# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
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data_230427_wq_xgd_zlz_0m
_database_code_depnum_ccdc_archive 'CCDC 2322228'
loop_
_audit_author_name
_audit_author_address
'lingzi zhao' 'Northwestern polytechnical university'
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 O3 S'
_chemical_formula_sum            'C20 H24 O3 S'
_chemical_formula_weight         344.45
_chemical_absolute_configuration ad
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.243(2)
_cell_length_b                   8.030(3)
_cell_length_c                   19.073(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.875(10)
_cell_angle_gamma                90
_cell_volume                     952.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5107
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.6853.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5375
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.186
_diffrn_reflns_theta_max         25.186
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      193.0
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                2746
_reflns_number_total             3180
_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 V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 956 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0922
_refine_ls_restrained_S_all      1.121
_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)+(0.1295P)²+2.0004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2420
_refine_ls_wR_factor_ref         0.2547
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2457(3) 0.5018(3) -0.01651(10) 0.0285(5) Uani 1 1 d . . . . .
O2 O 0.2523(13) 0.6538(8) -0.0569(4) 0.0385(17) Uani 1 1 d . . . . .
O1 O 0.2379(13) 0.3468(9) -0.0564(4) 0.0415(19) Uani 1 1 d . . . . .
O004 O 0.3842(10) 0.5282(10) 0.5841(3) 0.0408(18) Uani 1 1 d . . . . .
C2 C 0.3581(14) 0.4569(11) 0.1159(6) 0.046(3) Uani 1 1 d . . . . .
H2A H 0.450973 0.489887 0.158274 0.055 Uiso 1 1 calc R U . . .
H2B H 0.335390 0.334945 0.117508 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6468(14) 0.4542(11) 0.6803(4) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.4627(11) 0.5023(16) 0.0514(4) 0.0339(16) Uani 1 1 d . . . . .
H1A H 0.573709 0.419492 0.041395 0.041 Uiso 1 1 calc R U . . .
H1B H 0.530187 0.613707 0.056161 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1406(13) 0.5479(10) 0.1144(4) 0.031(2) Uani 1 1 d . . . . .
H3 H 0.170544 0.670252 0.116737 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0341(11) 0.5091(15) 0.0408(3) 0.0282(15) Uani 1 1 d . . . . .
H4A H -0.070966 0.596932 0.025499 0.034 Uiso 1 1 calc R U . . .
H4B H -0.041834 0.400865 0.040726 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9142(17) 0.5220(18) 0.7748(5) 0.053(3) Uani 1 1 d . . . . .
H17 H 1.058075 0.549944 0.790639 0.064 Uiso 1 1 calc R U . . .
C16 C 0.8564(16) 0.502(2) 0.7014(5) 0.054(2) Uani 1 1 d . . . . .
H16 H 0.958181 0.520249 0.667936 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3762(16) 0.4154(15) 0.4642(5) 0.046(2) Uani 1 1 d . . . . .
H10 H 0.503406 0.352384 0.475224 0.055 Uiso 1 1 calc R U . . .
C5 C -0.0045(12) 0.5061(18) 0.1727(4) 0.0379(18) Uani 1 1 d . . . . .
H5A H -0.057048 0.390347 0.165955 0.045 Uiso 1 1 calc R U . . .
H5B H -0.131174 0.580691 0.168205 0.045 Uiso 1 1 calc R U . . .
C14 C 0.5807(17) 0.4322(15) 0.6009(5) 0.048(3) Uani 1 1 d . . . . .
H14A H 0.696458 0.473027 0.572942 0.058 Uiso 1 1 calc R U . . .
H14B H 0.555026 0.313095 0.589850 0.058 Uiso 1 1 calc R U . . .
C9 C 0.2704(18) 0.4093(14) 0.3952(5) 0.045(2) Uani 1 1 d . . . . .
H9 H 0.329784 0.345232 0.359703 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0029(16) 0.5987(15) 0.4316(5) 0.046(3) Uani 1 1 d . . . . .
H13 H -0.120903 0.665254 0.420186 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0778(14) 0.498(2) 0.3793(4) 0.044(2) Uani 1 1 d . . . . .
C12 C 0.1037(16) 0.6062(15) 0.5014(5) 0.044(2) Uani 1 1 d . . . . .
H12 H 0.045555 0.670891 0.536874 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2935(13) 0.5133(19) 0.5151(4) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.1078(16) 0.5231(17) 0.2478(4) 0.047(3) Uani 1 1 d . . . . .
H6A H 0.230618 0.444784 0.252888 0.057 Uiso 1 1 calc R U . . .
H6B H 0.166250 0.637342 0.253698 0.057 Uiso 1 1 calc R U . . .
C7 C -0.0349(16) 0.490(2) 0.3051(4) 0.052(3) Uani 1 1 d . . . . .
H7A H -0.099355 0.377846 0.297774 0.062 Uiso 1 1 calc R U . . .
H7B H -0.153621 0.571925 0.301514 0.062 Uiso 1 1 calc R U . . .
C18 C 0.7701(17) 0.502(2) 0.8215(4) 0.054(3) Uani 1 1 d . . . . .
H18 H 0.811691 0.521117 0.869887 0.065 Uiso 1 1 calc R U . . .
C19 C 0.5572(19) 0.4543(15) 0.8009(5) 0.054(3) Uani 1 1 d . . . . .
H19 H 0.457362 0.434059 0.834878 0.065 Uiso 1 1 calc R U . . .
C20 C 0.4962(18) 0.4370(18) 0.7279(5) 0.056(3) Uani 1 1 d . . . . .
H20 H 0.350968 0.413456 0.712015 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
S1 O2 1.446(7) . ?
S1 O1 1.457(7) . ?
S1 C1 1.793(7) . ?
S1 C4 1.785(7) . ?
O004 C14 1.461(12) . ?
O004 C11 1.393(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.487(13) . ?
C2 C3 1.540(11) . ?
C15 C16 1.390(13) . ?
C15 C14 1.545(12) . ?
C15 C20 1.367(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C4 1.535(10) . ?
C3 C5 1.529(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.425(13) . ?
C17 C18 1.327(15) . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.422(13) . ?
C10 C11 1.384(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.547(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C8 1.407(15) . ?
C13 H13 0.9500 . ?
C13 C8 1.396(16) . ?
C13 C12 1.423(13) . ?
C8 C7 1.527(10) . ?
C12 H12 0.9500 . ?
C12 C11 1.406(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.492(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C19 1.407(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.420(14) . ?
C20 H20 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
O2 S1 O1 116.4(3) . . ?
O2 S1 C1 109.2(5) . . ?
O2 S1 C4 110.7(5) . . ?
O1 S1 C1 111.6(5) . . ?
O1 S1 C4 110.7(5) . . ?
C4 S1 C1 96.4(3) . . ?
C11 O004 C14 115.4(8) . . ?
H2A C2 H2B 108.4 . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C1 C2 C3 108.5(8) . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C16 C15 C14 118.8(8) . . ?
C20 C15 C16 121.3(8) . . ?
C20 C15 C14 119.8(8) . . ?
S1 C1 H1A 111.0 . . ?
S1 C1 H1B 111.0 . . ?
C2 C1 S1 103.8(6) . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C2 C3 H3 107.7 . . ?
C4 C3 C2 103.5(7) . . ?
C4 C3 H3 107.7 . . ?
C5 C3 C2 117.3(7) . . ?
C5 C3 H3 107.7 . . ?
C5 C3 C4 112.5(6) . . ?
S1 C4 H4A 110.5 . . ?
S1 C4 H4B 110.5 . . ?
C3 C4 S1 106.4(5) . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.6 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C18 C17 C16 121.0(9) . . ?
C15 C16 C17 118.0(9) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C11 C10 C9 119.9(9) . . ?
C3 C5 H5A 108.8 . . ?
C3 C5 H5B 108.8 . . ?
C3 C5 C6 113.8(7) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
O004 C14 C15 107.7(7) . . ?
O004 C14 H14A 110.2 . . ?
O004 C14 H14B 110.2 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.2(9) . . ?
C8 C9 H9 119.9 . . ?
C8 C13 H13 118.5 . . ?
C8 C13 C12 123.0(9) . . ?
C12 C13 H13 118.5 . . ?
C9 C8 C7 119.7(10) . . ?
C13 C8 C9 118.1(8) . . ?
C13 C8 C7 122.1(10) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 C13 116.8(9) . . ?
C11 C12 H12 121.6 . . ?
O004 C11 C12 113.6(9) . . ?
C10 C11 O004 124.5(10) . . ?
C10 C11 C12 121.9(8) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C5 114.3(8) . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 C8 114.5(8) . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(9) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 121.0 . . ?
C18 C19 C20 117.9(9) . . ?
C20 C19 H19 121.0 . . ?
C15 C20 C19 119.9(10) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?

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
O2 S1 C1 C2 131.2(7) . . . . ?
O2 S1 C4 C3 -102.0(7) . . . . ?
O1 S1 C1 C2 -98.8(7) . . . . ?
O1 S1 C4 C3 127.4(7) . . . . ?
C2 C3 C4 S1 -34.7(8) . . . . ?
C2 C3 C5 C6 53.0(14) . . . . ?
C1 S1 C4 C3 11.3(8) . . . . ?
C1 C2 C3 C4 49.8(10) . . . . ?
C1 C2 C3 C5 174.3(9) . . . . ?
C3 C2 C1 S1 -40.6(10) . . . . ?
C3 C5 C6 C7 177.4(11) . . . . ?
C4 S1 C1 C2 16.6(9) . . . . ?
C4 C3 C5 C6 172.8(10) . . . . ?
C17 C18 C19 C20 -4(2) . . . . ?
C16 C15 C14 O004 -128.9(12) . . . . ?
C16 C15 C20 C19 -5.3(19) . . . . ?
C16 C17 C18 C19 3(2) . . . . ?
C10 C9 C8 C13 3.9(18) . . . . ?
C10 C9 C8 C7 -179.7(11) . . . . ?
C5 C3 C4 S1 -162.3(8) . . . . ?
C5 C6 C7 C8 177.1(14) . . . . ?
C14 O004 C11 C10 0.4(16) . . . . ?
C14 O004 C11 C12 179.4(10) . . . . ?
C14 C15 C16 C17 179.8(12) . . . . ?
C14 C15 C20 C19 178.9(10) . . . . ?
C9 C10 C11 O004 -180.0(10) . . . . ?
C9 C10 C11 C12 1.1(19) . . . . ?
C9 C8 C7 C6 -50(2) . . . . ?
C13 C8 C7 C6 126.3(14) . . . . ?
C13 C12 C11 O004 179.3(10) . . . . ?
C13 C12 C11 C10 -1.7(18) . . . . ?
C8 C13 C12 C11 3.6(17) . . . . ?
C12 C13 C8 C9 -4.7(19) . . . . ?
C12 C13 C8 C7 179.1(12) . . . . ?
C11 O004 C14 C15 -175.9(9) . . . . ?
C11 C10 C9 C8 -2.2(17) . . . . ?
C18 C17 C16 C15 -3(2) . . . . ?
C18 C19 C20 C15 5.0(18) . . . . ?
C20 C15 C16 C17 4(2) . . . . ?
C20 C15 C14 O004 47.0(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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