# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_190302f
_database_code_depnum_ccdc_archive 'CCDC 2286937'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2024-04-22 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O3 S'
_chemical_formula_weight         388.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.0326(14)
_cell_length_b                   14.2112(13)
_cell_length_c                   8.6778(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.655(2)
_cell_angle_gamma                90.00
_cell_volume                     1967.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2083
_cell_measurement_theta_min      2.553
_cell_measurement_theta_max      25.199

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_T_max  0.9636
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9630
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3476
_reflns_number_gt                1894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0409P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3476
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15277(5) 0.45786(5) 0.12625(8) 0.0472(2) Uani 1 1 d . . .
O1 O 0.21756(11) 0.66086(12) 0.21986(19) 0.0433(5) Uani 1 1 d . . .
O2 O 0.21680(12) 0.46526(13) 0.2526(2) 0.0565(6) Uani 1 1 d . . .
C3 C 0.12050(17) 0.74565(18) 0.0664(3) 0.0372(7) Uani 1 1 d . . .
O3 O 0.08045(13) 0.40010(13) 0.1433(2) 0.0628(6) Uani 1 1 d . . .
C10 C 0.29720(17) 0.78521(19) 0.3482(3) 0.0418(7) Uani 1 1 d . . .
H10 H 0.3029 0.8502 0.3566 0.050 Uiso 1 1 calc R . .
C23 C 0.28116(19) 0.44063(18) -0.0547(3) 0.0452(8) Uani 1 1 d . . .
H23 H 0.3113 0.4781 0.0189 0.054 Uiso 1 1 calc R . .
C2 C 0.14862(17) 0.65179(18) 0.1137(3) 0.0397(7) Uani 1 1 d . . .
C4 C 0.05572(18) 0.7753(2) -0.0411(3) 0.0460(8) Uani 1 1 d . . .
H4 H 0.0201 0.7324 -0.0953 0.055 Uiso 1 1 calc R . .
C18 C 0.19947(18) 0.41531(17) -0.0352(3) 0.0407(7) Uani 1 1 d . . .
C9 C 0.23464(17) 0.75723(18) 0.2465(3) 0.0378(7) Uani 1 1 d . . .
C11 C 0.35812(17) 0.7326(2) 0.4483(3) 0.0408(7) Uani 1 1 d . . .
C12 C 0.41778(18) 0.7817(2) 0.5441(3) 0.0519(8) Uani 1 1 d . . .
H12 H 0.4177 0.8471 0.5412 0.062 Uiso 1 1 calc R . .
C7 C 0.16369(19) 0.90607(19) 0.1225(3) 0.0478(8) Uani 1 1 d . . .
H7 H 0.1992 0.9492 0.1765 0.057 Uiso 1 1 calc R . .
C22 C 0.3180(2) 0.41048(19) -0.1828(3) 0.0517(8) Uani 1 1 d . . .
H22 H 0.3730 0.4275 -0.1943 0.062 Uiso 1 1 calc R . .
C5 C 0.04645(19) 0.8707(2) -0.0642(3) 0.0519(8) Uani 1 1 d . . .
H5 H 0.0036 0.8926 -0.1352 0.062 Uiso 1 1 calc R . .
C20 C 0.1934(2) 0.3294(2) -0.2732(4) 0.0579(9) Uani 1 1 d . . .
H20 H 0.1635 0.2913 -0.3461 0.070 Uiso 1 1 calc R . .
C16 C 0.36175(18) 0.6342(2) 0.4559(3) 0.0476(8) Uani 1 1 d . . .
H16 H 0.3235 0.5986 0.3929 0.057 Uiso 1 1 calc R . .
C6 C 0.09962(19) 0.9351(2) 0.0162(3) 0.0522(8) Uani 1 1 d . . .
H6 H 0.0917 0.9991 -0.0024 0.063 Uiso 1 1 calc R . .
C8 C 0.17342(17) 0.80905(18) 0.1465(3) 0.0366(7) Uani 1 1 d . . .
C15 C 0.42094(19) 0.5897(2) 0.5552(3) 0.0539(8) Uani 1 1 d . . .
H15 H 0.4216 0.5243 0.5584 0.065 Uiso 1 1 calc R . .
C14 C 0.47957(19) 0.6391(2) 0.6506(3) 0.0547(8) Uani 1 1 d . . .
C21 C 0.2739(2) 0.3549(2) -0.2955(3) 0.0507(8) Uani 1 1 d . . .
C1 C 0.11714(17) 0.56781(18) 0.0671(3) 0.0447(8) Uani 1 1 d . . .
H1 H 0.0706 0.5691 -0.0058 0.054 Uiso 1 1 calc R . .
C19 C 0.1558(2) 0.35880(19) -0.1457(3) 0.0534(8) Uani 1 1 d . . .
H19 H 0.1011 0.3408 -0.1336 0.064 Uiso 1 1 calc R . .
C13 C 0.47696(19) 0.7361(2) 0.6429(3) 0.0590(9) Uani 1 1 d . . .
H13 H 0.5158 0.7712 0.7056 0.071 Uiso 1 1 calc R . .
C24 C 0.3130(2) 0.3250(2) -0.4385(3) 0.0773(11) Uani 1 1 d . . .
H24A H 0.3105 0.2577 -0.4477 0.116 Uiso 1 1 calc R . .
H24B H 0.3704 0.3451 -0.4309 0.116 Uiso 1 1 calc R . .
H24C H 0.2829 0.3530 -0.5280 0.116 Uiso 1 1 calc R . .
C17 C 0.5439(2) 0.5893(3) 0.7626(4) 0.0842(12) Uani 1 1 d . . .
H17A H 0.5993 0.6073 0.7410 0.126 Uiso 1 1 calc R . .
H17B H 0.5375 0.5224 0.7506 0.126 Uiso 1 1 calc R . .
H17C H 0.5355 0.6067 0.8668 0.126 Uiso 1 1 calc R . .


_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 1.4302(18) . ?
S1 O3 1.440(2) . ?
S1 C1 1.724(3) . ?
S1 C18 1.759(3) . ?
O1 C2 1.373(3) . ?
O1 C9 1.411(3) . ?
C3 C8 1.378(3) . ?
C3 C4 1.392(3) . ?
C3 C2 1.454(3) . ?
C10 C9 1.330(3) . ?
C10 C11 1.449(3) . ?
C23 C22 1.377(4) . ?
C23 C18 1.385(4) . ?
C2 C1 1.343(3) . ?
C4 C5 1.376(4) . ?
C18 C19 1.386(3) . ?
C9 C8 1.446(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.400(4) . ?
C12 C13 1.377(4) . ?
C7 C6 1.375(3) . ?
C7 C8 1.401(3) . ?
C22 C21 1.394(4) . ?
C5 C6 1.390(4) . ?
C20 C21 1.373(4) . ?
C20 C19 1.376(4) . ?
C16 C15 1.372(3) . ?
C15 C14 1.382(4) . ?
C14 C13 1.380(4) . ?
C14 C17 1.520(4) . ?
C21 C24 1.504(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
O2 S1 O3 119.18(12) . . ?
O2 S1 C1 110.69(12) . . ?
O3 S1 C1 107.49(13) . . ?
O2 S1 C18 107.82(13) . . ?
O3 S1 C18 107.22(13) . . ?
C1 S1 C18 103.24(12) . . ?
C2 O1 C9 109.36(19) . . ?
C8 C3 C4 121.5(2) . . ?
C8 C3 C2 107.4(2) . . ?
C4 C3 C2 131.1(2) . . ?
C9 C10 C11 131.5(3) . . ?
C22 C23 C18 120.2(3) . . ?
C1 C2 O1 122.6(2) . . ?
C1 C2 C3 129.3(2) . . ?
O1 C2 C3 108.1(2) . . ?
C5 C4 C3 117.3(3) . . ?
C23 C18 C19 119.0(3) . . ?
C23 C18 S1 119.4(2) . . ?
C19 C18 S1 121.6(2) . . ?
C10 C9 O1 121.4(2) . . ?
C10 C9 C8 132.0(3) . . ?
O1 C9 C8 106.6(2) . . ?
C12 C11 C16 116.7(3) . . ?
C12 C11 C10 118.8(3) . . ?
C16 C11 C10 124.5(3) . . ?
C13 C12 C11 121.8(3) . . ?
C6 C7 C8 117.4(3) . . ?
C23 C22 C21 121.0(3) . . ?
C4 C5 C6 121.5(3) . . ?
C21 C20 C19 121.7(3) . . ?
C15 C16 C11 120.9(3) . . ?
C7 C6 C5 121.3(3) . . ?
C3 C8 C7 121.0(2) . . ?
C3 C8 C9 108.5(2) . . ?
C7 C8 C9 130.5(3) . . ?
C16 C15 C14 122.0(3) . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 C17 120.8(3) . . ?
C15 C14 C17 121.7(3) . . ?
C20 C21 C22 117.9(3) . . ?
C20 C21 C24 121.0(3) . . ?
C22 C21 C24 121.0(3) . . ?
C2 C1 S1 127.7(2) . . ?
C20 C19 C18 120.1(3) . . ?
C12 C13 C14 121.0(3) . . ?

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
C9 O1 C2 C1 -179.2(2) . . . . ?
C9 O1 C2 C3 1.3(3) . . . . ?
C8 C3 C2 C1 -179.7(3) . . . . ?
C4 C3 C2 C1 -1.8(5) . . . . ?
C8 C3 C2 O1 -0.3(3) . . . . ?
C4 C3 C2 O1 177.6(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 -177.8(3) . . . . ?
C22 C23 C18 C19 0.5(4) . . . . ?
C22 C23 C18 S1 -177.96(19) . . . . ?
O2 S1 C18 C23 -33.6(2) . . . . ?
O3 S1 C18 C23 -163.1(2) . . . . ?
C1 S1 C18 C23 83.6(2) . . . . ?
O2 S1 C18 C19 148.0(2) . . . . ?
O3 S1 C18 C19 18.6(3) . . . . ?
C1 S1 C18 C19 -94.8(2) . . . . ?
C11 C10 C9 O1 0.0(4) . . . . ?
C11 C10 C9 C8 179.8(3) . . . . ?
C2 O1 C9 C10 178.1(2) . . . . ?
C2 O1 C9 C8 -1.7(3) . . . . ?
C9 C10 C11 C12 179.7(3) . . . . ?
C9 C10 C11 C16 -0.1(5) . . . . ?
C16 C11 C12 C13 -0.7(4) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C18 C23 C22 C21 0.5(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
C10 C11 C16 C15 -179.3(2) . . . . ?
C8 C7 C6 C5 0.2(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C4 C3 C8 C7 0.1(4) . . . . ?
C2 C3 C8 C7 178.3(2) . . . . ?
C4 C3 C8 C9 -178.9(2) . . . . ?
C2 C3 C8 C9 -0.8(3) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C6 C7 C8 C9 178.7(3) . . . . ?
C10 C9 C8 C3 -178.3(3) . . . . ?
O1 C9 C8 C3 1.5(3) . . . . ?
C10 C9 C8 C7 2.8(5) . . . . ?
O1 C9 C8 C7 -177.4(3) . . . . ?
C11 C16 C15 C14 -0.5(4) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C16 C15 C14 C17 178.8(3) . . . . ?
C19 C20 C21 C22 1.3(4) . . . . ?
C19 C20 C21 C24 -177.8(3) . . . . ?
C23 C22 C21 C20 -1.4(4) . . . . ?
C23 C22 C21 C24 177.7(3) . . . . ?
O1 C2 C1 S1 0.5(4) . . . . ?
C3 C2 C1 S1 179.8(2) . . . . ?
O2 S1 C1 C2 7.9(3) . . . . ?
O3 S1 C1 C2 139.6(3) . . . . ?
C18 S1 C1 C2 -107.3(3) . . . . ?
C21 C20 C19 C18 -0.3(4) . . . . ?
C23 C18 C19 C20 -0.6(4) . . . . ?
S1 C18 C19 C20 177.8(2) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C15 C14 C13 C12 0.2(4) . . . . ?
C17 C14 C13 C12 -178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.043
