# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2118351'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-07 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         'C13 H12 N2 O S'
_chemical_formula_sum            'C13 H12 N2 O S'
_chemical_formula_weight         244.31

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.7010(7)
_cell_length_b                   6.1737(2)
_cell_length_c                   20.5621(7)
_cell_angle_alpha                90
_cell_angle_beta                 120.2510(10)
_cell_angle_gamma                90
_cell_volume                     2379.68(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7862
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker-Nonius Roper CCD camera on κ-goniostat
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            14482
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.483
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2733
_reflns_number_gt                2135
_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       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Furrugia, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0489P)²+3.2440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
S1 S 0.85800(3) -0.09908(8) 0.78181(3) 0.02245(15) Uani 1 1 d . . . . .
O1 O 0.76288(7) -0.3351(2) 0.58932(7) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.70821(8) -0.0329(2) 0.52555(8) 0.0159(3) Uani 1 1 d D . . . .
H1N H 0.7144(11) -0.075(3) 0.4884(9) 0.019 Uiso 1 1 d D U . . .
N2 N 0.67130(8) 0.1546(2) 0.51973(8) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.78855(10) 0.0308(3) 0.70586(10) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.80619(10) 0.2427(3) 0.70051(10) 0.0161(4) Uani 1 1 d . . . . .
H2 H 0.775166 0.341418 0.662650 0.019 Uiso 1 1 calc R U . . .
C3 C 0.87732(11) 0.2952(3) 0.75935(11) 0.0207(4) Uani 1 1 d . . . . .
H3 H 0.898686 0.433152 0.764425 0.025 Uiso 1 1 calc R U . . .
C4 C 0.91085(11) 0.1266(3) 0.80700(11) 0.0231(4) Uani 1 1 d . . . . .
H4 H 0.957872 0.133490 0.849115 0.028 Uiso 1 1 calc R U . . .
C5 C 0.72254(10) -0.0913(3) 0.65132(10) 0.0173(4) Uani 1 1 d . . . . .
H5A H 0.680107 0.003200 0.632768 0.021 Uiso 1 1 calc R U . . .
H5B H 0.715862 -0.218487 0.676450 0.021 Uiso 1 1 calc R U . . .
C6 C 0.73159(9) -0.1645(3) 0.58591(10) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.65120(9) 0.2643(3) 0.45938(10) 0.0154(4) Uani 1 1 d . . . . .
H7 H 0.663291 0.215637 0.423386 0.018 Uiso 1 1 calc R U . . .
C8 C 0.60975(9) 0.4640(3) 0.44529(10) 0.0152(4) Uani 1 1 d . . . . .
C9 C 0.59172(10) 0.5855(3) 0.38072(10) 0.0187(4) Uani 1 1 d . . . . .
H9 H 0.606794 0.538547 0.346936 0.022 Uiso 1 1 calc R U . . .
C10 C 0.55192(10) 0.7745(3) 0.36554(11) 0.0218(4) Uani 1 1 d . . . . .
H10 H 0.540404 0.856906 0.321835 0.026 Uiso 1 1 calc R U . . .
C11 C 0.52907(10) 0.8427(3) 0.41398(11) 0.0230(4) Uani 1 1 d . . . . .
H11 H 0.501324 0.970803 0.403190 0.028 Uiso 1 1 calc R U . . .
C12 C 0.54681(10) 0.7232(3) 0.47877(11) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.531266 0.770478 0.512128 0.026 Uiso 1 1 calc R U . . .
C13 C 0.58706(10) 0.5357(3) 0.49452(10) 0.0185(4) Uani 1 1 d . . . . .
H13 H 0.599311 0.455472 0.538846 0.022 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 C4 1.711(2) . ?
S1 C1 1.7270(18) . ?
O1 C6 1.236(2) . ?
N1 C6 1.351(2) . ?
N1 N2 1.378(2) . ?
N1 H1N 0.878(9) . ?
N2 C7 1.282(2) . ?
C1 C2 1.383(3) . ?
C1 C5 1.503(3) . ?
C2 C3 1.439(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.522(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.467(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
C4 S1 C1 92.41(9) . . ?
C6 N1 N2 121.20(15) . . ?
C6 N1 H1N 118.0(14) . . ?
N2 N1 H1N 120.6(14) . . ?
C7 N2 N1 115.29(15) . . ?
C2 C1 C5 127.82(16) . . ?
C2 C1 S1 111.15(14) . . ?
C5 C1 S1 120.74(13) . . ?
C1 C2 C3 111.65(17) . . ?
C1 C2 H2 124.2 . . ?
C3 C2 H2 124.2 . . ?
C4 C3 C2 113.01(18) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 S1 111.77(15) . . ?
C3 C4 H4 124.1 . . ?
S1 C4 H4 124.1 . . ?
C1 C5 C6 108.04(14) . . ?
C1 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
C1 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
O1 C6 N1 120.41(16) . . ?
O1 C6 C5 120.98(16) . . ?
N1 C6 C5 118.50(16) . . ?
N2 C7 C8 120.74(16) . . ?
N2 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C13 118.96(17) . . ?
C9 C8 C7 119.28(16) . . ?
C13 C8 C7 121.76(16) . . ?
C10 C9 C8 120.56(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.09(18) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.97(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.15(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.27(17) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?

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
C6 N1 N2 C7 -179.16(16) . . . . ?
C4 S1 C1 C2 0.03(14) . . . . ?
C4 S1 C1 C5 174.32(15) . . . . ?
C5 C1 C2 C3 -173.57(17) . . . . ?
S1 C1 C2 C3 0.22(19) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 S1 0.5(2) . . . . ?
C1 S1 C4 C3 -0.29(16) . . . . ?
C2 C1 C5 C6 79.0(2) . . . . ?
S1 C1 C5 C6 -94.25(16) . . . . ?
N2 N1 C6 O1 177.98(15) . . . . ?
N2 N1 C6 C5 -5.7(2) . . . . ?
C1 C5 C6 O1 85.5(2) . . . . ?
C1 C5 C6 N1 -90.79(19) . . . . ?
N1 N2 C7 C8 178.32(15) . . . . ?
N2 C7 C8 C9 176.84(17) . . . . ?
N2 C7 C8 C13 -3.8(3) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 179.42(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C7 C8 C13 C12 -178.80(17) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.064

