# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_s_1159_20231023
_database_code_depnum_ccdc_archive 'CCDC 2305694'
loop_
_audit_author_name
_audit_author_address
lichengbo
;huaqiao university
China
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 O2 S'
_chemical_formula_sum            'C22 H20 O2 S'
_chemical_formula_weight         348.44
_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 0.0181 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'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.1661(7)
_cell_length_b                   5.6830(2)
_cell_length_c                   17.2863(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.5930(10)
_cell_angle_gamma                90
_cell_volume                     1768.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.073
_cell_measurement_theta_min      2.454
_shelx_estimated_absorpt_T_max   0.570
_shelx_estimated_absorpt_T_min   0.533
_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1234 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.7465.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18252
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.0555
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3132
_reflns_number_total             3191
_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       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+1.0093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.31954(2) 0.31287(6) 0.73623(2) 0.01800(12) Uani 1 1 d . . . . .
O1 O 0.33611(5) 0.4593(2) 0.80425(6) 0.0265(2) Uani 1 1 d . . . . .
O2 O 0.29855(5) 0.07138(19) 0.74692(6) 0.0261(2) Uani 1 1 d . . . . .
C1 C -0.00008(8) 0.7885(3) 0.90121(9) 0.0264(3) Uani 1 1 d . . . . .
H1 H -0.036313 0.815174 0.935146 0.032 Uiso 1 1 calc R U . . .
C2 C -0.00163(8) 0.5825(3) 0.85776(8) 0.0233(3) Uani 1 1 d . . . . .
H2 H -0.039087 0.468364 0.862088 0.028 Uiso 1 1 calc R U . . .
C3 C 0.05107(7) 0.5421(2) 0.80814(8) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.049071 0.401548 0.778192 0.023 Uiso 1 1 calc R U . . .
C4 C 0.10724(7) 0.7072(2) 0.80185(8) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.16723(7) 0.6691(2) 0.75375(8) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.201071 0.795464 0.751324 0.022 Uiso 1 1 calc R U . . .
C6 C 0.17921(7) 0.4773(2) 0.71338(8) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.145034 0.350328 0.711862 0.022 Uiso 1 1 calc R U . . .
C7 C 0.24546(7) 0.4554(2) 0.66992(8) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.262439 0.617591 0.658509 0.021 Uiso 1 1 calc R U . . .
C8 C 0.39733(7) 0.3154(2) 0.68466(8) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.44442(7) 0.5093(2) 0.69204(8) 0.0189(3) Uani 1 1 d . . . . .
H9 H 0.434493 0.639644 0.723480 0.023 Uiso 1 1 calc R U . . .
C10 C 0.50616(7) 0.5088(3) 0.65263(8) 0.0209(3) Uani 1 1 d . . . . .
H10 H 0.538155 0.641759 0.656496 0.025 Uiso 1 1 calc R U . . .
C11 C 0.52214(8) 0.3168(3) 0.60743(8) 0.0212(3) Uani 1 1 d . . . . .
C12 C 0.59066(8) 0.3177(3) 0.56698(9) 0.0300(4) Uani 1 1 d . . . . .
H12A H 0.598020 0.160879 0.545700 0.045 Uiso 1 1 calc R U . . .
H12B H 0.633913 0.359846 0.604480 0.045 Uiso 1 1 calc R U . . .
H12C H 0.584628 0.432938 0.524441 0.045 Uiso 1 1 calc R U . . .
C13 C 0.05459(9) 0.9549(3) 0.89482(9) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.055744 1.096582 0.924124 0.031 Uiso 1 1 calc R U . . .
C14 C 0.10772(8) 0.9139(3) 0.84541(8) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.145001 1.028768 0.841244 0.026 Uiso 1 1 calc R U . . .
C15 C 0.23391(7) 0.3199(2) 0.59411(8) 0.0170(3) Uani 1 1 d . . . . .
C16 C 0.19483(7) 0.1081(3) 0.58765(8) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.171960 0.052552 0.630507 0.024 Uiso 1 1 calc R U . . .
C17 C 0.18902(8) -0.0221(3) 0.51930(9) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.161461 -0.164670 0.515109 0.031 Uiso 1 1 calc R U . . .
C18 C 0.22355(8) 0.0560(3) 0.45685(9) 0.0274(3) Uani 1 1 d . . . . .
H18 H 0.220840 -0.035095 0.410488 0.033 Uiso 1 1 calc R U . . .
C19 C 0.26187(8) 0.2671(3) 0.46255(9) 0.0263(3) Uani 1 1 d . . . . .
H19 H 0.284892 0.321932 0.419701 0.032 Uiso 1 1 calc R U . . .
C20 C 0.26679(7) 0.3991(3) 0.53068(8) 0.0206(3) Uani 1 1 d . . . . .
H20 H 0.292812 0.544520 0.533970 0.025 Uiso 1 1 calc R U . . .
C21 C 0.41113(8) 0.1238(3) 0.63922(8) 0.0204(3) Uani 1 1 d . . . . .
H21 H 0.378173 -0.006690 0.634112 0.025 Uiso 1 1 calc R U . . .
C22 C 0.47382(8) 0.1254(3) 0.60125(8) 0.0228(3) Uani 1 1 d . . . . .
H22 H 0.483953 -0.006300 0.570517 0.027 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 O1 1.4395(11) . ?
S1 O2 1.4427(11) . ?
S1 C7 1.8367(14) . ?
S1 C8 1.7677(13) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(2) . ?
C1 C13 1.386(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3863(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.4008(19) . ?
C4 C5 1.4714(19) . ?
C4 C14 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.328(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.5056(17) . ?
C7 H7 1.0000 . ?
C7 C15 1.5104(18) . ?
C8 C9 1.3904(19) . ?
C8 C21 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.3871(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(2) . ?
C11 C12 1.5060(19) . ?
C11 C22 1.393(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 C20 1.3910(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C22 H22 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 118.40(6) . . ?
O1 S1 C7 108.16(6) . . ?
O1 S1 C8 108.20(6) . . ?
O2 S1 C7 108.37(6) . . ?
O2 S1 C8 108.34(6) . . ?
C8 S1 C7 104.50(6) . . ?
C2 C1 H1 120.2 . . ?
C13 C1 H1 120.2 . . ?
C13 C1 C2 119.70(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.50(14) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.47(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 123.15(12) . . ?
C14 C4 C3 118.34(13) . . ?
C14 C4 C5 118.47(12) . . ?
C4 C5 H5 116.5 . . ?
C6 C5 C4 127.08(13) . . ?
C6 C5 H5 116.5 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.84(12) . . ?
C7 C6 H6 119.1 . . ?
S1 C7 H7 108.1 . . ?
C6 C7 S1 107.05(9) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C15 116.52(11) . . ?
C15 C7 S1 108.85(9) . . ?
C15 C7 H7 108.1 . . ?
C9 C8 S1 118.90(10) . . ?
C21 C8 S1 119.76(10) . . ?
C21 C8 C9 121.32(12) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.76(13) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.21(13) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 120.22(13) . . ?
C22 C11 C10 118.56(13) . . ?
C22 C11 C12 121.22(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13 120.1 . . ?
C1 C13 C14 119.83(14) . . ?
C14 C13 H13 120.1 . . ?
C4 C14 H14 119.4 . . ?
C13 C14 C4 121.15(14) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C7 121.35(12) . . ?
C20 C15 C7 119.61(12) . . ?
C20 C15 C16 118.91(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.65(13) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.97(14) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.72(14) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.26(14) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.48(14) . . ?
C19 C20 H20 119.8 . . ?
C8 C21 H21 120.5 . . ?
C8 C21 C22 118.99(13) . . ?
C22 C21 H21 120.5 . . ?
C11 C22 H22 119.4 . . ?
C21 C22 C11 121.15(13) . . ?
C21 C22 H22 119.4 . . ?

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
S1 C7 C15 C16 77.47(13) . . . . ?
S1 C7 C15 C20 -98.35(13) . . . . ?
S1 C8 C9 C10 178.83(10) . . . . ?
S1 C8 C21 C22 -177.84(10) . . . . ?
O1 S1 C7 C6 -60.16(10) . . . . ?
O1 S1 C7 C15 173.11(8) . . . . ?
O1 S1 C8 C9 -26.57(13) . . . . ?
O1 S1 C8 C21 152.12(11) . . . . ?
O2 S1 C7 C6 69.37(10) . . . . ?
O2 S1 C7 C15 -57.37(10) . . . . ?
O2 S1 C8 C9 -156.11(11) . . . . ?
O2 S1 C8 C21 22.58(13) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C13 C14 C4 -0.1(2) . . . . ?
C2 C1 C13 C14 -0.4(2) . . . . ?
C2 C3 C4 C5 176.42(13) . . . . ?
C2 C3 C4 C14 -1.3(2) . . . . ?
C3 C4 C5 C6 -3.2(2) . . . . ?
C3 C4 C14 C13 0.9(2) . . . . ?
C4 C5 C6 C7 -176.46(12) . . . . ?
C5 C4 C14 C13 -176.91(12) . . . . ?
C5 C6 C7 S1 92.59(14) . . . . ?
C5 C6 C7 C15 -145.36(14) . . . . ?
C6 C7 C15 C16 -43.62(18) . . . . ?
C6 C7 C15 C20 140.55(13) . . . . ?
C7 S1 C8 C9 88.51(12) . . . . ?
C7 S1 C8 C21 -92.80(12) . . . . ?
C7 C15 C16 C17 -175.59(12) . . . . ?
C7 C15 C20 C19 174.77(12) . . . . ?
C8 S1 C7 C6 -175.27(9) . . . . ?
C8 S1 C7 C15 58.00(10) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C8 C21 C22 C11 -0.8(2) . . . . ?
C9 C8 C21 C22 0.8(2) . . . . ?
C9 C10 C11 C12 -178.31(13) . . . . ?
C9 C10 C11 C22 1.2(2) . . . . ?
C10 C11 C22 C21 -0.2(2) . . . . ?
C12 C11 C22 C21 179.32(13) . . . . ?
C13 C1 C2 C3 0.0(2) . . . . ?
C14 C4 C5 C6 174.51(14) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C16 C15 C20 C19 -1.1(2) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C21 C8 C9 C10 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
