# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_lzj037
_database_code_depnum_ccdc_archive 'CCDC 2284569'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-07-26 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O3 S'
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.5669(3)
_cell_length_b                   8.0829(2)
_cell_length_c                   11.7127(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.0000(10)
_cell_angle_gamma                90
_cell_volume                     920.87(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      4.10
_cell_measurement_theta_max      68.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.728
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14671
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.100
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_full        67.679
_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 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3277
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.942

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0298P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3277
_refine_ls_number_parameters     239
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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
S S 0.68029(4) 0.63723(6) 0.76519(4) 0.01714(12) Uani 1 1 d . . . . .
O1 O 0.46093(15) 0.6377(3) 0.47498(13) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.72637(16) 0.7299(2) 0.68291(15) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.72069(16) 0.6969(2) 0.89023(15) 0.0262(4) Uani 1 1 d . . . . .
N N 0.37778(19) 0.4263(2) 0.55746(17) 0.0215(4) Uani 1 1 d D . . . .
H1N H 0.354(3) 0.360(4) 0.493(2) 0.038(8) Uiso 1 1 d D . . . .
C1 C 0.4430(2) 0.5712(3) 0.5609(2) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.49124(17) 0.6382(3) 0.69538(16) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.4349(2) 0.5130(3) 0.75727(19) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.4358(2) 0.5072(3) 0.87560(19) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.478066 0.592778 0.933646 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3736(2) 0.3738(3) 0.9079(2) 0.0256(5) Uani 1 1 d . . . . .
H5 H 0.372298 0.368220 0.988503 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3133(2) 0.2488(3) 0.8228(2) 0.0286(5) Uani 1 1 d . . . . .
H6 H 0.273336 0.157170 0.847155 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3096(2) 0.2536(3) 0.7024(2) 0.0270(5) Uani 1 1 d . . . . .
H7 H 0.267156 0.168386 0.644150 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3708(2) 0.3885(3) 0.67198(19) 0.0192(4) Uani 1 1 d . . . . .
C11 C 0.7369(2) 0.4246(3) 0.7704(2) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.676993 0.367962 0.691937 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8848(2) 0.4274(3) 0.7771(2) 0.0273(5) Uani 1 1 d . . . . .
H12A H 0.887294 0.484743 0.703337 0.033 Uiso 1 1 calc R U . . .
H12B H 0.944353 0.489123 0.851851 0.033 Uiso 1 1 calc R U . . .
C13 C 0.9385(3) 0.2512(4) 0.7825(3) 0.0424(7) Uani 1 1 d . . . . .
H13A H 0.883306 0.193078 0.704383 0.051 Uiso 1 1 calc R U . . .
H13B H 1.034952 0.254823 0.789630 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9316(3) 0.1550(4) 0.8916(2) 0.0419(7) Uani 1 1 d . . . . .
H14A H 0.963117 0.040043 0.889866 0.050 Uiso 1 1 calc R U . . .
H14B H 0.993378 0.206786 0.970260 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7861(3) 0.1535(4) 0.8856(3) 0.0390(6) Uani 1 1 d . . . . .
H15A H 0.784241 0.095532 0.959383 0.047 Uiso 1 1 calc R U . . .
H15B H 0.726485 0.091636 0.811016 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7298(3) 0.3288(3) 0.8807(3) 0.0320(5) Uani 1 1 d . . . . .
H16A H 0.784021 0.387611 0.958745 0.038 Uiso 1 1 calc R U . . .
H16B H 0.633190 0.323264 0.872998 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4452(2) 0.8193(3) 0.7010(2) 0.0195(4) Uani 1 1 d . . . . .
H21A H 0.495831 0.864468 0.785204 0.023 Uiso 1 1 calc R U . . .
H21B H 0.467635 0.887988 0.641452 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2926(2) 0.8277(3) 0.6701(2) 0.0202(4) Uani 1 1 d . . . . .
C23 C 0.2413(3) 0.8236(3) 0.7633(2) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.303230 0.816779 0.847666 0.033 Uiso 1 1 calc R U . . .
C24 C 0.1007(3) 0.8292(4) 0.7340(3) 0.0370(6) Uani 1 1 d . . . . .
H24 H 0.067103 0.825272 0.798290 0.044 Uiso 1 1 calc R U . . .
C25 C 0.0099(3) 0.8405(4) 0.6122(3) 0.0445(7) Uani 1 1 d . . . . .
H25 H -0.086324 0.843979 0.592112 0.053 Uiso 1 1 calc R U . . .
C26 C 0.0597(3) 0.8467(5) 0.5192(3) 0.0458(7) Uani 1 1 d . . . . .
H26 H -0.002515 0.855823 0.435048 0.055 Uiso 1 1 calc R U . . .
C27 C 0.1994(2) 0.8397(4) 0.5482(2) 0.0306(5) Uani 1 1 d . . . . .
H27 H 0.232230 0.843182 0.483429 0.037 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
S O3 1.4392(16) . ?
S O2 1.4470(16) . ?
S C11 1.813(2) . ?
S C2 1.8393(17) . ?
O1 C1 1.219(3) . ?
N C1 1.352(3) . ?
N C8 1.405(3) . ?
C1 C2 1.552(3) . ?
C2 C3 1.498(3) . ?
C2 C21 1.552(3) . ?
C3 C4 1.383(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.396(3) . ?
C7 C8 1.383(3) . ?
C11 C12 1.533(3) . ?
C11 C16 1.534(3) . ?
C12 C13 1.526(4) . ?
C13 C14 1.522(4) . ?
C14 C15 1.511(4) . ?
C15 C16 1.529(4) . ?
C21 C22 1.510(3) . ?
C22 C27 1.385(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.389(4) . ?
C24 C25 1.377(4) . ?
C25 C26 1.383(4) . ?
C26 C27 1.381(4) . ?

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
O3 S O2 117.45(10) . . ?
O3 S C11 108.73(10) . . ?
O2 S C11 108.69(10) . . ?
O3 S C2 106.84(9) . . ?
O2 S C2 106.93(9) . . ?
C11 S C2 107.82(11) . . ?
C1 N C8 112.10(18) . . ?
O1 C1 N 126.8(2) . . ?
O1 C1 C2 126.1(2) . . ?
N C1 C2 107.09(18) . . ?
C3 C2 C1 102.74(18) . . ?
C3 C2 C21 115.25(16) . . ?
C1 C2 C21 112.84(17) . . ?
C3 C2 S 110.49(14) . . ?
C1 C2 S 108.59(12) . . ?
C21 C2 S 106.83(15) . . ?
C4 C3 C8 120.4(2) . . ?
C4 C3 C2 131.3(2) . . ?
C8 C3 C2 108.36(18) . . ?
C3 C4 C5 118.7(2) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C7 122.0(2) . . ?
C8 C7 C6 116.8(2) . . ?
C7 C8 C3 122.0(2) . . ?
C7 C8 N 128.4(2) . . ?
C3 C8 N 109.61(19) . . ?
C12 C11 C16 110.40(18) . . ?
C12 C11 S 107.69(16) . . ?
C16 C11 S 112.50(16) . . ?
C13 C12 C11 110.1(2) . . ?
C14 C13 C12 111.9(2) . . ?
C15 C14 C13 110.3(2) . . ?
C14 C15 C16 111.6(3) . . ?
C15 C16 C11 110.7(2) . . ?
C22 C21 C2 110.83(17) . . ?
C27 C22 C23 118.1(2) . . ?
C27 C22 C21 120.9(2) . . ?
C23 C22 C21 121.1(2) . . ?
C24 C23 C22 120.7(2) . . ?
C25 C24 C23 120.2(2) . . ?
C24 C25 C26 119.5(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C22 121.2(2) . . ?

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
C8 N C1 O1 -177.8(2) . . . . ?
C8 N C1 C2 2.2(2) . . . . ?
O1 C1 C2 C3 176.9(2) . . . . ?
N C1 C2 C3 -3.1(2) . . . . ?
O1 C1 C2 C21 52.2(3) . . . . ?
N C1 C2 C21 -127.79(18) . . . . ?
O1 C1 C2 S -66.0(3) . . . . ?
N C1 C2 S 113.98(16) . . . . ?
O3 S C2 C3 -66.93(17) . . . . ?
O2 S C2 C3 166.51(15) . . . . ?
C11 S C2 C3 49.78(17) . . . . ?
O3 S C2 C1 -178.89(16) . . . . ?
O2 S C2 C1 54.55(18) . . . . ?
C11 S C2 C1 -62.17(17) . . . . ?
O3 S C2 C21 59.13(15) . . . . ?
O2 S C2 C21 -67.42(15) . . . . ?
C11 S C2 C21 175.85(13) . . . . ?
C1 C2 C3 C4 -175.8(2) . . . . ?
C21 C2 C3 C4 -52.6(3) . . . . ?
S C2 C3 C4 68.6(3) . . . . ?
C1 C2 C3 C8 2.9(2) . . . . ?
C21 C2 C3 C8 126.00(19) . . . . ?
S C2 C3 C8 -112.80(16) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C5 179.52(19) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C6 C7 C8 N -177.8(2) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
C2 C3 C8 C7 179.39(19) . . . . ?
C4 C3 C8 N 177.04(19) . . . . ?
C2 C3 C8 N -1.8(2) . . . . ?
C1 N C8 C7 178.4(2) . . . . ?
C1 N C8 C3 -0.3(2) . . . . ?
O3 S C11 C12 -87.06(15) . . . . ?
O2 S C11 C12 41.87(16) . . . . ?
C2 S C11 C12 157.45(13) . . . . ?
O3 S C11 C16 34.81(19) . . . . ?
O2 S C11 C16 163.75(16) . . . . ?
C2 S C11 C16 -80.67(17) . . . . ?
C16 C11 C12 C13 56.5(3) . . . . ?
S C11 C12 C13 179.68(17) . . . . ?
C11 C12 C13 C14 -57.1(3) . . . . ?
C12 C13 C14 C15 56.7(4) . . . . ?
C13 C14 C15 C16 -56.1(3) . . . . ?
C14 C15 C16 C11 56.6(3) . . . . ?
C12 C11 C16 C15 -56.4(3) . . . . ?
S C11 C16 C15 -176.76(17) . . . . ?
C3 C2 C21 C22 -45.3(2) . . . . ?
C1 C2 C21 C22 72.3(2) . . . . ?
S C2 C21 C22 -168.47(14) . . . . ?
C2 C21 C22 C27 -86.3(3) . . . . ?
C2 C21 C22 C23 93.6(2) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C21 C22 C23 C24 -179.2(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
C23 C22 C27 C26 -0.3(4) . . . . ?
C21 C22 C27 C26 179.7(3) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.035



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CDCl3, PE'
