# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 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_mimi210
_database_code_depnum_ccdc_archive 'CCDC 2312261'
loop_
_audit_author_name
_audit_author_address
'Vladimir B. Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H22 Co I N6 S2, C2 H3 N, I'
_chemical_formula_sum            'C11 H25 Co I2 N7 S2'
_chemical_formula_weight         632.23

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.9236(4)
_cell_length_b                   10.5945(4)
_cell_length_c                   11.4418(5)
_cell_angle_alpha                62.637(3)
_cell_angle_beta                 75.464(4)
_cell_angle_gamma                79.855(3)
_cell_volume                     1031.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    46277
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      35.94

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    4.035
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5978
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Stadivari
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23335
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5981
_reflns_number_gt                5149
_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       
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_cell_refinement       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.1, Darmstadt 2022
;

_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)+(0.0404P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5981
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0609
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_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
I1 I 0.23226(2) 0.59365(2) -0.02429(2) 0.01363(4) Uani 1 1 d . . . . .
I2 I 0.08454(2) 0.35734(2) 0.70972(2) 0.01504(5) Uani 1 1 d . . . . .
Co Co 0.30042(3) 0.31105(3) 0.15347(3) 0.01032(7) Uani 1 1 d . . . . .
S1 S 0.43253(6) 0.38309(6) 0.45917(6) 0.01428(11) Uani 1 1 d . . . . .
S2 S 0.50639(7) 0.20457(8) -0.18463(7) 0.02685(15) Uani 1 1 d . . . . .
N1 N 0.41753(18) 0.34792(18) 0.24031(18) 0.0103(3) Uani 1 1 d . . . . .
H10 H 0.5070 0.3596 0.2072 0.012 Uiso 1 1 calc R U . . .
N2 N 0.21910(19) 0.3341(2) 0.39331(19) 0.0144(4) Uani 1 1 d . . . . .
H20 H 0.1731 0.3304 0.4712 0.017 Uiso 1 1 calc R U . . .
N3 N 0.15311(19) 0.3191(2) 0.30372(19) 0.0124(4) Uani 1 1 d . . . . .
H3 H 0.0897 0.4063 0.2664 0.015 Uiso 1 1 calc R U . . .
N4 N 0.1838(2) 0.2451(2) 0.07951(19) 0.0153(4) Uani 1 1 d . . . . .
H40 H 0.1156 0.3256 0.0377 0.018 Uiso 1 1 calc R U . . .
N5 N 0.2710(2) 0.2102(2) -0.0245(2) 0.0201(4) Uani 1 1 d . . . . .
H50 H 0.2388 0.1751 -0.0677 0.024 Uiso 1 1 calc R U . . .
N6 N 0.44719(19) 0.27558(19) 0.02580(18) 0.0128(4) Uani 1 1 d . . . . .
H60 H 0.5353 0.2854 0.0195 0.015 Uiso 1 1 calc R U . . .
C1 C 0.3574(2) 0.3546(2) 0.3508(2) 0.0099(4) Uani 1 1 d . . . . .
C2 C 0.0661(2) 0.1935(2) 0.3791(2) 0.0136(4) Uani 1 1 d . . . . .
H2 H 0.1280 0.1070 0.4225 0.016 Uiso 1 1 calc R U . . .
C3 C 0.0026(2) 0.1715(3) 0.2813(2) 0.0172(5) Uani 1 1 d . . . . .
H3A H -0.0689 0.1013 0.3346 0.021 Uiso 1 1 calc R U . . .
H3B H -0.0461 0.2628 0.2283 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1029(2) 0.1210(2) 0.1839(2) 0.0168(5) Uani 1 1 d . . . . .
H4 H 0.1696 0.0445 0.2341 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4074(2) 0.2362(2) -0.0503(2) 0.0162(5) Uani 1 1 d . . . . .
C6 C 0.6138(2) 0.3844(3) 0.3789(2) 0.0186(5) Uani 1 1 d . . . . .
H6A H 0.6247 0.4580 0.2859 0.028 Uiso 1 1 calc R U . . .
H6B H 0.6461 0.2911 0.3798 0.028 Uiso 1 1 calc R U . . .
H6C H 0.6692 0.4049 0.4272 0.028 Uiso 1 1 calc R U . . .
C7 C -0.0473(2) 0.2124(2) 0.4882(2) 0.0170(5) Uani 1 1 d . . . . .
H7A H -0.0047 0.2078 0.5587 0.025 Uiso 1 1 calc R U . . .
H7B H -0.1114 0.1364 0.5266 0.025 Uiso 1 1 calc R U . . .
H7C H -0.0991 0.3051 0.4496 0.025 Uiso 1 1 calc R U . . .
C8 C 0.0263(3) 0.0598(3) 0.1242(3) 0.0208(5) Uani 1 1 d . . . . .
H8A H -0.0409 0.1329 0.0758 0.031 Uiso 1 1 calc R U . . .
H8B H -0.0232 -0.0219 0.1962 0.031 Uiso 1 1 calc R U . . .
H8C H 0.0937 0.0287 0.0619 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6763(3) 0.2413(3) -0.1891(3) 0.0260(6) Uani 1 1 d . . . . .
H9A H 0.7424 0.2276 -0.2626 0.039 Uiso 1 1 calc R U . . .
H9B H 0.7052 0.1765 -0.1038 0.039 Uiso 1 1 calc R U . . .
H9C H 0.6751 0.3400 -0.2032 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4941(3) -0.0100(2) 0.3528(3) 0.0202(5) Uani 1 1 d . . . . .
C11 C 0.6444(3) -0.0022(3) 0.3054(3) 0.0246(5) Uani 1 1 d . . . . .
H11A H 0.6638 0.0860 0.2231 0.037 Uiso 1 1 calc R U . . .
H11B H 0.6835 -0.0842 0.2868 0.037 Uiso 1 1 calc R U . . .
H11C H 0.6870 -0.0031 0.3743 0.037 Uiso 1 1 calc R U . . .
N7 N 0.3772(2) -0.0145(2) 0.3886(3) 0.0295(5) Uani 1 1 d . . . . .


_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
I1 Co 2.8174(4) . ?
Co N1 1.8938(18) . ?
Co N6 1.9080(19) . ?
Co N4 1.9659(19) . ?
Co N3 1.9822(19) . ?
S1 C1 1.753(2) . ?
S1 C6 1.802(2) . ?
S2 C5 1.744(2) . ?
S2 C9 1.780(3) . ?
N1 C1 1.283(3) . ?
N1 H10 0.8800 . ?
N2 C1 1.357(3) . ?
N2 N3 1.424(3) . ?
N2 H20 0.8800 . ?
N3 C2 1.495(3) . ?
N3 H3 1.0000 . ?
N4 N5 1.441(3) . ?
N4 C4 1.499(3) . ?
N4 H40 1.0000 . ?
N5 C5 1.361(3) . ?
N5 H50 0.8800 . ?
N6 C5 1.285(3) . ?
N6 H60 0.8800 . ?
C2 C7 1.520(3) . ?
C2 C3 1.532(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.519(3) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N7 1.131(3) . ?
C10 C11 1.457(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
N1 Co N6 96.02(8) . . ?
N1 Co N4 172.15(8) . . ?
N6 Co N4 83.24(8) . . ?
N1 Co N3 83.21(8) . . ?
N6 Co N3 171.84(8) . . ?
N4 Co N3 96.40(8) . . ?
N1 Co I1 98.96(5) . . ?
N6 Co I1 95.13(6) . . ?
N4 Co I1 88.89(6) . . ?
N3 Co I1 93.01(6) . . ?
C1 S1 C6 100.41(11) . . ?
C5 S2 C9 101.94(12) . . ?
C1 N1 Co 115.42(15) . . ?
C1 N1 H10 122.3 . . ?
Co N1 H10 122.3 . . ?
C1 N2 N3 115.69(18) . . ?
C1 N2 H20 122.2 . . ?
N3 N2 H20 122.2 . . ?
N2 N3 C2 109.62(17) . . ?
N2 N3 Co 107.73(13) . . ?
C2 N3 Co 115.05(14) . . ?
N2 N3 H3 108.1 . . ?
C2 N3 H3 108.1 . . ?
Co N3 H3 108.1 . . ?
N5 N4 C4 110.70(17) . . ?
N5 N4 Co 108.96(13) . . ?
C4 N4 Co 113.10(14) . . ?
N5 N4 H40 108.0 . . ?
C4 N4 H40 108.0 . . ?
Co N4 H40 108.0 . . ?
C5 N5 N4 114.27(18) . . ?
C5 N5 H50 122.9 . . ?
N4 N5 H50 122.9 . . ?
C5 N6 Co 114.82(16) . . ?
C5 N6 H60 122.6 . . ?
Co N6 H60 122.6 . . ?
N1 C1 N2 117.6(2) . . ?
N1 C1 S1 128.13(17) . . ?
N2 C1 S1 114.30(16) . . ?
N3 C2 C7 111.11(18) . . ?
N3 C2 C3 109.65(18) . . ?
C7 C2 C3 110.80(18) . . ?
N3 C2 H2 108.4 . . ?
C7 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C4 C3 C2 116.87(19) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
N4 C4 C8 112.8(2) . . ?
N4 C4 C3 107.29(18) . . ?
C8 C4 C3 111.6(2) . . ?
N4 C4 H4 108.3 . . ?
C8 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
N6 C5 N5 118.4(2) . . ?
N6 C5 S2 128.91(18) . . ?
N5 C5 S2 112.68(17) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N7 C10 C11 179.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N6 Co N1 C1 -168.97(15) . . . . ?
N3 Co N1 C1 2.86(15) . . . . ?
I1 Co N1 C1 94.85(15) . . . . ?
C1 N2 N3 C2 132.67(19) . . . . ?
C1 N2 N3 Co 6.8(2) . . . . ?
C4 N4 N5 C5 -127.7(2) . . . . ?
Co N4 N5 C5 -2.7(2) . . . . ?
Co N1 C1 N2 0.4(2) . . . . ?
Co N1 C1 S1 178.62(12) . . . . ?
N3 N2 C1 N1 -5.1(3) . . . . ?
N3 N2 C1 S1 176.43(14) . . . . ?
C6 S1 C1 N1 -4.5(2) . . . . ?
C6 S1 C1 N2 173.74(16) . . . . ?
N2 N3 C2 C7 60.8(2) . . . . ?
Co N3 C2 C7 -177.64(15) . . . . ?
N2 N3 C2 C3 -176.38(17) . . . . ?
Co N3 C2 C3 -54.8(2) . . . . ?
N3 C2 C3 C4 69.2(3) . . . . ?
C7 C2 C3 C4 -167.80(19) . . . . ?
N5 N4 C4 C8 -50.7(3) . . . . ?
Co N4 C4 C8 -173.33(16) . . . . ?
N5 N4 C4 C3 -174.07(18) . . . . ?
Co N4 C4 C3 63.3(2) . . . . ?
C2 C3 C4 N4 -73.7(2) . . . . ?
C2 C3 C4 C8 162.2(2) . . . . ?
Co N6 C5 N5 -6.4(3) . . . . ?
Co N6 C5 S2 175.64(14) . . . . ?
N4 N5 C5 N6 6.1(3) . . . . ?
N4 N5 C5 S2 -175.69(15) . . . . ?
C9 S2 C5 N6 -0.1(3) . . . . ?
C9 S2 C5 N5 -178.11(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H10 I1 0.88 2.85 3.6891(17) 161.0 2_665
N2 H20 I2 0.88 2.78 3.6368(19) 165.1 .
N3 H3 I2 1.00 2.86 3.7665(19) 150.5 2_566
N5 H50 I2 0.88 2.99 3.543(2) 122.4 1_554
N6 H60 I1 0.88 2.85 3.6798(18) 157.4 2_665
C2 H2 N7 1.00 2.60 3.457(3) 143.2 .
C3 H3B I1 0.99 3.01 3.866(2) 144.9 2_565
C6 H6A I1 0.98 3.22 3.872(2) 125.4 2_665
C6 H6C S1 0.98 3.00 3.617(2) 122.3 2_666
C7 H7A I2 0.98 3.17 4.056(2) 150.9 .
C7 H7C I2 0.98 3.19 4.048(2) 146.7 2_566
C8 H8A I1 0.98 3.07 3.958(3) 152.0 2_565
C8 H8B I2 0.98 3.33 4.158(2) 143.7 2_556
C11 H11A I1 0.98 3.27 4.203(3) 159.1 2_665

_refine_diff_density_max         1.426
_refine_diff_density_min         -1.553
_refine_diff_density_rms         0.127

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_ov_sasa1073tritf20june22_auto
_database_code_depnum_ccdc_archive 'CCDC 2313267'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-12-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '1,2,4-triazolium triflate'
_chemical_name_systematic        
'4H-1,2,4-triazol-4-ium trifluoromethanesulfonate'
_chemical_formula_moiety         'C F3 O3 S, C2 H4 N3'
_chemical_formula_sum            'C3 H4 F3 N3 O3 S'
_chemical_formula_weight         219.15
_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 0.0181 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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.28976(18)
_cell_length_b                   8.2702(3)
_cell_length_c                   8.6996(2)
_cell_angle_alpha                88.420(3)
_cell_angle_beta                 88.373(3)
_cell_angle_gamma                88.468(3)
_cell_volume                     380.16(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      77.5130
_cell_measurement_theta_min      5.0270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.158
_diffrn_reflns_theta_min         5.088
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1522
_reflns_number_total             1616
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.082
_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)+(0.0700P)²+0.1756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.62886(8) 0.26099(5) 0.79607(5) 0.02053(18) Uani 1 1 d . . . . .
F1 F 0.3991(3) 0.2392(2) 0.53478(18) 0.0507(4) Uani 1 1 d . . . . .
F2 F 0.7681(3) 0.12249(18) 0.54131(16) 0.0486(4) Uani 1 1 d . . . . .
F3 F 0.7318(3) 0.38266(18) 0.52294(16) 0.0452(4) Uani 1 1 d . . . . .
O1 O 0.4668(3) 0.39950(16) 0.82961(17) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.5249(3) 0.10812(16) 0.84755(17) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.8908(3) 0.28083(17) 0.82940(17) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.6305(4) 0.2510(3) 0.5865(2) 0.0322(5) Uani 1 1 d . . . . .
N1 N -0.1569(3) 0.83712(19) 0.8408(2) 0.0243(4) Uani 1 1 d . . . . .
H1 H -0.287(5) 0.905(3) 0.851(3) 0.030(6) Uiso 1 1 d . . . . .
N2 N 0.0826(3) 0.6295(2) 0.82142(19) 0.0228(4) Uani 1 1 d . . . . .
H2 H 0.138(5) 0.540(4) 0.816(3) 0.032(7) Uiso 1 1 d . . . . .
N3 N 0.2409(3) 0.7574(2) 0.81165(19) 0.0244(4) Uani 1 1 d . . . . .
C1 C -0.1551(3) 0.6768(2) 0.8398(2) 0.0231(4) Uani 1 1 d . . . . .
H1A H -0.297531 0.609389 0.850402 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0878(4) 0.8827(2) 0.8234(2) 0.0233(4) Uani 1 1 d . . . . .
H2A H 0.140141 0.991750 0.820221 0.028 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 O1 1.4438(14) . ?
S1 O2 1.4468(14) . ?
S1 O3 1.4383(14) . ?
S1 C3 1.827(2) . ?
F1 C3 1.323(3) . ?
F2 C3 1.334(3) . ?
F3 C3 1.327(3) . ?
N1 H1 0.88(3) . ?
N1 C1 1.326(2) . ?
N1 C2 1.361(2) . ?
N2 H2 0.79(3) . ?
N2 N3 1.366(2) . ?
N2 C1 1.313(2) . ?
N3 C2 1.302(2) . ?
C1 H1A 0.9500 . ?
C2 H2A 0.9500 . ?

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
O1 S1 O2 113.87(8) . . ?
O1 S1 C3 104.18(10) . . ?
O2 S1 C3 103.66(9) . . ?
O3 S1 O1 114.53(8) . . ?
O3 S1 O2 115.14(8) . . ?
O3 S1 C3 103.50(10) . . ?
F1 C3 S1 111.61(16) . . ?
F1 C3 F2 108.45(18) . . ?
F1 C3 F3 108.23(18) . . ?
F2 C3 S1 109.84(15) . . ?
F3 C3 S1 110.30(14) . . ?
F3 C3 F2 108.33(18) . . ?
C1 N1 H1 128.8(17) . . ?
C1 N1 C2 106.97(16) . . ?
C2 N1 H1 124.3(17) . . ?
N3 N2 H2 120(2) . . ?
C1 N2 H2 128(2) . . ?
C1 N2 N3 111.91(16) . . ?
C2 N3 N2 103.46(15) . . ?
N1 C1 H1A 126.8 . . ?
N2 C1 N1 106.42(16) . . ?
N2 C1 H1A 126.8 . . ?
N1 C2 H2A 124.4 . . ?
N3 C2 N1 111.23(16) . . ?
N3 C2 H2A 124.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88(3) 1.93(3) 2.768(2) 159(2) 1_465 yes
N2 H2 O1 0.79(3) 2.07(3) 2.747(2) 143(3) . yes

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
O1 S1 C3 F1 -57.34(17) . . . . ?
O1 S1 C3 F2 -177.65(14) . . . . ?
O1 S1 C3 F3 63.01(17) . . . . ?
O2 S1 C3 F1 62.07(17) . . . . ?
O2 S1 C3 F2 -58.24(17) . . . . ?
O2 S1 C3 F3 -177.58(14) . . . . ?
O3 S1 C3 F1 -177.40(14) . . . . ?
O3 S1 C3 F2 62.29(17) . . . . ?
O3 S1 C3 F3 -57.05(17) . . . . ?
N2 N3 C2 N1 0.4(2) . . . . ?
N3 N2 C1 N1 0.7(2) . . . . ?
C1 N1 C2 N3 0.0(2) . . . . ?
C1 N2 N3 C2 -0.6(2) . . . . ?
C2 N1 C1 N2 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sasa107_imidazolium_triflate
_database_code_depnum_ccdc_archive 'CCDC 2313285'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Imidazolium triflate'
_chemical_formula_moiety         'C F3 O3 S, C3 H5 N2'
_chemical_formula_sum            'C4 H5 F3 N2 O3 S'
_chemical_formula_weight         218.16
_chemical_absolute_configuration ?
_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 0.0181 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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.11650(10)
_cell_length_b                   8.11650(10)
_cell_length_c                   24.8628(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1637.90(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.949
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             880
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.235
_diffrn_reflns_theta_min         5.734
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.562
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                1671
_reflns_number_total             1743
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.097
_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)+(0.0579P)²+1.9169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 0.51291(9) 0.52942(9) 0.60946(3) 0.0182(2) Uani 1 1 d . . . . .
F1 F 0.4285(5) 0.4446(6) 0.70620(11) 0.0867(15) Uani 1 1 d . . . . .
F2 F 0.4938(7) 0.2417(5) 0.65405(19) 0.0980(17) Uani 1 1 d . . . . .
F3 F 0.2657(5) 0.3613(6) 0.64574(18) 0.0869(15) Uani 1 1 d . . . . .
O1 O 0.4155(4) 0.6757(4) 0.61635(12) 0.0391(8) Uani 1 1 d . . . . .
O2 O 0.6809(3) 0.5455(4) 0.62536(12) 0.0362(7) Uani 1 1 d . . . . .
O3 O 0.4857(3) 0.4507(3) 0.55826(10) 0.0295(6) Uani 1 1 d . . . . .
C4 C 0.4249(7) 0.3858(6) 0.65736(18) 0.0429(12) Uani 1 1 d . . . . .
N1 N 0.4451(4) 0.8957(4) 0.70494(12) 0.0226(7) Uani 1 1 d . . . . .
H1 H 0.390(7) 0.860(7) 0.676(2) 0.041(15) Uiso 1 1 d . . . . .
N2 N 0.6409(4) 0.9765(4) 0.75632(13) 0.0242(7) Uani 1 1 d . . . . .
H2 H 0.739(8) 0.991(7) 0.770(2) 0.050(16) Uiso 1 1 d . . . . .
C1 C 0.6064(5) 0.8950(5) 0.71149(15) 0.0232(8) Uani 1 1 d . . . . .
H1A H 0.684341 0.844718 0.688156 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3738(4) 0.9816(5) 0.74647(14) 0.0244(8) Uani 1 1 d . . . . .
H2A H 0.259458 1.001641 0.751412 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4966(5) 1.0318(5) 0.77874(14) 0.0259(7) Uani 1 1 d . . . . .
H3 H 0.485672 1.093798 0.810959 0.031 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 O1 1.436(3) . ?
S1 O2 1.425(3) . ?
S1 O3 1.441(2) . ?
S1 C4 1.813(4) . ?
F1 C4 1.305(5) . ?
F2 C4 1.299(7) . ?
F3 C4 1.339(7) . ?
N1 H1 0.90(6) . ?
N1 C1 1.320(5) . ?
N1 C2 1.374(5) . ?
N2 H2 0.87(6) . ?
N2 C1 1.326(5) . ?
N2 C3 1.373(5) . ?
C1 H1A 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.343(5) . ?
C3 H3 0.9500 . ?

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
O1 S1 O3 112.81(16) . . ?
O1 S1 C4 103.7(2) . . ?
O2 S1 O1 114.7(2) . . ?
O2 S1 O3 115.59(17) . . ?
O2 S1 C4 104.7(2) . . ?
O3 S1 C4 103.58(19) . . ?
F1 C4 S1 111.6(3) . . ?
F1 C4 F3 106.1(4) . . ?
F2 C4 S1 111.6(3) . . ?
F2 C4 F1 112.2(5) . . ?
F2 C4 F3 105.5(5) . . ?
F3 C4 S1 109.5(4) . . ?
C1 N1 H1 126(4) . . ?
C1 N1 C2 109.1(3) . . ?
C2 N1 H1 124(4) . . ?
C1 N2 H2 126(4) . . ?
C1 N2 C3 108.9(3) . . ?
C3 N2 H2 126(4) . . ?
N1 C1 N2 108.1(3) . . ?
N1 C1 H1A 126.0 . . ?
N2 C1 H1A 126.0 . . ?
N1 C2 H2A 126.6 . . ?
C3 C2 N1 106.9(3) . . ?
C3 C2 H2A 126.6 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.0(3) . . ?
C2 C3 H3 126.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.90(6) 2.11(5) 2.846(4) 138(5) . yes

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
O1 S1 C4 F1 -57.4(5) . . . . ?
O1 S1 C4 F2 176.2(4) . . . . ?
O1 S1 C4 F3 59.8(4) . . . . ?
O2 S1 C4 F1 63.2(5) . . . . ?
O2 S1 C4 F2 -63.3(5) . . . . ?
O2 S1 C4 F3 -179.7(4) . . . . ?
O3 S1 C4 F1 -175.3(4) . . . . ?
O3 S1 C4 F2 58.2(5) . . . . ?
O3 S1 C4 F3 -58.2(4) . . . . ?
N1 C2 C3 N2 0.3(4) . . . . ?
C1 N1 C2 C3 -0.5(5) . . . . ?
C1 N2 C3 C2 0.1(4) . . . . ?
C2 N1 C1 N2 0.6(5) . . . . ?
C3 N2 C1 N1 -0.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ov_sasa1047_auto
_database_code_depnum_ccdc_archive 'CCDC 2313265'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '1,2,4-triazolium hydrogensulfate'
_chemical_name_systematic        '1H-1,2,4-triazol-1-ium hydrogen sulfate'
_chemical_formula_moiety         'H O4 S, C2 H4 N3'
_chemical_formula_sum            'C2 H5 N3 O4 S'
_chemical_formula_weight         167.15
_chemical_melting_point          370.15
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'
O O 0.0492 0.0322 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.50504(8)
_cell_length_b                   5.29352(7)
_cell_length_c                   16.91686(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.1450(10)
_cell_angle_gamma                90
_cell_volume                     582.408(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5210
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      79.9910
_cell_measurement_theta_min      5.1990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6348
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.246
_diffrn_reflns_theta_min         5.230
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1235
_reflns_number_total             1251
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.5903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.64135(5) 0.10314(7) 0.66163(2) 0.00998(14) Uani 1 1 d . . . . .
O1 O 0.84324(17) 0.0525(2) 0.69844(7) 0.0142(3) Uani 1 1 d . . . . .
O2 O 0.62819(18) 0.0200(2) 0.58013(6) 0.0147(3) Uani 1 1 d . . . . .
O3 O 0.47413(18) 0.0152(2) 0.70963(7) 0.0158(3) Uani 1 1 d . . . . .
O4 O 0.62310(18) 0.3983(2) 0.65524(7) 0.0141(3) Uani 1 1 d . . . . .
H4 H 0.632(5) 0.457(6) 0.7040(18) 0.045(8) Uiso 1 1 d . . . . .
N1 N 1.1647(2) 0.2872(3) 0.57361(8) 0.0148(3) Uani 1 1 d . . . . .
N2 N 1.1204(2) 0.4496(3) 0.63363(8) 0.0148(3) Uani 1 1 d . . . . .
H2 H 1.065(4) 0.400(5) 0.6764(17) 0.037(7) Uiso 1 1 d . . . . .
N3 N 1.2471(2) 0.6783(3) 0.54480(9) 0.0148(3) Uani 1 1 d . . . . .
H3 H 1.284(4) 0.802(5) 0.5173(16) 0.032(7) Uiso 1 1 d . . . . .
C1 C 1.2423(2) 0.4340(3) 0.52019(10) 0.0139(3) Uani 1 1 d . . . . .
H1 H 1.289547 0.377634 0.470426 0.017 Uiso 1 1 calc R U . . .
C2 C 1.1694(2) 0.6829(3) 0.61665(10) 0.0163(3) Uani 1 1 d . . . . .
H2A H 1.152700 0.827106 0.649339 0.020 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 O1 1.4668(12) . ?
S1 O2 1.4484(11) . ?
S1 O3 1.4473(11) . ?
S1 O4 1.5703(12) . ?
O4 H4 0.88(3) . ?
N1 N2 1.366(2) . ?
N1 C1 1.301(2) . ?
N2 H2 0.86(3) . ?
N2 C2 1.309(2) . ?
N3 H3 0.84(3) . ?
N3 C1 1.359(2) . ?
N3 C2 1.326(2) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9500 . ?

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
O1 S1 O4 106.07(7) . . ?
O2 S1 O1 112.57(7) . . ?
O2 S1 O4 103.53(7) . . ?
O3 S1 O1 112.31(7) . . ?
O3 S1 O2 113.92(7) . . ?
O3 S1 O4 107.58(7) . . ?
S1 O4 H4 106(2) . . ?
C1 N1 N2 103.35(14) . . ?
N1 N2 H2 122.4(19) . . ?
C2 N2 N1 112.01(14) . . ?
C2 N2 H2 125.6(19) . . ?
C1 N3 H3 125.2(18) . . ?
C2 N3 H3 127.7(18) . . ?
C2 N3 C1 106.98(15) . . ?
N1 C1 N3 111.24(15) . . ?
N1 C1 H1 124.4 . . ?
N3 C1 H1 124.4 . . ?
N2 C2 N3 106.41(15) . . ?
N2 C2 H2A 126.8 . . ?
N3 C2 H2A 126.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O1 0.88(3) 1.73(3) 2.6115(16) 176(3) 2_656 yes
N2 H2 O3 0.86(3) 2.04(3) 2.7558(18) 140(3) 2_656 yes
N3 H3 O2 0.84(3) 1.99(3) 2.7831(19) 156(2) 3_766 yes

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 N2 C2 N3 0.05(19) . . . . ?
N2 N1 C1 N3 -0.10(18) . . . . ?
C1 N1 N2 C2 0.03(18) . . . . ?
C1 N3 C2 N2 -0.11(18) . . . . ?
C2 N3 C1 N1 0.14(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ov_sasa1039_auto-copy
_database_code_depnum_ccdc_archive 'CCDC 2313264'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-12-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '1,2,4-triazolium benzensulfonate'
_chemical_name_systematic        '1H-1,2,4-triazol-1-ium benzenesulfonate'
_chemical_formula_moiety         'C6 H5 O3 S, C2 H4 N3'
_chemical_formula_sum            'C8 H9 N3 O3 S'
_chemical_formula_weight         227.24
_chemical_melting_point          417.15
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'
O O 0.0492 0.0322 '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'

_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                   5.31130(10)
_cell_length_b                   22.0575(4)
_cell_length_c                   8.18530(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.4580(10)
_cell_angle_gamma                90
_cell_volume                     958.06(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6520
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      79.1520
_cell_measurement_theta_min      5.7310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.727
_diffrn_reflns_theta_min         4.008
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1911
_reflns_number_total             2046
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2046
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.062
_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)+(0.0985P)²+1.2068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N3-H3 = N2-H2
 0.91 with sigma of 0.02
2. Restrained planarity
 C4", C5", C6", C7, C8
 with sigma of 0.05
 C4, C5, C6', C7", C8"
 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
Uiso(C6') = Uiso(C6) = Uiso(C6")
4. Others
 Fixed Sof: C4(0.25) H4(0.25) C4"(0.25) H4"(0.25) C4'(0.5) H4'(0.5) C5(0.25)
 H5(0.25) C5"(0.25) H5"(0.25) C5'(0.5) H5'(0.5) C6(0.5) H6(0.5) C6"(0.25)
 H6"(0.25) C6'(0.25) H6'(0.25) C7(0.25) H7(0.25) C7"(0.25) H7"(0.25) C7'(0.5)
 H7'(0.5) C8(0.25) H8(0.25) C8"(0.25) H8"(0.25) C8'(0.5) H8'(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C4"(H4"), C4'(H4'), C5(H5), C5"(H5"), C5'(H5'), C6(H6), C6"(H6"),
 C6'(H6'), C7(H7), C7"(H7"), C7'(H7'), C8(H8), C8"(H8"), C8'(H8'), C1(H1),
 C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.38667(10) 0.58421(3) 0.25580(6) 0.0182(2) Uani 1 1 d . . . . .
O1 O 0.5410(3) 0.56454(8) 0.3975(2) 0.0235(4) Uani 1 1 d . . . . .
O2 O 0.1202(3) 0.57268(8) 0.2715(2) 0.0223(4) Uani 1 1 d . . . . .
O3 O 0.4830(3) 0.56061(10) 0.1040(2) 0.0296(5) Uani 1 1 d . . . . .
C3 C 0.4188(6) 0.66387(14) 0.2471(4) 0.0424(8) Uani 1 1 d . . . . .
C4 C 0.688(3) 0.6862(7) 0.2485(16) 0.033(3) Uani 0.25 1 d . . P A -3
H4 H 0.829070 0.659667 0.249489 0.040 Uiso 0.25 1 calc R U P A -3
C4" C 0.514(3) 0.6904(6) 0.383(2) 0.043(3) Uani 0.25 1 d . . P A -2
H4" H 0.587180 0.667801 0.471332 0.052 Uiso 0.25 1 calc R U P A -2
C4' C 0.6279(13) 0.6950(3) 0.3147(11) 0.0263(13) Uani 0.5 1 d . . P A -1
H4' H 0.767960 0.672842 0.359338 0.032 Uiso 0.5 1 calc R U P A -1
C5 C 0.712(3) 0.7483(7) 0.2483(16) 0.045(4) Uani 0.25 1 d . . P A -3
H5 H 0.872671 0.767077 0.248843 0.054 Uiso 0.25 1 calc R U P A -3
C5" C 0.499(3) 0.7531(7) 0.386(2) 0.051(4) Uani 0.25 1 d . . P A -2
H5" H 0.549394 0.769571 0.489382 0.061 Uiso 0.25 1 calc R U P A -2
C5' C 0.6331(17) 0.7586(4) 0.3175(15) 0.058(3) Uani 0.5 1 d . . P A -1
H5' H 0.736738 0.780167 0.395003 0.070 Uiso 0.5 1 calc R U P A -1
C6 C 0.4839(16) 0.7878(4) 0.2048(10) 0.0478(15) Uiso 0.5 1 d . . P A -1
H6 H 0.537908 0.824952 0.159285 0.057 Uiso 0.5 1 calc R U P A -1
C6" C 0.441(3) 0.7890(9) 0.295(2) 0.0478(15) Uiso 0.25 1 d . . P A -2
H6" H 0.431128 0.831303 0.315794 0.057 Uiso 0.25 1 calc R U P A -2
C6' C 0.430(4) 0.7926(11) 0.2470(16) 0.0478(15) Uiso 0.25 1 d . . P A -3
H6' H 0.438925 0.835647 0.246666 0.057 Uiso 0.25 1 calc R U P A -3
C7 C 0.370(2) 0.7531(6) 0.1058(15) 0.036(2) Uiso 0.25 1 d . . P A -2
H7 H 0.334216 0.775669 0.008644 0.043 Uiso 0.25 1 calc R U P A -2
C7" C 0.191(3) 0.7625(6) 0.2463(15) 0.039(3) Uiso 0.25 1 d . . P A -3
H7" H 0.041784 0.786014 0.249837 0.047 Uiso 0.25 1 calc R U P A -3
C7' C 0.2493(14) 0.7631(3) 0.1550(9) 0.0408(14) Uiso 0.5 1 d . . P A -1
H7' H 0.113761 0.787707 0.114603 0.049 Uiso 0.5 1 calc R U P A -1
C8 C 0.370(4) 0.6903(6) 0.1064(17) 0.046(4) Uani 0.25 1 d . . P A -2
H8 H 0.335676 0.667557 0.009396 0.055 Uiso 0.25 1 calc R U P A -2
C8" C 0.173(3) 0.6992(6) 0.2406(19) 0.033(3) Uani 0.25 1 d . . P A -3
H8" H 0.014464 0.679262 0.233021 0.039 Uiso 0.25 1 calc R U P A -3
C8' C 0.2268(13) 0.7006(3) 0.1684(10) 0.0267(13) Uani 0.5 1 d . . P A -1
H8' H 0.078968 0.681507 0.123742 0.032 Uiso 0.5 1 calc R U P A -1
N1 N 0.7723(4) 0.57509(10) 0.7525(2) 0.0217(5) Uani 1 1 d . . . . .
N2 N 0.9250(4) 0.56687(9) 0.6240(2) 0.0183(4) Uani 1 1 d D . . . .
H2 H 0.860(8) 0.5672(18) 0.521(3) 0.056(12) Uiso 1 1 d D . . . .
N3 N 1.1629(4) 0.55585(9) 0.8358(2) 0.0191(4) Uani 1 1 d D . . . .
H3 H 1.296(5) 0.5523(16) 0.906(4) 0.036(9) Uiso 1 1 d D . . . .
C1 C 0.9251(5) 0.56805(11) 0.8801(3) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.875982 0.571071 0.990044 0.024 Uiso 1 1 calc R U . . .
C2 C 1.1574(4) 0.55507(10) 0.6732(3) 0.0192(5) Uani 1 1 d . . . . .
H2A H 1.295332 0.547429 0.605969 0.023 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 O1 1.4572(17) . ?
S1 O2 1.4492(18) . ?
S1 O3 1.4600(18) . ?
S1 C3 1.767(3) . ?
C3 C4 1.513(15) . ?
C3 C4" 1.335(13) . ?
C3 C4' 1.400(6) . ?
C3 C8 1.307(12) . ?
C3 C8" 1.519(15) . ?
C3 C8' 1.434(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.38(2) . ?
C4" H4" 0.9500 . ?
C4" C5" 1.39(2) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.402(10) . ?
C5 H5 0.9500 . ?
C5 C6' 1.79(3) . ?
C5" H5" 0.9500 . ?
C5" C6" 1.12(2) . ?
C5' H5' 0.9500 . ?
C5' C6 1.353(13) . ?
C6 H6 0.9500 . ?
C6 C7' 1.404(11) . ?
C6" H6" 0.9500 . ?
C6" C7 1.76(2) . ?
C6' H6' 0.9500 . ?
C6' C7" 1.43(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(18) . ?
C7" H7" 0.9500 . ?
C7" C8" 1.40(2) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.388(9) . ?
C8 H8 0.9500 . ?
C8" H8" 0.9500 . ?
C8' H8' 0.9500 . ?
N1 N2 1.368(3) . ?
N1 C1 1.304(3) . ?
N2 H2 0.898(19) . ?
N2 C2 1.308(3) . ?
N3 H3 0.894(19) . ?
N3 C1 1.356(3) . ?
N3 C2 1.330(3) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9500 . ?

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
O1 S1 O3 111.44(11) . . ?
O1 S1 C3 106.03(12) . . ?
O2 S1 O1 113.30(11) . . ?
O2 S1 O3 113.09(11) . . ?
O2 S1 C3 105.92(14) . . ?
O3 S1 C3 106.39(15) . . ?
C4 C3 S1 114.6(7) . . ?
C4 C3 C8" 130.1(9) . . ?
C4" C3 S1 115.9(6) . . ?
C4' C3 S1 123.3(3) . . ?
C4' C3 C8' 115.9(4) . . ?
C8 C3 S1 117.6(6) . . ?
C8 C3 C4" 126.2(9) . . ?
C8" C3 S1 115.3(6) . . ?
C8' C3 S1 120.8(3) . . ?
C3 C4 H4 122.9 . . ?
C5 C4 C3 114.2(14) . . ?
C5 C4 H4 122.9 . . ?
C3 C4" H4" 122.2 . . ?
C3 C4" C5" 115.7(12) . . ?
C5" C4" H4" 122.2 . . ?
C3 C4' H4' 119.6 . . ?
C5' C4' C3 120.8(6) . . ?
C5' C4' H4' 119.6 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6' 118.0(14) . . ?
C6' C5 H5 121.0 . . ?
C4" C5" H5" 112.5 . . ?
C6" C5" C4" 135.0(18) . . ?
C6" C5" H5" 112.5 . . ?
C4' C5' H5' 121.5 . . ?
C6 C5' C4' 117.0(8) . . ?
C6 C5' H5' 121.5 . . ?
C5' C6 H6 120.0 . . ?
C5' C6 C7' 120.0(8) . . ?
C7' C6 H6 120.0 . . ?
C5" C6" H6" 126.0 . . ?
C5" C6" C7 107.9(17) . . ?
C7 C6" H6" 126.0 . . ?
C5 C6' H6' 120.4 . . ?
C7" C6' C5 119.2(16) . . ?
C7" C6' H6' 120.4 . . ?
C6" C7 H7 121.8 . . ?
C8 C7 C6" 116.5(12) . . ?
C8 C7 H7 121.8 . . ?
C6' C7" H7" 119.2 . . ?
C8" C7" C6' 121.5(15) . . ?
C8" C7" H7" 119.2 . . ?
C6 C7' H7' 121.9 . . ?
C8' C7' C6 116.2(7) . . ?
C8' C7' H7' 121.9 . . ?
C3 C8 C7 116.7(11) . . ?
C3 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
C3 C8" H8" 121.6 . . ?
C7" C8" C3 116.9(12) . . ?
C7" C8" H8" 121.6 . . ?
C3 C8' H8' 118.8 . . ?
C7' C8' C3 122.3(5) . . ?
C7' C8' H8' 118.8 . . ?
C1 N1 N2 103.37(19) . . ?
N1 N2 H2 120(3) . . ?
C2 N2 N1 111.85(19) . . ?
C2 N2 H2 128(3) . . ?
C1 N3 H3 125(2) . . ?
C2 N3 H3 128(2) . . ?
C2 N3 C1 106.81(19) . . ?
N1 C1 N3 111.4(2) . . ?
N1 C1 H1 124.3 . . ?
N3 C1 H1 124.3 . . ?
N2 C2 N3 106.6(2) . . ?
N2 C2 H2A 126.7 . . ?
N3 C2 H2A 126.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.898(19) 1.94(3) 2.697(3) 141(4) . yes
N3 H3 O3 0.894(19) 1.88(2) 2.720(3) 157(3) 1_656 yes

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
S1 C3 C4 C5 -177.5(6) . . . . ?
S1 C3 C4" C5" -169.3(9) . . . . ?
S1 C3 C4' C5' -174.1(7) . . . . ?
S1 C3 C8 C7 173.4(11) . . . . ?
S1 C3 C8" C7" 175.2(9) . . . . ?
S1 C3 C8' C7' -178.0(6) . . . . ?
O1 S1 C3 C4 53.2(6) . . . . ?
O1 S1 C3 C4" -16.0(10) . . . . ?
O1 S1 C3 C4' 24.7(6) . . . . ?
O1 S1 C3 C8 158.1(11) . . . . ?
O1 S1 C3 C8" -126.4(7) . . . . ?
O1 S1 C3 C8' -155.2(5) . . . . ?
O2 S1 C3 C4 173.8(6) . . . . ?
O2 S1 C3 C4" 104.7(10) . . . . ?
O2 S1 C3 C4' 145.4(5) . . . . ?
O2 S1 C3 C8 -81.3(11) . . . . ?
O2 S1 C3 C8" -5.7(7) . . . . ?
O2 S1 C3 C8' -34.6(5) . . . . ?
O3 S1 C3 C4 -65.6(6) . . . . ?
O3 S1 C3 C4" -134.7(10) . . . . ?
O3 S1 C3 C4' -94.0(6) . . . . ?
O3 S1 C3 C8 39.3(11) . . . . ?
O3 S1 C3 C8" 114.9(7) . . . . ?
O3 S1 C3 C8' 86.0(5) . . . . ?
C3 C4 C5 C6' 0.2(8) . . . . ?
C3 C4" C5" C6" -7.3(15) . . . . ?
C3 C4' C5' C6 -23.8(14) . . . . ?
C4 C3 C8" C7" -4.3(18) . . . . ?
C4 C5 C6' C7" 0.1(8) . . . . ?
C4" C3 C8 C7 -13(3) . . . . ?
C4" C5" C6" C7 -3.5(11) . . . . ?
C4' C3 C8' C7' 2.0(11) . . . . ?
C4' C5' C6 C7' 34.5(13) . . . . ?
C5 C6' C7" C8" -2.4(15) . . . . ?
C5" C6" C7 C8 6.9(17) . . . . ?
C5' C6 C7' C8' -26.4(12) . . . . ?
C6 C7' C8' C3 7.7(12) . . . . ?
C6" C7 C8 C3 1(2) . . . . ?
C6' C7" C8" C3 4.1(18) . . . . ?
C8 C3 C4" C5" 17(2) . . . . ?
C8" C3 C4 C5 2.0(15) . . . . ?
C8' C3 C4' C5' 5.9(12) . . . . ?
N1 N2 C2 N3 -0.6(3) . . . . ?
N2 N1 C1 N3 -0.1(3) . . . . ?
C1 N1 N2 C2 0.4(3) . . . . ?
C1 N3 C2 N2 0.5(3) . . . . ?
C2 N3 C1 N1 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ext2304
_database_code_depnum_ccdc_archive 'CCDC 2312262'
loop_
_audit_author_name
_audit_author_address
'Michael Ferguson'
;University of Alberta
Canada
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
'2-[(1S,2R)-2-(difluoromethyl)cyclohexyl]pyridinium chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 F2 N, Cl'
_chemical_formula_sum            'C12 H16 Cl F2 N'
_chemical_formula_weight         247.71

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

_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, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   7.9234(2)
_cell_length_b                   7.9234(2)
_cell_length_c                   19.6691(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1234.83(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      5.58
_cell_measurement_theta_max      73.39

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    2.753
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.677
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6092
_exptl_absorpt_correction_T_max  0.7959
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48552
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         5.583
_diffrn_reflns_theta_max         73.607
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2479
_reflns_number_gt                2477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.5169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.07(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2479
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.148
_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
Cl1 Cl 0.58837(9) 0.54801(8) 0.51143(4) 0.03046(18) Uani 1 1 d . . . . .
F1 F 0.3031(3) 0.1543(3) 0.55017(14) 0.0573(7) Uani 1 1 d . . . . .
F2 F 0.3019(3) 0.0648(5) 0.65346(13) 0.0690(8) Uani 1 1 d . . . . .
N1 N 0.5406(3) 0.2157(3) 0.44323(13) 0.0258(5) Uani 1 1 d . . . . .
H1 H 0.569(5) 0.298(6) 0.472(2) 0.037(10) Uiso 1 1 d . . . . .
C1 C 0.5630(4) 0.0514(4) 0.45824(16) 0.0239(6) Uani 1 1 d . . . . .
C2 C 0.5134(4) -0.0665(4) 0.41018(18) 0.0301(6) Uani 1 1 d . . . . .
H2 H 0.525233 -0.183624 0.419393 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4466(4) -0.0136(5) 0.34872(18) 0.0344(7) Uani 1 1 d . . . . .
H3 H 0.414835 -0.094485 0.315461 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4259(4) 0.1569(4) 0.33554(16) 0.0342(7) Uani 1 1 d . . . . .
H4 H 0.380015 0.194489 0.293568 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4734(4) 0.2697(4) 0.38458(16) 0.0288(6) Uani 1 1 d . . . . .
H5 H 0.458661 0.387152 0.377024 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6432(4) -0.0003(4) 0.52477(14) 0.0254(6) Uani 1 1 d . . . . .
H6 H 0.700471 -0.110189 0.515049 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5132(4) -0.0402(4) 0.58164(15) 0.0295(6) Uani 1 1 d . . . . .
H7 H 0.435375 -0.129632 0.564183 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6084(5) -0.1133(5) 0.64307(17) 0.0380(7) Uani 1 1 d . . . . .
H8A H 0.527761 -0.130425 0.680902 0.046 Uiso 1 1 calc R U . . .
H8B H 0.655303 -0.224859 0.630618 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7521(5) 0.0009(5) 0.66743(17) 0.0381(8) Uani 1 1 d . . . . .
H9A H 0.704395 0.107411 0.685440 0.046 Uiso 1 1 calc R U . . .
H9B H 0.813772 -0.055670 0.704794 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8742(4) 0.0409(4) 0.61003(17) 0.0331(7) Uani 1 1 d . . . . .
H10A H 0.931987 -0.064106 0.595751 0.040 Uiso 1 1 calc R U . . .
H10B H 0.961119 0.120583 0.626650 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7840(4) 0.1180(4) 0.54899(17) 0.0303(6) Uani 1 1 d . . . . .
H11A H 0.865771 0.136629 0.511672 0.036 Uiso 1 1 calc R U . . .
H11B H 0.735333 0.228592 0.561813 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4071(5) 0.1103(5) 0.6018(2) 0.0438(9) Uani 1 1 d . . . . .
H12 H 0.480066 0.207458 0.615516 0.053 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
F1 C12 1.354(5) . ?
F2 C12 1.363(5) . ?
N1 C5 1.340(4) . ?
N1 C1 1.347(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.512(4) . ?
C2 C3 1.385(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.368(5) . ?
C6 C11 1.533(4) . ?
C6 C7 1.553(4) . ?
C7 C12 1.512(5) . ?
C7 C8 1.537(5) . ?
C8 C9 1.531(5) . ?
C9 C10 1.520(5) . ?
C10 C11 1.525(4) . ?

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 N1 C1 123.3(3) . . ?
N1 C1 C2 117.7(3) . . ?
N1 C1 C6 120.5(3) . . ?
C2 C1 C6 121.8(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 120.3(3) . . ?
C5 C4 C3 118.2(3) . . ?
N1 C5 C4 120.5(3) . . ?
C1 C6 C11 114.2(2) . . ?
C1 C6 C7 113.6(2) . . ?
C11 C6 C7 112.5(2) . . ?
C12 C7 C8 111.3(3) . . ?
C12 C7 C6 113.4(3) . . ?
C8 C7 C6 108.5(3) . . ?
C9 C8 C7 112.8(3) . . ?
C10 C9 C8 111.3(3) . . ?
C9 C10 C11 111.7(3) . . ?
C10 C11 C6 109.9(3) . . ?
F1 C12 F2 104.8(3) . . ?
F1 C12 C7 110.2(3) . . ?
F2 C12 C7 109.1(3) . . ?

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 C1 C2 0.0(4) . . . . ?
C5 N1 C1 C6 178.6(3) . . . . ?
N1 C1 C2 C3 1.2(5) . . . . ?
C6 C1 C2 C3 -177.4(3) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C1 N1 C5 C4 -1.2(5) . . . . ?
C3 C4 C5 N1 1.1(5) . . . . ?
N1 C1 C6 C11 -36.1(4) . . . . ?
C2 C1 C6 C11 142.4(3) . . . . ?
N1 C1 C6 C7 94.7(3) . . . . ?
C2 C1 C6 C7 -86.7(3) . . . . ?
C1 C6 C7 C12 -63.2(4) . . . . ?
C11 C6 C7 C12 68.5(3) . . . . ?
C1 C6 C7 C8 172.6(2) . . . . ?
C11 C6 C7 C8 -55.8(3) . . . . ?
C12 C7 C8 C9 -71.3(4) . . . . ?
C6 C7 C8 C9 54.2(4) . . . . ?
C7 C8 C9 C10 -55.1(4) . . . . ?
C8 C9 C10 C11 55.3(4) . . . . ?
C9 C10 C11 C6 -56.2(4) . . . . ?
C1 C6 C11 C10 -171.3(3) . . . . ?
C7 C6 C11 C10 57.4(3) . . . . ?
C8 C7 C12 F1 -169.6(3) . . . . ?
C6 C7 C12 F1 67.8(4) . . . . ?
C8 C7 C12 F2 -55.0(4) . . . . ?
C6 C7 C12 F2 -177.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl1 0.89(5) 2.14(5) 2.979(3) 158(4) . yes

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol / diethyl ether'
####################################################################### 
# 
# 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_sasa1033_auto
_database_code_depnum_ccdc_archive 'CCDC 2313263'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-12-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Imidazolium chloride'
_chemical_name_systematic        '1H-imidazol-3-ium chloride'
_chemical_formula_moiety         '8(Cl), 8(C3 H5 N2)'
_chemical_formula_sum            'C24 H40 Cl8 N16'
_chemical_formula_weight         836.32
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.02464(13)
_cell_length_b                   16.29449(16)
_cell_length_c                   16.72956(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.8607(10)
_cell_angle_gamma                90
_cell_volume                     3898.32(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20708
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      79.4860
_cell_measurement_theta_min      4.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42260
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.151
_diffrn_reflns_theta_min         3.463
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -67.00   0.50    0.44    --  -50.49-135.00-167.00  110
  2  ω    -93.00 -18.00   0.50    0.44    --  -50.49 134.00  79.00  150
  3  ω   -122.00 -68.00   0.50    0.44    --  -50.49-134.00  12.00  108
  4  ω     39.00 100.00   0.50    0.44    --   50.49-134.00  12.00  122
  5  ω     40.00 100.00   0.50    0.44    --   50.49-135.00-167.00  120
  6  ω   -143.00 -89.00   0.50    1.75    --  -90.00-135.00-167.00  108
  7  ω     77.00 105.00   0.50    1.75    --  111.50-134.00  12.00   56
  8  ω    109.00 134.00   0.50    1.75    --  111.50 135.00-101.00   50
  9  ω    106.00 144.00   0.50    1.75    --  111.50 134.00  79.00   76
 10  ω     89.00 118.00   0.50    1.75    --  111.50-135.00-167.00   58
 11  ω   -122.00 -74.00   0.50    0.44    --  -50.49-125.00  30.00   96
 12  ω    -55.00  20.00   0.50    0.44    --  -50.49  19.00  60.00  150
 13  ω    -96.00 -44.00   0.50    0.44    --  -50.49   0.00   0.00  104
 14  ω   -138.00-113.00   0.50    1.75    --  -90.00   0.00  60.00   50
 15  ω    -67.00 -18.00   0.50    1.75    --  -90.00  30.00-150.00   98
 16  ω     47.00 105.00   0.50    1.75    --  111.50 -94.00-150.00  116
 17  ω     41.00  67.00   0.50    1.75    --  111.50 -77.00-180.00   52
 18  ω     40.00  65.00   0.50    1.75    --  111.50 -30.00-150.00   50
 19  ω     44.00  76.00   0.50    1.75    --  111.50 -45.00-180.00   64
 20  ω     71.00 118.00   0.50    1.75    --  111.50   0.00-180.00   94
 21  ω     41.00  68.00   0.50    1.75    --  111.50 -94.00-180.00   54
 22  ω     46.00  71.00   0.50    1.75    --  111.50 -45.00-120.00   50
 23  ω     84.00 117.00   0.50    1.75    --  111.50   0.00 -30.00   66
 24  ω     41.00 106.00   0.50    1.75    --  111.50 -95.00 164.46  130
 25  ω     91.00 123.00   0.50    1.75    --  111.50 -61.00 -30.00   64
 26  ω     75.00 105.00   0.50    1.75    --  111.50 -94.00-120.00   60
 27  ω     42.00  67.00   0.50    1.75    --  111.50 -94.00-120.00   50
 28  ω    139.00 165.00   0.50    1.75    --  111.50  30.00   0.00   52
 29  ω     41.00 107.00   0.50    1.75    --  111.50-104.00 -33.17  132
 30  ω     48.00  76.00   0.50    1.75    --  111.50 -94.00 -90.00   56
 31  ω     80.00 106.00   0.50    1.75    --  111.50 -94.00 -90.00   52
 32  ω     68.00 110.00   0.50    1.75    --  111.50   0.00 -60.00   84
 33  ω     41.00  73.00   0.50    1.75    --  111.50 -45.00-150.00   64
 34  ω     72.00  98.00   0.50    1.75    --  111.50 -94.00-180.00   52
 35  ω    109.00 135.00   0.50    1.75    --  111.50  30.00   0.00   52
 36  ω     46.00  72.00   0.50    1.75    --  111.50 -61.00 -30.00   52
 37  ω     41.00  66.00   0.50    1.75    --  111.50 -30.00 120.00   50
 38  ω     40.00  65.00   0.50    1.75    --  111.50 -30.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7362
_reflns_number_total             8330
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8330
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+2.8404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N46-H46 = N48-H48
 0.91 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N21(H21), N19(H19), N32(H32), N30(H30), N35(H35), N25(H25), N10(H10),
 C29(H29), C20(H20), C45(H45), C33(H33), C13(H13), C22(H22), C14(H14), C18(H18),
  C11(H11), C23(H23), C31(H31), C28(H28), C16(H16), C34(H34), C38(H38),
 C36(H36), C9(H9), C26(H26), C24(H24), C39(H39), C47(H47), C43(H43), C41(H41),
 C44(H44)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.81200(3) 0.00105(3) 0.85108(3) 0.02469(11) Uani 1 1 d . . . . .
Cl2 Cl 1.10446(3) 0.14780(3) 0.51909(3) 0.02586(11) Uani 1 1 d . . . . .
Cl3 Cl 0.54701(3) 0.51252(3) 0.82720(3) 0.02285(10) Uani 1 1 d . . . . .
Cl4 Cl 1.00740(3) 0.50548(3) 0.79547(3) 0.02490(11) Uani 1 1 d . . . . .
Cl5 Cl 0.63038(3) 0.16439(3) 0.52683(3) 0.02931(11) Uani 1 1 d . . . . .
Cl6 Cl 0.37333(3) 0.31484(3) 0.52150(3) 0.02797(11) Uani 1 1 d . . . . .
Cl7 Cl 0.85619(3) 0.30907(3) 0.52148(3) 0.02631(11) Uani 1 1 d . . . . .
Cl8 Cl 0.32950(3) -0.00851(3) 0.85120(3) 0.02962(11) Uani 1 1 d . . . . .
N12 N 0.83008(11) 0.25735(10) 0.68764(10) 0.0234(3) Uani 1 1 d . . . . .
N17 N 0.90509(11) 0.06481(10) 0.41919(11) 0.0249(3) Uani 1 1 d . . . . .
N21 N 0.57476(11) 0.34459(10) 0.75310(10) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.570010 0.396174 0.766837 0.031 Uiso 1 1 calc R U . . .
N19 N 0.59117(11) 0.23795(10) 0.68370(11) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.599088 0.206651 0.643550 0.031 Uiso 1 1 calc R U . . .
N27 N 0.33388(12) 0.24807(11) 0.67820(11) 0.0261(3) Uani 1 1 d . . . . .
N32 N 1.06275(11) 0.33441(10) 0.74365(10) 0.0250(3) Uani 1 1 d . . . . .
H32 H 1.058609 0.386537 0.755793 0.030 Uiso 1 1 calc R U . . .
N30 N 1.07505(11) 0.22511(11) 0.67664(10) 0.0257(3) Uani 1 1 d . . . . .
H30 H 1.080699 0.192238 0.636735 0.031 Uiso 1 1 calc R U . . .
N15 N 0.78183(12) 0.09799(11) 0.44999(11) 0.0270(4) Uani 1 1 d . . . . .
N37 N 0.67900(11) 0.08336(11) 0.94888(11) 0.0279(4) Uani 1 1 d . . . . .
N35 N 0.53502(12) 0.05253(11) 0.92391(11) 0.0294(4) Uani 1 1 d . . . . .
H35 H 0.482156 0.024902 0.908702 0.035 Uiso 1 1 calc R U . . .
N25 N 0.33019(12) 0.16718(11) 0.77848(11) 0.0310(4) Uani 1 1 d . . . . .
H25 H 0.334183 0.122654 0.809152 0.037 Uiso 1 1 calc R U . . .
N10 N 0.82618(11) 0.18241(11) 0.79164(12) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.826425 0.139018 0.823016 0.036 Uiso 1 1 calc R U . . .
N42 N 0.75155(13) 0.44950(13) 0.91944(13) 0.0362(4) Uani 1 1 d . . . . .
N40 N 0.88765(15) 0.45464(12) 0.90679(14) 0.0384(5) Uani 1 1 d . . . . .
N46 N 1.14105(13) 0.13632(12) 0.96414(12) 0.0360(4) Uani 1 1 d D . . . .
C29 C 1.06879(14) 0.20048(12) 0.75321(13) 0.0275(4) Uani 1 1 d . . . . .
H29 H 1.069521 0.145584 0.772516 0.033 Uiso 1 1 calc R U . . .
C20 C 0.58868(14) 0.31927(13) 0.68287(13) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.595711 0.353493 0.639230 0.032 Uiso 1 1 calc R U . . .
C45 C 1.17038(14) 0.07056(15) 0.93312(13) 0.0326(5) Uani 1 1 d . . . . .
H45 H 1.232289 0.061388 0.931616 0.039 Uiso 1 1 calc R U . . .
C33 C 1.06137(13) 0.26951(12) 0.79604(12) 0.0253(4) Uani 1 1 d . . . . .
H33 H 1.056248 0.272502 0.851171 0.030 Uiso 1 1 calc R U . . .
C13 C 0.82114(14) 0.30919(12) 0.74909(13) 0.0272(4) Uani 1 1 d . . . . .
H13 H 0.817538 0.367367 0.746127 0.033 Uiso 1 1 calc R U . . .
C22 C 0.56886(14) 0.27775(13) 0.80136(13) 0.0276(4) Uani 1 1 d . . . . .
H22 H 0.559294 0.278581 0.854912 0.033 Uiso 1 1 calc R U . . .
C14 C 0.75402(14) 0.04984(12) 0.37958(13) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.691705 0.034152 0.350024 0.034 Uiso 1 1 calc R U . . .
C18 C 0.83146(15) 0.02896(13) 0.36015(13) 0.0292(4) Uani 1 1 d . . . . .
H18 H 0.834453 -0.004225 0.314351 0.035 Uiso 1 1 calc R U . . .
C11 C 0.83324(13) 0.18101(13) 0.71479(14) 0.0289(4) Uani 1 1 d . . . . .
H11 H 0.839499 0.133280 0.684347 0.035 Uiso 1 1 calc R U . . .
C23 C 0.57936(14) 0.21046(13) 0.75756(13) 0.0274(4) Uani 1 1 d . . . . .
H23 H 0.578706 0.154904 0.774585 0.033 Uiso 1 1 calc R U . . .
C31 C 1.07124(14) 0.30617(13) 0.67243(13) 0.0275(4) Uani 1 1 d . . . . .
H31 H 1.074118 0.338529 0.626053 0.033 Uiso 1 1 calc R U . . .
C28 C 0.30791(14) 0.29435(13) 0.73572(13) 0.0288(4) Uani 1 1 d . . . . .
H28 H 0.294121 0.351378 0.731946 0.035 Uiso 1 1 calc R U . . .
N48 N 1.02430(15) 0.05558(17) 0.91989(15) 0.0544(7) Uani 1 1 d D . . . .
C16 C 0.87408(14) 0.10624(13) 0.47268(12) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.911251 0.136748 0.519417 0.032 Uiso 1 1 calc R U . . .
C34 C 0.54634(14) 0.13098(13) 0.95518(12) 0.0275(4) Uani 1 1 d . . . . .
H34 H 0.498987 0.165280 0.963824 0.033 Uiso 1 1 calc R U . . .
C38 C 0.63698(14) 0.15004(13) 0.97122(13) 0.0281(4) Uani 1 1 d . . . . .
H38 H 0.666263 0.200215 0.993766 0.034 Uiso 1 1 calc R U . . .
C36 C 0.61647(16) 0.02533(13) 0.92038(13) 0.0310(4) Uani 1 1 d . . . . .
H36 H 0.627943 -0.027083 0.900680 0.037 Uiso 1 1 calc R U . . .
C9 C 0.81842(15) 0.26216(14) 0.81469(13) 0.0310(4) Uani 1 1 d . . . . .
H9 H 0.812329 0.280673 0.866602 0.037 Uiso 1 1 calc R U . . .
C26 C 0.34693(14) 0.17122(13) 0.70527(14) 0.0300(4) Uani 1 1 d . . . . .
H26 H 0.365144 0.126718 0.677062 0.036 Uiso 1 1 calc R U . . .
C24 C 0.30565(14) 0.24362(14) 0.79861(13) 0.0315(4) Uani 1 1 d . . . . .
H24 H 0.290003 0.258099 0.847660 0.038 Uiso 1 1 calc R U . . .
C39 C 0.89477(15) 0.41245(15) 0.97845(14) 0.0357(5) Uani 1 1 d . . . . .
H39 H 0.950111 0.389787 1.016051 0.043 Uiso 1 1 calc R U . . .
C47 C 1.05085(15) 0.12656(16) 0.95610(13) 0.0360(5) Uani 1 1 d . . . . .
H47 H 1.012426 0.164412 0.973557 0.043 Uiso 1 1 calc R U . . .
C43 C 0.80864(16) 0.40900(15) 0.98582(14) 0.0351(5) Uani 1 1 d . . . . .
H43 H 0.791041 0.382967 1.029499 0.042 Uiso 1 1 calc R U . . .
C41 C 0.7993(2) 0.47658(14) 0.87204(15) 0.0443(6) Uani 1 1 d . . . . .
H41 H 0.775076 0.506775 0.821418 0.053 Uiso 1 1 calc R U . . .
C44 C 1.0990(2) 0.01977(15) 0.90455(15) 0.0488(7) Uani 1 1 d . . . . .
H44 H 1.099797 -0.031830 0.878352 0.059 Uiso 1 1 calc R U . . .
H27 H 0.344(2) 0.2658(18) 0.631(2) 0.048(8) Uiso 1 1 d . . . . .
H37 H 0.740(2) 0.0805(19) 0.952(2) 0.056(9) Uiso 1 1 d . . . . .
H17 H 0.963(2) 0.0608(19) 0.4219(19) 0.051(8) Uiso 1 1 d . . . . .
H12 H 0.8373(18) 0.2714(16) 0.6396(18) 0.035(7) Uiso 1 1 d . . . . .
H15 H 0.742(2) 0.120(2) 0.475(2) 0.062(9) Uiso 1 1 d . . . . .
H40 H 0.927(2) 0.466(2) 0.887(2) 0.062(10) Uiso 1 1 d . . . . .
H48 H 0.9655(17) 0.034(3) 0.906(3) 0.101(14) Uiso 1 1 d D . . . .
H46 H 1.178(2) 0.1821(17) 0.989(2) 0.088(13) Uiso 1 1 d D . . . .
H42 H 0.691(2) 0.459(2) 0.911(2) 0.064(10) Uiso 1 1 d . . . . .


_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
N12 C13 1.369(3) . ?
N12 C11 1.320(3) . ?
N12 H12 0.87(3) . ?
N17 C18 1.368(3) . ?
N17 C16 1.315(3) . ?
N17 H17 0.86(3) . ?
N21 H21 0.8800 . ?
N21 C20 1.321(3) . ?
N21 C22 1.375(3) . ?
N19 H19 0.8800 . ?
N19 C20 1.325(3) . ?
N19 C23 1.376(3) . ?
N27 C28 1.370(3) . ?
N27 C26 1.326(3) . ?
N27 H27 0.89(3) . ?
N32 H32 0.8800 . ?
N32 C33 1.378(3) . ?
N32 C31 1.319(3) . ?
N30 H30 0.8800 . ?
N30 C29 1.373(3) . ?
N30 C31 1.323(3) . ?
N15 C14 1.370(3) . ?
N15 C16 1.327(3) . ?
N15 H15 0.91(3) . ?
N37 C38 1.365(3) . ?
N37 C36 1.315(3) . ?
N37 H37 0.90(3) . ?
N35 H35 0.8800 . ?
N35 C34 1.372(3) . ?
N35 C36 1.320(3) . ?
N25 H25 0.8800 . ?
N25 C26 1.325(3) . ?
N25 C24 1.370(3) . ?
N10 H10 0.8800 . ?
N10 C11 1.322(3) . ?
N10 C9 1.371(3) . ?
N42 C43 1.349(3) . ?
N42 C41 1.298(3) . ?
N42 H42 0.90(3) . ?
N40 C39 1.357(3) . ?
N40 C41 1.325(4) . ?
N40 H40 0.79(3) . ?
N46 C45 1.324(3) . ?
N46 C47 1.330(3) . ?
N46 H46 0.945(19) . ?
C29 H29 0.9500 . ?
C29 C33 1.356(3) . ?
C20 H20 0.9500 . ?
C45 H45 0.9500 . ?
C45 C44 1.323(4) . ?
C33 H33 0.9500 . ?
C13 H13 0.9500 . ?
C13 C9 1.349(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.355(3) . ?
C14 H14 0.9500 . ?
C14 C18 1.344(3) . ?
C18 H18 0.9500 . ?
C11 H11 0.9500 . ?
C23 H23 0.9500 . ?
C31 H31 0.9500 . ?
C28 H28 0.9500 . ?
C28 C24 1.347(3) . ?
N48 C47 1.310(4) . ?
N48 C44 1.357(4) . ?
N48 H48 0.911(19) . ?
C16 H16 0.9500 . ?
C34 H34 0.9500 . ?
C34 C38 1.341(3) . ?
C38 H38 0.9500 . ?
C36 H36 0.9500 . ?
C9 H9 0.9500 . ?
C26 H26 0.9500 . ?
C24 H24 0.9500 . ?
C39 H39 0.9500 . ?
C39 C43 1.338(3) . ?
C47 H47 0.9500 . ?
C43 H43 0.9500 . ?
C41 H41 0.9500 . ?
C44 H44 0.9500 . ?

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
C13 N12 H12 126.7(18) . . ?
C11 N12 C13 108.94(18) . . ?
C11 N12 H12 124.1(18) . . ?
C18 N17 H17 126(2) . . ?
C16 N17 C18 109.51(17) . . ?
C16 N17 H17 124(2) . . ?
C20 N21 H21 125.3 . . ?
C20 N21 C22 109.34(17) . . ?
C22 N21 H21 125.3 . . ?
C20 N19 H19 125.6 . . ?
C20 N19 C23 108.89(17) . . ?
C23 N19 H19 125.6 . . ?
C28 N27 H27 127.0(19) . . ?
C26 N27 C28 108.92(18) . . ?
C26 N27 H27 124.0(19) . . ?
C33 N32 H32 125.3 . . ?
C31 N32 H32 125.3 . . ?
C31 N32 C33 109.35(17) . . ?
C29 N30 H30 125.5 . . ?
C31 N30 H30 125.5 . . ?
C31 N30 C29 109.09(17) . . ?
C14 N15 H15 124(2) . . ?
C16 N15 C14 108.69(17) . . ?
C16 N15 H15 128(2) . . ?
C38 N37 H37 125(2) . . ?
C36 N37 C38 109.43(17) . . ?
C36 N37 H37 126(2) . . ?
C34 N35 H35 125.6 . . ?
C36 N35 H35 125.6 . . ?
C36 N35 C34 108.77(17) . . ?
C26 N25 H25 125.6 . . ?
C26 N25 C24 108.89(18) . . ?
C24 N25 H25 125.6 . . ?
C11 N10 H10 125.4 . . ?
C11 N10 C9 109.21(18) . . ?
C9 N10 H10 125.4 . . ?
C43 N42 H42 125(2) . . ?
C41 N42 C43 109.8(2) . . ?
C41 N42 H42 125(2) . . ?
C39 N40 H40 129(3) . . ?
C41 N40 C39 108.7(2) . . ?
C41 N40 H40 122(3) . . ?
C45 N46 C47 108.4(2) . . ?
C45 N46 H46 126(2) . . ?
C47 N46 H46 126(2) . . ?
N30 C29 H29 126.5 . . ?
C33 C29 N30 106.91(17) . . ?
C33 C29 H29 126.5 . . ?
N21 C20 N19 108.34(18) . . ?
N21 C20 H20 125.8 . . ?
N19 C20 H20 125.8 . . ?
N46 C45 H45 125.7 . . ?
C44 C45 N46 108.5(2) . . ?
C44 C45 H45 125.7 . . ?
N32 C33 H33 126.8 . . ?
C29 C33 N32 106.30(17) . . ?
C29 C33 H33 126.8 . . ?
N12 C13 H13 126.4 . . ?
C9 C13 N12 107.15(18) . . ?
C9 C13 H13 126.4 . . ?
N21 C22 H22 126.7 . . ?
C23 C22 N21 106.52(18) . . ?
C23 C22 H22 126.7 . . ?
N15 C14 H14 126.4 . . ?
C18 C14 N15 107.14(17) . . ?
C18 C14 H14 126.4 . . ?
N17 C18 H18 126.7 . . ?
C14 C18 N17 106.59(18) . . ?
C14 C18 H18 126.7 . . ?
N12 C11 N10 108.24(18) . . ?
N12 C11 H11 125.9 . . ?
N10 C11 H11 125.9 . . ?
N19 C23 H23 126.5 . . ?
C22 C23 N19 106.90(18) . . ?
C22 C23 H23 126.5 . . ?
N32 C31 N30 108.35(18) . . ?
N32 C31 H31 125.8 . . ?
N30 C31 H31 125.8 . . ?
N27 C28 H28 126.5 . . ?
C24 C28 N27 106.97(19) . . ?
C24 C28 H28 126.5 . . ?
C47 N48 C44 108.4(2) . . ?
C47 N48 H48 126(3) . . ?
C44 N48 H48 126(3) . . ?
N17 C16 N15 108.08(18) . . ?
N17 C16 H16 126.0 . . ?
N15 C16 H16 126.0 . . ?
N35 C34 H34 126.5 . . ?
C38 C34 N35 106.95(17) . . ?
C38 C34 H34 126.5 . . ?
N37 C38 H38 126.6 . . ?
C34 C38 N37 106.70(18) . . ?
C34 C38 H38 126.6 . . ?
N37 C36 N35 108.14(18) . . ?
N37 C36 H36 125.9 . . ?
N35 C36 H36 125.9 . . ?
N10 C9 H9 126.8 . . ?
C13 C9 N10 106.45(18) . . ?
C13 C9 H9 126.8 . . ?
N27 C26 H26 125.9 . . ?
N25 C26 N27 108.20(19) . . ?
N25 C26 H26 125.9 . . ?
N25 C24 H24 126.5 . . ?
C28 C24 N25 107.02(19) . . ?
C28 C24 H24 126.5 . . ?
N40 C39 H39 126.7 . . ?
C43 C39 N40 106.6(2) . . ?
C43 C39 H39 126.7 . . ?
N46 C47 H47 126.0 . . ?
N48 C47 N46 108.0(2) . . ?
N48 C47 H47 126.0 . . ?
N42 C43 H43 126.5 . . ?
C39 C43 N42 107.0(2) . . ?
C39 C43 H43 126.5 . . ?
N42 C41 N40 107.9(2) . . ?
N42 C41 H41 126.1 . . ?
N40 C41 H41 126.1 . . ?
C45 C44 N48 106.8(2) . . ?
C45 C44 H44 126.6 . . ?
N48 C44 H44 126.6 . . ?

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
N12 C13 C9 N10 0.2(2) . . . . ?
N21 C22 C23 N19 -0.1(2) . . . . ?
N27 C28 C24 N25 -0.1(2) . . . . ?
N30 C29 C33 N32 0.4(2) . . . . ?
N15 C14 C18 N17 0.0(2) . . . . ?
N35 C34 C38 N37 0.5(2) . . . . ?
N40 C39 C43 N42 -0.6(3) . . . . ?
N46 C45 C44 N48 -0.8(3) . . . . ?
C29 N30 C31 N32 0.0(2) . . . . ?
C20 N21 C22 C23 -0.2(2) . . . . ?
C20 N19 C23 C22 0.5(2) . . . . ?
C45 N46 C47 N48 -0.4(2) . . . . ?
C33 N32 C31 N30 0.2(2) . . . . ?
C13 N12 C11 N10 0.3(2) . . . . ?
C22 N21 C20 N19 0.6(2) . . . . ?
C14 N15 C16 N17 -0.2(2) . . . . ?
C18 N17 C16 N15 0.2(2) . . . . ?
C11 N12 C13 C9 -0.3(2) . . . . ?
C11 N10 C9 C13 -0.1(2) . . . . ?
C23 N19 C20 N21 -0.6(2) . . . . ?
C31 N32 C33 C29 -0.4(2) . . . . ?
C31 N30 C29 C33 -0.2(2) . . . . ?
C28 N27 C26 N25 -0.1(2) . . . . ?
C16 N17 C18 C14 -0.1(2) . . . . ?
C16 N15 C14 C18 0.1(2) . . . . ?
C34 N35 C36 N37 0.5(2) . . . . ?
C38 N37 C36 N35 -0.2(2) . . . . ?
C36 N37 C38 C34 -0.2(2) . . . . ?
C36 N35 C34 C38 -0.6(2) . . . . ?
C9 N10 C11 N12 -0.1(2) . . . . ?
C26 N27 C28 C24 0.1(2) . . . . ?
C26 N25 C24 C28 0.0(2) . . . . ?
C24 N25 C26 N27 0.1(2) . . . . ?
C39 N40 C41 N42 -0.1(3) . . . . ?
C47 N46 C45 C44 0.8(2) . . . . ?
C47 N48 C44 C45 0.6(3) . . . . ?
C43 N42 C41 N40 -0.3(3) . . . . ?
C41 N42 C43 C39 0.5(3) . . . . ?
C41 N40 C39 C43 0.4(3) . . . . ?
C44 N48 C47 N46 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ov_sp_[im][etso3]_auto
_database_code_depnum_ccdc_archive 'CCDC 2313266'
loop_
_audit_author_name
_audit_author_address
'Saliha Saher'
;Monash University
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '1,2,4-triazolium ethanesulfonate'
_chemical_name_systematic        '1H-1,2,4-triazol-1-ium ethanesulfonate'
_chemical_formula_moiety         'C2 H5 O3 S, C2 H4 N3'
_chemical_formula_sum            'C4 H9 N3 O3 S'
_chemical_formula_weight         179.20
_chemical_melting_point          366.15
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'
O O 0.0492 0.0322 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.16580(10)
_cell_length_b                   11.1478(2)
_cell_length_c                   13.9104(2)
_cell_angle_alpha                81.6110(10)
_cell_angle_beta                 82.7060(10)
_cell_angle_gamma                77.9530(10)
_cell_volume                     771.17(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19106
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      79.4890
_cell_measurement_theta_min      4.0440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.510
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.191
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30549
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.916
_diffrn_reflns_theta_min         4.086
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2971
_reflns_number_total             3301
_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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5A), C6(H6A)
1.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.98389(5) 0.23896(2) 0.55504(2) 0.01417(13) Uani 1 1 d . . . . .
O1 O 1.08363(17) 0.20459(9) 0.65132(6) 0.0223(2) Uani 1 1 d . . . . .
O2 O 1.01988(17) 0.36301(8) 0.51319(6) 0.0182(2) Uani 1 1 d . . . . .
O3 O 0.71231(18) 0.22129(9) 0.55686(7) 0.0264(2) Uani 1 1 d . . . . .
C3 C 1.1908(3) 0.13697(12) 0.47791(11) 0.0254(3) Uani 1 1 d . . . . .
H3A H 1.378074 0.145161 0.477616 0.030 Uiso 1 1 calc R U . . .
H3B H 1.177307 0.050762 0.504034 0.030 Uiso 1 1 calc R U . . .
C4 C 1.1133(4) 0.16390(17) 0.37364(12) 0.0420(4) Uani 1 1 d . . . . .
H4A H 1.235155 0.107748 0.332724 0.063 Uiso 1 1 calc R U . . .
H4B H 1.124039 0.249562 0.347891 0.063 Uiso 1 1 calc R U . . .
H4C H 0.931011 0.151713 0.373272 0.063 Uiso 1 1 calc R U . . .
S2 S -0.01081(5) 0.73336(2) 0.04844(2) 0.01427(13) Uani 1 1 d . . . . .
O4 O 0.10013(18) 0.69016(9) 0.14188(6) 0.0232(2) Uani 1 1 d . . . . .
O5 O 0.01575(17) 0.86089(8) 0.01379(6) 0.0179(2) Uani 1 1 d . . . . .
O6 O -0.28172(17) 0.71383(9) 0.05156(7) 0.0255(2) Uani 1 1 d . . . . .
C7 C 0.1914(3) 0.64208(12) -0.03749(10) 0.0246(3) Uani 1 1 d . . . . .
H7A H 0.378226 0.651629 -0.039151 0.030 Uiso 1 1 calc R U . . .
H7B H 0.184231 0.553940 -0.016659 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1005(4) 0.67936(16) -0.13951(12) 0.0388(4) Uani 1 1 d . . . . .
H8A H 0.224789 0.632166 -0.186019 0.058 Uiso 1 1 calc R U . . .
H8B H 0.096070 0.767881 -0.158566 0.058 Uiso 1 1 calc R U . . .
H8C H -0.077809 0.662001 -0.139551 0.058 Uiso 1 1 calc R U . . .
N1 N 1.3435(2) -0.01230(11) 0.81447(8) 0.0214(2) Uani 1 1 d . . . . .
N2 N 1.4596(2) 0.07901(10) 0.76147(8) 0.0183(2) Uani 1 1 d . . . . .
H2 H 1.380(4) 0.1252(17) 0.7130(13) 0.034(5) Uiso 1 1 d . . . . .
N3 N 1.7078(2) 0.00248(10) 0.87359(8) 0.0191(2) Uani 1 1 d . . . . .
H3 H 1.827(4) -0.0132(17) 0.9106(14) 0.037(5) Uiso 1 1 d . . . . .
C1 C 1.5011(2) -0.05716(12) 0.88228(9) 0.0204(3) Uani 1 1 d . . . . .
H1 H 1.474714 -0.123244 0.931590 0.025 Uiso 1 1 calc R U . . .
C2 C 1.6765(2) 0.08840(12) 0.79711(9) 0.0206(3) Uani 1 1 d . . . . .
H2A H 1.789262 0.145627 0.772865 0.025 Uiso 1 1 calc R U . . .
N4 N 0.3464(2) 0.48605(11) 0.31247(8) 0.0213(3) Uani 1 1 d . . . . .
N5 N 0.4737(2) 0.57078(10) 0.25552(8) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.399(4) 0.6159(17) 0.2054(14) 0.040(5) Uiso 1 1 d . . . . .
N6 N 0.7152(2) 0.49742(10) 0.37018(8) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.833(4) 0.4832(17) 0.4087(14) 0.037(5) Uiso 1 1 d . . . . .
C5 C 0.5002(2) 0.44291(12) 0.38183(9) 0.0198(3) Uani 1 1 d . . . . .
H5A H 0.466148 0.381157 0.433928 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6935(2) 0.57808(12) 0.29021(9) 0.0204(3) Uani 1 1 d . . . . .
H6A H 0.813810 0.630892 0.263279 0.024 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 O1 1.4661(9) . ?
S1 O2 1.4596(9) . ?
S1 O3 1.4534(9) . ?
S1 C3 1.7730(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.525(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
S2 O4 1.4633(9) . ?
S2 O5 1.4619(9) . ?
S2 O6 1.4549(9) . ?
S2 C7 1.7746(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 N2 1.3649(15) . ?
N1 C1 1.2999(17) . ?
N2 H2 0.877(19) . ?
N2 C2 1.3102(16) . ?
N3 H3 0.83(2) . ?
N3 C1 1.3555(16) . ?
N3 C2 1.3256(17) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9500 . ?
N4 N5 1.3644(15) . ?
N4 C5 1.3013(16) . ?
N5 H5 0.88(2) . ?
N5 C6 1.3105(16) . ?
N6 H6 0.84(2) . ?
N6 C5 1.3550(16) . ?
N6 C6 1.3253(17) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?

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
O1 S1 C3 105.83(6) . . ?
O2 S1 O1 111.48(5) . . ?
O2 S1 C3 105.90(6) . . ?
O3 S1 O1 112.03(5) . . ?
O3 S1 O2 113.16(5) . . ?
O3 S1 C3 107.91(6) . . ?
S1 C3 H3A 109.3 . . ?
S1 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 S1 111.72(10) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 S2 C7 105.99(6) . . ?
O5 S2 O4 111.53(5) . . ?
O5 S2 C7 105.83(6) . . ?
O6 S2 O4 112.02(5) . . ?
O6 S2 O5 113.06(5) . . ?
O6 S2 C7 107.88(6) . . ?
S2 C7 H7A 109.3 . . ?
S2 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 S2 111.58(9) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 N2 103.58(10) . . ?
N1 N2 H2 119.3(12) . . ?
C2 N2 N1 111.64(10) . . ?
C2 N2 H2 128.9(12) . . ?
C1 N3 H3 124.7(13) . . ?
C2 N3 H3 128.4(13) . . ?
C2 N3 C1 106.88(11) . . ?
N1 C1 N3 111.29(11) . . ?
N1 C1 H1 124.4 . . ?
N3 C1 H1 124.4 . . ?
N2 C2 N3 106.61(11) . . ?
N2 C2 H2A 126.7 . . ?
N3 C2 H2A 126.7 . . ?
C5 N4 N5 103.55(10) . . ?
N4 N5 H5 119.7(12) . . ?
C6 N5 N4 111.65(10) . . ?
C6 N5 H5 128.5(12) . . ?
C5 N6 H6 124.8(13) . . ?
C6 N6 H6 128.3(13) . . ?
C6 N6 C5 106.91(10) . . ?
N4 C5 N6 111.27(11) . . ?
N4 C5 H5A 124.4 . . ?
N6 C5 H5A 124.4 . . ?
N5 C6 N6 106.62(11) . . ?
N5 C6 H6A 126.7 . . ?
N6 C6 H6A 126.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.877(19) 1.848(19) 2.6599(13) 153.2(17) . yes
N3 H3 O5 0.83(2) 2.04(2) 2.7689(13) 146.1(18) 1_746 yes
N5 H5 O4 0.88(2) 1.86(2) 2.6614(13) 151.0(17) . yes
N6 H6 O2 0.84(2) 2.02(2) 2.7607(13) 146.9(18) . yes

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
O1 S1 C3 C4 -178.79(11) . . . . ?
O2 S1 C3 C4 -60.34(12) . . . . ?
O3 S1 C3 C4 61.12(12) . . . . ?
O4 S2 C7 C8 -178.89(10) . . . . ?
O5 S2 C7 C8 -60.32(11) . . . . ?
O6 S2 C7 C8 60.96(12) . . . . ?
N1 N2 C2 N3 0.62(14) . . . . ?
N2 N1 C1 N3 0.18(14) . . . . ?
C1 N1 N2 C2 -0.50(15) . . . . ?
C1 N3 C2 N2 -0.48(14) . . . . ?
C2 N3 C1 N1 0.19(15) . . . . ?
N4 N5 C6 N6 0.50(14) . . . . ?
N5 N4 C5 N6 0.16(14) . . . . ?
C5 N4 N5 C6 -0.41(15) . . . . ?
C5 N6 C6 N5 -0.38(14) . . . . ?
C6 N6 C5 N4 0.13(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
