# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_AA_1_RT
_database_code_depnum_ccdc_archive 'CCDC 2528299'
loop_
_audit_author_name
_audit_author_address
'Jan Janczak'
;Institute of Low Temperature and Structure Research, Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2026-02-03 deposited with the CCDC.	2026-05-19 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         'C11 H12 N2 S'
_chemical_formula_sum            'C11 H12 N2 S'
_chemical_formula_weight         204.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.7572(5)
_cell_length_b                   7.7852(3)
_cell_length_c                   20.6357(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.650(6)
_cell_angle_gamma                90
_cell_volume                     1075.90(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2424
_cell_measurement_theta_min      3.2810
_cell_measurement_theta_max      24.4320

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            8353
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         29.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2613
_reflns_number_gt                1556
_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       
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.3158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2613
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.79532(10) 0.71433(8) 0.45272(3) 0.0581(2) Uani 1 1 d . . . . .
C1 C 0.5908(3) 0.8337(3) 0.42784(9) 0.0390(5) Uani 1 1 d . . . . .
N1 N 0.3992(3) 0.7784(2) 0.41424(8) 0.0408(4) Uani 1 1 d . . . . .
C2 C 0.2754(4) 0.9150(3) 0.39437(12) 0.0551(6) Uani 1 1 d . . . . .
H2 H 0.138049 0.910234 0.381997 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3893(4) 1.0544(3) 0.39626(12) 0.0566(7) Uani 1 1 d . . . . .
H3 H 0.345714 1.165334 0.385479 0.068 Uiso 1 1 calc R U . . .
N2 N 0.5826(3) 1.0058(2) 0.41692(9) 0.0461(5) Uani 1 1 d . . . . .
C4 C 0.7557(4) 1.1195(3) 0.42399(14) 0.0684(8) Uani 1 1 d . . . . .
H4A H 0.846818 1.085494 0.461513 0.103 Uiso 1 1 calc R U . . .
H4B H 0.712995 1.235507 0.429563 0.103 Uiso 1 1 calc R U . . .
H4C H 0.821189 1.112185 0.385557 0.103 Uiso 1 1 calc R U . . .
C5 C 0.3323(4) 0.6016(3) 0.41990(10) 0.0483(6) Uani 1 1 d . . . . .
H5A H 0.215807 0.600982 0.442738 0.058 Uiso 1 1 calc R U . . .
H5B H 0.436780 0.537027 0.446063 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2807(3) 0.5131(2) 0.35470(10) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.0952(4) 0.4406(3) 0.33703(12) 0.0513(6) Uani 1 1 d . . . . .
H7 H -0.002392 0.451367 0.364596 0.062 Uiso 1 1 calc R U . . .
C8 C 0.0526(4) 0.3519(3) 0.27854(13) 0.0662(8) Uani 1 1 d . . . . .
H8 H -0.072816 0.302970 0.267240 0.079 Uiso 1 1 calc R U . . .
C9 C 0.1948(5) 0.3363(3) 0.23737(13) 0.0663(8) Uani 1 1 d . . . . .
H9 H 0.166051 0.276718 0.198175 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3797(5) 0.4086(3) 0.25410(13) 0.0655(8) Uani 1 1 d . . . . .
H10 H 0.476103 0.398729 0.226065 0.079 Uiso 1 1 calc R U . . .
C11 C 0.4229(4) 0.4959(3) 0.31243(11) 0.0540(6) Uani 1 1 d . . . . .
H11 H 0.548929 0.543779 0.323579 0.065 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 C1 1.687(2) . ?
C1 N1 1.358(3) . ?
C1 N2 1.359(3) . ?
N1 C2 1.381(3) . ?
N1 C5 1.458(3) . ?
C2 C3 1.328(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.372(3) . ?
C3 H3 0.9300 . ?
N2 C4 1.458(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.511(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.379(3) . ?
C6 C11 1.388(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 N2 105.15(18) . . ?
N1 C1 S1 127.47(16) . . ?
N2 C1 S1 127.38(18) . . ?
C1 N1 C2 109.92(18) . . ?
C1 N1 C5 125.41(19) . . ?
C2 N1 C5 124.7(2) . . ?
C3 C2 N1 107.2(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 107.9(2) . . ?
C2 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
C1 N2 C3 109.85(19) . . ?
C1 N2 C4 124.6(2) . . ?
C3 N2 C4 125.5(2) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 113.36(17) . . ?
N1 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N1 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C11 118.4(2) . . ?
C7 C6 C5 121.1(2) . . ?
C11 C6 C5 120.4(2) . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?

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
N2 C1 N1 C2 0.8(2) . . . . ?
S1 C1 N1 C2 -179.06(17) . . . . ?
N2 C1 N1 C5 -178.95(18) . . . . ?
S1 C1 N1 C5 1.2(3) . . . . ?
C1 N1 C2 C3 -0.6(3) . . . . ?
C5 N1 C2 C3 179.1(2) . . . . ?
N1 C2 C3 N2 0.2(3) . . . . ?
N1 C1 N2 C3 -0.7(2) . . . . ?
S1 C1 N2 C3 179.16(17) . . . . ?
N1 C1 N2 C4 -178.6(2) . . . . ?
S1 C1 N2 C4 1.2(3) . . . . ?
C2 C3 N2 C1 0.3(3) . . . . ?
C2 C3 N2 C4 178.2(2) . . . . ?
C1 N1 C5 C6 -105.5(2) . . . . ?
C2 N1 C5 C6 74.8(3) . . . . ?
N1 C5 C6 C7 -124.1(2) . . . . ?
N1 C5 C6 C11 59.0(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -176.6(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C6 -0.5(4) . . . . ?
C7 C6 C11 C10 0.1(3) . . . . ?
C5 C6 C11 C10 177.1(2) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046

