# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# 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. 
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#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1858041'
loop_
_audit_author_name
_audit_author_address
'Dr. Tapan Kumar Mondal'
;Jadavpur University
India
;
_audit_update_record             
;
2018-07-25 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 N3 O S'
_chemical_formula_weight         343.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.8363(12)
_cell_length_b                   5.1256(4)
_cell_length_c                   20.6360(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.118(3)
_cell_angle_gamma                90
_cell_volume                     1631.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7213
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.12

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega/Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52254
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         27.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3605
_reflns_number_gt                2727
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0496P)²+0.4310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_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
S1 S 0.57300(3) 0.75082(9) 0.46995(2) 0.04830(15) Uani 1 1 d . . . . .
O1 O 0.39501(10) -0.1641(3) 0.23367(7) 0.0714(4) Uani 1 1 d . . . . .
N1 N 0.67545(9) 0.8860(3) 0.39355(7) 0.0487(3) Uani 1 1 d . . . . .
N2 N 0.44607(13) 0.2907(4) 0.36891(10) 0.0816(6) Uani 1 1 d . . . . .
C1 C 0.69679(10) 1.0379(3) 0.45016(8) 0.0446(4) Uani 1 1 d . . . . .
C2 C 0.76140(12) 1.2285(4) 0.46145(10) 0.0560(5) Uani 1 1 d . . . . .
H2 H 0.793728 1.261597 0.429930 0.067 Uiso 1 1 calc R U . . .
C3 C 0.77623(12) 1.3658(4) 0.51981(10) 0.0607(5) Uani 1 1 d . . . . .
H3 H 0.819242 1.492979 0.527859 0.073 Uiso 1 1 calc R U . . .
C4 C 0.72813(12) 1.3188(4) 0.56744(10) 0.0578(5) Uani 1 1 d . . . . .
H4 H 0.739525 1.415782 0.606557 0.069 Uiso 1 1 calc R U . . .
C5 C 0.66418(11) 1.1320(4) 0.55772(9) 0.0517(4) Uani 1 1 d . . . . .
H5 H 0.632449 1.100076 0.589686 0.062 Uiso 1 1 calc R U . . .
C6 C 0.64858(10) 0.9921(3) 0.49832(8) 0.0438(4) Uani 1 1 d . . . . .
C7 C 0.61230(10) 0.7295(3) 0.39766(9) 0.0440(4) Uani 1 1 d . . . . .
C8 C 0.57758(11) 0.5373(3) 0.34567(8) 0.0460(4) Uani 1 1 d . . . . .
C9 C 0.50429(13) 0.3902(4) 0.35525(9) 0.0547(5) Uani 1 1 d . . . . .
C10 C 0.61445(12) 0.5060(4) 0.29356(9) 0.0531(4) Uani 1 1 d . . . . .
H10 H 0.661461 0.614193 0.293127 0.064 Uiso 1 1 calc R U . . .
C11 C 0.59105(12) 0.3267(4) 0.23785(9) 0.0505(4) Uani 1 1 d . . . . .
C12 C 0.63887(13) 0.3337(4) 0.18760(10) 0.0582(5) Uani 1 1 d . . . . .
H12 H 0.685471 0.447325 0.191146 0.070 Uiso 1 1 calc R U . . .
C13 C 0.61625(13) 0.1742(4) 0.13469(10) 0.0581(5) Uani 1 1 d . . . . .
H13 H 0.646530 0.180011 0.101014 0.070 Uiso 1 1 calc R U . . .
C14 C 0.54659(11) -0.0018(4) 0.13023(9) 0.0511(4) Uani 1 1 d . . . . .
C15 C 0.51941(13) -0.1755(4) 0.07647(10) 0.0587(5) Uani 1 1 d . . . . .
H15 H 0.546795 -0.175107 0.041089 0.070 Uiso 1 1 calc R U . . .
C16 C 0.45323(13) -0.3428(4) 0.07667(10) 0.0625(5) Uani 1 1 d . . . . .
H16 H 0.436199 -0.458019 0.041302 0.075 Uiso 1 1 calc R U . . .
C17 C 0.40969(13) -0.3470(4) 0.12875(10) 0.0598(5) Uani 1 1 d . . . . .
H17 H 0.364657 -0.464587 0.127643 0.072 Uiso 1 1 calc R U . . .
C18 C 0.43338(12) -0.1778(4) 0.18141(9) 0.0523(4) Uani 1 1 d . . . . .
C19 C 0.50327(11) 0.0008(3) 0.18350(8) 0.0471(4) Uani 1 1 d . . . . .
N3 N 0.52522(9) 0.1648(3) 0.23628(7) 0.0503(4) Uani 1 1 d . . . . .
C20 C 0.32762(15) -0.3457(5) 0.23540(12) 0.0787(7) Uani 1 1 d . . . . .
H20A H 0.305838 -0.316217 0.274570 0.118 Uiso 1 1 calc R U . . .
H20B H 0.281557 -0.323299 0.196593 0.118 Uiso 1 1 calc R U . . .
H20C H 0.349998 -0.519999 0.236219 0.118 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
S1 C6 1.7282(17) . ?
S1 C7 1.7453(18) . ?
O1 C18 1.354(2) . ?
O1 C20 1.422(3) . ?
N1 C7 1.300(2) . ?
N1 C1 1.381(2) . ?
N2 C9 1.143(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.404(2) . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.468(2) . ?
C8 C10 1.345(2) . ?
C8 C9 1.435(2) . ?
C10 C11 1.453(3) . ?
C10 H10 0.9300 . ?
C11 N3 1.327(2) . ?
C11 C12 1.417(3) . ?
C12 C13 1.346(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.412(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.411(3) . ?
C14 C19 1.422(2) . ?
C15 C16 1.355(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.429(3) . ?
C19 N3 1.357(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C6 S1 C7 88.88(8) . . ?
C18 O1 C20 117.44(17) . . ?
C7 N1 C1 109.70(14) . . ?
N1 C1 C2 124.44(16) . . ?
N1 C1 C6 115.90(14) . . ?
C2 C1 C6 119.67(16) . . ?
C3 C2 C1 118.67(18) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.30(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.30(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.68(17) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 121.38(15) . . ?
C5 C6 S1 129.59(13) . . ?
C1 C6 S1 109.03(12) . . ?
N1 C7 C8 122.17(16) . . ?
N1 C7 S1 116.49(13) . . ?
C8 C7 S1 121.31(12) . . ?
C10 C8 C9 124.00(17) . . ?
C10 C8 C7 120.39(16) . . ?
C9 C8 C7 115.61(15) . . ?
N2 C9 C8 172.3(2) . . ?
C8 C10 C11 129.00(17) . . ?
C8 C10 H10 115.5 . . ?
C11 C10 H10 115.5 . . ?
N3 C11 C12 123.04(17) . . ?
N3 C11 C10 118.21(16) . . ?
C12 C11 C10 118.74(17) . . ?
C13 C12 C11 119.39(18) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.07(18) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 123.27(17) . . ?
C15 C14 C19 119.93(18) . . ?
C13 C14 C19 116.80(17) . . ?
C16 C15 C14 119.67(19) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.81(18) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 120.18(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
O1 C18 C17 124.81(18) . . ?
O1 C18 C19 115.28(16) . . ?
C17 C18 C19 119.90(18) . . ?
N3 C19 C14 123.06(16) . . ?
N3 C19 C18 118.45(16) . . ?
C14 C19 C18 118.49(16) . . ?
C11 N3 C19 117.62(15) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036

