#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:45:00 +0300 (Fri, 06 May 2016) $
#$Revision: 182635 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/47/7224724.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.
#
data_7224724
loop_
_publ_author_name
'Anioła, Michalina'
'Katrusiak, Andrzej'
_publ_section_title
;
 Pressure-preferred symmetric reactions of 4,4′-bipyridine
 hydrobromide
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3223
_journal_paper_doi               10.1039/C6CE00356G
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C12 H14 Br2 N2'
_chemical_formula_sum            'C12 H14 Br2 N2'
_chemical_formula_weight         346.07
_chemical_name_common            'N,N-dimethylbipyridinium dibromide'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-17 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.947(3)
_cell_length_b                   8.068(8)
_cell_length_c                   13.411(5)
_cell_measurement_pressure       350000
_cell_measurement_reflns_used    2131
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      3.05
_cell_volume                     640.0(8)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'Mercury 2008'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.218
_diffrn_measured_fraction_theta_max 0.218
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method
; 
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168; 
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2281
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2131
_diffrn_reflns_theta_full        27.23
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    6.308
_exptl_absorpt_correction_T_max  0.352
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.35(5) GPa
 (350000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     39
_refine_ls_number_reflns         313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0879
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1797P)²+1.5200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2298
_refine_ls_wR_factor_ref         0.2400
_reflns_number_gt                285
_reflns_number_total             313
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00356g2.cif
_cod_data_source_block           035
_cod_depositor_comments
'Adding full bibliography for 7224724--7224729.cif.'
_cod_original_cell_volume        640.0(7)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7224724
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.3234(3) 0.4189(5) 0.32436(12) 0.042(3) Uani 1 1 d .
N1 N 0.983(2) 0.233(4) 0.5694(10) 0.040(4) Uiso 1 1 d .
C2 C 0.863(3) 0.158(5) 0.6350(13) 0.041(5) Uiso 1 1 d .
H2 H 0.9219 0.1616 0.7019 0.049 Uiso 1 1 calc R
C3 C 0.674(3) 0.081(5) 0.6155(14) 0.043(5) Uiso 1 1 d .
H3 H 0.5850 0.0528 0.6659 0.052 Uiso 1 1 calc R
C4 C 0.608(2) 0.042(3) 0.5132(10) 0.019(3) Uiso 1 1 d .
C5 C 0.726(3) 0.116(4) 0.4449(13) 0.035(5) Uiso 1 1 d .
H5 H 0.6861 0.0944 0.3774 0.042 Uiso 1 1 calc R
C6 C 0.909(2) 0.225(5) 0.4715(11) 0.037(5) Uiso 1 1 d .
H6 H 0.9734 0.2884 0.4239 0.045 Uiso 1 1 calc R
C7 C 1.178(3) 0.358(5) 0.5981(13) 0.044(5) Uiso 1 1 d .
H7A H 1.2388 0.3953 0.5384 0.053 Uiso 1 1 calc R
H7B H 1.2947 0.3047 0.6414 0.053 Uiso 1 1 calc R
H7C H 1.1205 0.4511 0.6321 0.053 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.053(2) 0.025(12) 0.0475(17) -0.0041(13) 0.0081(13) -0.0090(12)
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'
Br Br -0.2901 2.4595 '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_3
C2 N1 C6 118.7(18) .
C2 N1 C7 124.6(15) .
C6 N1 C7 115.6(18) .
C3 C2 N1 126.9(17) .
C2 C3 C4 116.9(18) .
C5 C4 C3 116(2) .
C5 C4 C4 123.2(16) 3_656
C3 C4 C4 119.0(17) 3_656
C4 C5 C6 123.0(16) .
N1 C6 C5 116(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.33(3) .
N1 C6 1.34(2) .
N1 C7 1.56(4) .
C2 C3 1.28(3) .
C3 C4 1.42(2) .
C4 C5 1.35(3) .
C4 C4 1.46(4) 3_656
C5 C6 1.41(4) .
