# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc28kwrh
_database_code_depnum_ccdc_archive 'CCDC 2102567'
loop_
_audit_author_name
_audit_author_address
aaaaaaaaa
;jiangsu normal university
China
;
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 O4 S'
_chemical_formula_weight         418.49

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                   15.137(2)
_cell_length_b                   16.348(2)
_cell_length_c                   8.7649(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.271(2)
_cell_angle_gamma                90.00
_cell_volume                     2151.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4919
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.14

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10685
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3788
_reflns_number_gt                2991
_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)+(0.0695P)²+0.4469P] 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         3788
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13553(3) 0.54049(3) 0.40085(6) 0.05172(18) Uani 1 1 d . . .
O1 O 0.66267(10) 0.37010(12) 0.0926(2) 0.0797(5) Uani 1 1 d . . .
O2 O 0.05454(10) 0.50130(9) 0.33588(16) 0.0632(4) Uani 1 1 d . . .
O3 O 0.21212(10) 0.53540(9) 0.32168(17) 0.0657(4) Uani 1 1 d . . .
O4 O 0.17330(11) 0.36492(10) 1.11546(18) 0.0708(4) Uani 1 1 d . . .
C1 C 0.04799(18) 0.89689(14) 0.4819(3) 0.0779(7) Uani 1 1 d . . .
H1A H -0.0054 0.9015 0.5298 0.117 Uiso 1 1 calc R . .
H1B H 0.0391 0.9227 0.3827 0.117 Uiso 1 1 calc R . .
H1C H 0.0962 0.9232 0.5450 0.117 Uiso 1 1 calc R . .
C2 C 0.06987(14) 0.80837(13) 0.4632(2) 0.0565(5) Uani 1 1 d . . .
C3 C 0.14388(15) 0.78512(14) 0.4000(3) 0.0699(6) Uani 1 1 d . . .
H3A H 0.1806 0.8254 0.3673 0.084 Uiso 1 1 calc R . .
C4 C 0.16618(14) 0.70423(14) 0.3827(3) 0.0664(6) Uani 1 1 d . . .
H4A H 0.2175 0.6904 0.3405 0.080 Uiso 1 1 calc R . .
C5 C 0.11133(13) 0.64404(12) 0.4287(2) 0.0496(5) Uani 1 1 d . . .
C6 C 0.03558(15) 0.66586(14) 0.4921(3) 0.0678(6) Uani 1 1 d . . .
H6A H -0.0019 0.6257 0.5230 0.081 Uiso 1 1 calc R . .
C7 C 0.01605(16) 0.74716(14) 0.5094(3) 0.0722(7) Uani 1 1 d . . .
H7A H -0.0346 0.7614 0.5532 0.087 Uiso 1 1 calc R . .
C8 C 0.16159(13) 0.49822(12) 0.5840(2) 0.0514(5) Uani 1 1 d . . .
H8A H 0.1197 0.5001 0.6529 0.062 Uiso 1 1 calc R . .
C9 C 0.23948(13) 0.46375(12) 0.6265(2) 0.0507(5) Uani 1 1 d . . .
H9A H 0.2825 0.4699 0.5605 0.061 Uiso 1 1 calc R . .
C10 C 0.26499(12) 0.41667(11) 0.7675(2) 0.0474(4) Uani 1 1 d . . .
C11 C 0.21022(13) 0.41126(12) 0.8818(2) 0.0519(5) Uani 1 1 d . . .
H11A H 0.1560 0.4388 0.8698 0.062 Uiso 1 1 calc R . .
C12 C 0.23401(14) 0.36588(12) 1.0137(2) 0.0524(5) Uani 1 1 d . . .
C13 C 0.31416(14) 0.32421(13) 1.0329(2) 0.0584(5) Uani 1 1 d . . .
H13A H 0.3307 0.2936 1.1214 0.070 Uiso 1 1 calc R . .
C14 C 0.36903(14) 0.32856(13) 0.9198(3) 0.0573(5) Uani 1 1 d . . .
H14A H 0.4228 0.3003 0.9330 0.069 Uiso 1 1 calc R . .
C15 C 0.34684(12) 0.37376(12) 0.7861(2) 0.0484(5) Uani 1 1 d . . .
C16 C 0.40455(13) 0.37479(12) 0.6695(2) 0.0522(5) Uani 1 1 d . . .
C17 C 0.45211(13) 0.37468(13) 0.5700(3) 0.0546(5) Uani 1 1 d . . .
C18 C 0.50612(12) 0.37525(12) 0.4476(2) 0.0515(5) Uani 1 1 d . . .
C19 C 0.48302(14) 0.42154(14) 0.3180(3) 0.0631(6) Uani 1 1 d . . .
H19A H 0.4321 0.4538 0.3114 0.076 Uiso 1 1 calc R . .
C20 C 0.53335(14) 0.42152(14) 0.1975(3) 0.0638(6) Uani 1 1 d . . .
H20A H 0.5161 0.4534 0.1110 0.077 Uiso 1 1 calc R . .
C21 C 0.60867(13) 0.37455(13) 0.2050(3) 0.0569(5) Uani 1 1 d . . .
C22 C 0.63299(16) 0.32775(17) 0.3348(3) 0.0775(7) Uani 1 1 d . . .
H22A H 0.6841 0.2957 0.3410 0.093 Uiso 1 1 calc R . .
C23 C 0.58313(15) 0.32779(16) 0.4539(3) 0.0709(7) Uani 1 1 d . . .
H23A H 0.6006 0.2959 0.5403 0.085 Uiso 1 1 calc R . .
C24 C 0.64064(18) 0.41581(19) -0.0441(3) 0.0818(7) Uani 1 1 d . . .
H24A H 0.6849 0.4068 -0.1116 0.123 Uiso 1 1 calc R . .
H24B H 0.6385 0.4729 -0.0194 0.123 Uiso 1 1 calc R . .
H24C H 0.5835 0.3987 -0.0940 0.123 Uiso 1 1 calc R . .
C25 C 0.1955(2) 0.32291(17) 1.2569(3) 0.0892(9) Uani 1 1 d . . .
H25A H 0.1470 0.3270 1.3172 0.134 Uiso 1 1 calc R . .
H25B H 0.2479 0.3470 1.3124 0.134 Uiso 1 1 calc R . .
H25C H 0.2068 0.2664 1.2368 0.134 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 O3 1.4269(15) . ?
S1 O2 1.4356(15) . ?
S1 C8 1.746(2) . ?
S1 C5 1.756(2) . ?
O1 C21 1.359(2) . ?
O1 C24 1.416(3) . ?
O4 C12 1.360(2) . ?
O4 C25 1.420(3) . ?
C1 C2 1.498(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.365(3) . ?
C2 C7 1.383(3) . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(3) . ?
C6 C7 1.374(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.317(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.466(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.382(3) . ?
C10 C15 1.415(3) . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(3) . ?
C13 C14 1.373(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.390(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.426(3) . ?
C16 C17 1.199(3) . ?
C17 C18 1.428(3) . ?
C18 C19 1.373(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.379(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.381(3) . ?
C22 C23 1.364(3) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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 S1 O2 119.12(10) . . ?
O3 S1 C8 108.73(9) . . ?
O2 S1 C8 105.68(9) . . ?
O3 S1 C5 108.69(9) . . ?
O2 S1 C5 107.62(9) . . ?
C8 S1 C5 106.29(10) . . ?
C21 O1 C24 119.10(18) . . ?
C12 O4 C25 118.25(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.5(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 121.4(2) . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 S1 120.20(17) . . ?
C6 C5 S1 120.19(15) . . ?
C7 C6 C5 119.64(19) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C2 121.7(2) . . ?
C6 C7 H7A 119.2 . . ?
C2 C7 H7A 119.2 . . ?
C9 C8 S1 121.28(15) . . ?
C9 C8 H8A 119.4 . . ?
S1 C8 H8A 119.4 . . ?
C8 C9 C10 126.43(18) . . ?
C8 C9 H9A 116.8 . . ?
C10 C9 H9A 116.8 . . ?
C11 C10 C15 118.80(18) . . ?
C11 C10 C9 121.80(17) . . ?
C15 C10 C9 119.38(17) . . ?
C10 C11 C12 121.59(18) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
O4 C12 C11 115.38(17) . . ?
O4 C12 C13 124.73(19) . . ?
C11 C12 C13 119.87(18) . . ?
C14 C13 C12 119.20(19) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C13 C14 C15 122.16(18) . . ?
C13 C14 H14A 118.9 . . ?
C15 C14 H14A 118.9 . . ?
C14 C15 C10 118.38(18) . . ?
C14 C15 C16 120.38(17) . . ?
C10 C15 C16 121.23(18) . . ?
C17 C16 C15 178.8(2) . . ?
C16 C17 C18 178.0(2) . . ?
C19 C18 C23 117.6(2) . . ?
C19 C18 C17 120.97(18) . . ?
C23 C18 C17 121.4(2) . . ?
C18 C19 C20 121.76(19) . . ?
C18 C19 H19A 119.1 . . ?
C20 C19 H19A 119.1 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
O1 C21 C20 124.6(2) . . ?
O1 C21 C22 116.42(18) . . ?
C20 C21 C22 118.9(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C18 120.7(2) . . ?
C22 C23 H23A 119.6 . . ?
C18 C23 H23A 119.6 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C7 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C4 179.4(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 S1 177.37(18) . . . . ?
O3 S1 C5 C4 -3.0(2) . . . . ?
O2 S1 C5 C4 -133.31(17) . . . . ?
C8 S1 C5 C4 113.84(18) . . . . ?
O3 S1 C5 C6 174.79(18) . . . . ?
O2 S1 C5 C6 44.5(2) . . . . ?
C8 S1 C5 C6 -68.3(2) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
S1 C5 C6 C7 -178.2(2) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 179.8(2) . . . . ?
O3 S1 C8 C9 -4.2(2) . . . . ?
O2 S1 C8 C9 124.82(18) . . . . ?
C5 S1 C8 C9 -121.00(18) . . . . ?
S1 C8 C9 C10 -171.12(15) . . . . ?
C8 C9 C10 C11 -7.3(3) . . . . ?
C8 C9 C10 C15 171.0(2) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 C12 179.09(18) . . . . ?
C25 O4 C12 C11 -176.8(2) . . . . ?
C25 O4 C12 C13 4.5(3) . . . . ?
C10 C11 C12 O4 -179.07(18) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
O4 C12 C13 C14 178.5(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C13 C14 C15 C16 -178.22(19) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
C9 C10 C15 C14 -179.06(18) . . . . ?
C11 C10 C15 C16 177.78(18) . . . . ?
C9 C10 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 102(12) . . . . ?
C10 C15 C16 C17 -76(12) . . . . ?
C15 C16 C17 C18 54(16) . . . . ?
C16 C17 C18 C19 27(6) . . . . ?
C16 C17 C18 C23 -152(6) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 C20 -178.6(2) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C24 O1 C21 C20 -0.8(3) . . . . ?
C24 O1 C21 C22 179.2(2) . . . . ?
C19 C20 C21 O1 179.9(2) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
O1 C21 C22 C23 -179.8(2) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
C17 C18 C23 C22 178.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.039
