# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2427348'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 N3 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         265.33

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9257(17)
_cell_length_b                   15.649(12)
_cell_length_c                   9.9843(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.460(18)
_cell_angle_gamma                90
_cell_volume                     1297.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1110
_cell_measurement_theta_min      3.5699
_cell_measurement_theta_max      28.9155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_T_min  0.61190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_reflns_number            7375
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.577
_diffrn_reflns_theta_max         28.979
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2991
_reflns_number_gt                2234
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
; 
SUPERFLIP 
L. Palatinus and G. Chapuis, J. Appl. Crystallogr., 2007, 40, 786-790.
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.1051P)²+0.3058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2991
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1968
_refine_ls_wR_factor_gt          0.1797
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.12899(8) 0.03328(4) 0.38122(6) 0.0487(3) Uani 1 1 d . . . . .
O2 O -0.0776(2) -0.04880(14) 0.12943(17) 0.0604(6) Uani 1 1 d . . . . .
O1 O -0.0713(2) -0.18423(13) 0.21076(18) 0.0613(6) Uani 1 1 d . . . . .
C10 C 0.5789(4) 0.2157(3) 0.7110(4) 0.0822(11) Uani 1 1 d . . . . .
H10A H 0.6778 0.2351 0.7016 0.099 Uiso 1 1 calc R U . . .
H10B H 0.5520 0.2555 0.7733 0.099 Uiso 1 1 calc R U . . .
N2 N 0.1465(3) -0.20487(16) 0.5077(2) 0.0548(6) Uani 1 1 d . . . . .
C1 C 0.2656(3) -0.06573(17) 0.5994(2) 0.0436(6) Uani 1 1 d . . . . .
N3 N 0.3306(3) 0.08994(16) 0.6335(2) 0.0661(7) Uani 1 1 d . . . . .
C2 C 0.3471(3) -0.10056(18) 0.7376(3) 0.0562(7) Uani 1 1 d . . . . .
C5 C 0.1624(3) -0.12024(16) 0.4877(2) 0.0427(6) Uani 1 1 d . . . . .
N1 N 0.4086(4) -0.13178(19) 0.8475(3) 0.0863(10) Uani 1 1 d . . . . .
C3 C 0.2587(3) 0.02053(17) 0.5576(2) 0.0464(6) Uani 1 1 d . . . . .
C4 C 0.0804(3) -0.07532(17) 0.3634(2) 0.0436(6) Uani 1 1 d . . . . .
C9 C 0.4457(5) 0.2148(3) 0.5651(4) 0.0867(11) Uani 1 1 d . . . . .
H9A H 0.4226 0.2729 0.5295 0.104 Uiso 1 1 calc R U . . .
H9B H 0.4803 0.1828 0.4984 0.104 Uiso 1 1 calc R U . . .
C7 C -0.1836(4) -0.0747(2) -0.0105(3) 0.0733(10) Uani 1 1 d . . . . .
H7A H -0.2102 -0.0262 -0.0737 0.110 Uiso 1 1 calc R U . . .
H7B H -0.1316 -0.1173 -0.0477 0.110 Uiso 1 1 calc R U . . .
H7C H -0.2802 -0.0982 -0.0042 0.110 Uiso 1 1 calc R U . . .
C11 C 0.6041(4) 0.1281(3) 0.7775(4) 0.0761(10) Uani 1 1 d . . . . .
H11A H 0.6500 0.0913 0.7244 0.091 Uiso 1 1 calc R U . . .
H11B H 0.6807 0.1320 0.8756 0.091 Uiso 1 1 calc R U . . .
C6 C -0.0281(3) -0.10973(17) 0.2320(2) 0.0459(6) Uani 1 1 d . . . . .
C8 C 0.3002(4) 0.1762(2) 0.5722(4) 0.0747(10) Uani 1 1 d . . . . .
H8A H 0.2186 0.1735 0.4761 0.090 Uiso 1 1 calc R U . . .
H8B H 0.2592 0.2118 0.6306 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4524(4) 0.0889(2) 0.7784(3) 0.0657(8) Uani 1 1 d . . . . .
H12A H 0.4728 0.0305 0.8129 0.079 Uiso 1 1 calc R U . . .
H12B H 0.4140 0.1206 0.8430 0.079 Uiso 1 1 calc R U . . .
H1A H 0.087(3) -0.2347(16) 0.434(3) 0.043(7) Uiso 1 1 d . . . . .
H1B H 0.217(4) -0.2329(19) 0.579(3) 0.059(8) Uiso 1 1 d . . . . .


_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 C3 1.729(2) . ?
S1 C4 1.747(3) . ?
O2 C6 1.350(3) . ?
O2 C7 1.430(3) . ?
O1 C6 1.222(3) . ?
C10 C11 1.504(5) . ?
C10 C9 1.506(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N2 C5 1.355(4) . ?
N2 H1A 0.86(3) . ?
N2 H1B 0.88(3) . ?
C1 C3 1.408(4) . ?
C1 C2 1.413(3) . ?
C1 C5 1.438(3) . ?
N3 C3 1.345(3) . ?
N3 C12 1.458(3) . ?
N3 C8 1.466(4) . ?
C2 N1 1.142(3) . ?
C5 C4 1.380(3) . ?
C4 C6 1.421(3) . ?
C9 C8 1.457(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 C12 1.489(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 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
C3 S1 C4 92.30(11) . . ?
C6 O2 C7 117.2(2) . . ?
C11 C10 C9 110.8(3) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C5 N2 H1A 117.8(17) . . ?
C5 N2 H1B 122(2) . . ?
H1A N2 H1B 117(3) . . ?
C3 C1 C2 127.6(2) . . ?
C3 C1 C5 113.1(2) . . ?
C2 C1 C5 118.9(2) . . ?
C3 N3 C12 125.4(2) . . ?
C3 N3 C8 122.0(2) . . ?
C12 N3 C8 112.4(2) . . ?
N1 C2 C1 177.0(3) . . ?
N2 C5 C4 125.5(2) . . ?
N2 C5 C1 122.5(2) . . ?
C4 C5 C1 111.9(2) . . ?
N3 C3 C1 130.3(2) . . ?
N3 C3 S1 119.0(2) . . ?
C1 C3 S1 110.65(17) . . ?
C5 C4 C6 126.5(2) . . ?
C5 C4 S1 111.95(18) . . ?
C6 C4 S1 121.49(18) . . ?
C8 C9 C10 111.1(3) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C10 112.9(3) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O1 C6 O2 123.2(2) . . ?
O1 C6 C4 125.9(2) . . ?
O2 C6 C4 110.9(2) . . ?
C9 C8 N3 111.7(3) . . ?
C9 C8 H8A 109.3 . . ?
N3 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N3 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N3 C12 C11 109.8(2) . . ?
N3 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?

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
C3 C1 C5 N2 -177.4(2) . . . . ?
C2 C1 C5 N2 -3.4(4) . . . . ?
C3 C1 C5 C4 0.5(3) . . . . ?
C2 C1 C5 C4 174.4(2) . . . . ?
C12 N3 C3 C1 8.1(5) . . . . ?
C8 N3 C3 C1 -176.2(3) . . . . ?
C12 N3 C3 S1 -174.6(2) . . . . ?
C8 N3 C3 S1 1.1(4) . . . . ?
C2 C1 C3 N3 3.0(5) . . . . ?
C5 C1 C3 N3 176.3(3) . . . . ?
C2 C1 C3 S1 -174.4(2) . . . . ?
C5 C1 C3 S1 -1.1(3) . . . . ?
C4 S1 C3 N3 -176.7(2) . . . . ?
C4 S1 C3 C1 1.1(2) . . . . ?
N2 C5 C4 C6 -3.8(4) . . . . ?
C1 C5 C4 C6 178.4(2) . . . . ?
N2 C5 C4 S1 178.1(2) . . . . ?
C1 C5 C4 S1 0.3(3) . . . . ?
C3 S1 C4 C5 -0.8(2) . . . . ?
C3 S1 C4 C6 -179.0(2) . . . . ?
C11 C10 C9 C8 52.1(5) . . . . ?
C9 C10 C11 C12 -51.7(4) . . . . ?
C7 O2 C6 O1 -1.1(4) . . . . ?
C7 O2 C6 C4 178.1(2) . . . . ?
C5 C4 C6 O1 3.7(4) . . . . ?
S1 C4 C6 O1 -178.4(2) . . . . ?
C5 C4 C6 O2 -175.5(2) . . . . ?
S1 C4 C6 O2 2.4(3) . . . . ?
C10 C9 C8 N3 -55.7(4) . . . . ?
C3 N3 C8 C9 -117.3(3) . . . . ?
C12 N3 C8 C9 58.9(4) . . . . ?
C3 N3 C12 C11 119.7(4) . . . . ?
C8 N3 C12 C11 -56.4(4) . . . . ?
C10 C11 C12 N3 53.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7C N1 0.96 2.68 3.504(5) 144.4 1_454
C8 H8A S1 0.97 2.41 2.973(3) 116.8 .
C12 H12A N1 0.97 2.65 3.572(5) 157.9 .
N2 H1A O1 0.86(3) 2.30(3) 2.908(3) 127(2) .
N2 H1A N1 0.86(3) 2.58(3) 3.334(4) 146(2) 4
N2 H1B O1 0.88(3) 2.27(3) 3.119(3) 163(2) 4_656
C7 H7C N1 0.96 2.68 3.504(5) 144.4 1_454
C8 H8A S1 0.97 2.41 2.973(3) 116.8 .
C12 H12A N1 0.97 2.65 3.572(5) 157.9 .
N2 H1A O1 0.86(3) 2.30(3) 2.908(3) 127(2) .
N2 H1A N1 0.86(3) 2.58(3) 3.334(4) 146(2) 4
N2 H1B O1 0.88(3) 2.27(3) 3.119(3) 163(2) 4_656

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.059

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

