#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220642.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_2220642
loop_
_publ_author_name
'Soleimannejad, Janet'
'Aghabozorg, Hossein'
'Morsali, Ali'
'Hemmati, Foruzan'
'Manteghi, Faranak'
_publ_section_title
;
 4,4'-Bipyridinium bis(2-carboxypyridine-3-carboxylate)
;
_journal_coeditor_code           SU2083
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o153
_journal_paper_doi               10.1107/S1600536808042220
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H10 N2 2+, 2C7 H4 N O4 -'
_chemical_formula_moiety         'C10 H10 N2 2+, 2(C7 H4 N O4 -)'
_chemical_formula_sum            'C24 H18 N4 O8'
_chemical_formula_weight         490.42
_chemical_name_systematic
;
4,4'-Bipyridinium bis(2-carboxypyridine-3-carboxylate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.310(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6675(2)
_cell_length_b                   13.7755(5)
_cell_length_c                   11.5887(4)
_cell_measurement_reflns_used    7505
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.35
_cell_volume                     1021.57(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18931
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.4079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2053
_reflns_number_total             2327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2083.cif
_cod_data_source_block           I
_cod_original_cell_volume        1021.56(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220642
_cod_database_fobs_code          2220642
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.27652(15) 0.50895(8) 0.56149(9) 0.0150(2) Uani d . 1 . .
N N2 0.15565(15) 0.51345(8) 0.31494(9) 0.0165(2) Uani d . 1 . .
H H2A 0.1890 0.5153 0.3913 0.020 Uiso d R 1 . .
O O1 0.38783(15) 0.30360(6) 0.50820(8) 0.0223(2) Uani d . 1 . .
O O2 0.08964(13) 0.29549(6) 0.56245(7) 0.0182(2) Uani d . 1 . .
O O3 0.45903(15) 0.26665(6) 0.77965(8) 0.0227(2) Uani d . 1 . .
O O4 0.47246(15) 0.35410(6) 0.94390(8) 0.0224(2) Uani d . 1 . .
H H4A 0.5120 0.2999 0.9777 0.027 Uiso d R 1 . .
C C1 0.31214(17) 0.42864(8) 0.63036(10) 0.0135(2) Uani d . 1 . .
C C2 0.38515(17) 0.43413(8) 0.75593(10) 0.0137(2) Uani d . 1 . .
C C3 0.41707(18) 0.52530(9) 0.80969(11) 0.0155(3) Uani d . 1 . .
H H3 0.4647 0.5310 0.8947 0.019 Uiso calc R 1 . .
C C4 0.37892(18) 0.60781(9) 0.73843(11) 0.0166(3) Uani d . 1 . .
H H4 0.3994 0.6707 0.7735 0.020 Uiso calc R 1 . .
C C5 0.31027(18) 0.59644(9) 0.61490(11) 0.0161(3) Uani d . 1 . .
H H5 0.2860 0.6528 0.5658 0.019 Uiso calc R 1 . .
C C6 0.26464(18) 0.33299(9) 0.56194(10) 0.0151(3) Uani d . 1 . .
C C7 0.44097(18) 0.34292(8) 0.82870(10) 0.0148(2) Uani d . 1 . .
C C8 0.13421(18) 0.59568(9) 0.25032(11) 0.0177(3) Uani d . 1 . .
H H8 0.1612 0.6565 0.2904 0.021 Uiso calc R 1 . .
C C9 0.07338(19) 0.59273(9) 0.12624(11) 0.0170(3) Uani d . 1 . .
H H9 0.0595 0.6512 0.0812 0.020 Uiso calc R 1 . .
C C10 0.03217(17) 0.50302(9) 0.06698(10) 0.0148(3) Uani d . 1 . .
C C11 0.05390(19) 0.41949(9) 0.13730(11) 0.0180(3) Uani d . 1 . .
H H11 0.0250 0.3576 0.1002 0.022 Uiso calc R 1 . .
C C12 0.11771(19) 0.42708(9) 0.26137(11) 0.0187(3) Uani d . 1 . .
H H12 0.1347 0.3699 0.3090 0.022 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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
C5 N1 C1 . . 119.02(10) ?
C12 N2 C8 . . 121.10(10) ?
C12 N2 H2A . . 118.2 ?
C8 N2 H2A . . 120.7 ?
C7 O4 H4A . . 108.0 ?
N1 C1 C2 . . 121.58(10) ?
N1 C1 C6 . . 115.20(10) ?
C2 C1 C6 . . 123.21(10) ?
C3 C2 C1 . . 118.59(10) ?
C3 C2 C7 . . 121.43(10) ?
C1 C2 C7 . . 119.84(10) ?
C4 C3 C2 . . 119.61(11) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 118.40(11) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 122.79(11) ?
N1 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
O1 C6 O2 . . 127.57(11) ?
O1 C6 C1 . . 118.49(11) ?
O2 C6 C1 . . 113.81(10) ?
O3 C7 O4 . . 124.97(11) ?
O3 C7 C2 . . 120.13(10) ?
O4 C7 C2 . . 114.88(10) ?
N2 C8 C9 . . 120.66(11) ?
N2 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C10 . . 119.71(11) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C11 C10 C9 . . 117.85(11) ?
C11 C10 C10 . 3_565 120.96(13) ?
C9 C10 C10 . 3_565 121.19(13) ?
C12 C11 C10 . . 119.75(11) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
N2 C12 C11 . . 120.93(11) ?
N2 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
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 C5 . 1.3446(15) ?
N1 C1 . 1.3457(15) ?
N2 C12 . 1.3330(16) ?
N2 C8 . 1.3432(16) ?
N2 H2A . 0.8501 ?
O1 C6 . 1.2303(15) ?
O2 C6 . 1.2775(15) ?
O3 C7 . 1.2165(15) ?
O4 C7 . 1.3009(14) ?
O4 H4A . 0.8501 ?
C1 C2 . 1.4009(16) ?
C1 C6 . 1.5245(16) ?
C2 C3 . 1.3915(16) ?
C2 C7 . 1.5007(15) ?
C3 C4 . 1.3857(16) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3840(17) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C8 C9 . 1.3807(17) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.4030(17) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3938(17) ?
C10 C10 3_565 1.492(2) ?
C11 C12 . 1.3841(17) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
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
N2 H2A N1 . 0.85 1.90 2.7430(14) 174.9
O4 H4A O2 4_666 0.85 1.64 2.4782(12) 170.9
C3 H3 O4 3_667 0.95 2.40 3.2055(15) 143.0
C4 H4 O2 2_556 0.95 2.55 3.4324(15) 155.0
C9 H9 O1 2_555 0.95 2.41 3.3405(15) 166.0
C11 H11 O1 4_565 0.95 2.52 3.4610(15) 170.0
C12 H12 O3 4_565 0.95 2.19 2.9004(15) 131.0
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
C5 N1 C1 C2 . . . . -0.59(17) ?
C5 N1 C1 C6 . . . . 178.63(10) ?
N1 C1 C2 C3 . . . . 1.26(17) ?
C6 C1 C2 C3 . . . . -177.90(10) ?
N1 C1 C2 C7 . . . . -174.57(10) ?
C6 C1 C2 C7 . . . . 6.27(17) ?
C1 C2 C3 C4 . . . . -0.83(17) ?
C7 C2 C3 C4 . . . . 174.93(11) ?
C2 C3 C4 C5 . . . . -0.21(17) ?
C1 N1 C5 C4 . . . . -0.53(18) ?
C3 C4 C5 N1 . . . . 0.93(18) ?
N1 C1 C6 O1 . . . . 75.36(14) ?
C2 C1 C6 O1 . . . . -105.43(13) ?
N1 C1 C6 O2 . . . . -100.72(12) ?
C2 C1 C6 O2 . . . . 78.49(14) ?
C3 C2 C7 O3 . . . . -162.59(11) ?
C1 C2 C7 O3 . . . . 13.12(17) ?
C3 C2 C7 O4 . . . . 15.52(16) ?
C1 C2 C7 O4 . . . . -168.77(11) ?
C12 N2 C8 C9 . . . . -0.43(18) ?
N2 C8 C9 C10 . . . . 0.43(18) ?
C8 C9 C10 C11 . . . . 0.31(18) ?
C8 C9 C10 C10 . . . 3_565 -179.48(13) ?
C9 C10 C11 C12 . . . . -1.05(18) ?
C10 C10 C11 C12 3_565 . . . 178.75(13) ?
C8 N2 C12 C11 . . . . -0.34(18) ?
C10 C11 C12 N2 . . . . 1.09(19) ?
