# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_AH5_C474
_database_code_depnum_ccdc_archive 'CCDC 2345919'
loop_
_audit_author_name
_audit_author_address
'Vaclav Eigner'
;Institute of Physics AS CR, v v i  Czech Republic
Czech Republic
;
_audit_update_record             
;
2024-04-05 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

_cell_length_a                   11.5536(3)
_cell_length_b                   14.1661(4)
_cell_length_c                   16.4150(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.1406(11)
_cell_angle_gamma                90
_cell_volume                     2675.83(13)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

_chemical_formula_sum            'C14 H10 N2 O S2'
_chemical_formula_moiety         'C14 H10 N2 O S2'
_chemical_compound_source        .
_chemical_formula_weight         286.38


_cell_measurement_reflns_used    305
_cell_measurement_theta_min      11.66
_cell_measurement_theta_max      59.65
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.206
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_max          0.420

_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1183.995
_exptl_absorpt_coefficient_mu    3.544

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.48
_diffrn_measurement_device_type  'Bruker Kappa Apex4'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Apex4 (Bruker AXS, 2021)'
_computing_cell_refinement       'Apex4 (Bruker AXS, 2021)'
_computing_data_reduction        'Apex4 (Bruker AXS, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            45299
_diffrn_reflns_av_unetI/netI     0.046
_reflns_number_total             5105
_diffrn_reflns_av_R_equivalents  0.038

_diffrn_reflns_theta_min         4.129
_diffrn_reflns_theta_max         70.564
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        70.564
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.16
_oxford_diffrn_Wilson_scale      49.68

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.53
_refine_diff_density_max         0.33

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     8
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5105
_oxford_refine_ls_R_factor_ref   0.0347
_refine_ls_R_factor_all          0.0347
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_all         0.0869
_refine_ls_goodness_of_fit_ref   0.9912
_refine_ls_shift/su_max          0.0009791
_refine_ls_shift/su_mean         0.0000619

_oxford_reflns_number_all        5105
_oxford_refine_ls_R_factor_all   0.0347
_oxford_refine_ls_wR_factor_all  0.0869

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4812
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0853


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.43P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.54387(12) 0.71859(10) 0.69042(9) 0.0226 1.0000 Uani . . . . . .
C2 C 0.57458(14) 0.75953(11) 0.61841(10) 0.0308 1.0000 Uani . . . . . .
C3 C 0.68778(15) 0.75127(12) 0.59733(11) 0.0375 1.0000 Uani . . . . . .
C4 C 0.77053(14) 0.70503(11) 0.64890(12) 0.0368 1.0000 Uani . . . . . .
C5 C 0.74013(13) 0.66470(12) 0.72041(11) 0.0345 1.0000 Uani . . . . . .
C6 C 0.62668(13) 0.66995(11) 0.74111(9) 0.0275 1.0000 Uani . . . . . .
C7 C 0.42338(12) 0.73306(10) 0.71390(8) 0.0219 1.0000 Uani D . . . . .
O8 O 0.37093(9) 0.80823(7) 0.70151(7) 0.0320 1.0000 Uani . . . . . .
N9 N 0.37619(10) 0.65851(9) 0.75038(7) 0.0233 1.0000 Uani D . . . . .
N10 N 0.27017(10) 0.67114(9) 0.78168(7) 0.0228 1.0000 Uani D . . . . .
C11 C 0.21992(12) 0.59572(10) 0.80343(8) 0.0226 1.0000 Uani . . . . . .
C12 C 0.11210(12) 0.59940(10) 0.84122(8) 0.0220 1.0000 Uani . . . . . .
S13 S 0.05453(3) 0.70641(3) 0.87070(3) 0.0351 1.0000 Uani . . . . . .
C14 C -0.06067(13) 0.64845(11) 0.90816(9) 0.0281 1.0000 Uani . . . . . .
C15 C -0.16054(15) 0.67702(13) 0.94644(12) 0.0396 1.0000 Uani . . . . . .
C16 C -0.22623(14) 0.60165(13) 0.96258(11) 0.0381 1.0000 Uani . . . . . .
S17 S -0.17076(3) 0.49574(3) 0.93288(3) 0.0354 1.0000 Uani . . . . . .
C18 C -0.05321(12) 0.55224(10) 0.89711(8) 0.0235 1.0000 Uani . . . . . .
C19 C 0.04653(12) 0.52334(10) 0.85947(9) 0.0251 1.0000 Uani . . . . . .
C21 C 0.04897(11) 0.85254(10) 0.61231(8) 0.0206 1.0000 Uani . . . . . .
C22 C -0.02541(13) 0.88782(11) 0.54827(9) 0.0294 1.0000 Uani . . . . . .
C23 C -0.04102(16) 0.83954(13) 0.47476(10) 0.0395 1.0000 Uani . . . . . .
C24 C 0.01737(16) 0.75550(13) 0.46478(10) 0.0387 1.0000 Uani . . . . . .
C25 C 0.08955(15) 0.71926(12) 0.52855(10) 0.0347 1.0000 Uani . . . . . .
C26 C 0.10544(13) 0.76672(10) 0.60251(9) 0.0271 1.0000 Uani . . . . . .
C27 C 0.06519(11) 0.91100(10) 0.68808(8) 0.0215 1.0000 Uani D . . . . .
O28 O 0.00641(10) 0.98216(8) 0.69665(7) 0.0325 1.0000 Uani . . . . . .
N29 N 0.15044(10) 0.88331(8) 0.74522(7) 0.0225 1.0000 Uani D . . . . .
N30 N 0.15973(10) 0.93100(8) 0.81875(7) 0.0242 1.0000 Uani D . . . . .
C31 C 0.25131(12) 0.91481(10) 0.86608(9) 0.0248 1.0000 Uani . . . . . .
C32 C 0.26245(12) 0.95848(10) 0.94615(9) 0.0248 1.0000 Uani . . . . . .
S33 S 0.14427(4) 1.01610(3) 0.98172(3) 0.0395 1.0000 Uani . . . . . .
C34 C 0.22340(16) 1.03992(12) 1.07383(10) 0.0362 1.0000 Uani . . . . . .
C35 C 0.2003(2) 1.08533(14) 1.14817(12) 0.0544 1.0000 Uani . . . . . .
C36 C 0.2954(2) 1.08627(14) 1.20135(11) 0.0579 1.0000 Uani . . . . . .
S37 S 0.41447(5) 1.03228(4) 1.16551(3) 0.0485 1.0000 Uani . . . . . .
C38 C 0.33482(15) 1.00638(11) 1.07401(9) 0.0298 1.0000 Uani . . . . . .
C39 C 0.35762(13) 0.95846(10) 1.00164(9) 0.0265 1.0000 Uani . . . . . .
H111 H 0.2533 0.5340 0.7969 0.0287 1.0000 Uiso R . . . . .
H61 H 0.6077 0.6427 0.7900 0.0342 1.0000 Uiso R . . . . .
H51 H 0.7981 0.6316 0.7571 0.0429 1.0000 Uiso R . . . . .
H41 H 0.8484 0.7012 0.6318 0.0427 1.0000 Uiso R . . . . .
H31 H 0.7095 0.7784 0.5493 0.0455 1.0000 Uiso R . . . . .
H21 H 0.5158 0.7936 0.5833 0.0369 1.0000 Uiso R . . . . .
H191 H 0.0640 0.4608 0.8489 0.0324 1.0000 Uiso R . . . . .
H151 H -0.1785 0.7381 0.9586 0.0486 1.0000 Uiso R . . . . .
H161 H -0.2957 0.6048 0.9885 0.0474 1.0000 Uiso R . . . . .
H391 H 0.4287 0.9278 0.9937 0.0334 1.0000 Uiso R . . . . .
H351 H 0.1246 1.1079 1.1579 0.0642 1.0000 Uiso R . . . . .
H361 H 0.2987 1.1121 1.2529 0.0699 1.0000 Uiso R . . . . .
H311 H 0.3137 0.8749 0.8504 0.0303 1.0000 Uiso R . . . . .
H261 H 0.1545 0.7394 0.6481 0.0344 1.0000 Uiso R . . . . .
H251 H 0.1307 0.6657 0.5203 0.0411 1.0000 Uiso R . . . . .
H241 H 0.0042 0.7257 0.4123 0.0455 1.0000 Uiso R . . . . .
H231 H -0.0938 0.8643 0.4303 0.0478 1.0000 Uiso R . . . . .
H221 H -0.0691 0.9425 0.5566 0.0357 1.0000 Uiso R . . . . .
H91 H 0.4089(13) 0.6052(10) 0.7541(10) 0.0287(18) 1.0000 Uiso D . . . . .
H291 H 0.2017(13) 0.8434(12) 0.7342(9) 0.0281(18) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13115(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.391(2) yes
C1 . C6 . 1.393(2) yes
C1 . C7 . 1.4916(19) yes
C2 . C3 . 1.387(2) yes
C2 . H21 . 0.977 no
C3 . C4 . 1.384(3) yes
C3 . H31 . 0.931 no
C4 . C5 . 1.379(3) yes
C4 . H41 . 0.968 no
C5 . C6 . 1.385(2) yes
C5 . H51 . 0.979 no
C6 . H61 . 0.934 no
C7 . O8 . 1.2331(17) yes
C7 . N9 . 1.3525(18) yes
N9 . N10 . 1.3817(16) yes
N9 . H91 . 0.844(14) no
N10 . C11 . 1.2819(19) yes
C11 . C12 . 1.4414(19) yes
C11 . H111 . 0.965 no
C12 . S13 . 1.7414(14) yes
C12 . C19 . 1.366(2) yes
S13 . C14 . 1.7236(15) yes
C14 . C15 . 1.421(2) yes
C14 . C18 . 1.379(2) yes
C15 . C16 . 1.350(2) yes
C15 . H151 . 0.915 no
C16 . S17 . 1.7190(18) yes
C16 . H161 . 0.942 no
S17 . C18 . 1.7242(14) yes
C18 . C19 . 1.4159(19) yes
C19 . H191 . 0.928 no
C21 . C22 . 1.390(2) yes
C21 . C26 . 1.396(2) yes
C21 . C27 . 1.4920(19) yes
C22 . C23 . 1.385(2) yes
C22 . H221 . 0.941 no
C23 . C24 . 1.385(3) yes
C23 . H231 . 0.973 no
C24 . C25 . 1.378(3) yes
C24 . H241 . 0.959 no
C25 . C26 . 1.385(2) yes
C25 . H251 . 0.912 no
C26 . H261 . 0.978 no
C27 . O28 . 1.2306(17) yes
C27 . N29 . 1.3558(18) yes
N29 . N30 . 1.3790(16) yes
N29 . H291 . 0.851(14) no
N30 . C31 . 1.2761(19) yes
C31 . C32 . 1.448(2) yes
C31 . H311 . 0.969 no
C32 . S33 . 1.7362(15) yes
C32 . C39 . 1.363(2) yes
S33 . C34 . 1.7286(18) yes
C34 . C35 . 1.425(2) yes
C34 . C38 . 1.372(3) yes
C35 . C36 . 1.341(3) yes
C35 . H351 . 0.958 no
C36 . S37 . 1.723(3) yes
C36 . H361 . 0.919 no
S37 . C38 . 1.7291(15) yes
C38 . C39 . 1.413(2) yes
C39 . H391 . 0.949 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 120.01(13) yes
C2 . C1 . C7 . 118.51(13) yes
C6 . C1 . C7 . 121.37(13) yes
C1 . C2 . C3 . 119.64(15) yes
C1 . C2 . H21 . 119.3 no
C3 . C2 . H21 . 121.0 no
C2 . C3 . C4 . 120.16(15) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 119.3 no
C3 . C4 . C5 . 120.14(14) yes
C3 . C4 . H41 . 117.3 no
C5 . C4 . H41 . 122.6 no
C4 . C5 . C6 . 120.36(15) yes
C4 . C5 . H51 . 120.6 no
C6 . C5 . H51 . 119.0 no
C1 . C6 . C5 . 119.63(14) yes
C1 . C6 . H61 . 121.1 no
C5 . C6 . H61 . 119.2 no
C1 . C7 . O8 . 122.16(12) yes
C1 . C7 . N9 . 115.45(12) yes
O8 . C7 . N9 . 122.38(13) yes
C7 . N9 . N10 . 118.00(12) yes
C7 . N9 . H91 . 122.4(9) no
N10 . N9 . H91 . 119.6(9) no
N9 . N10 . C11 . 115.75(12) yes
N10 . C11 . C12 . 121.35(13) yes
N10 . C11 . H111 . 121.9 no
C12 . C11 . H111 . 116.8 no
C11 . C12 . S13 . 121.15(11) yes
C11 . C12 . C19 . 125.71(13) yes
S13 . C12 . C19 . 113.12(10) yes
C12 . S13 . C14 . 90.62(7) yes
S13 . C14 . C15 . 134.88(13) yes
S13 . C14 . C18 . 111.38(11) yes
C15 . C14 . C18 . 113.73(14) yes
C14 . C15 . C16 . 110.77(15) yes
C14 . C15 . H151 . 125.0 no
C16 . C15 . H151 . 124.2 no
C15 . C16 . S17 . 113.84(12) yes
C15 . C16 . H161 . 124.6 no
S17 . C16 . H161 . 121.6 no
C16 . S17 . C18 . 90.95(7) yes
S17 . C18 . C14 . 110.71(11) yes
S17 . C18 . C19 . 135.32(12) yes
C14 . C18 . C19 . 113.97(13) yes
C18 . C19 . C12 . 110.90(13) yes
C18 . C19 . H191 . 123.8 no
C12 . C19 . H191 . 125.3 no
C22 . C21 . C26 . 119.32(13) yes
C22 . C21 . C27 . 117.00(13) yes
C26 . C21 . C27 . 123.67(13) yes
C21 . C22 . C23 . 120.33(15) yes
C21 . C22 . H221 . 119.3 no
C23 . C22 . H221 . 120.2 no
C22 . C23 . C24 . 120.05(15) yes
C22 . C23 . H231 . 119.9 no
C24 . C23 . H231 . 120.0 no
C23 . C24 . C25 . 119.89(15) yes
C23 . C24 . H241 . 116.4 no
C25 . C24 . H241 . 123.7 no
C24 . C25 . C26 . 120.57(15) yes
C24 . C25 . H251 . 119.0 no
C26 . C25 . H251 . 120.3 no
C21 . C26 . C25 . 119.80(14) yes
C21 . C26 . H261 . 120.1 no
C25 . C26 . H261 . 120.1 no
C21 . C27 . O28 . 121.37(12) yes
C21 . C27 . N29 . 116.45(12) yes
O28 . C27 . N29 . 122.14(13) yes
C27 . N29 . N30 . 117.30(11) yes
C27 . N29 . H291 . 121.5(9) no
N30 . N29 . H291 . 120.7(9) no
N29 . N30 . C31 . 116.11(12) yes
N30 . C31 . C32 . 118.50(13) yes
N30 . C31 . H311 . 122.7 no
C32 . C31 . H311 . 118.8 no
C31 . C32 . S33 . 119.84(11) yes
C31 . C32 . C39 . 127.38(14) yes
S33 . C32 . C39 . 112.76(11) yes
C32 . S33 . C34 . 90.90(8) yes
S33 . C34 . C35 . 135.40(17) yes
S33 . C34 . C38 . 110.91(12) yes
C35 . C34 . C38 . 113.69(18) yes
C34 . C35 . C36 . 110.9(2) yes
C34 . C35 . H351 . 122.4 no
C36 . C35 . H351 . 126.6 no
C35 . C36 . S37 . 113.94(14) yes
C35 . C36 . H361 . 124.6 no
S37 . C36 . H361 . 121.5 no
C36 . S37 . C38 . 90.67(9) yes
S37 . C38 . C34 . 110.77(12) yes
S37 . C38 . C39 . 135.02(14) yes
C34 . C38 . C39 . 114.20(14) yes
C38 . C39 . C32 . 111.19(14) yes
C38 . C39 . H391 . 124.3 no
C32 . C39 . H391 . 124.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N9 . H91 . O28 4_546 161.9(16) 0.844(14) 2.123(15) 2.937(2) yes
N29 . H291 . O8 . 151.8(16) 0.851(14) 2.132(15) 2.909(2) yes
N29 . H291 . N10 . 137.9(14) 0.851(14) 2.660(17) 3.340(2) yes
C6 . H61 . O28 4_546 126 0.93 2.65 3.281(2) yes
C11 . H111 . N29 4_546 170 0.97 2.53 3.486(2) yes
C19 . H191 . O8 4_546 169 0.93 2.46 3.372(2) yes
C26 . H261 . N10 . 174 0.97 2.65 3.620(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
