# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_T3_4_CN
_database_code_depnum_ccdc_archive 'CCDC 2225259'
loop_
_audit_author_name
_audit_author_address
'SATPAL SINGH BADSARA'
;University of Rajasthan
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H14 N2 S'
_chemical_formula_sum            'C21 H14 N2 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         326.40

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'

_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                   7.2200(5)
_cell_length_b                   8.7796(5)
_cell_length_c                   13.7287(9)
_cell_angle_alpha                104.304(2)
_cell_angle_beta                 98.521(2)
_cell_angle_gamma                98.162(2)
_cell_volume                     819.35(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9007
_cell_measurement_theta_min      2.903
_cell_measurement_theta_max      27.884
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36858
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         27.941
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3919
_reflns_number_gt                3483
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0548P)²+0.2417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S S 0.25696(4) 0.81698(3) 0.83542(2) 0.02607(10) Uani 1 1 d . . . . .
N1 N 0.04016(15) 0.38186(12) 0.65979(8) 0.0250(2) Uani 1 1 d . . . . .
H1A H -0.044(2) 0.314(2) 0.6114(13) 0.035(4) Uiso 1 1 d . . . . .
N2 N -0.71420(15) 0.85105(13) 0.50805(9) 0.0306(2) Uani 1 1 d . . . . .
C1 C 0.20063(17) 0.34828(14) 0.71279(9) 0.0245(2) Uani 1 1 d . . . . .
C2 C 0.26849(19) 0.20462(15) 0.70098(11) 0.0318(3) Uani 1 1 d . . . . .
H2A H 0.204435 0.110154 0.649783 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4333(2) 0.20663(17) 0.76739(12) 0.0376(3) Uani 1 1 d . . . . .
H3A H 0.483172 0.111019 0.761732 0.045 Uiso 1 1 calc R U . . .
C4 C 0.52848(19) 0.34543(18) 0.84263(11) 0.0373(3) Uani 1 1 d . . . . .
H4A H 0.639292 0.341361 0.888126 0.045 Uiso 1 1 calc R U . . .
C5 C 0.46412(18) 0.48906(16) 0.85209(10) 0.0304(3) Uani 1 1 d . . . . .
H5A H 0.530779 0.583618 0.902388 0.037 Uiso 1 1 calc R U . . .
C6 C 0.29771(16) 0.49062(14) 0.78521(9) 0.0233(2) Uani 1 1 d . . . . .
C7 C 0.19308(16) 0.61389(13) 0.77136(9) 0.0225(2) Uani 1 1 d . . . . .
C8 C 0.03614(16) 0.54250(13) 0.69498(8) 0.0220(2) Uani 1 1 d . . . . .
C9 C 0.17745(15) 0.83058(13) 0.95303(9) 0.0222(2) Uani 1 1 d . . . . .
C10 C 0.04296(17) 0.71410(14) 0.96896(10) 0.0270(2) Uani 1 1 d . . . . .
H10A H -0.008781 0.618251 0.916140 0.032 Uiso 1 1 calc R U . . .
C11 C -0.01526(19) 0.73870(16) 1.06252(11) 0.0326(3) Uani 1 1 d . . . . .
H11A H -0.107119 0.659317 1.073834 0.039 Uiso 1 1 calc R U . . .
C12 C 0.0601(2) 0.87893(17) 1.13983(10) 0.0341(3) Uani 1 1 d . . . . .
H12A H 0.020352 0.895114 1.203976 0.041 Uiso 1 1 calc R U . . .
C13 C 0.19264(19) 0.99449(16) 1.12322(10) 0.0317(3) Uani 1 1 d . . . . .
H13A H 0.243281 1.090656 1.175949 0.038 Uiso 1 1 calc R U . . .
C14 C 0.25243(16) 0.97150(14) 1.03040(9) 0.0260(2) Uani 1 1 d . . . . .
H14A H 0.344140 1.051341 1.019422 0.031 Uiso 1 1 calc R U . . .
C15 C -0.12351(16) 0.61176(13) 0.65564(8) 0.0211(2) Uani 1 1 d . . . . .
C16 C -0.08889(17) 0.75264(14) 0.62555(9) 0.0262(2) Uani 1 1 d . . . . .
H16A H 0.038662 0.803030 0.629870 0.031 Uiso 1 1 calc R U . . .
C17 C -0.23830(17) 0.81950(14) 0.58955(9) 0.0267(2) Uani 1 1 d . . . . .
H17A H -0.213837 0.914836 0.568878 0.032 Uiso 1 1 calc R U . . .
C18 C -0.42491(16) 0.74532(13) 0.58399(8) 0.0229(2) Uani 1 1 d . . . . .
C19 C -0.46186(17) 0.60575(14) 0.61464(9) 0.0242(2) Uani 1 1 d . . . . .
H19A H -0.589488 0.556477 0.611222 0.029 Uiso 1 1 calc R U . . .
C20 C -0.31149(16) 0.53934(13) 0.65010(9) 0.0235(2) Uani 1 1 d . . . . .
H20A H -0.336306 0.444036 0.670756 0.028 Uiso 1 1 calc R U . . .
C21 C -0.58376(17) 0.80769(14) 0.54262(9) 0.0253(2) Uani 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
S C7 1.7427(12) . ?
S C9 1.7747(12) . ?
N1 C8 1.3793(14) . ?
N1 C1 1.3827(15) . ?
N1 H1A 0.865(17) . ?
N2 C21 1.1471(16) . ?
C1 C2 1.3983(16) . ?
C1 C6 1.4044(17) . ?
C2 C3 1.3826(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3879(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4039(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4386(15) . ?
C7 C8 1.3777(16) . ?
C8 C15 1.4720(15) . ?
C9 C10 1.3886(17) . ?
C9 C14 1.3936(16) . ?
C10 C11 1.3862(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3826(18) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C20 1.3973(16) . ?
C15 C16 1.3994(16) . ?
C16 C17 1.3848(16) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3933(17) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3946(16) . ?
C18 C21 1.4410(15) . ?
C19 C20 1.3852(15) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

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
C7 S C9 103.71(5) . . ?
C8 N1 C1 109.27(10) . . ?
C8 N1 H1A 124.8(11) . . ?
C1 N1 H1A 125.9(11) . . ?
N1 C1 C2 129.87(12) . . ?
N1 C1 C6 107.76(10) . . ?
C2 C1 C6 122.35(11) . . ?
C3 C2 C1 116.80(13) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C2 C3 C4 121.84(12) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 121.22(12) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 118.11(13) . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 H5A 120.9 . . ?
C5 C6 C1 119.59(11) . . ?
C5 C6 C7 133.60(12) . . ?
C1 C6 C7 106.81(10) . . ?
C8 C7 C6 107.18(10) . . ?
C8 C7 S 126.18(9) . . ?
C6 C7 S 126.59(9) . . ?
C7 C8 N1 108.94(10) . . ?
C7 C8 C15 129.52(10) . . ?
N1 C8 C15 121.45(10) . . ?
C10 C9 C14 120.18(11) . . ?
C10 C9 S 123.89(9) . . ?
C14 C9 S 115.88(9) . . ?
C11 C10 C9 119.51(12) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.32(12) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 119.83(12) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.51(12) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C13 C14 C9 119.65(11) . . ?
C13 C14 H14A 120.2 . . ?
C9 C14 H14A 120.2 . . ?
C20 C15 C16 119.24(10) . . ?
C20 C15 C8 120.28(10) . . ?
C16 C15 C8 120.47(10) . . ?
C17 C16 C15 120.81(11) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C18 119.23(11) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
C19 C18 C17 120.69(10) . . ?
C19 C18 C21 118.62(10) . . ?
C17 C18 C21 120.64(10) . . ?
C20 C19 C18 119.66(11) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C15 120.37(10) . . ?
C19 C20 H20A 119.8 . . ?
C15 C20 H20A 119.8 . . ?
N2 C21 C18 177.21(13) . . ?

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
C8 N1 C1 C2 -177.11(12) . . . . ?
C8 N1 C1 C6 1.59(13) . . . . ?
N1 C1 C2 C3 -178.75(12) . . . . ?
C6 C1 C2 C3 2.71(18) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C1 1.06(18) . . . . ?
C4 C5 C6 C7 -178.75(12) . . . . ?
N1 C1 C6 C5 178.01(10) . . . . ?
C2 C1 C6 C5 -3.17(18) . . . . ?
N1 C1 C6 C7 -2.14(13) . . . . ?
C2 C1 C6 C7 176.69(11) . . . . ?
C5 C6 C7 C8 -178.26(13) . . . . ?
C1 C6 C7 C8 1.91(13) . . . . ?
C5 C6 C7 S 4.0(2) . . . . ?
C1 C6 C7 S -175.81(9) . . . . ?
C9 S C7 C8 100.35(11) . . . . ?
C9 S C7 C6 -82.35(11) . . . . ?
C6 C7 C8 N1 -0.96(13) . . . . ?
S C7 C8 N1 176.77(8) . . . . ?
C6 C7 C8 C15 175.56(11) . . . . ?
S C7 C8 C15 -6.71(18) . . . . ?
C1 N1 C8 C7 -0.37(13) . . . . ?
C1 N1 C8 C15 -177.23(10) . . . . ?
C7 S C9 C10 -18.70(11) . . . . ?
C7 S C9 C14 164.02(9) . . . . ?
C14 C9 C10 C11 -0.35(17) . . . . ?
S C9 C10 C11 -177.52(9) . . . . ?
C9 C10 C11 C12 0.08(18) . . . . ?
C10 C11 C12 C13 0.34(19) . . . . ?
C11 C12 C13 C14 -0.50(19) . . . . ?
C12 C13 C14 C9 0.22(18) . . . . ?
C10 C9 C14 C13 0.20(17) . . . . ?
S C9 C14 C13 177.58(9) . . . . ?
C7 C8 C15 C20 -127.20(13) . . . . ?
N1 C8 C15 C20 48.94(15) . . . . ?
C7 C8 C15 C16 51.37(17) . . . . ?
N1 C8 C15 C16 -132.49(12) . . . . ?
C20 C15 C16 C17 -0.69(18) . . . . ?
C8 C15 C16 C17 -179.27(11) . . . . ?
C15 C16 C17 C18 0.35(18) . . . . ?
C16 C17 C18 C19 0.30(18) . . . . ?
C16 C17 C18 C21 -177.21(11) . . . . ?
C17 C18 C19 C20 -0.60(17) . . . . ?
C21 C18 C19 C20 176.95(10) . . . . ?
C18 C19 C20 C15 0.26(17) . . . . ?
C16 C15 C20 C19 0.38(17) . . . . ?
C8 C15 C20 C19 178.97(10) . . . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.040

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

