . ?
C14 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
S3 C14 C13 C12 -177.4(2) . . . . ?
S3 C14 C9 C10 177.62(19) . . . . ?
S2 C4 C3 C2 -177.43(19) . . . . ?
Cl2 C16 C7 C5 -177.86(17) . . . . ?
Cl2 C16 C7 C8 1.7(3) . . . . ?
Cl2 C16 C15 S3 66.6(2) . . . . ?
Cl2 C16 C17 F3 176.9(2) . . . . ?
Cl2 C16 C17 F2 -61.2(2) . . . . ?
Cl2 C16 C17 F1 54.7(3) . . . . ?
C14 S3 C15 C16 76.5(2) . . . . ?
C5 C7 C8 S2 -0.7(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C5 C6 C1 C2 0.9(4) . . . . ?
C16 C7 C8 S2 179.65(17) . . . . ?
C7 C5 C4 S2 -0.6(2) . . . . ?
C7 C5 C4 C3 -178.5(2) . . . . ?
C7 C5 C6 C1 177.6(2) . . . . ?
C7 C16 C15 S3 -56.9(3) . . . . ?
C7 C16 C17 F3 -65.2(3) . . . . ?
C7 C16 C17 F2 56.6(3) . . . . ?
C7 C16 C17 F1 172.6(2) . . . . ?
O1 S3 C14 C13 -33.0(2) . . . . ?
O1 S3 C14 C9 147.2(2) . . . . ?
O1 S3 C15 C16 -169.39(18) . . . . ?
C4 S2 C8 C7 0.3(2) . . . . ?
C4 C5 C7 C16 -179.6(2) . . . . ?
C4 C5 C7 C8 0.8(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?
C15 S3 C14 C13 77.4(2) . . . . ?
C15 S3 C14 C9 -102.4(2) . . . . ?
C15 C16 C7 C5 -55.1(3) . . . . ?
C15 C16 C7 C8 124.5(3) . . . . ?
C15 C16 C17 F3 61.8(3) . . . . ?
C15 C16 C17 F2 -176.3(2) . . . . ?
C15 C16 C17 F1 -60.4(3) . . . . ?
C6 C5 C7 C16 2.1(4) . . . . ?
C6 C5 C7 C8 -177.5(2) . . . . ?
C6 C5 C4 S2 178.05(16) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C8 S2 C4 C5 0.17(18) . . . . ?
C8 S2 C4 C3 178.0(2) . . . . ?
O2 S3 C14 C13 -164.32(19) . . . . ?
O2 S3 C14 C9 15.8(2) . . . . ?
O2 S3 C15 C16 -41.2(2) . . . . ?
C13 C14 C9 C10 -2.2(4) . . . . ?
C13 C12 C11 C10 -1.1(4) . . . . ?
C13 C12 C11 C18 178.2(3) . . . . ?
C3 C2 C1 C6 -0.6(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C11 C10 C9 C14 0.3(4) . . . . ?
C17 C16 C7 C5 67.4(3) . . . . ?
C17 C16 C7 C8 -113.0(3) . . . . ?
C17 C16 C15 S3 179.49(17) . . . . ?
C9 C14 C13 C12 2.5(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C9 C10 C11 C18 -177.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
