#------------------------------------------------------------------------------
#$Date: 2025-06-26 05:35:09 +0300 (Thu, 26 Jun 2025) $
#$Revision: 300219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/35/2023532.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023532
loop_
_publ_author_name
'Khojabaeva, Gulnaz'
'Torambetov, Batirbay'
'Gonnade, Rajesh G.'
'Uzakbergenova, Zamira'
'Rasulov, Abdusamat'
'Kadirova, Shakhnoza'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 bis[2-amino-5-(ethylsulfanyl)-1,3,4-thiadiazol-3-ium]
 bis(perchlorato-\kO)bis(picolinato-κ2 N,O)copper(II)
;
_journal_coeditor_code           TX2099
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025004992
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          '(C4 H8 N3 S2)2 [Cu (C6 H4 N1 O2)2 (Cl O4)2]'
_chemical_formula_moiety         '2(C4 H8 N3 S2 +), C12 H8 Cl2 Cu N8 O12 S4'
_chemical_formula_sum            'C20 H24 Cl2 Cu N8 O12 S4'
_chemical_formula_weight         828.13
_chemical_name_systematic
;Bis[2-amino-5-(ethylsulfanyl)-1,3,4-thiadiazol-3-ium]
bis(perchlorato-κO)bis(picolinato-κ²N,O)copper(II)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90.5220(10)
_cell_angle_beta                 98.8180(10)
_cell_angle_gamma                99.4780(10)
_cell_formula_units_Z            1
_cell_length_a                   6.3100(2)
_cell_length_b                   9.8179(2)
_cell_length_c                   13.3493(4)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.57
_cell_volume                     805.57(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28717
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.515
_diffrn_reflns_theta_min         2.566
_exptl_absorpt_coefficient_mu    1.174
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0347
_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)+(0.0476P)²+0.4379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2937
_reflns_number_total             3315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2099.cif
_cod_data_source_block           I
_cod_database_code               2023532
_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.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.933
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.500000 0.500000 0.000000 0.04229(13) Uani d 1 . .
S S1 -0.22380(12) 0.45846(8) 0.36426(6) 0.0638(2) Uani d 1 . .
S S2 -0.33608(16) 0.66980(10) 0.50029(7) 0.0859(3) Uani d 1 . .
Cl Cl1 0.55824(9) 0.20197(6) 0.16167(5) 0.05452(17) Uani d 1 . .
O O1 0.3708(2) 0.55987(16) 0.11468(13) 0.0472(4) Uani d 1 . .
O O2 0.4332(3) 0.72184(19) 0.23898(14) 0.0593(5) Uani d 1 . .
O O3 0.7223(4) 0.1767(2) 0.24227(18) 0.0776(6) Uani d 1 . .
O O4 0.4945(4) 0.0857(2) 0.0948(2) 0.0889(7) Uani d 1 . .
O O5 0.3737(4) 0.2359(3) 0.1990(2) 0.0906(7) Uani d 1 . .
O O6 0.6536(3) 0.3183(2) 0.10864(18) 0.0729(6) Uani d 1 . .
N N3 -0.0062(4) 0.7053(2) 0.39137(18) 0.0620(6) Uani d 1 . .
N N4 0.0747(4) 0.4205(3) 0.24606(18) 0.0657(6) Uani d 1 . .
H H4A 0.189153 0.449554 0.219641 0.079 Uiso calc 1 . .
H H4B 0.008829 0.336685 0.234388 0.079 Uiso calc 1 . .
N N1 0.7410(3) 0.65204(18) 0.05284(14) 0.0404(4) Uani d 1 . .
N N2 0.0878(3) 0.6329(2) 0.32667(16) 0.0558(5) Uani d 1 . .
H H2 0.200239 0.671103 0.301887 0.067 Uiso calc 1 . .
C C1 0.6886(3) 0.7281(2) 0.12672(16) 0.0400(4) Uani d 1 . .
C C2 0.8134(4) 0.8502(2) 0.16490(19) 0.0488(5) Uani d 1 . .
H H2A 0.772326 0.900672 0.215821 0.059 Uiso calc 1 . .
C C3 1.0027(4) 0.8970(3) 0.1258(2) 0.0541(6) Uani d 1 . .
H H3 1.089572 0.980444 0.149272 0.065 Uiso calc 1 . .
C C4 1.0600(4) 0.8186(3) 0.0522(2) 0.0521(6) Uani d 1 . .
H H4 1.188109 0.847296 0.026328 0.063 Uiso calc 1 . .
C C5 0.9263(3) 0.6967(2) 0.01687(18) 0.0471(5) Uani d 1 . .
H H5 0.965821 0.643983 -0.033273 0.057 Uiso calc 1 . .
C C6 0.4818(4) 0.6673(2) 0.16415(17) 0.0434(5) Uani d 1 . .
C C7 0.0006(4) 0.5040(3) 0.30408(18) 0.0503(5) Uani d 1 . .
C C8 -0.1698(4) 0.6261(3) 0.4178(2) 0.0572(6) Uani d 1 . .
C C9 -0.218(3) 0.8510(10) 0.5248(9) 0.089(3) Uani d 0.5 A 1
H H9B -0.063195 0.856523 0.546730 0.106 Uiso calc 0.5 A 1
H H9A -0.236435 0.897343 0.460917 0.106 Uiso calc 0.5 A 1
C C10 -0.299(2) 0.9253(9) 0.5957(8) 0.124(4) Uani d 0.5 A 1
H H10A -0.232139 1.020680 0.596917 0.186 Uiso calc 0.5 A 1
H H10B -0.265597 0.888642 0.661633 0.186 Uiso calc 0.5 A 1
H H10C -0.453377 0.917710 0.577437 0.186 Uiso calc 0.5 A 1
C C9A -0.297(3) 0.869(2) 0.4976(17) 0.180(9) Uani d 0.5 A 2
H H9AA -0.241457 0.906202 0.437962 0.215 Uiso calc 0.5 A 2
H H9AB -0.424855 0.906473 0.508259 0.215 Uiso calc 0.5 A 2
C C10A -0.135(3) 0.878(2) 0.5860(14) 0.169(6) Uani d 0.5 A 2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 2_665 . 180.0 ?
O1 Cu1 N1 . 2_665 97.01(7) ?
O1 Cu1 N1 . . 82.99(7) ?
O1 Cu1 N1 2_665 2_665 82.99(7) ?
O1 Cu1 N1 2_665 . 97.01(7) ?
N1 Cu1 N1 2_665 . 180.0 ?
C7 S1 C8 . . 87.51(12) ?
C8 S2 C9 . . 99.3(4) ?
C8 S2 C9A . . 103.8(7) ?
O3 Cl1 O6 . . 106.67(13) ?
O4 Cl1 O3 . . 110.34(15) ?
O4 Cl1 O5 . . 109.73(15) ?
O4 Cl1 O6 . . 109.64(16) ?
O5 Cl1 O3 . . 111.56(16) ?
O5 Cl1 O6 . . 108.82(14) ?
C6 O1 Cu1 . . 114.18(13) ?
C8 N3 N2 . . 109.2(2) ?
H4A N4 H4B . . 120.0 ?
C7 N4 H4A . . 120.0 ?
C7 N4 H4B . . 120.0 ?
C1 N1 Cu1 . . 111.77(13) ?
C5 N1 Cu1 . . 129.29(15) ?
C5 N1 C1 . . 118.30(19) ?
N3 N2 H2 . . 121.1 ?
C7 N2 N3 . . 117.7(2) ?
C7 N2 H2 . . 121.1 ?
N1 C1 C2 . . 122.9(2) ?
N1 C1 C6 . . 114.28(18) ?
C2 C1 C6 . . 122.8(2) ?
C1 C2 H2A . . 120.8 ?
C1 C2 C3 . . 118.4(2) ?
C3 C2 H2A . . 120.8 ?
C2 C3 H3 . . 120.4 ?
C4 C3 C2 . . 119.1(2) ?
C4 C3 H3 . . 120.4 ?
C3 C4 H4 . . 120.3 ?
C3 C4 C5 . . 119.5(2) ?
C5 C4 H4 . . 120.3 ?
N1 C5 C4 . . 121.8(2) ?
N1 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
O1 C6 C1 . . 115.90(19) ?
O2 C6 O1 . . 125.3(2) ?
O2 C6 C1 . . 118.8(2) ?
N4 C7 S1 . . 124.9(2) ?
N2 C7 S1 . . 110.12(18) ?
N2 C7 N4 . . 125.0(2) ?
S2 C8 S1 . . 118.33(16) ?
N3 C8 S1 . . 115.4(2) ?
N3 C8 S2 . . 126.3(2) ?
S2 C9 H9B . . 107.8 ?
S2 C9 H9A . . 107.8 ?
H9B C9 H9A . . 107.1 ?
C10 C9 S2 . . 118.0(9) ?
C10 C9 H9B . . 107.8 ?
C10 C9 H9A . . 107.8 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
S2 C9A H9AA . . 113.7 ?
S2 C9A H9AB . . 113.7 ?
H9AA C9A H9AB . . 110.9 ?
C10A C9A S2 . . 89.9(15) ?
C10A C9A H9AA . . 113.7 ?
C10A C9A H9AB . . 113.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 2_665 1.9693(15) ?
Cu1 O1 . 1.9693(15) ?
Cu1 N1 . 1.9854(17) ?
Cu1 N1 2_665 1.9854(17) ?
S1 C7 . 1.731(2) ?
S1 C8 . 1.748(3) ?
S2 C8 . 1.730(3) ?
S2 C9 . 1.818(10) ?
S2 C9A . 1.93(2) ?
Cl1 O3 . 1.428(2) ?
Cl1 O4 . 1.408(2) ?
Cl1 O5 . 1.421(2) ?
Cl1 O6 . 1.444(2) ?
O1 C6 . 1.281(3) ?
O2 C6 . 1.231(3) ?
N3 N2 . 1.374(3) ?
N3 C8 . 1.284(3) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
N4 C7 . 1.310(3) ?
N1 C1 . 1.344(3) ?
N1 C5 . 1.341(3) ?
N2 H2 . 0.8600 ?
N2 C7 . 1.307(3) ?
C1 C2 . 1.368(3) ?
C1 C6 . 1.503(3) ?
C2 H2A . 0.9300 ?
C2 C3 . 1.387(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.369(4) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.379(3) ?
C5 H5 . 0.9300 ?
C9 H9B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 C10 . 1.394(12) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C9A H9AA . 0.9700 ?
C9A H9AB . 0.9700 ?
C9A C10A . 1.43(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4A O1 . 0.86 2.14 2.940(3) 155.6
N4 H4A O5 . 0.86 2.59 2.951(3) 106.2
N4 H4B O3 1_455 0.86 2.21 2.981(3) 149.6
N4 H4B O6 1_455 0.86 2.57 3.005(3) 112.7
N2 H2 O2 . 0.86 1.81 2.656(3) 169.9
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O1 C6 O2 . . . . -179.2(2) ?
Cu1 O1 C6 C1 . . . . -0.1(2) ?
Cu1 N1 C1 C2 . . . . -170.09(18) ?
Cu1 N1 C1 C6 . . . . 10.1(2) ?
Cu1 N1 C5 C4 . . . . 168.70(18) ?
N3 N2 C7 S1 . . . . 0.7(3) ?
N3 N2 C7 N4 . . . . -178.0(3) ?
N1 C1 C2 C3 . . . . -0.3(4) ?
N1 C1 C6 O1 . . . . -6.9(3) ?
N1 C1 C6 O2 . . . . 172.3(2) ?
N2 N3 C8 S1 . . . . -1.0(3) ?
N2 N3 C8 S2 . . . . 178.7(2) ?
C1 N1 C5 C4 . . . . -1.3(3) ?
C1 C2 C3 C4 . . . . -1.2(4) ?
C2 C1 C6 O1 . . . . 173.3(2) ?
C2 C1 C6 O2 . . . . -7.5(3) ?
C2 C3 C4 C5 . . . . 1.5(4) ?
C3 C4 C5 N1 . . . . -0.2(4) ?
C5 N1 C1 C2 . . . . 1.6(3) ?
C5 N1 C1 C6 . . . . -178.19(19) ?
C6 C1 C2 C3 . . . . 179.4(2) ?
C7 S1 C8 S2 . . . . -178.53(18) ?
C7 S1 C8 N3 . . . . 1.2(2) ?
C8 S1 C7 N4 . . . . 177.7(3) ?
C8 S1 C7 N2 . . . . -1.0(2) ?
C8 S2 C9 C10 . . . . -175.6(12) ?
C8 N3 N2 C7 . . . . 0.2(3) ?
C9 S2 C8 S1 . . . . -176.8(5) ?
C9 S2 C8 N3 . . . . 3.5(6) ?
C9A S2 C8 S1 . . . . -158.3(6) ?
C9A S2 C8 N3 . . . . 22.0(7) ?
