# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_2017961_0m
_audit_block_doi                 10.5517/ccdc.csd.cc24tmyk
_database_code_depnum_ccdc_archive 'CCDC 1990849'
loop_
_audit_author_name
_audit_author_address
aa
;Department of Medicinal Chemistry, China Pharmaceutical University
China
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2017-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'(Z)-(5-((4-chlorophenyl) sulfonyl)-4-phenylpent-3-en-1-yl) (trifluoromethyl)sulfane'
_chemical_formula_moiety         'C18 H16 Cl F3 O2 S2'
_chemical_formula_sum            'C18 H16 Cl F3 O2 S2'
_chemical_formula_weight         420.88
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.696(5)
_cell_length_b                   15.124(12)
_cell_length_c                   21.707(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.78(2)
_cell_angle_gamma                90
_cell_volume                     1861(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1336
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1734 before and 0.1043 after correction. The Ratio of minimum to maximum transmission is 0.2826. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_av_unetI/netI     0.1447
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7854
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.644
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2092
_reflns_number_total             3232
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.1057
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1830P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.2918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C7(H7A,H7B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C10(H10), C12(H12), C4(H4), C14(H14), C11(H11), C1(H1),
 C15(H15), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.7392(3) 0.49597(10) 0.59408(6) 0.0405(5) Uani 1 1 d . . . . .
S2 S 0.2041(3) 0.23505(11) 0.44177(6) 0.0496(5) Uani 1 1 d . . . . .
Cl1 Cl 1.2033(4) 0.59117(12) 0.85627(8) 0.0732(7) Uani 1 1 d . . . . .
O1 O 0.5027(7) 0.4676(3) 0.59829(18) 0.0514(11) Uani 1 1 d . . . . .
O2 O 0.7828(9) 0.5651(3) 0.55142(18) 0.0619(13) Uani 1 1 d . . . . .
F3 F 0.0493(11) 0.0902(3) 0.3968(2) 0.1104(19) Uani 1 1 d . . . . .
F2 F 0.0939(12) 0.0899(3) 0.4954(2) 0.1068(19) Uani 1 1 d . . . . .
F1 F 0.3847(11) 0.0770(3) 0.4433(3) 0.111(2) Uani 1 1 d . . . . .
C8 C 0.8664(10) 0.3187(3) 0.6076(2) 0.0358(12) Uani 1 1 d . . . . .
C9 C 0.9480(10) 0.3126(3) 0.6747(2) 0.0362(12) Uani 1 1 d . . . . .
C6 C 0.7485(10) 0.5055(3) 0.7195(2) 0.0381(13) Uani 1 1 d . . . . .
H6 H 0.6035 0.4740 0.7147 0.046 Uiso 1 1 calc R . . . .
C13 C 0.8752(11) 0.2716(4) 0.7783(3) 0.0441(14) Uani 1 1 d . . . . .
H13 H 0.7747 0.2453 0.8055 0.053 Uiso 1 1 calc R . . . .
C10 C 1.1665(10) 0.3449(4) 0.6992(2) 0.0408(13) Uani 1 1 d . . . . .
H10 H 1.2696 0.3702 0.6722 0.049 Uiso 1 1 calc R . . . .
C12 C 1.0868(11) 0.3048(4) 0.8017(3) 0.0444(14) Uani 1 1 d . . . . .
H12 H 1.1328 0.3035 0.8450 0.053 Uiso 1 1 calc R . . . .
C4 C 1.0687(11) 0.5755(4) 0.6743(3) 0.0459(14) Uani 1 1 d . . . . .
H4 H 1.1408 0.5926 0.6385 0.055 Uiso 1 1 calc R . . . .
C17 C 0.3712(10) 0.2562(4) 0.5153(2) 0.0417(14) Uani 1 1 d . . . . .
H17A H 0.3367 0.3171 0.5285 0.050 Uiso 1 1 calc R . . . .
H17B H 0.3174 0.2151 0.5464 0.050 Uiso 1 1 calc R . . . .
C14 C 0.8028(10) 0.2750(3) 0.7156(2) 0.0377(13) Uani 1 1 d . . . . .
H14 H 0.6534 0.2517 0.7003 0.045 Uiso 1 1 calc R . . . .
C5 C 0.8581(10) 0.5301(3) 0.6685(2) 0.0349(12) Uani 1 1 d . . . . .
C11 C 1.2354(11) 0.3410(4) 0.7612(2) 0.0439(14) Uani 1 1 d . . . . .
H11 H 1.3859 0.3631 0.7768 0.053 Uiso 1 1 calc R . . . .
C7 C 0.9133(10) 0.4038(3) 0.5751(2) 0.0394(13) Uani 1 1 d . . . . .
H7A H 0.8864 0.3937 0.5299 0.047 Uiso 1 1 calc R . . . .
H7B H 1.0818 0.4193 0.5850 0.047 Uiso 1 1 calc R . . . .
C1 C 0.8519(11) 0.5271(4) 0.7778(3) 0.0450(15) Uani 1 1 d . . . . .
H1 H 0.7772 0.5121 0.8136 0.054 Uiso 1 1 calc R . . . .
C16 C 0.6322(11) 0.2465(4) 0.5148(3) 0.0498(16) Uani 1 1 d . . . . .
H16A H 0.6680 0.1890 0.4961 0.060 Uiso 1 1 calc R . . . .
H16B H 0.6927 0.2940 0.4892 0.060 Uiso 1 1 calc R . . . .
C15 C 0.7513(10) 0.2516(4) 0.5790(3) 0.0438(14) Uani 1 1 d . . . . .
H15 H 0.7438 0.1993 0.6029 0.053 Uiso 1 1 calc R . . . .
C2 C 1.0647(11) 0.5707(4) 0.7832(3) 0.0438(14) Uani 1 1 d . . . . .
C3 C 1.1742(11) 0.5961(4) 0.7327(3) 0.0467(15) Uani 1 1 d . . . . .
H3 H 1.3197 0.6272 0.7378 0.056 Uiso 1 1 calc R . . . .
C18 C 0.1850(14) 0.1193(5) 0.4448(3) 0.064(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0456(10) 0.0368(8) 0.0380(7) 0.0054(6) -0.0008(6) 0.0009(7)
S2 0.0608(12) 0.0499(10) 0.0364(7) 0.0020(7) -0.0040(6) 0.0000(8)
Cl1 0.0899(15) 0.0652(12) 0.0587(10) -0.0246(9) -0.0216(9) 0.0133(10)
O1 0.044(3) 0.055(3) 0.053(2) -0.008(2) -0.0049(17) 0.003(2)
O2 0.091(4) 0.046(2) 0.046(2) 0.019(2) -0.003(2) 0.003(3)
F3 0.143(5) 0.078(3) 0.099(3) -0.023(3) -0.045(3) -0.025(3)
F2 0.177(6) 0.060(3) 0.084(3) 0.012(3) 0.009(3) -0.040(3)
F1 0.107(4) 0.059(3) 0.158(5) -0.030(3) -0.022(4) 0.022(3)
C8 0.037(3) 0.034(3) 0.038(3) -0.003(2) 0.006(2) 0.002(2)
C9 0.043(3) 0.026(3) 0.040(3) -0.007(2) 0.001(2) 0.002(2)
C6 0.038(3) 0.031(3) 0.046(3) -0.001(3) 0.007(2) -0.001(3)
C13 0.056(4) 0.034(3) 0.043(3) 0.002(3) 0.013(3) -0.003(3)
C10 0.039(3) 0.039(3) 0.045(3) -0.003(3) 0.009(2) 0.002(3)
C12 0.046(4) 0.040(3) 0.045(3) 0.003(3) -0.001(2) 0.005(3)
C4 0.052(4) 0.034(3) 0.052(3) 0.000(3) 0.004(3) -0.002(3)
C17 0.056(4) 0.035(3) 0.033(3) 0.003(2) 0.004(2) 0.000(3)
C14 0.039(3) 0.030(3) 0.044(3) 0.001(2) 0.003(2) -0.002(2)
C5 0.039(3) 0.026(3) 0.039(3) 0.001(2) 0.002(2) 0.001(2)
C11 0.046(4) 0.039(3) 0.044(3) -0.002(3) -0.008(2) 0.002(3)
C7 0.044(4) 0.037(3) 0.037(3) -0.001(2) 0.007(2) 0.002(3)
C1 0.057(4) 0.036(3) 0.043(3) -0.002(3) 0.009(3) 0.008(3)
C16 0.050(4) 0.053(4) 0.046(3) -0.021(3) 0.001(3) -0.006(3)
C15 0.041(4) 0.045(3) 0.043(3) -0.010(3) -0.001(2) -0.007(3)
C2 0.051(4) 0.031(3) 0.047(3) -0.005(3) -0.007(3) 0.008(3)
C3 0.044(4) 0.028(3) 0.066(4) -0.011(3) -0.004(3) -0.006(3)
C18 0.081(6) 0.044(4) 0.061(4) -0.012(3) -0.017(3) -0.001(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.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.426(5) . ?
S1 O2 1.434(4) . ?
S1 C5 1.764(5) . ?
S1 C7 1.782(6) . ?
S2 C17 1.803(5) . ?
S2 C18 1.755(7) . ?
Cl1 C2 1.727(6) . ?
F3 C18 1.309(8) . ?
F2 C18 1.339(9) . ?
F1 C18 1.308(9) . ?
C8 C9 1.486(7) . ?
C8 C7 1.505(7) . ?
C8 C15 1.328(8) . ?
C9 C10 1.392(8) . ?
C9 C14 1.393(8) . ?
C6 H6 0.9500 . ?
C6 C5 1.377(7) . ?
C6 C1 1.380(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.357(9) . ?
C13 C14 1.384(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.365(8) . ?
C12 H12 0.9500 . ?
C12 C11 1.393(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(8) . ?
C4 C3 1.383(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.495(8) . ?
C14 H14 0.9500 . ?
C11 H11 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1 0.9500 . ?
C1 C2 1.375(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.489(8) . ?
C15 H15 0.9500 . ?
C2 C3 1.369(9) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.1(3) . . ?
O1 S1 C5 107.9(2) . . ?
O1 S1 C7 109.3(3) . . ?
O2 S1 C5 107.6(3) . . ?
O2 S1 C7 106.5(3) . . ?
C5 S1 C7 105.6(3) . . ?
C18 S2 C17 100.0(3) . . ?
C9 C8 C7 117.3(5) . . ?
C15 C8 C9 120.2(5) . . ?
C15 C8 C7 122.5(5) . . ?
C10 C9 C8 122.1(5) . . ?
C10 C9 C14 117.7(5) . . ?
C14 C9 C8 120.1(5) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C1 119.2(5) . . ?
C1 C6 H6 120.4 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(5) . . ?
C14 C13 H13 119.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(5) . . ?
C11 C10 H10 119.4 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.8(5) . . ?
C11 C12 H12 120.6 . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
S2 C17 H17A 108.7 . . ?
S2 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C16 C17 S2 114.4(4) . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C6 C5 S1 119.6(4) . . ?
C6 C5 C4 121.5(5) . . ?
C4 C5 S1 118.8(4) . . ?
C10 C11 C12 120.5(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
S1 C7 H7A 108.4 . . ?
S1 C7 H7B 108.4 . . ?
C8 C7 S1 115.6(4) . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C6 C1 H1 120.5 . . ?
C2 C1 C6 118.9(5) . . ?
C2 C1 H1 120.5 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C15 C16 C17 110.3(5) . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C8 C15 C16 129.4(6) . . ?
C8 C15 H15 115.3 . . ?
C16 C15 H15 115.3 . . ?
C1 C2 Cl1 118.8(5) . . ?
C3 C2 Cl1 118.8(5) . . ?
C3 C2 C1 122.3(5) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.7(6) . . ?
C2 C3 H3 120.7 . . ?
F3 C18 S2 109.9(5) . . ?
F3 C18 F2 107.1(7) . . ?
F2 C18 S2 113.1(5) . . ?
F1 C18 S2 115.4(6) . . ?
F1 C18 F3 105.1(6) . . ?
F1 C18 F2 105.5(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
