# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2368900'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Taizhou university
China
;
_audit_update_record             
;
2024-07-08 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 O4 S'
_chemical_formula_sum            'C23 H26 O4 S'
_chemical_formula_weight         398.50
_chemical_absolute_configuration RM
_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           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                   11.2877(3)
_cell_length_b                   6.0439(2)
_cell_length_c                   15.4637(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.7840(10)
_cell_angle_gamma                90
_cell_volume                     1015.18(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.236
_cell_measurement_theta_min      5.659
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4222
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1469 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.5606.
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    1.304
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12360
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         4.070
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                3372
_reflns_number_total             3428
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.207(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.085
_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)+(0.0683P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C13(H13A,H13B), C1(H1A,H1B), C9(H9A,H9B), C2(H2A,H2B), C4(H4A,
 H4B), C8(H8A,H8B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C15(H15), C22(H22), C16(H16), C23(H23), C21(H21)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
2.e :
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S001 S 0.22393(5) 0.66465(13) 0.59741(4) 0.0374(2) Uani 1 1 d . . . . .
O2 O 0.1992(2) 0.4575(4) 0.63455(15) 0.0497(5) Uani 1 1 d . . . . .
O4 O 0.4411(2) 0.9960(5) 0.56271(15) 0.0590(6) Uani 1 1 d . . . . .
H4 H 0.508611 0.935380 0.575633 0.088 Uiso 1 1 calc GR . . . .
O3 O 0.1320(2) 0.8333(5) 0.58316(17) 0.0625(6) Uani 1 1 d . . . . .
O1 O 0.2859(2) 0.5159(6) 0.33062(16) 0.0720(8) Uani 1 1 d . . . . .
C19 C 0.3735(2) 0.6456(5) 0.82934(15) 0.0338(5) Uani 1 1 d . . . . .
H19 H 0.410424 0.516918 0.816253 0.041 Uiso 1 1 calc R . . . .
C14 C 0.3389(2) 0.8053(4) 0.76486(16) 0.0323(5) Uani 1 1 d . . . . .
C18 C 0.3546(2) 0.6713(5) 0.91574(15) 0.0348(5) Uani 1 1 d . . . . .
C10 C 0.3665(2) 0.7790(4) 0.67367(17) 0.0347(5) Uani 1 1 d . . . . .
C20 C 0.3922(3) 0.5094(5) 0.98356(18) 0.0431(6) Uani 1 1 d . . . . .
H20 H 0.427217 0.377901 0.971318 0.052 Uiso 1 1 calc R . . . .
C17 C 0.2998(2) 0.8710(5) 0.93524(18) 0.0382(6) Uani 1 1 d . . . . .
C11 C 0.4656(2) 0.6214(5) 0.67564(17) 0.0389(6) Uani 1 1 d . . . . .
C15 C 0.2785(3) 0.9983(5) 0.78321(19) 0.0401(6) Uani 1 1 d . . . . .
H15 H 0.251043 1.104330 0.738688 0.048 Uiso 1 1 calc R . . . .
C22 C 0.3253(3) 0.7446(7) 1.0872(2) 0.0562(9) Uani 1 1 d . . . . .
H22 H 0.317071 0.768521 1.144648 0.067 Uiso 1 1 calc R . . . .
C16 C 0.2607(2) 1.0282(5) 0.86604(19) 0.0419(6) Uani 1 1 d . . . . .
H16 H 0.221550 1.156126 0.877280 0.050 Uiso 1 1 calc R . . . .
C5 C 0.0801(3) 0.0885(5) 0.2994(2) 0.0478(7) Uani 1 1 d . . . . .
H5A H 0.157850 0.010360 0.310137 0.057 Uiso 1 1 calc R . . . .
H5B H 0.056199 0.090184 0.355053 0.057 Uiso 1 1 calc R . . . .
C6 C 0.0962(3) 0.3260(5) 0.27042(18) 0.0402(6) Uani 1 1 d . . . . .
H6 H 0.016885 0.401472 0.261434 0.048 Uiso 1 1 calc R . . . .
C13 C 0.3975(3) 1.0084(5) 0.6396(2) 0.0477(6) Uani 1 1 d . . . . .
H13A H 0.324136 1.099856 0.626096 0.057 Uiso 1 1 calc R . . . .
H13B H 0.459339 1.080350 0.687351 0.057 Uiso 1 1 calc R . . . .
C23 C 0.2872(3) 0.9017(6) 1.0232(2) 0.0496(7) Uani 1 1 d . . . . .
H23 H 0.252308 1.031643 1.037125 0.060 Uiso 1 1 calc R . . . .
C1 C 0.1283(3) 0.3272(6) 0.18053(19) 0.0523(7) Uani 1 1 d . . . . .
H1A H 0.133156 0.478736 0.161154 0.063 Uiso 1 1 calc R . . . .
H1B H 0.208227 0.258921 0.188015 0.063 Uiso 1 1 calc R . . . .
C21 C 0.3770(3) 0.5460(7) 1.0675(2) 0.0523(8) Uani 1 1 d . . . . .
H21 H 0.401227 0.438344 1.111803 0.063 Uiso 1 1 calc R . . . .
C12 C 0.5457(3) 0.5009(6) 0.6721(2) 0.0518(7) Uani 1 1 d . . . . .
H12 H 0.609120 0.405360 0.669320 0.062 Uiso 1 1 calc R . . . .
C9 C 0.2611(3) 0.6114(7) 0.4953(2) 0.0592(10) Uani 1 1 d . . . . .
H9A H 0.278703 0.750002 0.469697 0.071 Uiso 1 1 calc R . . . .
H9B H 0.334543 0.520275 0.507219 0.071 Uiso 1 1 calc R . . . .
C7 C 0.1897(3) 0.4503(6) 0.3420(2) 0.0471(7) Uani 1 1 d . . . . .
C2 C 0.0322(3) 0.2025(8) 0.10907(19) 0.0624(10) Uani 1 1 d . . . . .
H2A H -0.045191 0.282325 0.096357 0.075 Uiso 1 1 calc R . . . .
H2B H 0.058006 0.197780 0.054171 0.075 Uiso 1 1 calc R . . . .
C4 C -0.0178(3) -0.0325(7) 0.2271(2) 0.0614(9) Uani 1 1 d . . . . .
H4A H -0.097190 0.036928 0.220845 0.074 Uiso 1 1 calc R . . . .
H4B H -0.023323 -0.184756 0.245493 0.074 Uiso 1 1 calc R . . . .
C8 C 0.1577(3) 0.4958(8) 0.4290(2) 0.0636(10) Uani 1 1 d . . . . .
H8A H 0.084316 0.586877 0.417041 0.076 Uiso 1 1 calc R . . . .
H8B H 0.140100 0.357136 0.454619 0.076 Uiso 1 1 calc R . . . .
C3 C 0.0124(4) -0.0285(8) 0.1366(3) 0.0721(12) Uani 1 1 d . . . . .
H3A H 0.086012 -0.115178 0.140758 0.086 Uiso 1 1 calc R . . . .
H3B H -0.054735 -0.095413 0.091222 0.086 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
S001 O2 1.436(2) . ?
S001 O3 1.428(2) . ?
S001 C10 1.851(3) . ?
S001 C9 1.770(3) . ?
O4 H4 0.8200 . ?
O4 C13 1.407(4) . ?
O1 C7 1.214(4) . ?
C19 H19 0.9300 . ?
C19 C14 1.366(4) . ?
C19 C18 1.418(3) . ?
C14 C10 1.533(3) . ?
C14 C15 1.418(4) . ?
C18 C20 1.413(4) . ?
C18 C17 1.425(4) . ?
C10 C11 1.463(4) . ?
C10 C13 1.557(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C17 C16 1.409(4) . ?
C17 C23 1.417(4) . ?
C11 C12 1.174(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.354(5) . ?
C22 C21 1.403(5) . ?
C16 H16 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.529(4) . ?
C5 C4 1.527(5) . ?
C6 H6 0.9800 . ?
C6 C1 1.529(4) . ?
C6 C7 1.506(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C23 H23 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.521(5) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.500(4) . ?
C7 C8 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.494(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.528(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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 S001 C10 107.49(12) . . ?
O2 S001 C9 108.49(17) . . ?
O3 S001 O2 118.14(15) . . ?
O3 S001 C10 107.54(14) . . ?
O3 S001 C9 109.33(18) . . ?
C9 S001 C10 105.08(13) . . ?
C13 O4 H4 109.5 . . ?
C14 C19 H19 119.2 . . ?
C14 C19 C18 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C19 C14 C10 120.6(2) . . ?
C19 C14 C15 119.5(2) . . ?
C15 C14 C10 119.9(2) . . ?
C19 C18 C17 118.5(2) . . ?
C20 C18 C19 122.1(3) . . ?
C20 C18 C17 119.3(2) . . ?
C14 C10 S001 105.39(16) . . ?
C14 C10 C13 109.9(2) . . ?
C11 C10 S001 107.32(18) . . ?
C11 C10 C14 113.2(2) . . ?
C11 C10 C13 110.2(2) . . ?
C13 C10 S001 110.70(19) . . ?
C18 C20 H20 120.0 . . ?
C21 C20 C18 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 C23 123.2(3) . . ?
C23 C17 C18 118.5(3) . . ?
C12 C11 C10 175.7(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C23 C22 H22 119.7 . . ?
C23 C22 C21 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C17 C16 H16 119.0 . . ?
C15 C16 C17 121.9(3) . . ?
C15 C16 H16 119.0 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.8(3) . . ?
C5 C6 H6 107.6 . . ?
C1 C6 C5 110.3(3) . . ?
C1 C6 H6 107.6 . . ?
C7 C6 C5 111.6(2) . . ?
C7 C6 H6 107.6 . . ?
C7 C6 C1 112.0(2) . . ?
O4 C13 C10 113.6(3) . . ?
O4 C13 H13A 108.8 . . ?
O4 C13 H13B 108.8 . . ?
C10 C13 H13A 108.8 . . ?
C10 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C17 C23 H23 119.5 . . ?
C22 C23 C17 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C6 C1 H1A 109.4 . . ?
C6 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 C6 111.1(3) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C11 C12 H12 180.0 . . ?
S001 C9 H9A 109.3 . . ?
S001 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 S001 111.4(2) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
O1 C7 C6 122.1(3) . . ?
O1 C7 C8 120.7(3) . . ?
C6 C7 C8 117.2(2) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.8(3) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C5 C4 C3 111.4(3) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C9 C8 C7 111.3(3) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C2 C3 C4 111.4(3) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
