#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/51/2225156.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_2225156
loop_
_publ_author_name
'Zhu, Zhen'
'Wang, Feng-Qin'
'Zhao, Yong-Nan'
_publ_section_title
;
 4,4'-Bipyridine--3-nitrobenzoic acid (1/2)
;
_journal_coeditor_code           BG2325
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o546
_journal_paper_doi               10.1107/S1600536810003594
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H8 N2, 2C7 H5 N O4'
_chemical_formula_moiety         'C10 H8 N2, 2(C7 H5 N O4)'
_chemical_formula_sum            'C24 H18 N4 O8'
_chemical_formula_weight         490.42
_chemical_name_systematic
;
4,4'-Bipyridine--3-nitrobenzoic acid (1/2)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 112.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.489(7)
_cell_length_b                   6.7757(14)
_cell_length_c                   13.291(3)
_cell_measurement_reflns_used    2874
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      3.093
_cell_volume                     2208.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_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      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7177
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            purple--red
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1646
_reflns_number_total             1935
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bg2325.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2208.8(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2225156
_cod_database_fobs_code          2225156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.30213(4) 0.58310(15) 0.39895(8) 0.0316(3) Uani d . 1 . .
O O2 0.26214(4) 0.60692(13) 0.21797(8) 0.0238(3) Uani d D 1 . .
H H2 0.2955(4) 0.608(2) 0.2257(14) 0.036 Uiso d D 1 . .
O O3 0.01600(4) 0.66151(15) 0.13387(9) 0.0328(3) Uani d . 1 . .
O O4 0.06802(4) 0.65732(16) 0.04209(8) 0.0363(3) Uani d . 1 . .
N N1 0.06088(4) 0.64662(15) 0.12810(10) 0.0223(3) Uani d . 1 . .
N N2 0.13751(4) 0.10542(14) 0.27135(9) 0.0189(3) Uani d . 1 . .
C C1 0.26146(5) 0.59392(18) 0.31583(11) 0.0204(3) Uani d . 1 . .
C C2 0.20523(5) 0.59219(17) 0.31772(11) 0.0189(3) Uani d . 1 . .
C C3 0.19834(5) 0.56014(18) 0.41546(11) 0.0231(3) Uani d . 1 . .
H H3 0.2287 0.5420 0.4791 0.028 Uiso calc R 1 . .
C C4 0.14675(6) 0.55513(18) 0.41864(12) 0.0247(3) Uani d . 1 . .
H H4 0.1427 0.5334 0.4843 0.030 Uiso calc R 1 . .
C C5 0.10097(5) 0.58232(18) 0.32441(11) 0.0224(3) Uani d . 1 . .
H H5 0.0661 0.5781 0.3256 0.027 Uiso calc R 1 . .
C C6 0.10882(5) 0.61589(17) 0.22863(11) 0.0188(3) Uani d . 1 . .
C C7 0.15989(5) 0.62214(17) 0.22295(11) 0.0181(3) Uani d . 1 . .
H H7 0.1637 0.6458 0.1573 0.022 Uiso calc R 1 . .
C C8 0.09648(5) 0.14365(18) 0.17646(11) 0.0200(3) Uani d . 1 . .
H H8 0.1049 0.1696 0.1158 0.024 Uiso calc R 1 . .
C C9 0.04234(5) 0.14626(18) 0.16471(11) 0.0193(3) Uani d . 1 . .
H H9 0.0152 0.1758 0.0978 0.023 Uiso calc R 1 . .
C C10 0.02882(5) 0.10427(17) 0.25412(11) 0.0175(3) Uani d . 1 . .
C C11 0.07148(5) 0.06255(18) 0.35231(11) 0.0195(3) Uani d . 1 . .
H H11 0.0642 0.0326 0.4138 0.023 Uiso calc R 1 . .
C C12 0.12465(5) 0.06609(17) 0.35760(11) 0.0197(3) Uani d . 1 . .
H H12 0.1527 0.0400 0.4239 0.024 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
C1 O2 H2 . . 106.5(12) ?
O3 N1 O4 . . 123.21(12) ?
O3 N1 C6 . . 118.74(12) ?
O4 N1 C6 . . 118.05(10) ?
C12 N2 C8 . . 117.68(11) ?
O1 C1 O2 . . 124.35(13) ?
O1 C1 C2 . . 121.85(13) ?
O2 C1 C2 . . 113.79(12) ?
C7 C2 C3 . . 119.66(13) ?
C7 C2 C1 . . 120.54(12) ?
C3 C2 C1 . . 119.80(12) ?
C4 C3 C2 . . 120.68(13) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.38(13) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 117.93(12) ?
C6 C5 H5 . . 121.0 ?
C4 C5 H5 . . 121.0 ?
C7 C6 C5 . . 123.01(13) ?
C7 C6 N1 . . 118.22(12) ?
C5 C6 N1 . . 118.77(11) ?
C6 C7 C2 . . 118.33(13) ?
C6 C7 H7 . . 120.8 ?
C2 C7 H7 . . 120.8 ?
N2 C8 C9 . . 123.06(13) ?
N2 C8 H8 . . 118.5 ?
C9 C8 H8 . . 118.5 ?
C8 C9 C10 . . 119.38(12) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C9 C10 C11 . . 117.44(12) ?
C9 C10 C10 . 2 121.59(14) ?
C11 C10 C10 . 2 120.97(15) ?
C12 C11 C10 . . 119.56(13) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
N2 C12 C11 . . 122.87(12) ?
N2 C12 H12 . . 118.6 ?
C11 C12 H12 . . 118.6 ?
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
O1 C1 . 1.2197(17) ?
O2 C1 . 1.3106(17) ?
O2 H2 . 0.850(9) ?
O3 N1 . 1.2242(14) ?
O4 N1 . 1.2294(14) ?
N1 C6 . 1.4695(18) ?
N2 C12 . 1.3402(18) ?
N2 C8 . 1.3430(18) ?
C1 C2 . 1.4991(19) ?
C2 C7 . 1.388(2) ?
C2 C3 . 1.3954(19) ?
C3 C4 . 1.3835(19) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3839(19) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3838(18) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.3827(18) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.3938(19) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.3950(19) ?
C10 C10 2 1.489(2) ?
C11 C12 . 1.3836(18) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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
O2 H2 N2 4 0.850(10) 1.760(10) 2.608(2) 175(2)
C5 H5 O3 2 0.930 2.490 3.390(2) 162
C9 H9 O4 5_565 0.930 2.550 3.436(2) 159
C12 H12 O1 7_556 0.930 2.350 3.242(2) 160
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
O1 C1 C2 C7 . . . . 174.30(12) ?
O2 C1 C2 C7 . . . . -6.02(16) ?
O1 C1 C2 C3 . . . . -5.73(18) ?
O2 C1 C2 C3 . . . . 173.94(10) ?
C7 C2 C3 C4 . . . . 0.92(18) ?
C1 C2 C3 C4 . . . . -179.05(11) ?
C2 C3 C4 C5 . . . . -0.11(18) ?
C3 C4 C5 C6 . . . . -0.54(18) ?
C4 C5 C6 C7 . . . . 0.42(18) ?
C4 C5 C6 N1 . . . . -179.52(10) ?
O3 N1 C6 C7 . . . . -172.63(10) ?
O4 N1 C6 C7 . . . . 6.93(16) ?
O3 N1 C6 C5 . . . . 7.31(16) ?
O4 N1 C6 C5 . . . . -173.13(11) ?
C5 C6 C7 C2 . . . . 0.37(18) ?
N1 C6 C7 C2 . . . . -179.69(10) ?
C3 C2 C7 C6 . . . . -1.03(17) ?
C1 C2 C7 C6 . . . . 178.94(10) ?
C12 N2 C8 C9 . . . . 0.77(17) ?
N2 C8 C9 C10 . . . . -1.16(18) ?
C8 C9 C10 C11 . . . . 0.43(16) ?
C8 C9 C10 C10 . . . 2 -179.76(8) ?
C9 C10 C11 C12 . . . . 0.59(17) ?
C10 C10 C11 C12 2 . . . -179.22(8) ?
C8 N2 C12 C11 . . . . 0.33(17) ?
C10 C11 C12 N2 . . . . -1.01(18) ?
