# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2344626'
loop_
_audit_author_name
_audit_author_address
zhh
;Taizhou university
China
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 S'
_chemical_formula_weight         245.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   14.3166(4)
_cell_length_b                   10.3015(3)
_cell_length_c                   17.5450(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2587.58(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      5.86
_cell_measurement_theta_max      68.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.061
_shelx_estimated_absorpt_T_min   0.649
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21803
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.041
_diffrn_reflns_theta_max         68.414
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2369
_reflns_number_gt                2184
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0577P)²+0.5761P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2369
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.35983(3) 0.62622(4) 0.56256(2) 0.05068(19) Uani 1 1 d . . . . .
N2 N 0.23922(9) 0.58227(15) 0.44996(7) 0.0509(3) Uani 1 1 d . . . . .
N3 N 0.17237(9) 0.66011(14) 0.55985(7) 0.0487(3) Uani 1 1 d . . . . .
N4 N 0.34533(10) 0.72072(14) 0.64031(7) 0.0528(4) Uani 1 1 d . . . . .
C5 C 0.31923(10) 0.56839(15) 0.40338(7) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.46615(10) 0.54352(15) 0.29893(8) 0.0455(4) Uani 1 1 d . . . . .
C8 C 0.24793(10) 0.62560(13) 0.51857(8) 0.0408(3) Uani 1 1 d . . . . .
C6 C 0.35300(11) 0.44689(16) 0.38324(9) 0.0511(4) Uani 1 1 d . . . . .
H6 H 0.3261 0.3729 0.4043 0.061 Uiso 1 1 calc R U . . .
C4 C 0.35978(11) 0.67718(17) 0.37053(9) 0.0510(4) Uani 1 1 d . . . . .
H4 H 0.3382 0.7593 0.3837 0.061 Uiso 1 1 calc R U . . .
C1 C 0.53896(12) 0.53433(17) 0.24247(9) 0.0536(4) Uani 1 1 d . . . . .
C7 C 0.42631(11) 0.43429(16) 0.33217(9) 0.0513(4) Uani 1 1 d . . . . .
H7 H 0.4490 0.3522 0.3201 0.062 Uiso 1 1 calc R U . . .
C3 C 0.43170(11) 0.66517(16) 0.31863(9) 0.0502(4) Uani 1 1 d . . . . .
H3 H 0.4574 0.7391 0.2966 0.060 Uiso 1 1 calc R U . . .
C9 C 0.17201(12) 0.70611(19) 0.63843(9) 0.0573(4) Uani 1 1 d . . . . .
H9A H 0.1210 0.6643 0.6653 0.069 Uiso 1 1 calc R U . . .
H9B H 0.1598 0.7987 0.6383 0.069 Uiso 1 1 calc R U . . .
C10 C 0.26164(13) 0.6816(2) 0.68190(9) 0.0590(4) Uani 1 1 d . . . . .
H10A H 0.2593 0.7285 0.7298 0.071 Uiso 1 1 calc R U . . .
H10B H 0.2659 0.5898 0.6937 0.071 Uiso 1 1 calc R U . . .
C11 C 0.08128(12) 0.6651(2) 0.52235(11) 0.0675(5) Uani 1 1 d . . . . .
H11A H 0.0559 0.7511 0.5268 0.101 Uiso 1 1 calc R U . . .
H11B H 0.0398 0.6043 0.5462 0.101 Uiso 1 1 calc R U . . .
H11C H 0.0883 0.6434 0.4695 0.101 Uiso 1 1 calc R U . . .
C0 C 0.59583(14) 0.5344(2) 0.19405(11) 0.0667(5) Uani 1 1 d . . . . .
H0 H 0.6408 0.5345 0.1558 0.080 Uiso 1 1 calc R U . . .
C12 C 0.34915(16) 0.85960(18) 0.62229(13) 0.0742(6) Uani 1 1 d . . . . .
H12A H 0.4098 0.8808 0.6026 0.111 Uiso 1 1 calc R U . . .
H12B H 0.3376 0.9091 0.6677 0.111 Uiso 1 1 calc R U . . .
H12C H 0.3025 0.8798 0.5848 0.111 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 N4 1.6887(13) . ?
S1 C8 1.7783(14) . ?
N2 C8 1.2898(19) . ?
N2 C5 1.4143(19) . ?
N3 C8 1.349(2) . ?
N3 C9 1.4580(19) . ?
N3 C11 1.461(2) . ?
N4 C10 1.460(2) . ?
N4 C12 1.466(2) . ?
C5 C6 1.387(2) . ?
C5 C4 1.388(2) . ?
C2 C7 1.390(2) . ?
C2 C3 1.390(2) . ?
C2 C1 1.441(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.380(2) . ?
C4 H4 0.9300 . ?
C1 C0 1.177(2) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C9 C10 1.514(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C0 H0 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
N4 S1 C8 104.00(7) . . ?
C8 N2 C5 119.74(12) . . ?
C8 N3 C9 126.58(13) . . ?
C8 N3 C11 118.88(13) . . ?
C9 N3 C11 114.27(13) . . ?
C10 N4 C12 114.08(15) . . ?
C10 N4 S1 110.22(11) . . ?
C12 N4 S1 112.56(13) . . ?
C6 C5 C4 118.49(14) . . ?
C6 C5 N2 121.37(14) . . ?
C4 C5 N2 119.82(15) . . ?
C7 C2 C3 118.68(14) . . ?
C7 C2 C1 122.15(15) . . ?
C3 C2 C1 119.12(14) . . ?
N2 C8 N3 120.97(13) . . ?
N2 C8 S1 119.56(11) . . ?
N3 C8 S1 119.23(11) . . ?
C7 C6 C5 120.86(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C3 C4 C5 120.92(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C0 C1 C2 175.34(19) . . ?
C6 C7 C2 120.41(15) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C4 C3 C2 120.63(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N3 C9 C10 114.78(13) . . ?
N3 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
N4 C10 C9 113.43(13) . . ?
N4 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N4 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C0 H0 180.0 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 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
C8 S1 N4 C10 48.18(12) . . . . ?
C8 S1 N4 C12 -80.41(14) . . . . ?
C8 N2 C5 C6 110.36(18) . . . . ?
C8 N2 C5 C4 -76.26(19) . . . . ?
C5 N2 C8 N3 168.94(14) . . . . ?
C5 N2 C8 S1 -16.8(2) . . . . ?
C9 N3 C8 N2 177.79(16) . . . . ?
C11 N3 C8 N2 -8.5(2) . . . . ?
C9 N3 C8 S1 3.5(2) . . . . ?
C11 N3 C8 S1 177.20(13) . . . . ?
N4 S1 C8 N2 166.93(12) . . . . ?
N4 S1 C8 N3 -18.69(13) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
N2 C5 C6 C7 174.22(14) . . . . ?
C6 C5 C4 C3 0.4(2) . . . . ?
N2 C5 C4 C3 -173.18(14) . . . . ?
C5 C6 C7 C2 -1.3(2) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C1 C2 C7 C6 -176.52(15) . . . . ?
C5 C4 C3 C2 -1.0(2) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 177.75(14) . . . . ?
C8 N3 C9 C10 -15.4(3) . . . . ?
C11 N3 C9 C10 170.63(16) . . . . ?
C12 N4 C10 C9 61.30(19) . . . . ?
S1 N4 C10 C9 -66.46(17) . . . . ?
N3 C9 C10 N4 48.5(2) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041

