# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 
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data_pth_ab_py_300623_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2gh56c
_database_code_depnum_ccdc_archive 'CCDC 2278692'
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
dhandapanichemist@gmail.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 S'
_chemical_formula_sum            'C23 H17 N3 S'
_chemical_formula_weight         367.45
_chemical_melting_point          ?
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.3292(16)
_cell_length_b                   14.298(2)
_cell_length_c                   14.191(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.460(6)
_cell_angle_gamma                90
_cell_volume                     1880.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.570
_cell_measurement_theta_min      2.490
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.9005.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33902
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2661
_reflns_number_total             4647
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.055
_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)+(0.0411P)²+0.4958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C1(H1), C14(H14), C16(H16), C19(H19), C22(H22), C21(H21),
 C5(H5), C20(H20), C7(H7), C8(H8), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.58447(6) 0.77673(4) 0.28134(4) 0.0670(2) Uani 1 1 d . . . . .
N3 N 0.90504(16) 0.75849(11) 0.33878(11) 0.0504(4) Uani 1 1 d . . . . .
N1 N 0.49382(18) 0.25444(13) 0.45128(13) 0.0613(5) Uani 1 1 d . . . . .
C12 C 0.8236(2) 0.67944(13) 0.35686(13) 0.0452(5) Uani 1 1 d . . . . .
C11 C 0.6729(2) 0.68085(13) 0.33938(13) 0.0472(5) Uani 1 1 d . . . . .
C13 C 0.8889(2) 0.59670(14) 0.39078(14) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.988892 0.593666 0.402977 0.063 Uiso 1 1 calc R U . . .
C2 C 0.4431(2) 0.40761(14) 0.38885(13) 0.0484(5) Uani 1 1 d . . . . .
C9 C 0.6568(2) 0.52004(13) 0.39041(14) 0.0491(5) Uani 1 1 d . . . . .
C10 C 0.5920(2) 0.60382(14) 0.35760(14) 0.0510(5) Uani 1 1 d . . . . .
H10 H 0.491894 0.607578 0.347872 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7019(2) 0.86739(14) 0.32296(14) 0.0520(5) Uani 1 1 d . . . . .
C1 C 0.5823(2) 0.43387(14) 0.40665(14) 0.0528(5) Uani 1 1 d . . . . .
H1 H 0.642233 0.387390 0.434947 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3952(2) 0.31127(14) 0.40689(13) 0.0483(5) Uani 1 1 d . . . . .
C18 C 0.8486(2) 0.85004(14) 0.34488(13) 0.0498(5) Uani 1 1 d . . . . .
C14 C 0.8073(2) 0.51938(14) 0.40646(14) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.853780 0.464791 0.428504 0.064 Uiso 1 1 calc R U . . .
C16 C 1.1583(2) 0.74582(15) 0.42205(19) 0.0638(6) Uani 1 1 d . . . . .
H16 H 1.256431 0.740644 0.416798 0.077 Uiso 1 1 calc R U . . .
C15 C 1.0594(2) 0.74703(16) 0.33123(16) 0.0611(6) Uani 1 1 d . . . . .
H15A H 1.089606 0.797412 0.292156 0.073 Uiso 1 1 calc R U . . .
H15B H 1.072480 0.688942 0.297941 0.073 Uiso 1 1 calc R U . . .
C19 C 0.9377(2) 0.92549(15) 0.37355(15) 0.0615(6) Uani 1 1 d . . . . .
H19 H 1.035827 0.915742 0.390059 0.074 Uiso 1 1 calc R U . . .
C17 C 1.1212(3) 0.75123(17) 0.5071(2) 0.0683(7) Uani 1 1 d . . . . .
C3 C 0.3333(2) 0.46948(16) 0.34674(17) 0.0653(6) Uani 1 1 d . . . . .
C22 C 0.6471(2) 0.95697(15) 0.32836(15) 0.0622(6) Uani 1 1 d . . . . .
H22 H 0.548689 0.967282 0.313923 0.075 Uiso 1 1 calc R U . . .
C21 C 0.7372(3) 1.03086(16) 0.35493(16) 0.0670(6) Uani 1 1 d . . . . .
H21 H 0.700492 1.091172 0.357428 0.080 Uiso 1 1 calc R U . . .
N2 N 0.2415(2) 0.51600(16) 0.3130(2) 0.1038(8) Uani 1 1 d . . . . .
C5 C 0.2575(2) 0.28037(16) 0.37550(15) 0.0596(6) Uani 1 1 d . . . . .
H5 H 0.189005 0.321657 0.346760 0.071 Uiso 1 1 calc R U . . .
C20 C 0.8815(3) 1.01445(16) 0.37765(17) 0.0688(6) Uani 1 1 d . . . . .
H20 H 0.942704 1.064099 0.396147 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3234(3) 0.12936(17) 0.43247(17) 0.0722(7) Uani 1 1 d . . . . .
H7 H 0.302455 0.066657 0.441707 0.087 Uiso 1 1 calc R U . . .
C8 C 0.4564(2) 0.16621(17) 0.46382(17) 0.0693(6) Uani 1 1 d . . . . .
H8 H 0.524480 0.126710 0.495911 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2234(2) 0.18851(18) 0.38722(17) 0.0716(7) Uani 1 1 d . . . . .
H6 H 0.132367 0.166339 0.364446 0.086 Uiso 1 1 calc R U . . .
H17A H 1.019(3) 0.7567(15) 0.5173(15) 0.075(7) Uiso 1 1 d . . . . .
H17B H 1.193(3) 0.7496(16) 0.5628(18) 0.083(7) 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 C11 1.756(2) . ?
S1 C23 1.756(2) . ?
N3 C12 1.401(2) . ?
N3 C18 1.417(2) . ?
N3 C15 1.465(2) . ?
N1 C4 1.332(2) . ?
N1 C8 1.326(3) . ?
C12 C11 1.401(3) . ?
C12 C13 1.392(3) . ?
C11 C10 1.376(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C2 C1 1.349(3) . ?
C2 C4 1.479(3) . ?
C2 C3 1.432(3) . ?
C9 C10 1.398(3) . ?
C9 C1 1.446(3) . ?
C9 C14 1.396(3) . ?
C10 H10 0.9300 . ?
C23 C18 1.391(3) . ?
C23 C22 1.384(3) . ?
C1 H1 0.9300 . ?
C4 C5 1.384(3) . ?
C18 C19 1.394(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.498(3) . ?
C16 C17 1.294(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C17 H17A 0.98(2) . ?
C17 H17B 0.98(2) . ?
C3 N2 1.146(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.376(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(3) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.375(3) . ?
C7 C6 1.365(3) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?

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
C23 S1 C11 100.15(9) . . ?
C12 N3 C18 121.40(16) . . ?
C12 N3 C15 118.71(16) . . ?
C18 N3 C15 118.87(16) . . ?
C8 N1 C4 117.74(18) . . ?
C11 C12 N3 120.66(17) . . ?
C13 C12 N3 121.59(17) . . ?
C13 C12 C11 117.74(18) . . ?
C12 C11 S1 120.24(15) . . ?
C10 C11 S1 118.32(14) . . ?
C10 C11 C12 121.07(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.69(18) . . ?
C14 C13 H13 119.7 . . ?
C1 C2 C4 122.00(18) . . ?
C1 C2 C3 122.33(19) . . ?
C3 C2 C4 115.59(17) . . ?
C10 C9 C1 125.86(18) . . ?
C14 C9 C10 116.70(18) . . ?
C14 C9 C1 117.42(18) . . ?
C11 C10 C9 121.52(17) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C18 C23 S1 120.29(16) . . ?
C22 C23 S1 118.78(16) . . ?
C22 C23 C18 120.83(19) . . ?
C2 C1 C9 132.66(19) . . ?
C2 C1 H1 113.7 . . ?
C9 C1 H1 113.7 . . ?
N1 C4 C2 116.38(17) . . ?
N1 C4 C5 121.62(19) . . ?
C5 C4 C2 121.94(19) . . ?
C23 C18 N3 120.94(18) . . ?
C23 C18 C19 117.79(19) . . ?
C19 C18 N3 121.27(19) . . ?
C13 C14 C9 122.24(19) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C15 C16 H16 116.6 . . ?
C17 C16 H16 116.6 . . ?
C17 C16 C15 126.7(2) . . ?
N3 C15 C16 116.97(18) . . ?
N3 C15 H15A 108.1 . . ?
N3 C15 H15B 108.1 . . ?
C16 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C16 C17 H17A 120.5(13) . . ?
C16 C17 H17B 121.3(14) . . ?
H17A C17 H17B 118.2(19) . . ?
N2 C3 C2 177.2(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C22 C21 H21 120.4 . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H21 120.4 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.5 . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.3(2) . . ?
N1 C8 C7 124.2(2) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?

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 C11 C10 C9 170.30(15) . . . . ?
S1 C23 C18 N3 -3.2(3) . . . . ?
S1 C23 C18 C19 177.17(15) . . . . ?
S1 C23 C22 C21 -175.92(17) . . . . ?
N3 C12 C11 S1 7.6(3) . . . . ?
N3 C12 C11 C10 -179.49(17) . . . . ?
N3 C12 C13 C14 -178.82(18) . . . . ?
N3 C18 C19 C20 178.92(19) . . . . ?
N1 C4 C5 C6 -2.4(3) . . . . ?
C12 N3 C18 C23 -31.7(3) . . . . ?
C12 N3 C18 C19 147.85(19) . . . . ?
C12 N3 C15 C16 -83.3(2) . . . . ?
C12 C11 C10 C9 -2.7(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C11 S1 C23 C18 30.67(18) . . . . ?
C11 S1 C23 C22 -152.91(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C13 C12 C11 S1 -171.15(14) . . . . ?
C13 C12 C11 C10 1.7(3) . . . . ?
C2 C4 C5 C6 174.48(19) . . . . ?
C10 C9 C1 C2 6.5(4) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C23 S1 C11 C12 -32.95(18) . . . . ?
C23 S1 C11 C10 153.97(16) . . . . ?
C23 C18 C19 C20 -1.5(3) . . . . ?
C23 C22 C21 C20 -1.2(3) . . . . ?
C1 C2 C4 N1 7.1(3) . . . . ?
C1 C2 C4 C5 -169.95(19) . . . . ?
C1 C9 C10 C11 -176.36(19) . . . . ?
C1 C9 C14 C13 178.20(18) . . . . ?
C4 N1 C8 C7 1.2(4) . . . . ?
C4 C2 C1 C9 175.8(2) . . . . ?
C4 C5 C6 C7 2.3(3) . . . . ?
C18 N3 C12 C11 29.2(3) . . . . ?
C18 N3 C12 C13 -152.07(18) . . . . ?
C18 N3 C15 C16 85.3(2) . . . . ?
C18 C23 C22 C21 0.5(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C14 C9 C10 C11 1.9(3) . . . . ?
C14 C9 C1 C2 -171.7(2) . . . . ?
C15 N3 C12 C11 -162.45(18) . . . . ?
C15 N3 C12 C13 16.3(3) . . . . ?
C15 N3 C18 C23 159.94(18) . . . . ?
C15 N3 C18 C19 -20.5(3) . . . . ?
C17 C16 C15 N3 2.1(3) . . . . ?
C3 C2 C1 C9 -0.9(4) . . . . ?
C3 C2 C4 N1 -176.03(19) . . . . ?
C3 C2 C4 C5 6.9(3) . . . . ?
C22 C23 C18 N3 -179.56(18) . . . . ?
C22 C23 C18 C19 0.8(3) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C8 N1 C4 C2 -176.39(19) . . . . ?
C8 N1 C4 C5 0.7(3) . . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
C6 C7 C8 N1 -1.3(4) . . . . ?


_olex2_date_sample_data_collection 2023-06-30
_olex2_date_sample_submission    2023-06-09
_olex2_submission_original_sample_id PTH-AB-PY
_olex2_submission_special_instructions 'No special instructions were received'
