#------------------------------------------------------------------------------
#$Date: 2022-05-21 05:15:43 +0300 (Sat, 21 May 2022) $
#$Revision: 275595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567009.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_1567009
loop_
_publ_author_name
'Schuster, Sara A.'
'Nesterov, Volodymyr V.'
'Smucker, Bradley W.'
_publ_section_title
;
 1,1'-Methylenebis(4,4'-bipyridin-1-ium) dibromide
;
_journal_coeditor_code           BX4020
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x220526
_journal_paper_doi               10.1107/S2414314622005260
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C21 H18 N4 2+, 2Br -'
_chemical_formula_moiety         'C21 H18 N4 2+, 2(Br -)'
_chemical_formula_sum            'C21 H18 Br2 N4'
_chemical_formula_weight         486.21
_chemical_name_systematic
;
1,1'-Methylenebis(4,4'-bipyridin-1-ium) dibromide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0776(2)
_cell_length_b                   48.2301(5)
_cell_length_c                   4.5424(2)
_cell_measurement_reflns_used    18629
_cell_measurement_temperature    219.9(4)
_cell_measurement_theta_max      78.7160
_cell_measurement_theta_min      3.6820
_cell_volume                     3960.45(18)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      219.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            21913
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.887
_diffrn_reflns_theta_min         3.666
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro (Rigaku OD, 2021)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.255
_refine_ls_abs_structure_details
;
Flack x determined using 895 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.015(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0076P)²+10.8403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                2118
_reflns_number_total             2127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bx4020sup1.cif
_cod_data_source_block           I
_cod_database_code               1567009
_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   0.816
_shelx_estimated_absorpt_t_max   0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Br Br1 0.65219(2) 0.46137(2) 0.25829(7) 0.04764(12) Uani d 1 . .
N N1 0.53731(13) 0.52084(5) 0.8226(6) 0.0304(6) Uani d 1 . .
N N2 0.71760(17) 0.62446(6) -0.0002(10) 0.0532(8) Uani d 1 . .
C C1 0.500000 0.500000 1.0054(12) 0.0327(8) Uani d 1 . .
H H1A 0.463945 0.509067 1.130882 0.039 Uiso calc 0.5 . .
H H1B 0.536051 0.490934 1.130908 0.039 Uiso calc 0.5 . .
C C2 0.49878(16) 0.54322(6) 0.7299(10) 0.0360(7) Uani d 1 . .
H H2 0.449003 0.545007 0.778057 0.043 Uiso calc 1 . .
C C3 0.53289(17) 0.56327(6) 0.5653(8) 0.0370(8) Uani d 1 . .
H H3 0.506094 0.578632 0.502375 0.044 Uiso calc 1 . .
C C4 0.60776(15) 0.56086(5) 0.4907(10) 0.0318(6) Uani d 1 . .
C C5 0.64502(17) 0.53725(7) 0.5872(8) 0.0383(8) Uani d 1 . .
H H5 0.694617 0.534836 0.539168 0.046 Uiso calc 1 . .
C C6 0.60952(15) 0.51762(6) 0.7513(10) 0.0365(6) Uani d 1 . .
H H6 0.635047 0.501967 0.814337 0.044 Uiso calc 1 . .
C C7 0.64574(17) 0.58273(6) 0.3206(8) 0.0353(8) Uani d 1 . .
C C8 0.71058(19) 0.57758(7) 0.1703(9) 0.0425(8) Uani d 1 . .
H H8 0.731788 0.560015 0.174291 0.051 Uiso calc 1 . .
C C9 0.7435(2) 0.59865(7) 0.0146(12) 0.0515(9) Uani d 1 . .
H H9 0.786861 0.594616 -0.087262 0.062 Uiso calc 1 . .
C C10 0.6558(2) 0.62938(8) 0.1498(11) 0.0561(12) Uani d 1 . .
H H10 0.637202 0.647358 0.148926 0.067 Uiso calc 1 . .
C C11 0.6175(2) 0.60960(7) 0.3062(11) 0.0492(10) Uani d 1 . .
H H11 0.573509 0.614083 0.400858 0.059 Uiso calc 1 . .
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'
Br Br -0.6763 1.2805 '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'
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
C2 N1 C1 . . 119.1(2) ?
C2 N1 C6 . . 120.9(3) ?
C6 N1 C1 . . 120.0(2) ?
C10 N2 C9 . . 115.9(3) ?
N1 C1 N1 . 2_665 111.1(4) ?
N1 C1 H1A . . 109.4 ?
N1 C1 H1A 2_665 . 109.4 ?
N1 C1 H1B . . 109.4 ?
N1 C1 H1B 2_665 . 109.4 ?
H1A C1 H1B . . 108.0 ?
N1 C2 H2 . . 119.9 ?
N1 C2 C3 . . 120.1(3) ?
C3 C2 H2 . . 119.9 ?
C2 C3 H3 . . 119.7 ?
C2 C3 C4 . . 120.6(3) ?
C4 C3 H3 . . 119.7 ?
C3 C4 C7 . . 121.1(3) ?
C5 C4 C3 . . 117.3(3) ?
C5 C4 C7 . . 121.6(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 C4 . . 120.7(3) ?
C6 C5 H5 . . 119.6 ?
N1 C6 C5 . . 120.3(3) ?
N1 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C8 C7 C4 . . 121.7(3) ?
C8 C7 C11 . . 117.1(3) ?
C11 C7 C4 . . 121.2(3) ?
C7 C8 H8 . . 120.3 ?
C9 C8 C7 . . 119.4(3) ?
C9 C8 H8 . . 120.3 ?
N2 C9 C8 . . 124.4(3) ?
N2 C9 H9 . . 117.8 ?
C8 C9 H9 . . 117.8 ?
N2 C10 H10 . . 117.9 ?
N2 C10 C11 . . 124.3(3) ?
C11 C10 H10 . . 117.9 ?
C7 C11 H11 . . 120.5 ?
C10 C11 C7 . . 119.0(3) ?
C10 C11 H11 . . 120.5 ?
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 . 1.468(4) ?
N1 C2 . 1.352(4) ?
N1 C6 . 1.354(4) ?
N2 C9 . 1.332(4) ?
N2 C10 . 1.330(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2 . 0.9300 ?
C2 C3 . 1.369(5) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.400(4) ?
C4 C5 . 1.394(4) ?
C4 C7 . 1.477(4) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.365(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(4) ?
C7 C11 . 1.394(4) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.374(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C10 C11 . 1.376(5) ?
C11 H11 . 0.9300 ?
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 C2 C3 C4 . . . . 0.1(6) ?
N2 C10 C11 C7 . . . . 2.5(8) ?
C1 N1 C2 C3 . . . . 178.4(4) ?
C1 N1 C6 C5 . . . . -178.5(4) ?
C2 N1 C1 N1 . . . 2_665 87.1(3) ?
C2 N1 C6 C5 . . . . 1.0(6) ?
C2 C3 C4 C5 . . . . 0.9(6) ?
C2 C3 C4 C7 . . . . -178.2(4) ?
C3 C4 C5 C6 . . . . -0.9(6) ?
C3 C4 C7 C8 . . . . -160.1(4) ?
C3 C4 C7 C11 . . . . 20.1(6) ?
C4 C5 C6 N1 . . . . 0.1(6) ?
C4 C7 C8 C9 . . . . 179.8(4) ?
C4 C7 C11 C10 . . . . 178.7(4) ?
C5 C4 C7 C8 . . . . 20.9(6) ?
C5 C4 C7 C11 . . . . -158.9(4) ?
C6 N1 C1 N1 . . . 2_665 -93.5(3) ?
C6 N1 C2 C3 . . . . -1.0(6) ?
C7 C4 C5 C6 . . . . 178.1(4) ?
C7 C8 C9 N2 . . . . 0.9(7) ?
C8 C7 C11 C10 . . . . -1.1(6) ?
C9 N2 C10 C11 . . . . -2.1(8) ?
C10 N2 C9 C8 . . . . 0.3(7) ?
C11 C7 C8 C9 . . . . -0.4(6) ?

_cod_database_fobs_code 1567009
