# 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_B190
_database_code_depnum_ccdc_archive 'CCDC 2429110'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-05-19 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         'C28 H24 N2 O4 S2'
_chemical_formula_sum            'C28 H24 N2 O4 S2'
_chemical_formula_weight         516.61

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'
N N 0.0061 0.0033 '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'

_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                   5.3963(2)
_cell_length_b                   17.4674(7)
_cell_length_c                   13.4272(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.1140(12)
_cell_angle_gamma                90
_cell_volume                     1249.66(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.48
_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_T_max  0.6952
_exptl_absorpt_process_details   
;
 SADABS 2016/2 (Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10).
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            40667
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_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             3652
_reflns_number_gt                2961
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_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     
'w=1/[σ²(Fo²)+(0.0278P)²+1.1304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.89341(7) 0.64998(2) 0.65536(3) 0.01590(10) Uani 1 1 d . . . . .
O1 O 1.1517(2) 0.64153(7) 0.64233(9) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.7630(2) 0.71934(7) 0.62154(9) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.9227(2) 0.51770(7) 0.46045(9) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.7197(3) 0.57001(9) 0.59812(11) 0.0153(3) Uani 1 1 d . . . . .
H1A H 0.777680 0.522802 0.635504 0.018 Uiso 1 1 calc R U . . .
H1B H 0.539637 0.577055 0.602372 0.018 Uiso 1 1 calc R U . . .
C2 C 0.7512(3) 0.56105(9) 0.48869(11) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.5789(3) 0.60018(9) 0.40804(11) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.6115(3) 0.59090(10) 0.30699(12) 0.0211(3) Uani 1 1 d . . . . .
H4 H 0.747987 0.561394 0.291240 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4453(3) 0.62460(11) 0.23011(12) 0.0266(4) Uani 1 1 d . . . . .
H5 H 0.468936 0.618162 0.161994 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2446(3) 0.66764(10) 0.25201(13) 0.0255(4) Uani 1 1 d . . . . .
H6 H 0.129867 0.690060 0.199080 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2126(3) 0.67773(10) 0.35143(13) 0.0237(3) Uani 1 1 d . . . . .
H7 H 0.075786 0.707368 0.366597 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3794(3) 0.64480(9) 0.42935(12) 0.0190(3) Uani 1 1 d . . . . .
H8 H 0.357328 0.652754 0.497377 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8799(3) 0.63765(9) 0.78493(11) 0.0162(3) Uani 1 1 d . . . . .
C10 C 1.0664(3) 0.59501(10) 0.84302(12) 0.0231(3) Uani 1 1 d . . . . .
H10 H 1.194402 0.571003 0.813072 0.028 Uiso 1 1 calc R U . . .
C11 C 1.0621(4) 0.58812(12) 0.94589(13) 0.0296(4) Uani 1 1 d . . . . .
H11 H 1.187526 0.559001 0.986955 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8751(4) 0.62374(12) 0.98836(13) 0.0298(4) Uani 1 1 d . . . . .
H12 H 0.873832 0.619133 1.058781 0.036 Uiso 1 1 calc R U . . .
C13 C 0.6898(3) 0.66595(11) 0.92977(13) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.562440 0.690022 0.959995 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6900(3) 0.67319(10) 0.82659(12) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.563046 0.701779 0.785555 0.024 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 O2 1.4382(12) . ?
S1 O1 1.4394(12) . ?
S1 C9 1.7659(15) . ?
S1 C1 1.7867(15) . ?
N1 C2 1.2981(19) . ?
N1 N1 1.388(2) 3_766 ?
C1 C2 1.514(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.478(2) . ?
C3 C8 1.395(2) . ?
C3 C4 1.405(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 H14 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
O2 S1 O1 118.86(8) . . ?
O2 S1 C9 108.62(7) . . ?
O1 S1 C9 107.41(7) . . ?
O2 S1 C1 109.00(7) . . ?
O1 S1 C1 108.65(7) . . ?
C9 S1 C1 103.17(7) . . ?
C2 N1 N1 113.97(15) . 3_766 ?
C2 C1 S1 111.50(10) . . ?
C2 C1 H1A 109.3 . . ?
S1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
S1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 C3 116.78(13) . . ?
N1 C2 C1 122.60(13) . . ?
C3 C2 C1 120.59(13) . . ?
C8 C3 C4 118.76(14) . . ?
C8 C3 C2 121.62(14) . . ?
C4 C3 C2 119.59(14) . . ?
C5 C4 C3 120.32(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.44(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.61(15) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.51(16) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.33(15) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C10 C9 C14 121.93(15) . . ?
C10 C9 S1 118.65(12) . . ?
C14 C9 S1 119.37(12) . . ?
C9 C10 C11 118.68(16) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 119.92(17) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.93(16) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.04(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 118.49(16) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?

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
O2 S1 C1 C2 75.91(12) . . . . ?
O1 S1 C1 C2 -55.01(12) . . . . ?
C9 S1 C1 C2 -168.79(11) . . . . ?
N1 N1 C2 C3 -179.65(15) 3_766 . . . ?
N1 N1 C2 C1 -1.6(2) 3_766 . . . ?
S1 C1 C2 N1 92.51(16) . . . . ?
S1 C1 C2 C3 -89.52(15) . . . . ?
N1 C2 C3 C8 176.50(14) . . . . ?
C1 C2 C3 C8 -1.6(2) . . . . ?
N1 C2 C3 C4 -1.8(2) . . . . ?
C1 C2 C3 C4 -179.87(14) . . . . ?
C8 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 177.30(16) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C3 -1.0(3) . . . . ?
C4 C3 C8 C7 1.6(2) . . . . ?
C2 C3 C8 C7 -176.67(15) . . . . ?
O2 S1 C9 C10 -154.61(13) . . . . ?
O1 S1 C9 C10 -24.86(15) . . . . ?
C1 S1 C9 C10 89.81(14) . . . . ?
O2 S1 C9 C14 22.84(15) . . . . ?
O1 S1 C9 C14 152.59(13) . . . . ?
C1 S1 C9 C14 -92.73(14) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
S1 C9 C10 C11 177.18(14) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
S1 C9 C14 C13 -176.81(13) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.063



