# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 1835915'
loop_
_audit_author_name
_audit_author_address
'Manfredo Horner'
;Universidade Federal de Santa Maria
Brazil
;
_audit_update_record             
;
2018-04-09 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;

_audit_creation_date             2018-04-09T14:00:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2,3-diphenyl-1,3,4-thiadiazol-3-ium-5-thiolate'
;
_chemical_name_common            thiadiazol
_chemical_formula_moiety         'C14 H10 N2 S2'
_chemical_formula_sum            'C14 H10 N2 S2'
_chemical_formula_weight         270.36
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7734(3)
_cell_length_b                   10.4120(3)
_cell_length_c                   14.0300(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.5020(10)
_cell_angle_gamma                90
_cell_volume                     1270.65(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      3.177
_cell_measurement_theta_max      68.318
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.5022
_exptl_absorpt_correction_T_max  0.7531
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.26
_shelx_estimated_absorpt_T_max   0.534

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_number            16780
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.364
_diffrn_reflns_theta_max         68.341
_diffrn_reflns_theta_full        10
_diffrn_measured_fraction_theta_full 0.538
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.538
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.538
_diffrn_reflns_point_group_measured_fraction_max 0.965
_reflns_Friedel_coverage         0
_reflns_number_total             2255
_reflns_number_gt                2087
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0452P)²+0.5425P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
S4 S 0.61074(5) 0.62439(5) 0.62867(3) 0.04735(16) Uani 1 1 d . . . . .
S31 S 0.48730(6) 0.73456(5) 0.43511(4) 0.05465(18) Uani 1 1 d . . . . .
N1 N 0.34487(16) 0.55852(13) 0.64785(10) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.32557(18) 0.61773(15) 0.55917(11) 0.0443(4) Uani 1 1 d . . . . .
C14 C -0.0649(2) 0.4132(2) 0.72662(16) 0.0549(5) Uani 1 1 d . . . . .
H14 H -0.1562 0.3805 0.7436 0.066 Uiso 1 1 calc R U . . .
C13 C 0.0309(2) 0.4847(2) 0.79219(15) 0.0569(5) Uani 1 1 d . . . . .
H13 H 0.0039 0.5001 0.8531 0.068 Uiso 1 1 calc R U . . .
C12 C 0.1669(2) 0.53362(19) 0.76754(14) 0.0496(5) Uani 1 1 d . . . . .
H12 H 0.2311 0.5833 0.8109 0.06 Uiso 1 1 calc R U . . .
C11 C 0.20536(19) 0.50735(16) 0.67743(12) 0.0394(4) Uani 1 1 d . . . . .
C5 C 0.48554(19) 0.55105(16) 0.69426(12) 0.0390(4) Uani 1 1 d . . . . .
C51 C 0.53319(19) 0.48780(16) 0.78692(12) 0.0384(4) Uani 1 1 d . . . . .
C56 C 0.4762(2) 0.36770(18) 0.80784(14) 0.0471(4) Uani 1 1 d . . . . .
H56 H 0.4044 0.3266 0.7635 0.057 Uiso 1 1 calc R U . . .
C55 C 0.5264(2) 0.3102(2) 0.89430(14) 0.0538(5) Uani 1 1 d . . . . .
H55 H 0.4876 0.2303 0.9085 0.065 Uiso 1 1 calc R U . . .
C54 C 0.6338(2) 0.3698(2) 0.96033(14) 0.0545(5) Uani 1 1 d . . . . .
H54 H 0.6664 0.3306 1.019 0.065 Uiso 1 1 calc R U . . .
C16 C 0.1106(2) 0.43636(18) 0.61131(13) 0.0470(4) Uani 1 1 d . . . . .
H16 H 0.1383 0.4201 0.5507 0.056 Uiso 1 1 calc R U . . .
C15 C -0.0259(2) 0.3899(2) 0.63609(15) 0.0546(5) Uani 1 1 d . . . . .
H15 H -0.0916 0.3428 0.5918 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4582(2) 0.65946(17) 0.53701(13) 0.0421(4) Uani 1 1 d . . . . .
C52 C 0.6432(2) 0.54670(18) 0.85262(13) 0.0443(4) Uani 1 1 d . . . . .
H52 H 0.6835 0.626 0.8384 0.053 Uiso 1 1 calc R U . . .
C53 C 0.6927(2) 0.4872(2) 0.93924(14) 0.0520(5) Uani 1 1 d . . . . .
H53 H 0.7661 0.5269 0.9834 0.062 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S4 C5 1.7031(18) . ?
S4 C3 1.7689(18) . ?
S31 C3 1.6781(18) . ?
N1 C5 1.320(2) . ?
N1 N2 1.379(2) . ?
N1 C11 1.445(2) . ?
N2 C3 1.317(2) . ?
C14 C15 1.379(3) . ?
C14 C13 1.381(3) . ?
C14 H14 0.93 . ?
C13 C12 1.382(3) . ?
C13 H13 0.93 . ?
C12 C11 1.378(3) . ?
C12 H12 0.93 . ?
C11 C16 1.377(2) . ?
C5 C51 1.468(2) . ?
C51 C52 1.387(2) . ?
C51 C56 1.392(3) . ?
C56 C55 1.373(3) . ?
C56 H56 0.93 . ?
C55 C54 1.380(3) . ?
C55 H55 0.93 . ?
C54 C53 1.374(3) . ?
C54 H54 0.93 . ?
C16 C15 1.377(3) . ?
C16 H16 0.93 . ?
C15 H15 0.93 . ?
C52 C53 1.382(3) . ?
C52 H52 0.93 . ?
C53 H53 0.93 . ?

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
C5 S4 C3 90.30(8) . . ?
C5 N1 N2 117.90(15) . . ?
C5 N1 C11 127.52(14) . . ?
N2 N1 C11 114.53(13) . . ?
C3 N2 N1 110.63(14) . . ?
C15 C14 C13 120.37(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C13 C12 120.17(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C11 C12 C13 118.64(18) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C16 C11 C12 121.73(17) . . ?
C16 C11 N1 117.65(16) . . ?
C12 C11 N1 120.57(16) . . ?
N1 C5 C51 127.06(16) . . ?
N1 C5 S4 109.54(12) . . ?
C51 C5 S4 123.39(13) . . ?
C52 C51 C56 119.66(16) . . ?
C52 C51 C5 118.87(16) . . ?
C56 C51 C5 121.39(16) . . ?
C55 C56 C51 119.69(17) . . ?
C55 C56 H56 120.2 . . ?
C51 C56 H56 120.2 . . ?
C56 C55 C54 120.63(19) . . ?
C56 C55 H55 119.7 . . ?
C54 C55 H55 119.7 . . ?
C53 C54 C55 119.90(18) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C11 C16 C15 119.13(18) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C15 C14 119.93(19) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
N2 C3 S31 126.32(14) . . ?
N2 C3 S4 111.61(13) . . ?
S31 C3 S4 122.06(11) . . ?
C53 C52 C51 119.84(17) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C54 C53 C52 120.26(18) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 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
C5 N1 N2 C3 -0.9(2) . . . . ?
C11 N1 N2 C3 -178.88(14) . . . . ?
C15 C14 C13 C12 0.0(3) . . . . ?
C14 C13 C12 C11 -1.2(3) . . . . ?
C13 C12 C11 C16 1.4(3) . . . . ?
C13 C12 C11 N1 178.79(17) . . . . ?
C5 N1 C11 C16 -131.02(19) . . . . ?
N2 N1 C11 C16 46.7(2) . . . . ?
C5 N1 C11 C12 51.5(3) . . . . ?
N2 N1 C11 C12 -130.82(17) . . . . ?
N2 N1 C5 C51 -177.16(15) . . . . ?
C11 N1 C5 C51 0.5(3) . . . . ?
N2 N1 C5 S4 1.45(19) . . . . ?
C11 N1 C5 S4 179.09(13) . . . . ?
C3 S4 C5 N1 -1.16(13) . . . . ?
C3 S4 C5 C51 177.52(15) . . . . ?
N1 C5 C51 C52 -139.94(18) . . . . ?
S4 C5 C51 C52 41.6(2) . . . . ?
N1 C5 C51 C56 43.3(3) . . . . ?
S4 C5 C51 C56 -135.10(16) . . . . ?
C52 C51 C56 C55 1.7(3) . . . . ?
C5 C51 C56 C55 178.37(18) . . . . ?
C51 C56 C55 C54 -0.6(3) . . . . ?
C56 C55 C54 C53 -0.7(3) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
N1 C11 C16 C15 -177.82(17) . . . . ?
C11 C16 C15 C14 -0.9(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
N1 N2 C3 S31 178.85(13) . . . . ?
N1 N2 C3 S4 -0.04(18) . . . . ?
C5 S4 C3 N2 0.69(14) . . . . ?
C5 S4 C3 S31 -178.25(12) . . . . ?
C56 C51 C52 C53 -1.5(3) . . . . ?
C5 C51 C52 C53 -178.29(17) . . . . ?
C55 C54 C53 C52 0.8(3) . . . . ?
C51 C52 C53 C54 0.3(3) . . . . ?


# END of CIF
