# 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_ex-pm908
_database_code_depnum_ccdc_archive 'CCDC 2471164'
loop_
_audit_author_name
_audit_author_address
'Vikas Tyagi'
;Thapar Institute of Engineering and Technology
India
;
_audit_update_record             
;
2025-07-09 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_audit_creation_date             2025-03-06
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O4 S2'
_chemical_formula_sum            'C23 H21 N3 O4 S2'
_chemical_formula_weight         467.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5075(5)
_cell_length_b                   10.2822(5)
_cell_length_c                   15.6878(9)
_cell_angle_alpha                72.906(5)
_cell_angle_beta                 88.731(5)
_cell_angle_gamma                80.529(5)
_cell_volume                     1141.28(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5410
_cell_measurement_theta_min      3.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14961
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.079
_diffrn_reflns_theta_min         3.233
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  -6.00   0.50   12.65    --   -9.32  99.00  91.00   70
  2  ω      0.00  41.00   0.50   12.65    --    9.60 -99.00 -14.00   82
  3  ω    -23.00  36.00   0.50   12.65    --   -9.32  77.00  30.00  118
  4  ω     14.00  39.00   0.50   12.65    --    9.60 -99.00  60.00   50
  5  ω      9.00  56.00   0.50   12.65    --    9.60-125.00-150.00   94
  6  ω    -54.00  23.00   0.50   12.65    --    9.60 -38.00-120.00  154
  7  ω    -18.00   7.00   0.50   12.65    --    9.60 107.00 -48.26   50
  8  ω    -41.00  32.00   0.50   12.65    --    9.60 -77.00   0.00  146
  9  ω     -5.00  23.00   0.50   12.65    --    9.60  88.00-140.35   56
 10  ω    -11.00  35.00   0.50   12.65    --    9.60 -99.00  90.00   92
 11  ω     16.00  51.00   0.50   12.65    --    9.60-125.00 -60.00   70
 12  ω    -32.00  -5.00   0.50   12.65    --    9.60 -57.00-180.00   54
 13  ω      0.00  25.00   0.50   12.65    --    9.60 -57.00-180.00   50
 14  ω    -33.00  -5.00   0.50   12.65    --    9.60 123.00 106.03   56
 15  ω    -56.00  22.00   0.50   12.65    --    9.60 -19.00  90.00  156
 16  ω    -31.00  -5.00   0.50   12.65    --    9.60 -77.00 -30.00   52
 17  ω    -33.00  -8.00   0.50   12.65    --    9.60 120.00  43.13   50
 18  ω    -54.00 -14.00   0.50   12.65    --    9.60 -57.00-150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0654862000
_diffrn_orient_matrix_UB_12      -0.0316179000
_diffrn_orient_matrix_UB_13      0.0349872000
_diffrn_orient_matrix_UB_21      -0.0676370000
_diffrn_orient_matrix_UB_22      -0.0290969000
_diffrn_orient_matrix_UB_23      0.0279948000
_diffrn_orient_matrix_UB_31      0.0178466000
_diffrn_orient_matrix_UB_32      -0.0592359000
_diffrn_orient_matrix_UB_33      -0.0152160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2338
_reflns_number_total             4595
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N007(H007), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00E), C00W(H00F,H00J,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S001 S 0.18437(15) 0.73373(8) 0.83898(6) 0.0640(3) Uani 1 1 d . . . . .
S002 S 0.56011(15) 0.66851(8) 0.77720(7) 0.0692(4) Uani 1 1 d . . . . .
O003 O 0.0281(4) 0.8264(2) 0.79503(15) 0.0755(8) Uani 1 1 d . . . . .
O004 O 0.2628(4) 0.7535(2) 0.91470(16) 0.0871(9) Uani 1 1 d . . . . .
O005 O 0.6118(4) 0.6699(2) 0.86315(16) 0.0875(9) Uani 1 1 d . . . . .
N006 N 0.2671(4) 0.7538(2) 0.67396(17) 0.0554(7) Uani 1 1 d . . . . .
N007 N 0.1636(4) 1.0111(2) 0.38090(18) 0.0603(8) Uani 1 1 d . . . . .
H007 H 0.162225 1.074620 0.330842 0.072 Uiso 1 1 calc R U . . .
O008 O 0.6525(4) 0.7356(2) 0.69990(18) 0.0851(8) Uani 1 1 d . . . . .
N009 N 0.3439(4) 0.7538(2) 0.75845(17) 0.0577(8) Uani 1 1 d . . . . .
C00A C 0.2300(5) 0.8887(3) 0.5222(2) 0.0489(8) Uani 1 1 d . . . . .
C00B C 0.1140(5) 0.8193(3) 0.4855(2) 0.0530(9) Uani 1 1 d . . . . .
C00C C 0.2953(4) 0.8613(3) 0.6109(2) 0.0519(9) Uani 1 1 d . . . . .
H00C H 0.360453 0.922695 0.624146 0.062 Uiso 1 1 calc R U . . .
C00D C 0.2519(5) 1.0066(3) 0.4548(2) 0.0545(9) Uani 1 1 d . . . . .
H00D H 0.318269 1.072652 0.460301 0.065 Uiso 1 1 calc R U . . .
C00E C 0.0743(5) 0.8989(3) 0.3963(2) 0.0550(9) Uani 1 1 d . . . . .
C00F C 0.1430(5) 0.5644(3) 0.8642(2) 0.0551(9) Uani 1 1 d . . . . .
C00G C 0.0615(5) 0.5224(3) 0.8011(2) 0.0612(10) Uani 1 1 d . . . . .
H00G H 0.024715 0.584732 0.745837 0.073 Uiso 1 1 calc R U . . .
C00H C 0.0354(5) 0.3889(3) 0.8204(2) 0.0683(11) Uani 1 1 d . . . . .
H00H H -0.018788 0.360549 0.777691 0.082 Uiso 1 1 calc R U . . .
C00I C 0.0314(5) 0.7033(3) 0.5204(2) 0.0697(11) Uani 1 1 d . . . . .
H00I H 0.055105 0.648407 0.579007 0.084 Uiso 1 1 calc R U . . .
C00J C 0.5604(5) 0.4984(3) 0.7780(3) 0.0674(10) Uani 1 1 d . . . . .
C00K C 0.1948(5) 0.4728(3) 0.9464(2) 0.0715(12) Uani 1 1 d . . . . .
H00K H 0.249673 0.500828 0.989050 0.086 Uiso 1 1 calc R U . . .
C00L C 0.0887(5) 0.2943(3) 0.9029(3) 0.0659(10) Uani 1 1 d . . . . .
C00M C -0.0398(6) 0.8653(4) 0.3419(2) 0.0718(12) Uani 1 1 d . . . . .
H00M H -0.061343 0.918059 0.282632 0.086 Uiso 1 1 calc R U . . .
C00N C 0.1646(6) 0.3388(3) 0.9648(3) 0.0779(12) Uani 1 1 d . . . . .
H00N H 0.196781 0.277400 1.020952 0.094 Uiso 1 1 calc R U . . .
C00O C -0.0853(7) 0.6722(4) 0.4663(3) 0.0859(13) Uani 1 1 d . . . . .
H00O H -0.142641 0.596061 0.489040 0.103 Uiso 1 1 calc R U . . .
C00P C 0.5671(6) 0.3955(3) 0.8589(3) 0.0743(11) Uani 1 1 d . . . . .
H00P H 0.570395 0.417345 0.912287 0.089 Uiso 1 1 calc R U . . .
C00Q C -0.1205(6) 0.7528(4) 0.3771(3) 0.0820(13) Uani 1 1 d . . . . .
H00Q H -0.199755 0.728846 0.341710 0.098 Uiso 1 1 calc R U . . .
C00R C 0.5592(6) 0.4641(4) 0.6995(3) 0.0848(12) Uani 1 1 d . . . . .
H00R H 0.557433 0.531650 0.644867 0.102 Uiso 1 1 calc R U . . .
C00S C 0.5690(6) 0.2614(4) 0.8598(3) 0.0885(13) Uani 1 1 d . . . . .
H00S H 0.572397 0.193448 0.914411 0.106 Uiso 1 1 calc R U . . .
C00T C 0.5661(6) 0.2245(4) 0.7831(4) 0.0949(15) Uani 1 1 d . . . . .
C00U C 0.5608(6) 0.3264(5) 0.7029(4) 0.0954(14) Uani 1 1 d . . . . .
H00U H 0.558280 0.303225 0.650019 0.114 Uiso 1 1 calc R U . . .
C00V C 0.0598(7) 0.1461(3) 0.9230(3) 0.0993(15) Uani 1 1 d . . . . .
H00A H -0.016255 0.138014 0.877115 0.149 Uiso 1 1 calc R U . . .
H00B H 0.003209 0.118927 0.979546 0.149 Uiso 1 1 calc R U . . .
H00E H 0.174265 0.087476 0.925198 0.149 Uiso 1 1 calc R U . . .
C00W C 0.5602(8) 0.0759(4) 0.7856(4) 0.142(2) Uani 1 1 d . . . . .
H00F H 0.672708 0.018915 0.809850 0.213 Uiso 1 1 calc R U . . .
H00J H 0.540839 0.071898 0.726231 0.213 Uiso 1 1 calc R U . . .
H00L H 0.463353 0.043315 0.822400 0.213 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
S001 O003 1.429(2) . ?
S001 O004 1.418(2) . ?
S001 N009 1.713(3) . ?
S001 C00F 1.747(3) . ?
S002 O005 1.416(2) . ?
S002 O008 1.434(3) . ?
S002 N009 1.701(3) . ?
S002 C00J 1.745(4) . ?
N006 N009 1.457(3) . ?
N006 C00C 1.292(3) . ?
N007 C00D 1.334(4) . ?
N007 C00E 1.387(4) . ?
C00A C00B 1.438(4) . ?
C00A C00C 1.417(4) . ?
C00A C00D 1.385(4) . ?
C00B C00E 1.408(4) . ?
C00B C00I 1.397(5) . ?
C00E C00M 1.373(5) . ?
C00F C00G 1.381(4) . ?
C00F C00K 1.375(4) . ?
C00G C00H 1.362(4) . ?
C00H C00L 1.392(5) . ?
C00I C00O 1.369(5) . ?
C00J C00P 1.389(5) . ?
C00J C00R 1.377(5) . ?
C00K C00N 1.378(4) . ?
C00L C00N 1.359(5) . ?
C00L C00V 1.514(5) . ?
C00M C00Q 1.361(5) . ?
C00O C00Q 1.406(5) . ?
C00P C00S 1.373(5) . ?
C00R C00U 1.399(5) . ?
C00S C00T 1.366(6) . ?
C00T C00U 1.376(6) . ?
C00T C00W 1.524(6) . ?

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
O003 S001 N009 103.47(14) . . ?
O003 S001 C00F 109.22(17) . . ?
O004 S001 O003 119.93(15) . . ?
O004 S001 N009 106.31(17) . . ?
O004 S001 C00F 109.67(15) . . ?
N009 S001 C00F 107.41(14) . . ?
O005 S002 O008 120.55(18) . . ?
O005 S002 N009 106.08(16) . . ?
O005 S002 C00J 109.17(16) . . ?
O008 S002 N009 103.81(14) . . ?
O008 S002 C00J 108.49(18) . . ?
N009 S002 C00J 108.04(16) . . ?
C00C N006 N009 110.6(2) . . ?
C00D N007 C00E 110.3(3) . . ?
S002 N009 S001 122.84(15) . . ?
N006 N009 S001 110.3(2) . . ?
N006 N009 S002 112.59(19) . . ?
C00C C00A C00B 130.4(3) . . ?
C00D C00A C00B 106.2(3) . . ?
C00D C00A C00C 122.9(3) . . ?
C00E C00B C00A 106.8(3) . . ?
C00I C00B C00A 134.4(3) . . ?
C00I C00B C00E 118.7(3) . . ?
N006 C00C C00A 122.2(3) . . ?
N007 C00D C00A 109.9(3) . . ?
N007 C00E C00B 106.8(3) . . ?
C00M C00E N007 130.6(3) . . ?
C00M C00E C00B 122.5(3) . . ?
C00G C00F S001 120.0(2) . . ?
C00K C00F S001 119.7(3) . . ?
C00K C00F C00G 120.2(3) . . ?
C00H C00G C00F 119.6(3) . . ?
C00G C00H C00L 121.0(3) . . ?
C00O C00I C00B 118.5(3) . . ?
C00P C00J S002 119.5(3) . . ?
C00R C00J S002 120.9(3) . . ?
C00R C00J C00P 119.5(3) . . ?
C00F C00K C00N 119.2(3) . . ?
C00H C00L C00V 120.3(4) . . ?
C00N C00L C00H 118.4(3) . . ?
C00N C00L C00V 121.2(3) . . ?
C00Q C00M C00E 118.1(4) . . ?
C00L C00N C00K 121.6(3) . . ?
C00I C00O C00Q 121.5(4) . . ?
C00S C00P C00J 119.7(4) . . ?
C00M C00Q C00O 120.7(4) . . ?
C00J C00R C00U 119.2(4) . . ?
C00T C00S C00P 122.1(4) . . ?
C00S C00T C00U 118.1(4) . . ?
C00S C00T C00W 121.2(5) . . ?
C00U C00T C00W 120.6(5) . . ?
C00T C00U C00R 121.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.070
_oxdiff_exptl_absorpt_empirical_full_min 0.161
