# 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_3m
_database_code_depnum_ccdc_archive 'CCDC 2385529'
loop_
_audit_author_name
_audit_author_address
'Rishukumar Panday'
;Indian Institute of Science Education and Research, Pune
India
;
_audit_update_record             
;
2024-10-16 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;
_audit_creation_date             2024-10-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.291
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03233 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.33375 0.55836 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.244(3)
_cell_length_b                   20.111(7)
_cell_length_c                   7.539(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.061(15)
_cell_angle_gamma                90
_cell_volume                     1150.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1328
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.39
_cell_measurement_theta_min      4.40
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1434 before and 0.0796 after correction.
The Ratio of minimum to maximum transmission is 0.8022.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             514.980
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.384
_exptl_crystal_size_min          0.215
_diffrn_reflns_av_R_equivalents  0.1523
_diffrn_reflns_av_unetI/netI     0.1441
_diffrn_reflns_Laue_measured_fraction_full 0.9832
_diffrn_reflns_Laue_measured_fraction_max 0.9832
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6376
_diffrn_reflns_point_group_measured_fraction_full 0.9832
_diffrn_reflns_point_group_measured_fraction_max 0.9832
_diffrn_reflns_theta_full        66.5147
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         4.40
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9832
_diffrn_measured_fraction_theta_max 0.9832
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1057
_reflns_number_total             1990
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.0796
_refine_diff_density_min         -0.9811
_refine_diff_density_rms         0.2591
_refine_ls_d_res_high            0.8405
_refine_ls_d_res_low             10.0555
_refine_ls_goodness_of_fit_ref   1.0918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2053
_refine_ls_R_factor_gt           0.1145
_refine_ls_restrained_S_all      1.0918
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²+8.0297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.2219
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.7096(3) 0.57627(11) 0.1132(3) 0.0398(6) Uani 1.000000 .
O1 O 0.1359(7) 0.6597(3) 0.1238(9) 0.0457(16) Uani 1.000000 .
N1 N 0.1779(8) 0.7182(4) 0.1416(10) 0.0399(19) Uani 1.000000 .
C1 C 0.3456(5) 0.7369(3) 0.1420(7) 0.0293(18) Uani 1.000000 G
O2 O 0.0828(8) 0.7621(3) 0.1614(10) 0.061(2) Uani 1.000000 .
N2 N 0.7473(9) 0.6583(3) 0.1324(10) 0.0431(19) Uani 1.000000 .
H2 H 0.8504(9) 0.6723(3) 0.1381(10) 0.052(2) Uiso 1.000000 R
C2 C 0.3916(6) 0.8036(2) 0.1493(7) 0.039(2) Uani 1.000000 G
H2a H 0.3111(6) 0.8369(2) 0.1525(7) 0.046(3) Uiso 1.000000 R
C3 C 0.5553(6) 0.82158(18) 0.1519(8) 0.038(2) Uani 1.000000 G
H3 H 0.5867(6) 0.86719(18) 0.1569(8) 0.045(3) Uiso 1.000000 R
C4 C 0.6730(5) 0.7728(2) 0.1472(8) 0.036(2) Uani 1.000000 G
H4 H 0.7849(5) 0.7851(2) 0.1490(8) 0.043(2) Uiso 1.000000 R
C5 C 0.6271(6) 0.7061(2) 0.1399(7) 0.034(2) Uani 1.000000 .
C6 C 0.4633(6) 0.68809(18) 0.1373(7) 0.0326(19) Uani 1.000000 G
H6 H 0.4319(6) 0.64248(18) 0.1324(7) 0.039(2) Uiso 1.000000 R
C7 C 0.7617(7) 0.5515(3) 0.3550(6) 0.034(2) Uani 1.000000 .
C8 C 0.8828(7) 0.5852(2) 0.5120(8) 0.039(2) Uani 1.000000 G
H8 H 0.9385(7) 0.6243(2) 0.4924(8) 0.047(3) Uiso 1.000000 R
C9 C 0.9224(6) 0.5618(3) 0.6978(6) 0.048(2) Uani 1.000000 G
H9 H 1.0052(6) 0.5848(3) 0.8051(6) 0.057(3) Uiso 1.000000 R
C10 C 0.8410(8) 0.5047(3) 0.7265(6) 0.045(2) Uani 1.000000 G
H10 H 0.8681(8) 0.4886(3) 0.8535(6) 0.054(3) Uiso 1.000000 R
C11 C 0.7199(7) 0.4710(2) 0.5695(8) 0.044(2) Uani 1.000000 G
H11 H 0.6642(7) 0.4319(2) 0.5891(8) 0.053(3) Uiso 1.000000 R
C12 C 0.6802(6) 0.4944(3) 0.3837(7) 0.040(2) Uani 1.000000 G
H12 H 0.5975(6) 0.4713(3) 0.2764(7) 0.048(3) Uiso 1.000000 R


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 N2 1.674(7) . ?
S1 C7 1.773(4) . ?
O1 N1 1.219(8) . ?
N1 C1 1.431(7) . ?
N1 O2 1.228(8) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
N2 H2 0.8800 . ?
N2 C5 1.398(7) . ?
C2 H2a 0.9500 . ?
C2 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 H6 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 H8 0.9500 . ?
C8 C9 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 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
C7 S1 N2 103.1(3) . . ?
C1 N1 O1 119.0(6) . . ?
O2 N1 O1 122.7(7) . . ?
O2 N1 C1 118.3(7) . . ?
C2 C1 N1 120.1(5) . . ?
C6 C1 N1 119.9(5) . . ?
C6 C1 C2 120.0 . . ?
H2 N2 S1 117.6(2) . . ?
C5 N2 S1 124.8(5) . . ?
C5 N2 H2 117.6(3) . . ?
H2a C2 C1 120.00(15) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2a 120.00(15) . . ?
H3 C3 C2 120.00(15) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.00(15) . . ?
H4 C4 C3 120.00(15) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.00(15) . . ?
C4 C5 N2 118.6 . . ?
C6 C5 N2 121.4 . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C1 120.0 . . ?
H6 C6 C1 120.00(15) . . ?
H6 C6 C5 120.00(15) . . ?
C8 C7 S1 122.9 . . ?
C12 C7 S1 117.1 . . ?
C12 C7 C8 120.0 . . ?
H8 C8 C7 120.00(18) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.00(18) . . ?
H9 C9 C8 120.00(18) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.00(18) . . ?
H10 C10 C9 120.00(18) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.00(18) . . ?
H11 C11 C10 120.00(18) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.00(18) . . ?
C11 C12 C7 120.0 . . ?
H12 C12 C7 120.00(18) . . ?
H12 C12 C11 120.00(18) . . ?

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 N2 C5 C4 -177.1(4) . . . . ?
S1 N2 C5 C6 1.9(7) . . . . ?
S1 C7 C8 C9 -177.65(15) . . . . ?
S1 C7 C12 C11 177.78(15) . . . . ?
O1 N1 C1 C2 175.7(6) . . . . ?
O1 N1 C1 C6 -5.0(8) . . . . ?
N1 C1 C2 C3 179.3(4) . . . . ?
N1 C1 C6 C5 -179.3(4) . . . . ?
C1 C2 C3 C4 -0.0(4) . . . . ?
C1 C6 C5 N2 -179.0(4) . . . . ?
C1 C6 C5 C4 -0.0(4) . . . . ?
N2 C5 C4 C3 179.0(4) . . . . ?
C2 C3 C4 C5 -0.0(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C7 C12 C11 C10 -0.0(4) . . . . ?
C8 C9 C10 C11 -0.0(4) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
