# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_XSJ20220725
_database_code_depnum_ccdc_archive 'CCDC 2262177'
loop_
_audit_author_name
_audit_author_address
'lei wang'
;Yangzhou University
China
;
_audit_update_record             
;
2023-05-11 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O2 S'
_chemical_formula_sum            'C22 H23 N O2 S'
_chemical_formula_weight         365.47

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'
N N 0.0061 0.0033 '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                   16.6490(11)
_cell_length_b                   6.3815(5)
_cell_length_c                   18.6164(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.783(2)
_cell_angle_gamma                90
_cell_volume                     1967.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7916
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            26735
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3844
_reflns_number_gt                2635
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0508P)²+0.6429P] 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         3844
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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 -0.02240(12) 0.1804(4) 0.12172(11) 0.0529(5) Uani 1 1 d . . . . .
H1 H -0.0290 0.3186 0.1359 0.063 Uiso 1 1 calc R U . . .
C2 C -0.08627(13) 0.0723(4) 0.08682(12) 0.0595(6) Uani 1 1 d . . . . .
H2 H -0.1361 0.1384 0.0778 0.071 Uiso 1 1 calc R U . . .
C3 C -0.07788(13) -0.1324(4) 0.06493(11) 0.0545(6) Uani 1 1 d . . . . .
C4 C -0.14796(15) -0.2503(5) 0.02601(13) 0.0793(8) Uani 1 1 d . . . . .
H4A H -0.1789 -0.3153 0.0607 0.119 Uiso 1 1 calc R U . . .
H4B H -0.1279 -0.3560 -0.0042 0.119 Uiso 1 1 calc R U . . .
H4C H -0.1816 -0.1545 -0.0032 0.119 Uiso 1 1 calc R U . . .
C5 C -0.00361(14) -0.2257(4) 0.07938(12) 0.0587(6) Uani 1 1 d . . . . .
H5 H 0.0032 -0.3631 0.0645 0.070 Uiso 1 1 calc R U . . .
C6 C 0.06094(13) -0.1219(3) 0.11512(11) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.1103 -0.1895 0.1252 0.063 Uiso 1 1 calc R U . . .
C7 C 0.05181(11) 0.0825(3) 0.13572(10) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.14558(14) 0.0016(3) 0.30333(11) 0.0544(6) Uani 1 1 d . . . . .
H8A H 0.2004 -0.0452 0.2991 0.065 Uiso 1 1 calc R U . . .
H8B H 0.1082 -0.1062 0.2843 0.065 Uiso 1 1 calc R U . . .
C9 C 0.13341(12) 0.0539(4) 0.38145(11) 0.0516(5) Uani 1 1 d . . . . .
C10 C 0.11465(17) -0.1428(4) 0.42282(14) 0.0793(8) Uani 1 1 d . . . . .
H10A H 0.1120 -0.1085 0.4727 0.119 Uiso 1 1 calc R U . . .
H10B H 0.1564 -0.2448 0.4189 0.119 Uiso 1 1 calc R U . . .
H10C H 0.0638 -0.1994 0.4030 0.119 Uiso 1 1 calc R U . . .
C11 C 0.06723(12) 0.2160(4) 0.37305(11) 0.0548(6) Uani 1 1 d . . . . .
C12 C 0.01657(15) 0.2663(5) 0.42023(15) 0.0830(8) Uani 1 1 d . . . . .
H12A H -0.0227 0.3680 0.4088 0.100 Uiso 1 1 calc R U . . .
H12B H 0.0200 0.2001 0.4649 0.100 Uiso 1 1 calc R U . . .
C13 C 0.06640(16) 0.3136(4) 0.29993(12) 0.0736(7) Uani 1 1 d . . . . .
H13A H 0.0141 0.2959 0.2725 0.088 Uiso 1 1 calc R U . . .
H13B H 0.0787 0.4620 0.3038 0.088 Uiso 1 1 calc R U . . .
C14 C 0.21114(13) 0.1610(4) 0.41805(11) 0.0624(6) Uani 1 1 d . . . . .
H14A H 0.2562 0.0649 0.4179 0.075 Uiso 1 1 calc R U . . .
H14B H 0.2232 0.2840 0.3904 0.075 Uiso 1 1 calc R U . . .
C15 C 0.20182(13) 0.2234(4) 0.49280(13) 0.0663(7) Uani 1 1 d . . . . .
C16 C 0.18933(14) 0.2686(4) 0.55291(13) 0.0683(7) Uani 1 1 d . . . . .
C17 C 0.17081(13) 0.3183(4) 0.62476(12) 0.0616(6) Uani 1 1 d . . . . .
C18 C 0.19385(15) 0.5040(5) 0.65767(14) 0.0757(7) Uani 1 1 d . . . . .
H18 H 0.2221 0.6015 0.6329 0.091 Uiso 1 1 calc R U . . .
C19 C 0.17598(17) 0.5490(5) 0.72658(16) 0.0841(8) Uani 1 1 d . . . . .
H19 H 0.1922 0.6758 0.7480 0.101 Uiso 1 1 calc R U . . .
C20 C 0.13467(18) 0.4082(6) 0.76329(15) 0.0881(9) Uani 1 1 d . . . . .
H20 H 0.1233 0.4379 0.8101 0.106 Uiso 1 1 calc R U . . .
C21 C 0.10996(19) 0.2243(6) 0.73184(17) 0.0934(9) Uani 1 1 d . . . . .
H21 H 0.0806 0.1294 0.7567 0.112 Uiso 1 1 calc R U . . .
C22 C 0.12844(16) 0.1782(5) 0.66286(15) 0.0803(8) Uani 1 1 d . . . . .
H22 H 0.1121 0.0510 0.6419 0.096 Uiso 1 1 calc R U . . .
N1 N 0.12922(10) 0.2008(3) 0.26588(8) 0.0483(4) Uani 1 1 d . . . . .
O1 O 0.12345(10) 0.4355(2) 0.16225(8) 0.0676(5) Uani 1 1 d . . . . .
O2 O 0.20648(8) 0.1148(3) 0.16446(8) 0.0627(4) Uani 1 1 d . . . . .
S1 S 0.13439(3) 0.21991(9) 0.18005(3) 0.04929(19) 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 1.374(3) . ?
C1 C7 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.374(3) . ?
C3 C4 1.511(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 S1 1.764(2) . ?
C8 N1 1.463(3) . ?
C8 C9 1.525(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.508(3) . ?
C9 C10 1.522(3) . ?
C9 C14 1.558(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.317(3) . ?
C11 C13 1.496(3) . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 N1 1.465(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.471(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.194(3) . ?
C16 C17 1.438(3) . ?
C17 C18 1.371(4) . ?
C17 C22 1.379(3) . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.357(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 S1 1.6134(17) . ?
O1 S1 1.4225(16) . ?
O2 S1 1.4301(15) . ?

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 C7 119.7(2) . . ?
C2 C1 H1 120.2 . . ?
C7 C1 H1 120.2 . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C5 C3 C2 117.9(2) . . ?
C5 C3 C4 121.0(2) . . ?
C2 C3 C4 121.1(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 122.0(2) . . ?
C3 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C1 119.85(19) . . ?
C6 C7 S1 120.02(15) . . ?
C1 C7 S1 120.13(16) . . ?
N1 C8 C9 103.16(17) . . ?
N1 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
N1 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C11 C9 C10 115.68(19) . . ?
C11 C9 C8 102.56(16) . . ?
C10 C9 C8 110.83(19) . . ?
C11 C9 C14 108.08(19) . . ?
C10 C9 C14 110.14(19) . . ?
C8 C9 C14 109.19(17) . . ?
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 . . ?
C12 C11 C13 123.9(2) . . ?
C12 C11 C9 127.5(2) . . ?
C13 C11 C9 108.64(18) . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
N1 C13 C11 104.34(18) . . ?
N1 C13 H13A 110.9 . . ?
C11 C13 H13A 110.9 . . ?
N1 C13 H13B 110.9 . . ?
C11 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C15 C14 C9 111.73(18) . . ?
C15 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 175.8(2) . . ?
C15 C16 C17 177.4(3) . . ?
C18 C17 C22 117.7(2) . . ?
C18 C17 C16 122.0(2) . . ?
C22 C17 C16 120.3(3) . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.9(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C8 N1 C13 109.13(17) . . ?
C8 N1 S1 120.78(14) . . ?
C13 N1 S1 120.20(14) . . ?
O1 S1 O2 119.79(10) . . ?
O1 S1 N1 106.58(9) . . ?
O2 S1 N1 107.17(9) . . ?
O1 S1 C7 107.24(10) . . ?
O2 S1 C7 107.59(10) . . ?
N1 S1 C7 108.00(9) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.037

