# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc2h1zq8
_database_code_depnum_ccdc_archive 'CCDC 2295820'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan Che'
;Xinjiang University
China
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2021-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 N4 S'
_chemical_formula_sum            'C12 H14 N4 S'
_chemical_formula_weight         246.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.106(4)
_cell_length_b                   4.9258(12)
_cell_length_c                   16.520(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.557(12)
_cell_angle_gamma                90
_cell_volume                     1212.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5432
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      60.900
_cell_measurement_theta_min      4.723
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    1.461
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1607 before and 0.0917 after correction.
The Ratio of minimum to maximum transmission is 0.7101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10113
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.467
_diffrn_reflns_theta_min         4.723
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2170
_reflns_number_total             2776
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.134
_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)+(0.0577P)²+0.2572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N4(H4), C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.60292(3) -0.10134(10) 0.42929(3) 0.04218(17) Uani 1 1 d . . . . .
N1 N 0.65674(13) 1.1091(3) 0.79757(10) 0.0489(4) Uani 1 1 d . . . . .
H1 H 0.641601 1.244568 0.827197 0.059 Uiso 1 1 calc R U . . .
N2 N 0.65379(10) 0.4156(3) 0.61103(9) 0.0380(4) Uani 1 1 d . . . . .
N3 N 0.60901(9) 0.2621(3) 0.54749(9) 0.0375(3) Uani 1 1 d . . . . .
H3 H 0.550965 0.283919 0.531204 0.045 Uiso 1 1 calc R U . . .
N4 N 0.74165(10) 0.0541(3) 0.54048(10) 0.0443(4) Uani 1 1 d . . . . .
H4 H 0.764735 0.166398 0.579790 0.053 Uiso 1 1 calc R U . . .
C1 C 0.74242(15) 1.0083(4) 0.80094(12) 0.0462(5) Uani 1 1 d . . . . .
C2 C 0.82237(18) 1.0917(5) 0.84858(14) 0.0584(6) Uani 1 1 d . . . . .
H2 H 0.824059 1.237239 0.886556 0.070 Uiso 1 1 calc R U . . .
C3 C 0.89899(18) 0.9540(5) 0.83824(15) 0.0645(7) Uani 1 1 d . . . . .
H3A H 0.954718 1.005625 0.870051 0.077 Uiso 1 1 calc R U . . .
C4 C 0.89716(15) 0.7413(5) 0.78250(15) 0.0599(6) Uani 1 1 d . . . . .
H4A H 0.951441 0.651515 0.776778 0.072 Uiso 1 1 calc R U . . .
C5 C 0.81783(14) 0.6594(5) 0.73563(13) 0.0492(5) Uani 1 1 d . . . . .
H5 H 0.816972 0.513179 0.698003 0.059 Uiso 1 1 calc R U . . .
C6 C 0.73850(13) 0.7940(4) 0.74409(11) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.64576(13) 0.7701(4) 0.70627(11) 0.0396(4) Uani 1 1 d . . . . .
C8 C 0.59967(14) 0.9666(4) 0.74148(12) 0.0444(5) Uani 1 1 d . . . . .
H8 H 0.536859 0.997574 0.728297 0.053 Uiso 1 1 calc R U . . .
C9 C 0.60633(13) 0.5926(4) 0.64187(11) 0.0380(4) Uani 1 1 d . . . . .
H9 H 0.543873 0.605494 0.621434 0.046 Uiso 1 1 calc R U . . .
C10 C 0.65472(12) 0.0789(4) 0.51058(11) 0.0359(4) Uani 1 1 d . . . . .
C11 C 0.80115(13) -0.1437(5) 0.51323(14) 0.0512(5) Uani 1 1 d . . . . .
H11A H 0.791291 -0.149064 0.452490 0.061 Uiso 1 1 calc R U . . .
H11B H 0.787927 -0.326184 0.533363 0.061 Uiso 1 1 calc R U . . .
C12 C 0.89716(14) -0.0707(6) 0.54518(18) 0.0700(7) Uani 1 1 d . . . . .
H12A H 0.936987 -0.202646 0.525119 0.105 Uiso 1 1 calc R U . . .
H12B H 0.907354 -0.072949 0.605326 0.105 Uiso 1 1 calc R U . . .
H12C H 0.909775 0.111212 0.525915 0.105 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 C10 1.6896(19) . ?
N1 H1 0.8800 . ?
N1 C1 1.379(3) . ?
N1 C8 1.353(3) . ?
N2 N3 1.377(2) . ?
N2 C9 1.287(2) . ?
N3 H3 0.8800 . ?
N3 C10 1.343(2) . ?
N4 H4 0.8800 . ?
N4 C10 1.330(2) . ?
N4 C11 1.447(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C6 C7 1.441(3) . ?
C7 C8 1.376(3) . ?
C7 C9 1.428(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.503(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C1 N1 H1 125.4 . . ?
C8 N1 H1 125.4 . . ?
C8 N1 C1 109.15(16) . . ?
C9 N2 N3 116.01(16) . . ?
N2 N3 H3 120.3 . . ?
C10 N3 N2 119.39(15) . . ?
C10 N3 H3 120.3 . . ?
C10 N4 H4 117.5 . . ?
C10 N4 C11 124.92(17) . . ?
C11 N4 H4 117.5 . . ?
N1 C1 C2 129.6(2) . . ?
N1 C1 C6 107.93(18) . . ?
C2 C1 C6 122.4(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 106.32(18) . . ?
C5 C6 C1 118.75(19) . . ?
C5 C6 C7 134.93(18) . . ?
C8 C7 C6 106.43(18) . . ?
C8 C7 C9 124.58(19) . . ?
C9 C7 C6 128.92(17) . . ?
N1 C8 C7 110.17(19) . . ?
N1 C8 H8 124.9 . . ?
C7 C8 H8 124.9 . . ?
N2 C9 C7 121.26(18) . . ?
N2 C9 H9 119.4 . . ?
C7 C9 H9 119.4 . . ?
N3 C10 S1 120.58(14) . . ?
N4 C10 S1 123.06(14) . . ?
N4 C10 N3 116.34(16) . . ?
N4 C11 H11A 109.7 . . ?
N4 C11 H11B 109.7 . . ?
N4 C11 C12 110.04(19) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 -179.2(2) . . . . ?
N1 C1 C6 C5 179.50(17) . . . . ?
N1 C1 C6 C7 -0.2(2) . . . . ?
N2 N3 C10 S1 -176.85(12) . . . . ?
N2 N3 C10 N4 1.7(2) . . . . ?
N3 N2 C9 C7 -177.93(15) . . . . ?
C1 N1 C8 C7 -0.3(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C6 C7 C8 0.0(2) . . . . ?
C1 C6 C7 C9 176.85(18) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 -179.26(18) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 179.1(2) . . . . ?
C5 C6 C7 C8 -179.6(2) . . . . ?
C5 C6 C7 C9 -2.7(4) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C7 C8 N1 0.2(2) . . . . ?
C6 C7 C9 N2 2.7(3) . . . . ?
C8 N1 C1 C2 179.3(2) . . . . ?
C8 N1 C1 C6 0.3(2) . . . . ?
C8 C7 C9 N2 179.06(17) . . . . ?
C9 N2 N3 C10 178.01(16) . . . . ?
C9 C7 C8 N1 -176.86(17) . . . . ?
C10 N4 C11 C12 166.3(2) . . . . ?
C11 N4 C10 S1 -5.9(3) . . . . ?
C11 N4 C10 N3 175.56(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_chemical_compound_source        'room temperture'
