# 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_mo_k_290825_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2502392'
loop_
_audit_author_name
_audit_author_address
'Akram Khan'
;CSIR National Chemical Laboratory
India
;
_audit_update_record             
;
2025-11-12 deposited with the CCDC.	2026-03-18 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         'C17 H18 N2 O2 S'
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_weight         314.39

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.5177(2)
_cell_length_b                   8.2099(3)
_cell_length_c                   17.2362(8)
_cell_angle_alpha                85.431(2)
_cell_angle_beta                 84.675(2)
_cell_angle_gamma                80.4690(10)
_cell_volume                     765.05(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9846
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            41860
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.379
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3803
_reflns_number_gt                3470
_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, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0444P)²+0.6141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3803
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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 0.40153(6) 0.23216(4) 0.90841(2) 0.01268(10) Uani 1 1 d . . . . .
O1 O 0.22223(19) 0.08892(14) 0.69866(6) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.62404(19) 0.25665(14) 0.94235(6) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.2127(2) 0.18170(16) 0.62590(7) 0.0175(3) Uani 1 1 d . . . . .
N2 N 0.4119(2) 0.10628(15) 0.84768(7) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.4711(2) 0.24283(17) 0.51108(8) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.2844(3) 0.35514(18) 0.47730(9) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.128291 0.381200 0.505569 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3250(3) 0.42855(18) 0.40312(9) 0.0191(3) Uani 1 1 d . . . . .
H3 H 0.197827 0.505720 0.381055 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5523(3) 0.38939(18) 0.36078(9) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.579747 0.439058 0.309713 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7380(3) 0.27789(19) 0.39337(9) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.892372 0.250383 0.364335 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6994(3) 0.20580(18) 0.46855(9) 0.0164(3) Uani 1 1 d . . . . .
H6 H 0.828826 0.131239 0.490971 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4287(3) 0.16400(17) 0.58962(8) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.6220(3) 0.05258(18) 0.63354(8) 0.0154(3) Uani 1 1 d . . . . .
H8A H 0.769091 0.105556 0.636836 0.019 Uiso 1 1 calc R U . . .
H8B H 0.672722 -0.054753 0.609582 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4815(3) 0.03226(18) 0.71311(8) 0.0153(3) Uani 1 1 d . . . . .
H9 H 0.505780 -0.086852 0.732633 0.018 Uiso 1 1 calc R U . . .
C10 C 0.5535(3) 0.13748(18) 0.77294(8) 0.0162(3) Uani 1 1 d . . . . .
H10A H 0.732348 0.108741 0.779272 0.019 Uiso 1 1 calc R U . . .
H10B H 0.517311 0.256099 0.755329 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2609(3) 0.43233(17) 0.87283(8) 0.0135(3) Uani 1 1 d . . . . .
C12 C 0.3546(3) 0.57067(19) 0.89028(9) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.489338 0.559376 0.921893 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2484(4) 0.72598(19) 0.86086(10) 0.0268(4) Uani 1 1 d . . . . .
H13 H 0.311042 0.821871 0.872009 0.032 Uiso 1 1 calc R U . . .
C14 C 0.0509(3) 0.7407(2) 0.81521(10) 0.0284(4) Uani 1 1 d . . . . .
H14 H -0.020834 0.846990 0.795042 0.034 Uiso 1 1 calc R U . . .
C15 C -0.0433(3) 0.6015(2) 0.79859(10) 0.0252(3) Uani 1 1 d . . . . .
H15 H -0.179892 0.613255 0.767728 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0623(3) 0.44534(19) 0.82714(9) 0.0186(3) Uani 1 1 d . . . . .
H16 H 0.000330 0.349394 0.815736 0.022 Uiso 1 1 calc R U . . .
C17 C 0.1916(3) 0.1728(2) 0.98366(9) 0.0193(3) Uani 1 1 d . . . . .
H17A H 0.028879 0.181125 0.963854 0.029 Uiso 1 1 calc R U . . .
H17B H 0.180910 0.245766 1.026572 0.029 Uiso 1 1 calc R U . . .
H17C H 0.247667 0.058247 1.002642 0.029 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 1.4574(11) . ?
S1 N2 1.5194(13) . ?
S1 C17 1.7517(15) . ?
S1 C11 1.7844(14) . ?
O1 N1 1.4151(16) . ?
O1 C9 1.4669(17) . ?
N1 C7 1.2851(18) . ?
N2 C10 1.4706(18) . ?
C1 C6 1.3980(19) . ?
C1 C2 1.4006(19) . ?
C1 C7 1.4691(19) . ?
C2 C3 1.385(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.394(2) . ?
C7 C8 1.5048(19) . ?
C8 C9 1.5231(19) . ?
C9 C10 1.516(2) . ?
C11 C12 1.387(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.390(2) . ?

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 N2 120.96(7) . . ?
O2 S1 C17 108.64(7) . . ?
N2 S1 C17 104.65(7) . . ?
O2 S1 C11 106.02(7) . . ?
N2 S1 C11 110.89(7) . . ?
C17 S1 C11 104.54(7) . . ?
N1 O1 C9 108.65(10) . . ?
C7 N1 O1 109.37(12) . . ?
C10 N2 S1 116.56(10) . . ?
C6 C1 C2 118.87(13) . . ?
C6 C1 C7 120.24(13) . . ?
C2 C1 C7 120.89(12) . . ?
C3 C2 C1 120.65(13) . . ?
C2 C3 C4 120.09(14) . . ?
C5 C4 C3 119.81(14) . . ?
C4 C5 C6 120.34(14) . . ?
C5 C6 C1 120.23(13) . . ?
N1 C7 C1 121.05(13) . . ?
N1 C7 C8 113.91(13) . . ?
C1 C7 C8 125.00(12) . . ?
C7 C8 C9 100.62(11) . . ?
O1 C9 C10 108.96(11) . . ?
O1 C9 C8 104.51(11) . . ?
C10 C9 C8 112.85(12) . . ?
N2 C10 C9 108.52(12) . . ?
C12 C11 C16 121.71(13) . . ?
C12 C11 S1 119.22(11) . . ?
C16 C11 S1 119.06(11) . . ?
C11 C12 C13 119.04(15) . . ?
C14 C13 C12 119.84(15) . . ?
C13 C14 C15 120.76(14) . . ?
C16 C15 C14 120.00(16) . . ?
C15 C16 C11 118.65(15) . . ?

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
C9 O1 N1 C7 10.79(15) . . . . ?
O2 S1 N2 C10 -64.21(13) . . . . ?
C17 S1 N2 C10 172.96(11) . . . . ?
C11 S1 N2 C10 60.78(12) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C7 C1 C2 C3 -179.73(13) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C7 C1 C6 C5 178.62(13) . . . . ?
O1 N1 C7 C1 178.03(12) . . . . ?
O1 N1 C7 C8 0.32(16) . . . . ?
C6 C1 C7 N1 -171.97(13) . . . . ?
C2 C1 C7 N1 7.7(2) . . . . ?
C6 C1 C7 C8 5.5(2) . . . . ?
C2 C1 C7 C8 -174.90(13) . . . . ?
N1 C7 C8 C9 -10.49(16) . . . . ?
C1 C7 C8 C9 171.90(13) . . . . ?
N1 O1 C9 C10 104.02(13) . . . . ?
N1 O1 C9 C8 -16.86(14) . . . . ?
C7 C8 C9 O1 15.66(13) . . . . ?
C7 C8 C9 C10 -102.59(13) . . . . ?
S1 N2 C10 C9 -163.34(10) . . . . ?
O1 C9 C10 N2 65.56(14) . . . . ?
C8 C9 C10 N2 -178.82(11) . . . . ?
O2 S1 C11 C12 -8.06(13) . . . . ?
N2 S1 C11 C12 -141.10(12) . . . . ?
C17 S1 C11 C12 106.64(12) . . . . ?
O2 S1 C11 C16 170.91(11) . . . . ?
N2 S1 C11 C16 37.87(13) . . . . ?
C17 S1 C11 C16 -74.39(13) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
S1 C11 C12 C13 178.43(11) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
S1 C11 C16 C15 -178.92(11) . . . . ?

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
_geom_hbond_publ_flag
C8 H8A N1 0.99 2.61 3.5782(19) 165.5 1_655 yes
C17 H17A O2 0.98 2.27 3.2265(19) 163.8 1_455 yes

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.059

