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#$Date: 2023-05-05 14:23:02 +0300 (Fri, 05 May 2023) $
#$Revision: 283520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/90/1569035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
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data_1569035
loop_
_publ_author_name
'Sakhapov, Ilyas F.'
'Zagidullin, Almaz A.'
'Dobrynin, Alexey B.'
'Litvinov, Igor A.'
'Yakhvarov, Dmitry G.'
'Bondarenko, Mikhail A.'
'Novikov, Alexander S.'
'Fedin, Vladimir P.'
'Adonin, Sergey A.'
_publ_section_title
;
 Crystal Structures of
 3,3′,5,5′-Tetrabromo-4,4′-bipyridine and Co(II)
 Coordination Polymer Based Thereon
;
_journal_issue                   4
_journal_name_full               Crystals
_journal_page_first              704
_journal_paper_doi               10.3390/cryst13040704
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C10 H4 Br4 N2'
_chemical_formula_sum            'C10 H4 Br4 N2'
_chemical_formula_weight         471.79
_chemical_name_systematic        '3,5,3',5'- tetrabromo-[4,4']bipyridine'
_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           SHELXL-2018/3
_cell_angle_alpha                103.034(2)
_cell_angle_beta                 96.915(2)
_cell_angle_gamma                92.460(2)
_cell_formula_units_Z            4
_cell_length_a                   7.8725(4)
_cell_length_b                   10.9122(6)
_cell_length_c                   15.6053(8)
_cell_measurement_reflns_used    9113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.29
_cell_measurement_theta_min      2.59
_cell_volume                     1293.15(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            57634
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    12.421
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.1013
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.423
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.658
_refine_diff_density_min         -1.566
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         7528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0417
_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)+(0.0485P)²+3.4364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6176
_reflns_number_total             7528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           shelx
_cod_database_code               1569035
_shelx_shelxl_version_number     2018/3
_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'
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
C1A C 0.1348(5) 0.8259(4) 0.8335(3) 0.0147(7) Uani 1 1 d . . . . .
C1B C 0.2820(5) 0.2439(4) 0.6988(3) 0.0161(7) Uani 1 1 d . . . . .
C2A C 0.1269(5) 0.9498(4) 0.8820(3) 0.0192(8) Uani 1 1 d . . . . .
C2B C 0.3906(5) 0.2349(4) 0.7739(3) 0.0168(8) Uani 1 1 d . . . . .
C3A C 0.0116(6) 1.0283(4) 0.8524(3) 0.0237(9) Uani 1 1 d . . . . .
H3A H 0.008850 1.111375 0.887522 0.028 Uiso 1 1 calc R U . . .
C3B C 0.3392(6) 0.2719(4) 0.8573(3) 0.0209(8) Uani 1 1 d . . . . .
H3B H 0.415009 0.263721 0.907578 0.025 Uiso 1 1 calc R U . . .
N4A N -0.0954(5) 0.9930(4) 0.7773(3) 0.0242(8) Uani 1 1 d . . . . .
N4B N 0.1872(5) 0.3188(4) 0.8700(3) 0.0232(8) Uani 1 1 d . . . . .
C5A C -0.0921(5) 0.8744(5) 0.7310(3) 0.0231(9) Uani 1 1 d . . . . .
H5A H -0.169861 0.846310 0.677920 0.028 Uiso 1 1 calc R U . . .
C5B C 0.0812(6) 0.3278(4) 0.7982(3) 0.0238(9) Uani 1 1 d . . . . .
H5B H -0.026884 0.361214 0.805934 0.029 Uiso 1 1 calc R U . . .
C6A C 0.0195(5) 0.7902(4) 0.7566(3) 0.0186(8) Uani 1 1 d . . . . .
C6B C 0.1236(5) 0.2900(4) 0.7134(3) 0.0184(8) Uani 1 1 d . . . . .
C7A C 0.2624(5) 0.7419(4) 0.8617(3) 0.0137(7) Uani 1 1 d . . . . .
C7B C 0.3313(5) 0.2061(4) 0.6080(3) 0.0148(7) Uani 1 1 d . . . . .
C8A C 0.4208(5) 0.7317(4) 0.8299(3) 0.0156(7) Uani 1 1 d . . . . .
C8B C 0.4253(6) 0.2866(4) 0.5714(3) 0.0197(8) Uani 1 1 d . . . . .
C9A C 0.5393(5) 0.6554(4) 0.8590(3) 0.0200(8) Uani 1 1 d . . . . .
H9A H 0.646466 0.651477 0.836594 0.024 Uiso 1 1 calc R U . . .
C9B C 0.4653(6) 0.2491(4) 0.4860(3) 0.0211(9) Uani 1 1 d . . . . .
H9B H 0.529131 0.307064 0.462807 0.025 Uiso 1 1 calc R U . . .
N10A N 0.5097(5) 0.5870(4) 0.9171(2) 0.0216(7) Uani 1 1 d . . . . .
N10B N 0.4178(5) 0.1348(4) 0.4350(2) 0.0194(7) Uani 1 1 d . . . . .
C11A C 0.3587(6) 0.5925(4) 0.9469(3) 0.0186(8) Uani 1 1 d . . . . .
H11A H 0.335007 0.542695 0.987342 0.022 Uiso 1 1 calc R U . . .
C11B C 0.3264(5) 0.0548(4) 0.4683(3) 0.0172(8) Uani 1 1 d . . . . .
H11B H 0.289606 -0.026445 0.432042 0.021 Uiso 1 1 calc R U . . .
C12A C 0.2343(5) 0.6677(4) 0.9216(3) 0.0158(7) Uani 1 1 d . . . . .
C12B C 0.2832(5) 0.0861(4) 0.5541(3) 0.0145(7) Uani 1 1 d . . . . .
Br2A Br 0.27148(6) 1.01300(5) 0.98985(3) 0.02848(11) Uani 1 1 d . . . . .
Br2B Br 0.60569(5) 0.16518(4) 0.76520(3) 0.02030(10) Uani 1 1 d . . . . .
Br6A Br 0.00801(7) 0.62446(5) 0.68615(3) 0.03130(12) Uani 1 1 d . . . . .
Br6B Br -0.03959(6) 0.29927(5) 0.61581(3) 0.02662(11) Uani 1 1 d . . . . .
Br8A Br 0.47411(6) 0.82087(5) 0.74483(3) 0.02462(11) Uani 1 1 d . . . . .
Br8B Br 0.49412(7) 0.45347(4) 0.63642(3) 0.02966(12) Uani 1 1 d . . . . .
Br12 Br 0.02474(6) 0.66660(4) 0.96958(3) 0.02255(10) Uani 1 1 d . . . . .
Br13 Br 0.15949(5) -0.03315(4) 0.59671(3) 0.01921(10) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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'
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
C6A C1A C2A 115.1(4) . . ?
C6A C1A C7A 123.1(4) . . ?
C2A C1A C7A 121.8(4) . . ?
C6B C1B C2B 116.1(4) . . ?
C6B C1B C7B 121.7(4) . . ?
C2B C1B C7B 122.3(4) . . ?
C3A C2A C1A 120.8(4) . . ?
C3A C2A Br2A 118.4(4) . . ?
C1A C2A Br2A 120.8(3) . . ?
C3B C2B C1B 120.1(4) . . ?
C3B C2B Br2B 118.4(3) . . ?
C1B C2B Br2B 121.4(3) . . ?
N4A C3A C2A 123.1(4) . . ?
N4A C3A H3A 118.5 . . ?
C2A C3A H3A 118.5 . . ?
N4B C3B C2B 122.8(4) . . ?
N4B C3B H3B 118.6 . . ?
C2B C3B H3B 118.6 . . ?
C3A N4A C5A 116.9(4) . . ?
C5B N4B C3B 117.7(4) . . ?
N4A C5A C6A 123.2(4) . . ?
N4A C5A H5A 118.4 . . ?
C6A C5A H5A 118.4 . . ?
N4B C5B C6B 122.2(4) . . ?
N4B C5B H5B 118.9 . . ?
C6B C5B H5B 118.9 . . ?
C1A C6A C5A 120.8(4) . . ?
C1A C6A Br6A 120.3(3) . . ?
C5A C6A Br6A 118.9(3) . . ?
C5B C6B C1B 121.1(4) . . ?
C5B C6B Br6B 119.0(3) . . ?
C1B C6B Br6B 120.0(3) . . ?
C8A C7A C12A 115.1(4) . . ?
C8A C7A C1A 121.8(3) . . ?
C12A C7A C1A 123.1(3) . . ?
C8B C7B C12B 116.0(4) . . ?
C8B C7B C1B 122.7(4) . . ?
C12B C7B C1B 121.3(3) . . ?
C9A C8A C7A 120.8(4) . . ?
C9A C8A Br8A 119.1(3) . . ?
C7A C8A Br8A 120.1(3) . . ?
C9B C8B C7B 121.0(4) . . ?
C9B C8B Br8B 118.6(3) . . ?
C7B C8B Br8B 120.3(3) . . ?
N10A C9A C8A 122.7(4) . . ?
N10A C9A H9A 118.6 . . ?
C8A C9A H9A 118.6 . . ?
N10B C9B C8B 122.4(4) . . ?
N10B C9B H9B 118.8 . . ?
C8B C9B H9B 118.8 . . ?
C11A N10A C9A 117.8(4) . . ?
C9B N10B C11B 118.0(4) . . ?
N10A C11A C12A 122.8(4) . . ?
N10A C11A H11A 118.6 . . ?
C12A C11A H11A 118.6 . . ?
N10B C11B C12B 122.5(4) . . ?
N10B C11B H11B 118.8 . . ?
C12B C11B H11B 118.8 . . ?
C11A C12A C7A 120.8(4) . . ?
C11A C12A Br12 118.3(3) . . ?
C7A C12A Br12 121.0(3) . . ?
C11B C12B C7B 120.0(4) . . ?
C11B C12B Br13 119.8(3) . . ?
C7B C12B Br13 120.3(3) . . ?
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
C1A C6A 1.383(6) . ?
C1A C2A 1.400(6) . ?
C1A C7A 1.483(5) . ?
C1B C6B 1.389(6) . ?
C1B C2B 1.390(6) . ?
C1B C7B 1.488(5) . ?
C2A C3A 1.384(6) . ?
C2A Br2A 1.884(4) . ?
C2B C3B 1.387(6) . ?
C2B Br2B 1.893(4) . ?
C3A N4A 1.327(7) . ?
C3A H3A 0.9500 . ?
C3B N4B 1.341(6) . ?
C3B H3B 0.9500 . ?
N4A C5A 1.336(6) . ?
N4B C5B 1.339(6) . ?
C5A C6A 1.387(6) . ?
C5A H5A 0.9500 . ?
C5B C6B 1.381(6) . ?
C5B H5B 0.9500 . ?
C6A Br6A 1.885(4) . ?
C6B Br6B 1.895(4) . ?
C7A C8A 1.396(5) . ?
C7A C12A 1.398(5) . ?
C7B C8B 1.385(5) . ?
C7B C12B 1.395(6) . ?
C8A C9A 1.380(6) . ?
C8A Br8A 1.888(4) . ?
C8B C9B 1.381(6) . ?
C8B Br8B 1.894(4) . ?
C9A N10A 1.334(5) . ?
C9A H9A 0.9500 . ?
C9B N10B 1.330(6) . ?
C9B H9B 0.9500 . ?
N10A C11A 1.326(6) . ?
N10B C11B 1.338(5) . ?
C11A C12A 1.382(6) . ?
C11A H11A 0.9500 . ?
C11B C12B 1.392(5) . ?
C11B H11B 0.9500 . ?
C12A Br12 1.892(4) . ?
C12B Br13 1.877(4) . ?
