# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_KB137_0m
_database_code_depnum_ccdc_archive 'CCDC 2109329'
loop_
_audit_author_name
_audit_author_address
'Prakasha Reddy'
;Indrashil University
India
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O S'
_chemical_formula_sum            'C15 H15 N3 O S'
_chemical_formula_weight         285.36

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'
O O 0.0106 0.0060 '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                   6.6492(8)
_cell_length_b                   13.731(2)
_cell_length_c                   15.329(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.032(5)
_cell_angle_gamma                90
_cell_volume                     1373.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6640
_cell_measurement_theta_min      2.7075
_cell_measurement_theta_max      26.2625

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5122
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29104
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.707
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3402
_reflns_number_gt                2118
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0368P)²+0.7399P] 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         3402
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.3415(4) 0.61688(18) -0.03903(16) 0.0530(6) Uani 1 1 d . . . . .
C2 C 0.5525(4) 0.63025(19) -0.03602(18) 0.0619(7) Uani 1 1 d . . . . .
H2 H 0.603260 0.633281 -0.088436 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6817(4) 0.6387(2) 0.04357(18) 0.0628(7) Uani 1 1 d . . . . .
H3 H 0.821901 0.647100 0.047511 0.075 Uiso 1 1 calc R U . . .
C4 C 0.5945(4) 0.63415(18) 0.11913(16) 0.0534(6) Uani 1 1 d . . . . .
C5 C 0.3830(3) 0.62152(17) 0.11000(15) 0.0480(5) Uani 1 1 d . . . . .
C6 C 0.0116(4) 0.5901(3) -0.12730(18) 0.0810(10) Uani 1 1 d . . . . .
H6A H -0.049866 0.575242 -0.187721 0.122 Uiso 1 1 calc R U . . .
H6B H -0.051544 0.647322 -0.108556 0.122 Uiso 1 1 calc R U . . .
H6C H -0.007834 0.536343 -0.089765 0.122 Uiso 1 1 calc R U . . .
C7 C 0.4611(4) 0.62921(17) 0.25651(16) 0.0505(6) Uani 1 1 d . . . . .
C8 C 0.4380(4) 0.62909(17) 0.34935(15) 0.0508(6) Uani 1 1 d . . . . .
C9 C 0.6008(4) 0.64815(19) 0.41876(17) 0.0607(7) Uani 1 1 d . . . . .
H9 H 0.729051 0.661679 0.405885 0.073 Uiso 1 1 calc R U . . .
C10 C 0.5774(4) 0.64755(19) 0.50574(17) 0.0610(7) Uani 1 1 d . . . . .
H10 H 0.690019 0.660679 0.550359 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3888(4) 0.62772(18) 0.52874(15) 0.0546(6) Uani 1 1 d . . . . .
C12 C 0.2248(4) 0.6083(2) 0.45856(16) 0.0611(7) Uani 1 1 d . . . . .
H12 H 0.096700 0.594234 0.471356 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2481(4) 0.60967(19) 0.37183(15) 0.0575(7) Uani 1 1 d . . . . .
H13 H 0.135418 0.597402 0.326997 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1706(5) 0.6020(2) 0.63805(19) 0.0807(9) Uani 1 1 d . . . . .
H14A H 0.067668 0.647608 0.611378 0.121 Uiso 1 1 calc R U . . .
H14B H 0.182885 0.603383 0.701459 0.121 Uiso 1 1 calc R U . . .
H14C H 0.132382 0.537661 0.616456 0.121 Uiso 1 1 calc R U . . .
C15 C 0.5366(5) 0.6425(2) 0.68716(18) 0.0777(9) Uani 1 1 d . . . . .
H15A H 0.639004 0.593994 0.683980 0.117 Uiso 1 1 calc R U . . .
H15B H 0.492374 0.637073 0.743030 0.117 Uiso 1 1 calc R U . . .
H15C H 0.593245 0.706051 0.682146 0.117 Uiso 1 1 calc R U . . .
N1 N 0.2547(3) 0.61250(15) 0.03134(13) 0.0518(5) Uani 1 1 d . . . . .
N2 N 0.3106(3) 0.61862(14) 0.18919(12) 0.0512(5) Uani 1 1 d . . . . .
N3 N 0.3636(3) 0.62775(17) 0.61538(13) 0.0662(6) Uani 1 1 d . . . . .
S1 S 0.70493(10) 0.64249(6) 0.22987(5) 0.0669(3) Uani 1 1 d . . . . .
O1 O 0.2263(3) 0.60725(15) -0.12114(11) 0.0668(5) 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
C1 N1 1.318(3) . ?
C1 O1 1.349(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.356(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 S1 1.720(3) . ?
C5 N1 1.343(3) . ?
C5 N2 1.390(3) . ?
C6 O1 1.432(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N2 1.301(3) . ?
C7 C8 1.460(3) . ?
C7 S1 1.755(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9300 . ?
C11 N3 1.370(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.368(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.436(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.446(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
N1 C1 O1 120.0(2) . . ?
N1 C1 C2 124.7(2) . . ?
O1 C1 C2 115.3(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 S1 130.63(19) . . ?
C5 C4 S1 109.79(18) . . ?
N1 C5 N2 121.0(2) . . ?
N1 C5 C4 123.7(2) . . ?
N2 C5 C4 115.2(2) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 124.4(2) . . ?
N2 C7 S1 115.57(18) . . ?
C8 C7 S1 120.07(17) . . ?
C9 C8 C13 117.1(2) . . ?
C9 C8 C7 122.3(2) . . ?
C13 C8 C7 120.6(2) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
N3 C11 C10 121.9(2) . . ?
N3 C11 C12 121.5(2) . . ?
C10 C11 C12 116.6(2) . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C8 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C5 115.4(2) . . ?
C7 N2 C5 110.3(2) . . ?
C11 N3 C14 121.0(2) . . ?
C11 N3 C15 120.7(2) . . ?
C14 N3 C15 117.9(2) . . ?
C4 S1 C7 89.08(11) . . ?
C1 O1 C6 117.30(19) . . ?

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
N1 C1 C2 C3 0.6(4) . . . . ?
O1 C1 C2 C3 -178.7(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 S1 -179.6(2) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
S1 C4 C5 N1 -179.88(19) . . . . ?
C3 C4 C5 N2 -179.6(2) . . . . ?
S1 C4 C5 N2 0.0(3) . . . . ?
N2 C7 C8 C9 -174.9(2) . . . . ?
S1 C7 C8 C9 6.1(3) . . . . ?
N2 C7 C8 C13 4.9(4) . . . . ?
S1 C7 C8 C13 -174.07(19) . . . . ?
C13 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 N3 -179.5(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
N3 C11 C12 C13 179.0(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 0.9(4) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C7 C8 C13 C12 179.3(2) . . . . ?
O1 C1 N1 C5 179.1(2) . . . . ?
C2 C1 N1 C5 -0.2(4) . . . . ?
N2 C5 N1 C1 179.7(2) . . . . ?
C4 C5 N1 C1 -0.4(3) . . . . ?
C8 C7 N2 C5 -179.7(2) . . . . ?
S1 C7 N2 C5 -0.6(3) . . . . ?
N1 C5 N2 C7 -179.7(2) . . . . ?
C4 C5 N2 C7 0.4(3) . . . . ?
C10 C11 N3 C14 -176.6(3) . . . . ?
C12 C11 N3 C14 3.9(4) . . . . ?
C10 C11 N3 C15 -4.0(4) . . . . ?
C12 C11 N3 C15 176.5(3) . . . . ?
C3 C4 S1 C7 179.2(3) . . . . ?
C5 C4 S1 C7 -0.30(19) . . . . ?
N2 C7 S1 C4 0.5(2) . . . . ?
C8 C7 S1 C4 179.6(2) . . . . ?
N1 C1 O1 C6 -1.4(4) . . . . ?
C2 C1 O1 C6 177.9(3) . . . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040



