# 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_exp_13405
_database_code_depnum_ccdc_archive 'CCDC 2300262'
loop_
_audit_author_name
_audit_author_address
'Yao-Bin Shen'
;Zaozhuang University
China
;
_audit_update_record             
;
2023-10-10 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O4 S'
_chemical_formula_weight         496.56

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   8.3837(5)
_cell_length_b                   23.2508(12)
_cell_length_c                   12.2750(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.299(7)
_cell_angle_gamma                90
_cell_volume                     2318.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4632
_cell_measurement_theta_min      4.1930
_cell_measurement_theta_max      70.9100

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.579
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_T_min  0.90991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15189
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_full        67.246
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4149
_reflns_number_gt                3158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+1.0920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4149
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_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 0.88518(9) 0.59092(3) 0.13025(6) 0.0522(2) Uani 1 1 d . . . . .
N1 N 0.8980(3) 0.58791(9) 0.26723(18) 0.0437(5) Uani 1 1 d . . . . .
N2 N 0.7303(3) 0.54633(9) 0.59888(18) 0.0413(5) Uani 1 1 d . . . . .
O1 O 0.9850(3) 0.63813(11) 0.11543(19) 0.0732(7) Uani 1 1 d . . . . .
O2 O 0.9188(3) 0.53468(10) 0.09646(18) 0.0702(6) Uani 1 1 d . . . . .
O3 O 0.4907(2) 0.63117(8) 0.43909(16) 0.0496(5) Uani 1 1 d . . . . .
O4 O 0.8700(2) 0.72541(8) 0.73045(18) 0.0571(5) Uani 1 1 d . . . . .
C1 C 0.6794(4) 0.60818(12) 0.0660(2) 0.0471(6) Uani 1 1 d . . . . .
C2 C 0.6434(4) 0.65737(12) 0.0030(2) 0.0568(8) Uani 1 1 d . . . . .
H2 H 0.726842 0.682838 -0.002056 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4833(5) 0.66871(14) -0.0526(3) 0.0652(9) Uani 1 1 d . . . . .
H3 H 0.460043 0.701782 -0.096235 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3558(4) 0.63255(14) -0.0456(2) 0.0603(8) Uani 1 1 d . . . . .
C5 C 0.3939(4) 0.58387(15) 0.0189(3) 0.0739(10) Uani 1 1 d . . . . .
H5 H 0.310012 0.559027 0.025825 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5537(4) 0.57121(14) 0.0735(3) 0.0678(9) Uani 1 1 d . . . . .
H6 H 0.577339 0.537665 0.115708 0.081 Uiso 1 1 calc R U . . .
C7 C 0.1807(5) 0.64595(17) -0.1067(3) 0.0808(11) Uani 1 1 d . . . . .
H7A H 0.111443 0.613899 -0.100282 0.121 Uiso 1 1 calc R U . . .
H7B H 0.175111 0.653031 -0.184626 0.121 Uiso 1 1 calc R U . . .
H7C H 0.144065 0.679457 -0.074180 0.121 Uiso 1 1 calc R U . . .
C8 C 0.8459(3) 0.54227(11) 0.3254(2) 0.0407(6) Uani 1 1 d . . . . .
C9 C 0.8228(4) 0.48484(12) 0.2951(2) 0.0509(7) Uani 1 1 d . . . . .
H9 H 0.841192 0.470891 0.228249 0.061 Uiso 1 1 calc R U . . .
C10 C 0.7712(4) 0.44996(11) 0.3693(3) 0.0545(7) Uani 1 1 d . . . . .
H10 H 0.754097 0.411159 0.351865 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7434(3) 0.46990(11) 0.4689(2) 0.0487(7) Uani 1 1 d . . . . .
H11 H 0.708212 0.444238 0.516231 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7670(3) 0.52782(10) 0.5008(2) 0.0380(6) Uani 1 1 d . . . . .
C13 C 0.8201(3) 0.56452(10) 0.4257(2) 0.0350(5) Uani 1 1 d . . . . .
C14 C 0.8533(3) 0.62557(10) 0.4253(2) 0.0362(5) Uani 1 1 d . . . . .
C15 C 0.8964(3) 0.63810(11) 0.3295(2) 0.0413(6) Uani 1 1 d . . . . .
H15 H 0.921429 0.674688 0.307954 0.050 Uiso 1 1 calc R U . . .
C16 C 0.8510(3) 0.66918(10) 0.5144(2) 0.0387(6) Uani 1 1 d . . . . .
H16A H 0.821922 0.706190 0.478500 0.046 Uiso 1 1 calc R U . . .
H16B H 0.961322 0.672509 0.562509 0.046 Uiso 1 1 calc R U . . .
C17 C 0.7330(3) 0.65629(10) 0.5878(2) 0.0362(5) Uani 1 1 d . . . . .
C18 C 0.5509(3) 0.65714(10) 0.5245(2) 0.0381(6) Uani 1 1 d . . . . .
C19 C 0.4637(3) 0.69807(10) 0.5820(2) 0.0406(6) Uani 1 1 d . . . . .
C20 C 0.2965(3) 0.71028(12) 0.5588(3) 0.0497(7) Uani 1 1 d . . . . .
H20 H 0.221224 0.690454 0.503079 0.060 Uiso 1 1 calc R U . . .
C21 C 0.2462(3) 0.75272(12) 0.6209(3) 0.0562(8) Uani 1 1 d . . . . .
H21 H 0.134585 0.761005 0.608104 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3587(4) 0.78359(12) 0.7027(3) 0.0539(7) Uani 1 1 d . . . . .
H22 H 0.321275 0.812667 0.742153 0.065 Uiso 1 1 calc R U . . .
C23 C 0.5237(3) 0.77158(11) 0.7256(2) 0.0459(6) Uani 1 1 d . . . . .
H23 H 0.599078 0.792213 0.779902 0.055 Uiso 1 1 calc R U . . .
C24 C 0.5752(3) 0.72772(10) 0.6655(2) 0.0395(6) Uani 1 1 d . . . . .
C25 C 0.7439(3) 0.70624(11) 0.6719(2) 0.0401(6) Uani 1 1 d . . . . .
C26 C 0.7852(3) 0.60003(11) 0.6565(2) 0.0417(6) Uani 1 1 d . . . . .
H26 H 0.905589 0.599261 0.681586 0.050 Uiso 1 1 calc R U . . .
C27 C 0.7153(5) 0.59615(14) 0.7599(3) 0.0761(11) Uani 1 1 d . . . . .
H27A H 0.786852 0.615845 0.823102 0.091 Uiso 1 1 calc R U . . .
H27B H 0.607125 0.613753 0.744765 0.091 Uiso 1 1 calc R U . . .
C28 C 0.7048(6) 0.53552(16) 0.7849(3) 0.0857(12) Uani 1 1 d . . . . .
H28A H 0.609363 0.528154 0.814242 0.103 Uiso 1 1 calc R U . . .
H28B H 0.802567 0.523257 0.840310 0.103 Uiso 1 1 calc R U . . .
C29 C 0.6901(4) 0.50412(13) 0.6769(2) 0.0537(7) Uani 1 1 d . . . . .
H29A H 0.766229 0.472006 0.687370 0.064 Uiso 1 1 calc R U . . .
H29B H 0.579130 0.489612 0.648393 0.064 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 1.419(2) . ?
S1 O2 1.421(2) . ?
S1 N1 1.660(2) . ?
S1 C1 1.757(3) . ?
N1 C15 1.397(3) . ?
N1 C8 1.408(3) . ?
N2 C12 1.383(3) . ?
N2 C26 1.453(3) . ?
N2 C29 1.467(3) . ?
O3 C18 1.207(3) . ?
O4 C25 1.208(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.380(4) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 C7 1.507(5) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.387(4) . ?
C8 C13 1.400(3) . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(3) . ?
C13 C14 1.447(3) . ?
C14 C15 1.344(3) . ?
C14 C16 1.495(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.524(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.533(3) . ?
C17 C25 1.541(3) . ?
C17 C26 1.559(3) . ?
C18 C19 1.481(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.388(4) . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.484(3) . ?
C26 C27 1.527(4) . ?
C26 H26 0.9800 . ?
C27 C28 1.450(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.492(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 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
O1 S1 O2 120.57(15) . . ?
O1 S1 N1 105.65(13) . . ?
O2 S1 N1 106.81(13) . . ?
O1 S1 C1 108.08(15) . . ?
O2 S1 C1 108.82(14) . . ?
N1 S1 C1 105.99(12) . . ?
C15 N1 C8 107.8(2) . . ?
C15 N1 S1 120.82(18) . . ?
C8 N1 S1 126.53(18) . . ?
C12 N2 C26 125.4(2) . . ?
C12 N2 C29 119.8(2) . . ?
C26 N2 C29 110.7(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 S1 119.9(2) . . ?
C6 C1 S1 120.6(2) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 C7 121.1(3) . . ?
C3 C4 C7 121.2(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 123.4(3) . . ?
C9 C8 N1 129.1(3) . . ?
C13 C8 N1 107.6(2) . . ?
C10 C9 C8 116.0(3) . . ?
C10 C9 H9 122.0 . . ?
C8 C9 H9 122.0 . . ?
C9 C10 C11 122.8(2) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 121.8(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
N2 C12 C11 119.7(2) . . ?
N2 C12 C13 123.8(2) . . ?
C11 C12 C13 116.5(2) . . ?
C8 C13 C12 119.6(2) . . ?
C8 C13 C14 106.7(2) . . ?
C12 C13 C14 133.6(2) . . ?
C15 C14 C13 108.0(2) . . ?
C15 C14 C16 123.2(2) . . ?
C13 C14 C16 128.7(2) . . ?
C14 C15 N1 109.8(2) . . ?
C14 C15 H15 125.1 . . ?
N1 C15 H15 125.1 . . ?
C14 C16 C17 115.3(2) . . ?
C14 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C14 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 114.1(2) . . ?
C16 C17 C25 107.92(19) . . ?
C18 C17 C25 102.52(19) . . ?
C16 C17 C26 110.4(2) . . ?
C18 C17 C26 113.4(2) . . ?
C25 C17 C26 107.9(2) . . ?
O3 C18 C19 125.9(2) . . ?
O3 C18 C17 125.8(2) . . ?
C19 C18 C17 108.3(2) . . ?
C24 C19 C20 120.8(2) . . ?
C24 C19 C18 110.4(2) . . ?
C20 C19 C18 128.7(2) . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C20 C21 C22 121.5(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 118.1(3) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C19 C24 C23 121.1(2) . . ?
C19 C24 C25 109.4(2) . . ?
C23 C24 C25 129.5(2) . . ?
O4 C25 C24 126.2(2) . . ?
O4 C25 C17 125.1(2) . . ?
C24 C25 C17 108.7(2) . . ?
N2 C26 C27 102.3(2) . . ?
N2 C26 C17 116.4(2) . . ?
C27 C26 C17 112.6(2) . . ?
N2 C26 H26 108.4 . . ?
C27 C26 H26 108.4 . . ?
C17 C26 H26 108.4 . . ?
C28 C27 C26 106.8(3) . . ?
C28 C27 H27A 110.4 . . ?
C26 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
C26 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
C27 C28 C29 106.5(3) . . ?
C27 C28 H28A 110.4 . . ?
C29 C28 H28A 110.4 . . ?
C27 C28 H28B 110.4 . . ?
C29 C28 H28B 110.4 . . ?
H28A C28 H28B 108.6 . . ?
N2 C29 C28 105.7(2) . . ?
N2 C29 H29A 110.6 . . ?
C28 C29 H29A 110.6 . . ?
N2 C29 H29B 110.6 . . ?
C28 C29 H29B 110.6 . . ?
H29A C29 H29B 108.7 . . ?

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.050



