Short N···O hydrogen bonds in the 1:1 adduct of 4,4'-bipyridyl and oxalic acid
Cowan, John A.; Howard, Judith A. K.; Puschmann, Horst; Williams, Ian D.; Acta Crystallographica Section E 63 (2007) o1240–o1242; doi:10.1107/S1600536807005156

data_2212677
_publ_section_title
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 Short N&#x00B7;&#x00B7;&#x00B7;O hydrogen bonds in the 1:1 adduct of
 4,4'-bipyridyl and oxalic acid
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_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       \w
_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/[\s^2^(Fo^2^)+(0.0821P)^2^+0.9233P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_cod_data_source_file            sg2117.cif
_cod_data_source_block           I
_cod_depositor_comments
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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 
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_cod_database_code               2212677
_cod_database_fobs_code          2212677