# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_20230712zjl3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281475'
loop_
_audit_author_name
_audit_author_address
AYNU-zhanjl-a
;Anyang Normal University
China
;
_audit_update_record             
;
2023-07-14 deposited with the CCDC.	2026-01-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H10 N2 O4 S'
_chemical_formula_sum            'C12 H11 N2 O4 S'
_chemical_formula_weight         279.29
_chemical_absolute_configuration ad
_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 0.0033 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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.1939(3)
_cell_length_b                   12.7888(9)
_cell_length_c                   18.6760(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.318(2)
_cell_angle_gamma                90.00
_cell_volume                     1238.45(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5483
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.18
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.9183.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34424
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1938
_reflns_number_total             2103
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0378P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0825
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C5(H5), C6(H6), C12(H12), C11(H11), C3(H3), C2(H2), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.37255(11) 0.31310(4) 0.51263(4) 0.04750(17) Uani 1 d . . .
N1 N 0.5595(4) 0.33172(17) 0.58471(12) 0.0519(5) Uani 1 d . . .
H1 H 0.7172 0.3186 0.5762 0.062 Uiso 1 d . . R
O1 O 0.4489(4) 0.21572(14) 0.48342(11) 0.0597(5) Uani 1 d . . .
O3 O 0.8788(5) 0.6484(2) 0.29217(15) 0.0952(8) Uani 1 d . . .
O2 O 0.1131(3) 0.32832(14) 0.53155(10) 0.0558(5) Uani 1 d . . .
C10 C 0.6010(5) 0.5738(2) 0.36985(14) 0.0494(6) Uani 1 d . . .
C8 C 0.6438(5) 0.3983(2) 0.40670(15) 0.0558(7) Uani 1 d . . .
H8 H 0.7218 0.3330 0.4040 0.067 Uiso 1 calc . . R
C4 C 0.4760(8) 0.6108(3) 0.69811(18) 0.0854(11) Uani 1 d . . .
H4 H 0.4534 0.6732 0.7225 0.102 Uiso 1 calc . . R
C5 C 0.6732(8) 0.6013(3) 0.65227(18) 0.0799(10) Uani 1 d . . .
H5 H 0.7875 0.6563 0.6467 0.096 Uiso 1 calc . . R
C6 C 0.6992(6) 0.5100(2) 0.61496(17) 0.0625(7) Uani 1 d . . .
H6 H 0.8299 0.5036 0.5833 0.075 Uiso 1 calc . . R
C1 C 0.5340(5) 0.4282(2) 0.62399(14) 0.0498(6) Uani 1 d . . .
C7 C 0.4482(4) 0.41373(18) 0.45292(14) 0.0449(6) Uani 1 d . . .
C12 C 0.3294(5) 0.5097(2) 0.45646(16) 0.0576(7) Uani 1 d . . .
H12 H 0.1970 0.5196 0.4873 0.069 Uiso 1 calc . . R
C11 C 0.4063(5) 0.5911(2) 0.41450(16) 0.0602(7) Uani 1 d . . .
H11 H 0.3277 0.6563 0.4165 0.072 Uiso 1 calc . . R
N2 N 0.6890(5) 0.6622(2) 0.32626(13) 0.0655(7) Uani 1 d . . .
O4 O 0.5700(5) 0.74398(19) 0.32660(15) 0.0943(9) Uani 1 d . . .
C3 C 0.3137(7) 0.5288(3) 0.70788(19) 0.0849(11) Uani 1 d . . .
H3 H 0.1827 0.5356 0.7395 0.102 Uiso 1 calc . . R
C2 C 0.3411(6) 0.4361(3) 0.67164(15) 0.0682(8) Uani 1 d . . .
H2 H 0.2320 0.3800 0.6791 0.082 Uiso 1 calc . . R
C9 C 0.7224(6) 0.4786(2) 0.36505(16) 0.0597(7) Uani 1 d . . .
H9 H 0.8548 0.4693 0.3342 0.072 Uiso 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 N1 1.631(2) . ?
S1 O1 1.4251(19) . ?
S1 O2 1.4262(18) . ?
S1 C7 1.762(3) . ?
N1 H1 0.8601 . ?
N1 C1 1.445(3) . ?
O3 N2 1.217(3) . ?
C10 C11 1.365(4) . ?
C10 N2 1.481(3) . ?
C10 C9 1.375(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C8 C9 1.366(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(5) . ?
C4 C3 1.364(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.370(4) . ?
C1 C2 1.382(4) . ?
C7 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.376(4) . ?
C11 H11 0.9300 . ?
N2 O4 1.215(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.376(5) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?

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
N1 S1 C7 105.78(12) . . ?
O1 S1 N1 106.14(12) . . ?
O1 S1 O2 120.13(11) . . ?
O1 S1 C7 108.59(12) . . ?
O2 S1 N1 107.55(11) . . ?
O2 S1 C7 107.79(11) . . ?
S1 N1 H1 110.3 . . ?
C1 N1 S1 118.41(17) . . ?
C1 N1 H1 112.2 . . ?
C11 C10 N2 118.3(2) . . ?
C11 C10 C9 122.8(2) . . ?
C9 C10 N2 118.8(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.7 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.7 . . ?
C6 C1 N1 120.9(2) . . ?
C6 C1 C2 120.4(3) . . ?
C2 C1 N1 118.7(3) . . ?
C8 C7 S1 119.24(19) . . ?
C12 C7 S1 120.2(2) . . ?
C12 C7 C8 120.3(2) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
O3 N2 C10 117.5(3) . . ?
O4 N2 O3 123.7(3) . . ?
O4 N2 C10 118.8(3) . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C10 C9 H9 120.8 . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 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
S1 N1 C1 C6 -98.6(3) . . . . ?
S1 N1 C1 C2 82.1(3) . . . . ?
S1 C7 C12 C11 173.8(2) . . . . ?
N1 S1 C7 C8 88.6(2) . . . . ?
N1 S1 C7 C12 -85.9(2) . . . . ?
N1 C1 C2 C3 -178.7(3) . . . . ?
O1 S1 N1 C1 176.96(19) . . . . ?
O1 S1 C7 C8 -25.0(2) . . . . ?
O1 S1 C7 C12 160.6(2) . . . . ?
O2 S1 N1 C1 -53.3(2) . . . . ?
O2 S1 C7 C8 -156.6(2) . . . . ?
O2 S1 C7 C12 29.0(3) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C4 C3 C2 C1 -1.1(5) . . . . ?
C5 C4 C3 C2 -0.9(6) . . . . ?
C5 C6 C1 N1 179.8(3) . . . . ?
C5 C6 C1 C2 -0.9(5) . . . . ?
C6 C1 C2 C3 2.1(5) . . . . ?
C7 S1 N1 C1 61.7(2) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C7 C12 C11 C10 0.1(5) . . . . ?
C11 C10 N2 O3 172.9(3) . . . . ?
C11 C10 N2 O4 -6.8(4) . . . . ?
C11 C10 C9 C8 0.2(5) . . . . ?
N2 C10 C11 C12 -178.2(3) . . . . ?
N2 C10 C9 C8 178.5(2) . . . . ?
C3 C4 C5 C6 2.1(6) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C9 C10 N2 O3 -5.5(4) . . . . ?
C9 C10 N2 O4 174.8(3) . . . . ?
C9 C8 C7 S1 -173.6(2) . . . . ?
C9 C8 C7 C12 0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
