#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/26/2212677.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_2212677
loop_
_publ_author_name
'Cowan, John A.'
'Howard, Judith A. K.'
'Puschmann, Horst'
'Williams, Ian D.'
_publ_section_title
;
 Short N···O hydrogen bonds in the 1:1 adduct of
 4,4'-bipyridyl and oxalic acid
;
_journal_coeditor_code           SG2117
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1240
_journal_page_last               o1242
_journal_paper_doi               10.1107/S1600536807005156
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 N2 , C2 H2 O4'
_chemical_formula_moiety         'C10 H8 N2 , C2 H2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_name_common            '4,4-bipyridinium oxalate'
_chemical_name_systematic
;
4,4'-bipyridyl--oxalic acid (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                100.253(10)
_cell_angle_beta                 105.349(11)
_cell_angle_gamma                107.569(10)
_cell_formula_units_Z            3
_cell_length_a                   8.7365(18)
_cell_length_b                   9.9154(19)
_cell_length_c                   10.380(2)
_cell_measurement_reflns_used    874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.99
_cell_measurement_theta_min      10.11
_cell_volume                     793.5(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8434
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0699
_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)+(0.0821P)²+0.9233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1930
_reflns_number_gt                2523
_reflns_number_total             3601
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2117.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2212677
_cod_database_fobs_code          2212677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.0631(4) 0.9499(3) 0.1702(3) 0.0157(6) Uani d . 1
O O1 0.1464(3) 1.0696(2) 0.1636(2) 0.0204(5) Uani d . 1
O O2 -0.0932(3) 0.9108(2) 0.1751(2) 0.0195(5) Uani d . 1
H H1 -0.1252 0.9805 0.1745 0.080(18) Uiso calc R 1
C C2 0.1318(4) 0.8219(3) 0.1705(3) 0.0150(5) Uani d . 1
O O3 0.0336(3) 0.6941(2) 0.1412(2) 0.0247(5) Uani d . 1
O O4 0.2955(2) 0.8668(2) 0.2015(2) 0.0192(5) Uani d . 1
H H2 0.3248 0.7954 0.1933 0.10(2) Uiso calc R 1
N N1 0.4089(3) 0.6576(2) 0.1828(2) 0.0128(5) Uani d . 1
C C11 0.3087(4) 0.5142(3) 0.1246(3) 0.0148(6) Uani d . 1
H H11 0.1909 0.4881 0.0909 0.021(8) Uiso calc R 1
C C12 0.3763(3) 0.4040(3) 0.1134(3) 0.0136(5) Uani d . 1
H H12 0.3046 0.3057 0.0731 0.020(8) Uiso calc R 1
C C13 0.5547(3) 0.4431(3) 0.1638(3) 0.0112(5) Uani d . 1
C C14 0.6565(3) 0.5934(3) 0.2216(3) 0.0144(5) Uani d . 1
H H14 0.7748 0.6235 0.2536 0.022(8) Uiso calc R 1
C C15 0.5800(3) 0.6968(3) 0.2308(3) 0.0145(5) Uani d . 1
H H15 0.6485 0.7959 0.2712 0.014(7) Uiso calc R 1
N N2 0.7855(3) 0.1180(2) 0.1646(2) 0.0156(5) Uani d . 1
C C21 0.8754(4) 0.2565(3) 0.1681(3) 0.0178(6) Uani d . 1
H H21 0.9884 0.2805 0.1721 0.024(9) Uiso calc R 1
C C22 0.8046(4) 0.3642(3) 0.1659(3) 0.0163(6) Uani d . 1
H H22 0.8694 0.4587 0.1680 0.034(10) Uiso calc R 1
C C23 0.6351(3) 0.3295(3) 0.1604(3) 0.0130(5) Uani d . 1
C C24 0.5416(4) 0.1853(3) 0.1546(3) 0.0144(5) Uani d . 1
H H24 0.4277 0.1574 0.1485 0.023(9) Uiso calc R 1
C C25 0.6229(4) 0.0842(3) 0.1581(3) 0.0155(6) Uani d . 1
H H25 0.5613 -0.0113 0.1559 0.012(7) Uiso calc R 1
C C3 1.0356(3) 0.9366(3) 0.5023(3) 0.0142(5) Uani d . 1
O O5 0.9471(2) 0.8154(2) 0.5031(2) 0.0185(4) Uani d . 1
O O6 1.1925(2) 0.9765(2) 0.5046(2) 0.0192(5) Uani d . 1
H H3 1.2232 0.9060 0.5033 0.10(2) Uiso calc R 1
N N3 1.3099(3) 0.7691(2) 0.5027(2) 0.0155(5) Uani d . 1
C C31 1.2128(4) 0.6253(3) 0.4680(3) 0.0160(6) Uani d . 1
H H31 1.0951 0.5979 0.4446 0.013(7) Uiso calc R 1
C C32 1.2821(3) 0.5163(3) 0.4658(3) 0.0154(6) Uani d . 1
H H32 1.2116 0.4178 0.4415 0.030(9) Uiso calc R 1
C C33 1.4596(3) 0.5564(3) 0.5007(3) 0.0132(5) Uani d . 1
C C34 1.5585(3) 0.7073(3) 0.5373(3) 0.0143(5) Uani d . 1
H H34 1.6765 0.7387 0.5607 0.020(8) Uiso calc R 1
C C35 1.4788(4) 0.8091(3) 0.5382(3) 0.0161(6) Uani d . 1
H H35 1.5457 0.9089 0.5645 0.024(9) 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_3
_geom_angle
O1 C1 O2 . 125.6(3)
O1 C1 C2 . 122.3(3)
O2 C1 C2 . 112.1(2)
C1 O2 H1 . 109.5
O3 C2 O4 . 126.4(3)
O3 C2 C1 . 120.7(3)
O4 C2 C1 . 112.9(2)
C2 O4 H2 . 109.5
C11 N1 C15 . 119.5(2)
N1 C11 C12 . 121.9(3)
N1 C11 H11 . 119.0
C12 C11 H11 . 119.0
C11 C12 C13 . 119.2(2)
C11 C12 H12 . 120.4
C13 C12 H12 . 120.4
C14 C13 C12 . 117.8(2)
C14 C13 C23 . 120.4(2)
C12 C13 C23 . 121.8(2)
C15 C14 C13 . 119.7(3)
C15 C14 H14 . 120.1
C13 C14 H14 . 120.1
N1 C15 C14 . 121.8(2)
N1 C15 H15 . 119.1
C14 C15 H15 . 119.1
C25 N2 C21 . 118.6(2)
N2 C21 C22 . 122.1(3)
N2 C21 H21 . 119.0
C22 C21 H21 . 119.0
C21 C22 C23 . 119.5(2)
C21 C22 H22 . 120.3
C23 C22 H22 . 120.3
C24 C23 C22 . 118.3(2)
C24 C23 C13 . 120.1(2)
C22 C23 C13 . 121.7(2)
C25 C24 C23 . 118.5(3)
C25 C24 H24 . 120.8
C23 C24 H24 . 120.8
N2 C25 C24 . 123.1(2)
N2 C25 H25 . 118.4
C24 C25 H25 . 118.4
O5 C3 O6 . 126.3(2)
O5 C3 C3 2_776 121.0(3)
O6 C3 C3 2_776 112.7(3)
C3 O6 H3 . 109.5
C35 N3 C31 . 119.1(2)
N3 C31 C32 . 122.3(3)
N3 C31 H31 . 118.9
C32 C31 H31 . 118.9
C31 C32 C33 . 119.4(2)
C31 C32 H32 . 120.3
C33 C32 H32 . 120.3
C34 C33 C32 . 117.3(2)
C34 C33 C33 2_866 121.2(3)
C32 C33 C33 2_866 121.5(3)
C35 C34 C33 . 119.5(3)
C35 C34 H34 . 120.2
C33 C34 H34 . 120.2
N3 C35 C34 . 122.4(2)
N3 C35 H35 . 118.8
C34 C35 H35 . 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.215(3)
C1 O2 . 1.320(3)
C1 C2 . 1.559(4)
O2 H1 . 0.8200
C2 O3 . 1.226(3)
C2 O4 . 1.292(3)
O4 H2 . 0.8200
N1 C11 . 1.348(3)
N1 C15 . 1.349(3)
C11 C12 . 1.392(4)
C11 H11 . 0.9300
C12 C13 . 1.408(4)
C12 H12 . 0.9300
C13 C14 . 1.404(3)
C13 C23 . 1.497(4)
C14 C15 . 1.385(4)
C14 H14 . 0.9300
C15 H15 . 0.9300
N2 C25 . 1.337(4)
N2 C21 . 1.350(3)
C21 C22 . 1.386(4)
C21 H21 . 0.9300
C22 C23 . 1.399(4)
C22 H22 . 0.9300
C23 C24 . 1.398(4)
C24 C25 . 1.393(4)
C24 H24 . 0.9300
C25 H25 . 0.9300
C3 O5 . 1.220(3)
C3 O6 . 1.299(3)
C3 C3 2_776 1.563(5)
O6 H3 . 0.8200
N3 C35 . 1.334(4)
N3 C31 . 1.344(3)
C31 C32 . 1.388(4)
C31 H31 . 0.9300
C32 C33 . 1.406(4)
C32 H32 . 0.9300
C33 C34 . 1.404(4)
C33 C33 2_866 1.492(5)
C34 C35 . 1.389(4)
C34 H34 . 0.9300
C35 H35 . 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
_geom_hbond_publ_flag
O2 H1 N2 1_465 0.82 1.77 2.586(3) 174 y
O4 H2 N1 . 0.82 1.74 2.553(3) 174 y
O6 H3 N3 . 0.82 1.74 2.560(3) 174 y
C11 H11 O3 2_565 0.93 2.59 3.270(4) 130 y
C22 H22 O3 1_655 0.93 2.45 3.375(3) 172 y
C24 H24 O1 1_545 0.93 2.40 3.326(4) 171 y
C25 H25 O4 1_545 0.93 2.48 3.216(3) 136 y
C32 H32 O5 2_766 0.93 2.56 3.418(3) 153 y
C34 H34 O5 1_655 0.93 2.52 3.373(3) 153 y
C35 H35 O6 2_876 0.93 2.57 3.207(3) 126 y
