#------------------------------------------------------------------------------
#$Date: 2024-07-13 04:57:40 +0300 (Sat, 13 Jul 2024) $
#$Revision: 293406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312554.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_2312554
loop_
_publ_author_name
'Qin, Qiaoqi'
'Liu, Jiamin'
'Luan, Xinyu'
'Xu, Jianqiao'
'Jiang, Long'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of two iHOFs based on
 CH...NC hydrogen bonding.
;
_journal_coeditor_code           JX3084
_journal_issue                   8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624005850
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '(C14 H10 N3)2 [Sb Br5] '
_chemical_formula_moiety         '2(C14 H10 N3 +), Br5 Sb 2-'
_chemical_formula_sum            'C28 H20 Br5 N6 Sb'
_chemical_formula_weight         959.80
_chemical_name_systematic
;
Bis[4-cyano-N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           87
_space_group_name_Hall           '-I 4'
_space_group_name_H-M_alt        'I 4/m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8054(12)
_cell_length_b                   23.8054(12)
_cell_length_c                   7.3222(4)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      59.362
_cell_measurement_theta_min      4.572
_cell_volume                     4149.5(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32444
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.343
_diffrn_reflns_theta_min         4.571
_diffrn_source_current           3.57
_diffrn_source_power             0.24947160000000
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.567
_exptl_absorpt_correction_T_max  0.0979
_exptl_absorpt_correction_T_min  0.0216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1820
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.403
_refine_diff_density_min         -1.753
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0730
_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)+(0.1320P)²+37.3690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2203
_reflns_number_gt                2327
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3084sup1.cif
_cod_data_source_block           iHOFII
_cod_original_cell_volume        4149.5(5)
_cod_original_formula_sum        'C28 H20 Br5 N6 Sb1'
_cod_database_code               2312554
_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   0.583
_shelx_estimated_absorpt_t_max   0.863
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
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
N N1 0.4835(2) 0.3428(3) 0.5000 0.0304(12) Uani d 1 . .
N N2 0.6685(4) 0.2200(4) 0.5000 0.058(2) Uani d 1 . .
N N3 0.2405(4) 0.1467(4) 0.5000 0.061(2) Uani d 1 . .
C C1 0.5073(2) 0.3297(2) 0.6587(7) 0.0358(11) Uani d 1 . .
H H1 0.4903 0.3414 0.7696 0.043 Uiso calc 1 . .
C C2 0.5568(2) 0.2991(3) 0.6635(8) 0.0394(12) Uani d 1 . .
H H2 0.5740 0.2893 0.7762 0.047 Uiso calc 1 . .
C C3 0.5802(3) 0.2833(3) 0.5000 0.0328(15) Uani d 1 . .
C C4 0.6308(3) 0.2486(4) 0.5000 0.0414(18) Uani d 1 . .
C C5 0.4262(3) 0.3677(3) 0.5000 0.0314(14) Uani d 1 . .
H H5A 0.4210 0.3915 0.3903 0.038 Uiso calc 0.5 . .
H H5B 0.4210 0.3915 0.6097 0.038 Uiso calc 0.5 . .
C C6 0.3839(3) 0.3206(3) 0.5000 0.0309(14) Uani d 1 . .
C C7 0.3658(2) 0.2980(2) 0.3359(7) 0.0362(11) Uani d 1 . .
H H7 0.3782 0.3138 0.2237 0.043 Uiso calc 1 . .
C C8 0.3294(2) 0.2522(2) 0.3351(8) 0.0402(12) Uani d 1 . .
H H8 0.3167 0.2366 0.2231 0.048 Uiso calc 1 . .
C C9 0.3120(3) 0.2298(3) 0.5000 0.0369(16) Uani d 1 . .
C C10 0.2730(4) 0.1835(4) 0.5000 0.046(2) Uani d 1 . .
Sb Sb1 0.47999(9) 0.11701(9) 0.2488(3) 0.0244(5) Uani d 0.125 . .
Br Br1 0.46859(15) 0.18576(12) 0.5000 0.0377(7) Uani d 0.25 . .
Br Br2 0.46397(16) 0.21197(16) 0.0000 0.0418(8) Uani d 0.25 . .
Br Br3 0.4986(2) 0.03254(14) 0.5000 0.0523(9) Uani d 0.25 . .
Br Br4 0.5934(5) 0.1320(6) 0.218(2) 0.068(3) Uani d 0.125 . .
Br Br4A 0.3678(5) 0.0819(8) 0.257(3) 0.113(7) Uani d 0.125 . .
Sb Sb2 0.5000 0.5000 0.05741(14) 0.0210(3) Uani d 0.5 . .
Br Br5 0.41593(3) 0.41812(3) 0.0000 0.0347(3) Uani d 0.9 A 1
Br Br6 0.5000 0.5000 -0.2922(2) 0.0239(4) Uani d 0.45 A 1
Br Br7 0.5000 0.5000 0.5000 0.0259(6) Uani d 0.45 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
Br Br -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb 0.0887 4.4824 '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
C1 N1 C1 10_556 . 121.7(6) ?
C1 N1 C5 10_556 . 119.0(3) ?
C1 N1 C5 . . 119.0(3) ?
N1 C1 H1 . . 119.7 ?
N1 C1 C2 . . 120.5(5) ?
C2 C1 H1 . . 119.7 ?
C1 C2 H2 . . 121.1 ?
C3 C2 C1 . . 117.8(5) ?
C3 C2 H2 . . 121.1 ?
C2 C3 C2 . 10_556 121.5(7) ?
C2 C3 C4 10_556 . 119.3(4) ?
C2 C3 C4 . . 119.3(4) ?
N2 C4 C3 . . 177.3(10) ?
N1 C5 H5A . . 110.0 ?
N1 C5 H5B . . 110.0 ?
N1 C5 C6 . . 108.3(6) ?
H5A C5 H5B . . 108.4 ?
C6 C5 H5A . . 110.0 ?
C6 C5 H5B . . 110.0 ?
C7 C6 C5 10_556 . 119.8(3) ?
C7 C6 C5 . . 119.8(3) ?
C7 C6 C7 10_556 . 120.3(7) ?
C6 C7 H7 . . 120.0 ?
C6 C7 C8 . . 120.1(5) ?
C8 C7 H7 . . 120.0 ?
C7 C8 H8 . . 120.5 ?
C9 C8 C7 . . 119.0(5) ?
C9 C8 H8 . . 120.5 ?
C8 C9 C8 10_556 . 121.6(7) ?
C8 C9 C10 . . 119.2(4) ?
C8 C9 C10 10_556 . 119.2(4) ?
N3 C10 C9 . . 178.7(11) ?
Br1 Sb1 Br2 . . 86.42(9) ?
Br1 Sb1 Br3 . . 90.25(10) ?
Br1 Sb1 Br4 . . 94.8(3) ?
Br1 Sb1 Br4 . 16_545 87.8(3) ?
Br1 Sb1 Br4A . . 94.4(4) ?
Br3 Sb1 Br2 . . 176.05(12) ?
Br3 Sb1 Br4A . . 85.5(4) ?
Br4 Sb1 Br2 . . 88.6(3) ?
Br4 Sb1 Br2 16_545 . 95.0(3) ?
Br4 Sb1 Br3 . . 89.6(3) ?
Br4 Sb1 Br3 16_545 . 87.0(3) ?
Br4 Sb1 Br4 . 16_545 175.6(4) ?
Br4 Sb1 Br4A . . 169.5(5) ?
Br4 Sb1 Br4A 16_545 . 6.8(5) ?
Br4A Sb1 Br1 15 . 91.3(4) ?
Br4A Sb1 Br2 . . 96.8(4) ?
Br4A Sb1 Br2 15 . 90.3(5) ?
Br4A Sb1 Br3 15 . 87.7(5) ?
Br4A Sb1 Br4 15 16_545 174.6(7) ?
Br4A Sb1 Br4 15 . 4.0(7) ?
Br4A Sb1 Br4A 15 . 171.1(5) ?
Sb1 Br1 Sb1 10_556 . 95.89(15) ?
Sb1 Br2 Sb1 10 . 76.95(12) ?
Sb1 Br3 Sb1 . 10_556 83.54(13) ?
Br3 Br3 Sb1 9_656 10_556 137.27(10) ?
Br3 Br3 Sb1 9_656 . 137.27(10) ?
Sb1 Br4 Sb1 . 15 93.9(4) ?
Br4A Br4 Sb1 15 . 31(6) ?
Br4A Br4 Sb1 15 15 98(5) ?
Sb1 Br4A Sb1 16_545 . 98.8(5) ?
Br4 Br4A Sb1 16_545 . 76(5) ?
Br4 Br4A Sb1 16_545 16_545 145(6) ?
Sb2 Sb2 Br5 9_665 11_565 81.44(2) ?
Sb2 Sb2 Br5 9_665 3_655 81.44(2) ?
Sb2 Sb2 Br5 9_665 . 81.44(2) ?
Sb2 Sb2 Br5 9_665 9_665 81.44(2) ?
Sb2 Sb2 Br6 9_665 9_665 180.0 ?
Sb2 Sb2 Br6 9_665 . 0.0000(10) ?
Br5 Sb2 Br5 11_565 . 88.731(6) ?
Br5 Sb2 Br5 9_665 3_655 88.731(6) ?
Br5 Sb2 Br5 9_665 11_565 88.731(6) ?
Br5 Sb2 Br5 3_655 . 88.732(6) ?
Br5 Sb2 Br5 9_665 . 162.89(4) ?
Br5 Sb2 Br5 11_565 3_655 162.89(4) ?
Br6 Sb2 Br5 . 3_655 81.44(2) ?
Br6 Sb2 Br5 9_665 . 98.56(2) ?
Br6 Sb2 Br5 . 11_565 81.44(2) ?
Br6 Sb2 Br5 9_665 3_655 98.56(2) ?
Br6 Sb2 Br5 . . 81.44(2) ?
Br6 Sb2 Br5 9_665 11_565 98.56(2) ?
Br6 Sb2 Br5 . 9_665 81.44(2) ?
Br6 Sb2 Br5 9_665 9_665 98.56(2) ?
Br6 Sb2 Br6 9_665 . 180.0 ?
Sb2 Br5 Sb2 . 9_665 17.11(4) ?
Sb2 Br6 Sb2 9_665 . 0.0 ?
Br7 Br6 Sb2 1_554 . 180.0 ?
Br7 Br6 Sb2 1_554 9_665 180.0 ?
Br6 Br7 Br6 9_665 1_556 180.0 ?
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
N1 C1 10_556 1.330(6) ?
N1 C1 . 1.330(6) ?
N1 C5 . 1.488(9) ?
N2 C4 . 1.127(11) ?
N3 C10 . 1.169(12) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.386(8) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.372(7) ?
C3 C2 10_556 1.372(7) ?
C3 C4 . 1.461(10) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5 C6 . 1.507(10) ?
C6 C7 . 1.386(6) ?
C6 C7 10_556 1.386(6) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.394(7) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.383(7) ?
C9 C8 10_556 1.383(7) ?
C9 C10 . 1.442(11) ?
Sb1 Br1 . 2.477(3) ?
Sb1 Br2 . 2.928(4) ?
Sb1 Br3 . 2.761(3) ?
Sb1 Br4 16_545 2.736(15) ?
Sb1 Br4 . 2.733(11) ?
Sb1 Br4A 15 2.453(19) ?
Sb1 Br4A . 2.800(14) ?
Br1 Sb1 10_556 2.477(3) ?
Br2 Sb1 10 2.928(4) ?
Br3 Sb1 10_556 2.761(3) ?
Br3 Br3 9_656 1.550(7) ?
Br4 Sb1 15 2.736(15) ?
Br4 Br4A 15 0.33(3) ?
Br4A Sb1 16_545 2.454(19) ?
Br4A Br4 16_545 0.33(3) ?
Sb2 Sb2 9_665 0.841(2) ?
Sb2 Br5 11_565 2.8251(8) ?
Sb2 Br5 . 2.8251(8) ?
Sb2 Br5 9_665 2.8251(8) ?
Sb2 Br5 3_655 2.8251(8) ?
Sb2 Br6 . 2.560(2) ?
Sb2 Br6 9_665 1.719(2) ?
Br5 Sb2 9_665 2.8251(8) ?
Br6 Sb2 9_665 1.719(2) ?
Br6 Br7 1_554 1.5213(18) ?
Br7 Br6 9_665 1.5214(18) ?
Br7 Br6 1_556 1.5214(18) ?
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
_geom_hbond_publ_flag
C1 H1 Br5 1_556 0.95 3.05 3.924(4) 153.3 yes
C2 H2 N3 8_555 0.95 2.49 3.397(7) 160.0 yes
C5 H5A Br5 . 0.99 2.93 3.8568(19) 156.7 yes
C5 H5A Br6 2_665 0.99 3.27 3.910(5) 123.7 yes
C5 H5B Br5 ??? 0.99 2.93 3.8568(19) 156.7 yes
C5 H5B Br6 ??? 0.99 3.27 3.910(5) 123.7 yes
C7 H7 Br5 . 0.95 3.11 3.960(4) 149.3 yes
C8 H8 N2 7_544 0.95 2.46 3.371(6) 160.6 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.4(9) ?
N1 C5 C6 C7 . . . 10_556 88.2(6) ?
N1 C5 C6 C7 . . . . -88.2(6) ?
C1 N1 C1 C2 10_556 . . . -3.4(11) ?
C1 N1 C5 C6 10_556 . . . 87.1(5) ?
C1 N1 C5 C6 . . . . -87.1(5) ?
C1 C2 C3 C2 . . . 10_556 2.6(12) ?
C1 C2 C3 C4 . . . . -176.9(7) ?
C5 N1 C1 C2 . . . . 170.6(6) ?
C5 C6 C7 C8 . . . . 176.1(6) ?
C6 C7 C8 C9 . . . . -0.2(10) ?
C7 C6 C7 C8 10_556 . . . -0.2(11) ?
C7 C8 C9 C8 . . . 10_556 0.7(12) ?
C7 C8 C9 C10 . . . . 178.1(7) ?

_cod_database_fobs_code 2312554
