# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tpa-th-new-red
_database_code_depnum_ccdc_archive 'CCDC 2278085'
loop_
_audit_author_name
_audit_author_address
'Dr Venkatramaiah Nutalapati'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2023-06-30 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_tpa-th-new-red      
;
PROBLEM: No TEMP record and _measurement_temperature .NE. 293 Degree
RESPONSE: Crystal data were collected at low temperature 100K.
;
# end Validation Reply Form

_audit_creation_date             2017-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N3 O S'
_chemical_formula_sum            'C22 H17 N3 O S'
_chemical_formula_weight         371.44
_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      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                   9.4332(7)
_cell_length_b                   20.7152(16)
_cell_length_c                   9.7429(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.033(8)
_cell_angle_gamma                90
_cell_volume                     1799.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.4800
_cell_measurement_theta_min      3.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.269
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  51.00   1.00   18.00    --  -16.44  77.00  90.00   94
  2  ω    -43.00  51.00   1.00   18.00    --  -16.44  77.00-150.00   94
  3  ω    -43.00  51.00   1.00   18.00    --  -16.44  77.00 -30.00   94
  4  ω     -6.00  88.00   1.00   18.00    --   20.82  77.00  90.00   94
  5  ω     -6.00  88.00   1.00   18.00    --   20.82  77.00 -30.00   94
  6  ω     -6.00  88.00   1.00   18.00    --   20.82  77.00-150.00   94
  7  ω    -20.00  41.00   1.00   18.00    --   20.82 -99.00  60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0544543000
_diffrn_orient_matrix_UB_12      -0.0105714000
_diffrn_orient_matrix_UB_13      0.0652183000
_diffrn_orient_matrix_UB_21      -0.0381281000
_diffrn_orient_matrix_UB_22      0.0168093000
_diffrn_orient_matrix_UB_23      0.0409713000
_diffrn_orient_matrix_UB_31      -0.0435971000
_diffrn_orient_matrix_UB_32      -0.0279110000
_diffrn_orient_matrix_UB_33      -0.0001519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2268
_reflns_number_total             3164
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.089
_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)+(0.0251P)²+0.8481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C10(H10), C21(H21), C7(H7), C16(H16), C22(H22),
 C18(H18), C12(H12), C14(H14), C20(H20), C6(H6), C9(H9), C15(H15), C13(H13),
 C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.23612(10) 0.53586(5) 0.44528(10) 0.0223(3) Uani 1 1 d . . . . .
O1 O -0.3734(2) 0.45037(11) -0.0586(2) 0.0214(6) Uani 1 1 d . . . . .
N1 N -0.3355(3) 0.49751(13) 0.1667(3) 0.0189(7) Uani 1 1 d . . . . .
H1 H -0.4241 0.5128 0.1514 0.023 Uiso 1 1 calc R . . . .
N3 N 0.5517(3) 0.32761(13) 0.2724(3) 0.0181(7) Uani 1 1 d . . . . .
N2 N -0.0974(3) 0.47721(13) 0.2736(3) 0.0178(7) Uani 1 1 d . . . . .
H2 H -0.0085 0.4783 0.3357 0.021 Uiso 1 1 calc R . . . .
C4 C -0.0575(4) 0.40758(16) 0.0798(3) 0.0186(8) Uani 1 1 d . . . . .
H4 H -0.1139 0.3891 -0.0080 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2140(4) 0.42925(17) 0.2125(3) 0.0178(8) Uani 1 1 d . . . . .
H10 H 0.1897 0.4702 0.2369 0.021 Uiso 1 1 calc R . . . .
C3 C -0.1340(4) 0.44737(16) 0.1377(3) 0.0166(8) Uani 1 1 d . . . . .
C5 C 0.0993(4) 0.38841(17) 0.1314(3) 0.0178(8) Uani 1 1 d . . . . .
C8 C 0.4007(4) 0.34839(16) 0.2247(3) 0.0161(8) Uani 1 1 d . . . . .
C21 C 0.9041(4) 0.37128(16) 0.5637(4) 0.0215(9) Uani 1 1 d . . . . .
H21 H 1.0058 0.3750 0.5763 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2879(4) 0.30696(17) 0.1434(3) 0.0187(8) Uani 1 1 d . . . . .
H7 H 0.3122 0.2656 0.1212 0.022 Uiso 1 1 calc R . . . .
C16 C 0.7034(4) 0.23792(16) 0.2320(4) 0.0199(8) Uani 1 1 d . . . . .
H16 H 0.7313 0.2277 0.3302 0.024 Uiso 1 1 calc R . . . .
C17 C 0.6529(4) 0.34676(16) 0.4095(4) 0.0162(8) Uani 1 1 d . . . . .
C22 C 0.8062(4) 0.35336(16) 0.4299(4) 0.0174(8) Uani 1 1 d . . . . .
H22 H 0.8421 0.3456 0.3532 0.021 Uiso 1 1 calc R . . . .
C1 C -0.2204(4) 0.50436(16) 0.2956(4) 0.0167(8) Uani 1 1 d . . . . .
C18 C 0.6035(4) 0.35848(16) 0.5275(4) 0.0187(8) Uani 1 1 d . . . . .
H18 H 0.5026 0.3534 0.5170 0.022 Uiso 1 1 calc R . . . .
C12 C 0.5626(4) 0.30339(17) 0.0302(4) 0.0197(8) Uani 1 1 d . . . . .
H12 H 0.4984 0.3378 -0.0074 0.024 Uiso 1 1 calc R . . . .
C14 C 0.7142(4) 0.21559(18) -0.0058(4) 0.0240(9) Uani 1 1 d . . . . .
H14 H 0.7500 0.1909 -0.0673 0.029 Uiso 1 1 calc R . . . .
C20 C 0.8539(4) 0.38375(17) 0.6794(4) 0.0230(9) Uani 1 1 d . . . . .
H20 H 0.9206 0.3961 0.7690 0.028 Uiso 1 1 calc R . . . .
C6 C 0.1398(4) 0.32705(17) 0.0957(3) 0.0192(8) Uani 1 1 d . . . . .
H6 H 0.0660 0.2995 0.0390 0.023 Uiso 1 1 calc R . . . .
C11 C 0.6058(3) 0.28896(16) 0.1774(3) 0.0152(8) Uani 1 1 d . . . . .
C9 C 0.3617(4) 0.41041(16) 0.2570(3) 0.0167(8) Uani 1 1 d . . . . .
H9 H 0.4360 0.4389 0.3088 0.020 Uiso 1 1 calc R . . . .
C15 C 0.7592(4) 0.20217(17) 0.1415(4) 0.0220(9) Uani 1 1 d . . . . .
H15 H 0.8272 0.1690 0.1794 0.026 Uiso 1 1 calc R . . . .
C2 C -0.2940(4) 0.46365(16) 0.0650(4) 0.0178(8) Uani 1 1 d . . . . .
C13 C 0.6164(4) 0.26565(17) -0.0605(4) 0.0216(9) Uani 1 1 d . . . . .
H13 H 0.5856 0.2745 -0.1595 0.026 Uiso 1 1 calc R . . . .
C19 C 0.7029(4) 0.37756(16) 0.6597(4) 0.0220(9) Uani 1 1 d . . . . .
H19 H 0.6676 0.3863 0.7364 0.026 Uiso 1 1 calc R . . . .


_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 C1 1.648(3) . ?
O1 C2 1.224(4) . ?
N1 C1 1.374(4) . ?
N1 C2 1.371(4) . ?
N3 C8 1.414(4) . ?
N3 C17 1.421(4) . ?
N3 C11 1.438(4) . ?
N2 C3 1.399(4) . ?
N2 C1 1.367(4) . ?
C4 C3 1.335(4) . ?
C4 C5 1.453(4) . ?
C10 C5 1.398(4) . ?
C10 C9 1.374(4) . ?
C3 C2 1.482(4) . ?
C5 C6 1.403(4) . ?
C8 C7 1.396(4) . ?
C8 C9 1.401(4) . ?
C21 C22 1.380(4) . ?
C21 C20 1.383(5) . ?
C7 C6 1.384(4) . ?
C16 C11 1.389(4) . ?
C16 C15 1.381(4) . ?
C17 C22 1.401(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.381(4) . ?
C12 C11 1.389(4) . ?
C12 C13 1.394(5) . ?
C14 C15 1.385(5) . ?
C14 C13 1.375(5) . ?
C20 C19 1.380(5) . ?

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
C2 N1 C1 112.7(3) . . ?
C8 N3 C17 121.3(3) . . ?
C8 N3 C11 119.3(3) . . ?
C17 N3 C11 119.3(3) . . ?
C1 N2 C3 111.7(3) . . ?
C3 C4 C5 130.7(3) . . ?
C9 C10 C5 121.7(3) . . ?
N2 C3 C2 104.5(3) . . ?
C4 C3 N2 132.2(3) . . ?
C4 C3 C2 123.0(3) . . ?
C10 C5 C4 122.9(3) . . ?
C10 C5 C6 117.7(3) . . ?
C6 C5 C4 119.4(3) . . ?
C7 C8 N3 120.0(3) . . ?
C7 C8 C9 118.9(3) . . ?
C9 C8 N3 121.1(3) . . ?
C22 C21 C20 121.2(3) . . ?
C6 C7 C8 120.3(3) . . ?
C15 C16 C11 120.4(3) . . ?
C22 C17 N3 120.4(3) . . ?
C18 C17 N3 121.4(3) . . ?
C18 C17 C22 118.2(3) . . ?
C21 C22 C17 120.2(3) . . ?
N1 C1 S1 125.3(2) . . ?
N2 C1 S1 128.9(3) . . ?
N2 C1 N1 105.8(3) . . ?
C19 C18 C17 120.7(3) . . ?
C11 C12 C13 119.3(3) . . ?
C13 C14 C15 119.5(3) . . ?
C19 C20 C21 118.8(3) . . ?
C7 C6 C5 121.0(3) . . ?
C16 C11 N3 120.5(3) . . ?
C16 C11 C12 119.6(3) . . ?
C12 C11 N3 119.9(3) . . ?
C10 C9 C8 120.2(3) . . ?
C16 C15 C14 120.1(3) . . ?
O1 C2 N1 126.8(3) . . ?
O1 C2 C3 128.3(3) . . ?
N1 C2 C3 104.9(3) . . ?
C14 C13 C12 121.0(3) . . ?
C20 C19 C18 120.8(3) . . ?


_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.846


