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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_a
_audit_block_doi                 10.5517/ccdc.csd.cc29856z
_database_code_depnum_ccdc_archive 'CCDC 2123010'
loop_
_audit_author_name
_audit_author_address
'huang xin'
;shandong university of technology
China
;
_audit_update_record             
;
2021-11-19 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2021-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Cl N O2 S'
_chemical_formula_sum            'C20 H20 Cl N O2 S'
_chemical_formula_weight         373.88
_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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   9.4606(5)
_cell_length_b                   15.2394(8)
_cell_length_c                   13.4503(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.685(3)
_cell_angle_gamma                90
_cell_volume                     1836.98(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6070
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      58.983
_cell_measurement_theta_min      3.018
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1197 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.7457.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14195
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.251
_diffrn_reflns_theta_min         3.934
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2865
_reflns_number_total             3942
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.123
_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)+(0.0622P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          ?
_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:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
Cl1 Cl 0.46181(6) 0.06734(4) 0.08232(4) 0.0588(2) Uani 1 1 d . . . . .
S1 S 0.31113(5) 0.30655(3) 0.45331(4) 0.03224(16) Uani 1 1 d . . . . .
O1 O 0.65815(15) 0.15931(10) 0.58965(10) 0.0511(4) Uani 1 1 d . . . . .
O2 O 0.49611(17) 0.55967(9) 0.71266(13) 0.0612(5) Uani 1 1 d . . . . .
N1 N 0.51612(15) 0.37817(10) 0.69119(12) 0.0347(4) Uani 1 1 d . . . . .
C1 C 0.50801(18) 0.22647(13) 0.32422(14) 0.0331(4) Uani 1 1 d . . . . .
H1 H 0.502813 0.287733 0.335654 0.040 Uiso 1 1 calc R U . . .
C2 C 0.48859(19) 0.19581(13) 0.22462(15) 0.0367(5) Uani 1 1 d . . . . .
H2 H 0.472039 0.235499 0.167561 0.044 Uiso 1 1 calc R U . . .
C3 C 0.49349(19) 0.10655(14) 0.20866(15) 0.0369(5) Uani 1 1 d . . . . .
C4 C 0.5233(2) 0.04754(13) 0.29117(16) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.528356 -0.013673 0.279355 0.045 Uiso 1 1 calc R U . . .
C5 C 0.54553(18) 0.07972(12) 0.39083(15) 0.0329(5) Uani 1 1 d . . . . .
H5 H 0.568333 0.040139 0.448382 0.039 Uiso 1 1 calc R U . . .
C6 C 0.53523(17) 0.16871(12) 0.40865(14) 0.0284(4) Uani 1 1 d . . . . .
C7 C 0.56394(19) 0.19941(12) 0.51930(14) 0.0322(4) Uani 1 1 d . . . . .
C8 C 0.48386(18) 0.27471(12) 0.54262(14) 0.0296(4) Uani 1 1 d . . . . .
C9 C 0.55555(19) 0.31595(12) 0.63619(15) 0.0311(4) Uani 1 1 d . . . . .
H9 H 0.654596 0.295510 0.668375 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3706(2) 0.42014(13) 0.66796(18) 0.0451(6) Uani 1 1 d . . . . .
H10A H 0.338271 0.419533 0.731055 0.054 Uiso 1 1 calc R U . . .
H10B H 0.295619 0.387973 0.611155 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3834(2) 0.51295(15) 0.63456(18) 0.0598(7) Uani 1 1 d . . . . .
H11A H 0.407555 0.512780 0.568181 0.072 Uiso 1 1 calc R U . . .
H11B H 0.286405 0.543082 0.621430 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6382(2) 0.51750(13) 0.73644(17) 0.0485(6) Uani 1 1 d . . . . .
H12A H 0.713396 0.550969 0.791691 0.058 Uiso 1 1 calc R U . . .
H12B H 0.669734 0.516639 0.673032 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6301(2) 0.42558(12) 0.77329(15) 0.0365(5) Uani 1 1 d . . . . .
H13A H 0.728016 0.396326 0.787655 0.044 Uiso 1 1 calc R U . . .
H13B H 0.603881 0.426063 0.838894 0.044 Uiso 1 1 calc R U . . .
C14 C 0.18229(18) 0.23337(12) 0.48098(13) 0.0279(4) Uani 1 1 d . . . . .
C15 C 0.2262(2) 0.16755(13) 0.55609(14) 0.0358(5) Uani 1 1 d . . . . .
H15 H 0.328754 0.160555 0.595229 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1211(2) 0.11215(14) 0.57406(16) 0.0444(5) Uani 1 1 d . . . . .
H16 H 0.151356 0.067353 0.625666 0.053 Uiso 1 1 calc R U . . .
C17 C -0.0271(2) 0.12198(15) 0.51725(18) 0.0496(6) Uani 1 1 d . . . . .
H17 H -0.099370 0.084098 0.529693 0.059 Uiso 1 1 calc R U . . .
C18 C -0.0710(2) 0.18684(14) 0.44212(17) 0.0442(6) Uani 1 1 d . . . . .
H18 H -0.173788 0.192569 0.403018 0.053 Uiso 1 1 calc R U . . .
C19 C 0.03110(18) 0.24409(13) 0.42202(14) 0.0333(5) Uani 1 1 d . . . . .
C20 C -0.0188(2) 0.31477(13) 0.34105(16) 0.0449(6) Uani 1 1 d . . . . .
H20A H -0.002701 0.372226 0.375579 0.067 Uiso 1 1 calc R U . . .
H20B H -0.125099 0.307252 0.302326 0.067 Uiso 1 1 calc R U . . .
H20C H 0.038790 0.311102 0.292214 0.067 Uiso 1 1 calc R U . . .


_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
Cl1 C3 1.734(2) . ?
S1 C8 1.7582(16) . ?
S1 C14 1.7772(18) . ?
O1 C7 1.2339(19) . ?
O2 C11 1.425(2) . ?
O2 C12 1.430(2) . ?
N1 C9 1.328(2) . ?
N1 C10 1.458(2) . ?
N1 C13 1.463(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(3) . ?
C1 C6 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.500(2) . ?
C7 C8 1.463(2) . ?
C8 C9 1.375(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.501(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.496(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.389(2) . ?
C14 C19 1.405(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 C20 1.497(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C8 S1 C14 103.50(8) . . ?
C11 O2 C12 111.60(16) . . ?
C9 N1 C10 127.48(15) . . ?
C9 N1 C13 120.18(15) . . ?
C10 N1 C13 111.21(15) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.76(18) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.08(18) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 Cl1 119.21(16) . . ?
C2 C3 C4 121.57(19) . . ?
C4 C3 Cl1 119.22(17) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.45(19) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.25(18) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 122.61(17) . . ?
C5 C6 C1 118.81(17) . . ?
C5 C6 C7 118.45(16) . . ?
O1 C7 C6 117.60(16) . . ?
O1 C7 C8 121.35(16) . . ?
C8 C7 C6 121.05(15) . . ?
C7 C8 S1 120.11(13) . . ?
C9 C8 S1 125.24(15) . . ?
C9 C8 C7 114.65(15) . . ?
N1 C9 C8 133.79(17) . . ?
N1 C9 H9 113.1 . . ?
C8 C9 H9 113.1 . . ?
N1 C10 H10A 110.0 . . ?
N1 C10 H10B 110.0 . . ?
N1 C10 C11 108.45(17) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
O2 C11 C10 111.30(17) . . ?
O2 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 C13 110.52(17) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
N1 C13 C12 108.42(15) . . ?
N1 C13 H13A 110.0 . . ?
N1 C13 H13B 110.0 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C15 C14 S1 122.68(13) . . ?
C15 C14 C19 120.50(17) . . ?
C19 C14 S1 116.82(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.22(18) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.02(19) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.81(18) . . ?
C19 C18 H18 119.1 . . ?
C14 C19 C20 121.40(17) . . ?
C18 C19 C14 117.52(17) . . ?
C18 C19 C20 121.08(17) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Cl1 C3 C4 C5 -178.83(13) . . . . ?
S1 C8 C9 N1 9.7(3) . . . . ?
S1 C14 C15 C16 -179.71(15) . . . . ?
S1 C14 C19 C18 179.46(14) . . . . ?
S1 C14 C19 C20 -0.9(2) . . . . ?
O1 C7 C8 S1 -157.90(16) . . . . ?
O1 C7 C8 C9 22.8(3) . . . . ?
O2 C12 C13 N1 58.1(2) . . . . ?
N1 C10 C11 O2 -56.6(2) . . . . ?
C1 C2 C3 Cl1 177.50(14) . . . . ?
C1 C2 C3 C4 -2.6(3) . . . . ?
C1 C6 C7 O1 -141.87(18) . . . . ?
C1 C6 C7 C8 37.6(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C1 C6 C7 177.16(16) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 -2.7(3) . . . . ?
C4 C5 C6 C7 -178.71(15) . . . . ?
C5 C6 C7 O1 34.0(2) . . . . ?
C5 C6 C7 C8 -146.55(17) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C7 C8 S1 22.6(2) . . . . ?
C6 C7 C8 C9 -156.67(17) . . . . ?
C7 C8 C9 N1 -171.1(2) . . . . ?
C8 S1 C14 C15 -1.86(18) . . . . ?
C8 S1 C14 C19 178.83(14) . . . . ?
C9 N1 C10 C11 -109.4(2) . . . . ?
C9 N1 C13 C12 109.4(2) . . . . ?
C10 N1 C9 C8 3.8(3) . . . . ?
C10 N1 C13 C12 -59.3(2) . . . . ?
C11 O2 C12 C13 -58.2(2) . . . . ?
C12 O2 C11 C10 57.6(3) . . . . ?
C13 N1 C9 C8 -162.89(19) . . . . ?
C13 N1 C10 C11 58.3(2) . . . . ?
C14 S1 C8 C7 81.29(16) . . . . ?
C14 S1 C8 C9 -99.47(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C15 C14 C19 C20 179.74(17) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
C17 C18 C19 C20 -179.27(19) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
