# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 2450009'
loop_
_audit_author_name
_audit_author_address
'Balasubramani Alagesan'
;University of Hyderabad
India
;
_audit_update_record             
;
2025-11-17 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2025-04-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C16 H10 Cl N S'
_chemical_formula_sum            'C16 H10 Cl N S'
_chemical_formula_weight         283.783
_chemical_absolute_configuration unk
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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.6596(4)
_cell_length_b                   10.8313(5)
_cell_length_c                   16.1412(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1339.13(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.26
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1350 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.9245.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             585.270
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20879
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9991
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2571
_reflns_number_total             3201
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3549
_refine_diff_density_min         -0.3064
_refine_diff_density_rms         0.0877
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.35(7)
_refine_ls_d_res_high            0.7598
_refine_ls_d_res_low             8.9940
_refine_ls_goodness_of_fit_ref   0.9986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      0.9986
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0942
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00D(H00D), C00C(H00C), C00G(H00G), C00J(H00J),
 C00I(H00I), C00H(H00H), C009(H009), C00E(H00E)
;
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
S001 S 0.65886(7) 0.47921(5) 0.09681(3) 0.04913(16) Uani 1.000000 .
Cl1 Cl 0.68520(8) 0.68661(6) 0.36205(4) 0.0799(2) Uani 1.000000 .
N003 N 0.6692(2) 0.41762(12) 0.25026(8) 0.0347(3) Uani 1.000000 .
C004 C 0.7437(2) 0.34468(14) 0.31114(11) 0.0337(4) Uani 1.000000 .
C005 C 0.5286(2) 0.50031(14) 0.24468(11) 0.0384(4) Uani 1.000000 .
C006 C 0.8777(2) 0.27592(16) 0.27241(11) 0.0383(4) Uani 1.000000 .
C007 C 0.7544(2) 0.39418(16) 0.17603(11) 0.0376(4) Uani 1.000000 .
C008 C 0.4257(2) 0.53127(15) 0.31877(11) 0.0407(4) Uani 1.000000 .
C009 C 0.8830(2) 0.30985(17) 0.18706(11) 0.0440(4) Uani 1.000000 .
C00A C 0.7058(2) 0.33280(16) 0.39545(11) 0.0410(4) Uani 1.000000 .
C00B C 0.4869(3) 0.61288(16) 0.37839(12) 0.0450(5) Uani 1.000000 .
C00C C 0.9727(3) 0.19135(17) 0.32037(12) 0.0496(5) Uani 1.000000 .
C00D C 0.9343(3) 0.17952(18) 0.40306(12) 0.0505(5) Uani 1.000000 .
C00E C 0.5073(3) 0.53981(18) 0.16671(12) 0.0492(5) Uani 1.000000 .
C00F C 0.8029(3) 0.24945(19) 0.44021(11) 0.0477(5) Uani 1.000000 .
C00G C 0.2641(3) 0.47665(19) 0.33260(14) 0.0528(5) Uani 1.000000 .
C00H C 0.3956(3) 0.63642(18) 0.45010(13) 0.0534(5) Uani 1.000000 .
C00I C 0.2369(3) 0.57917(19) 0.46220(15) 0.0598(6) Uani 1.000000 .
C00J C 0.1715(3) 0.49975(19) 0.40405(15) 0.0648(6) Uani 1.000000 .
H00A H 0.6182(2) 0.37940(16) 0.42030(11) 0.0492(5) Uiso 1.000000 R
H00F H 0.7806(3) 0.23950(19) 0.49645(11) 0.0572(6) Uiso 1.000000 R
H00D H 0.9972(3) 0.12364(18) 0.43502(12) 0.0606(6) Uiso 1.000000 R
H00C H 1.0605(3) 0.14396(17) 0.29647(12) 0.0595(6) Uiso 1.000000 R
H00G H 0.2178(3) 0.42366(19) 0.29295(14) 0.0634(6) Uiso 1.000000 R
H00J H 0.0644(3) 0.46137(19) 0.41280(15) 0.0777(7) Uiso 1.000000 R
H00I H 0.1738(3) 0.59466(19) 0.51031(15) 0.0718(7) Uiso 1.000000 R
H00H H 0.4402(3) 0.69011(18) 0.48977(13) 0.0641(6) Uiso 1.000000 R
H009 H 0.9594(2) 0.28006(17) 0.14700(11) 0.0528(5) Uiso 1.000000 R
H00E H 0.4197(3) 0.59457(18) 0.15118(12) 0.0590(6) 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
S001 C007 1.7375(18) . ?
S001 C00E 1.747(2) . ?
Cl1 C00B 1.736(2) . ?
N003 C004 1.384(2) . ?
N003 C005 1.403(2) . ?
N003 C007 1.388(2) . ?
C004 C006 1.413(2) . ?
C004 C00A 1.398(3) . ?
C005 C008 1.471(3) . ?
C005 C00E 1.339(3) . ?
C006 C009 1.426(3) . ?
C006 C00C 1.403(2) . ?
C007 C009 1.355(2) . ?
C008 C00B 1.388(2) . ?
C008 C00G 1.390(3) . ?
C00A C00F 1.375(3) . ?
C00B C00H 1.377(3) . ?
C00C C00D 1.373(3) . ?
C00D C00F 1.395(3) . ?
C00G C00J 1.377(3) . ?
C00H C00I 1.378(3) . ?
C00I C00J 1.368(3) . ?

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
C00E S001 C007 90.21(9) . . ?
C005 N003 C004 136.59(15) . . ?
C007 N003 C004 108.32(14) . . ?
C007 N003 C005 114.97(14) . . ?
C006 C004 N003 106.64(15) . . ?
C00A C004 N003 131.14(16) . . ?
C00A C004 C006 122.23(16) . . ?
C008 C005 N003 120.29(15) . . ?
C00E C005 N003 110.97(17) . . ?
C00E C005 C008 128.74(16) . . ?
C009 C006 C004 108.19(15) . . ?
C00C C006 C004 118.46(17) . . ?
C00C C006 C009 133.33(17) . . ?
N003 C007 S001 109.90(13) . . ?
C009 C007 S001 139.47(15) . . ?
C009 C007 N003 110.60(15) . . ?
C00B C008 C005 121.86(16) . . ?
C00G C008 C005 120.71(17) . . ?
C00G C008 C00B 117.41(18) . . ?
C007 C009 C006 106.24(16) . . ?
C00F C00A C004 117.34(18) . . ?
C008 C00B Cl1 118.88(15) . . ?
C00H C00B Cl1 119.16(15) . . ?
C00H C00B C008 121.96(18) . . ?
C00D C00C C006 119.09(18) . . ?
C00F C00D C00C 121.46(18) . . ?
C005 C00E S001 113.94(15) . . ?
C00D C00F C00A 121.41(18) . . ?
C00J C00G C008 121.1(2) . . ?
C00I C00H C00B 118.9(2) . . ?
C00J C00I C00H 120.6(2) . . ?
C00I C00J C00G 120.0(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
