#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018228.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_2018228
loop_
_publ_author_name
'Androš, Lidija'
'Planinić, Pavica'
'Jurić, Marijana'
_publ_section_title
;
 The supramolecular architecture in 4,4'-bipyridinium bis(hydrogen
 oxalate)
;
_journal_coeditor_code           SU3065
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o337
_journal_page_last               o340
_journal_paper_doi               10.1107/S0108270111028162
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H10 N2 2+, 2C2 H O4 -'
_chemical_formula_moiety         'C10 H10 N2 2+, 2(C2 H O4)'
_chemical_formula_sum            'C14 H12 N2 O8'
_chemical_formula_weight         336.26
_chemical_name_common
;
4,4'-bipyridinium bis(hydrogen oxalate)
;
_chemical_name_systematic
;
4,4'-bipyridineium bis(2-hydroxy-2-oxoacetate)
;
_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
_cell_angle_alpha                116.081(7)
_cell_angle_beta                 97.214(5)
_cell_angle_gamma                97.487(5)
_cell_formula_units_Z            1
_cell_length_a                   3.6954(2)
_cell_length_b                   9.8579(7)
_cell_length_c                   10.4254(8)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0610
_cell_measurement_theta_min      3.9079
_cell_volume                     331.00(5)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
'PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_device_type
'Oxford Diffraction KM-4/Xcalibur diffractometer with a Sapphire3 detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2408
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0357
_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)+(0.0679P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1134
_reflns_number_total             1475
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3065.cif
_cod_data_source_block           I
_cod_original_cell_volume        331.00(4)
_cod_database_code               2018228
_cod_database_fobs_code          2018228
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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_thermal_displace_type
_atom_site_occupancy
N N1 0.5661(3) 0.36954(13) 0.65192(12) 0.0181(3) Uani 1.000
C C3 0.4629(4) 0.28742(15) 0.50631(14) 0.0189(4) Uani 1.000
C C4 0.2378(4) 0.14177(15) 0.44369(14) 0.0185(4) Uani 1.000
C C5 0.1201(4) 0.07872(14) 0.53168(14) 0.0154(4) Uani 1.000
C C6 0.2372(4) 0.16850(15) 0.68293(15) 0.0200(4) Uani 1.000
C C7 0.4580(4) 0.31361(16) 0.74039(15) 0.0224(4) Uani 1.000
O O1 0.8258(3) 0.12413(11) -0.07841(10) 0.0250(3) Uani 1.000
O O2 1.1664(3) 0.36004(11) 0.04696(11) 0.0275(3) Uani 1.000
O O3 0.9530(3) 0.38142(11) 0.29721(10) 0.0224(3) Uani 1.000
O O4 0.6039(3) 0.14264(11) 0.16365(10) 0.0245(3) Uani 1.000
C C1 0.9575(4) 0.25304(16) 0.04372(15) 0.0194(4) Uani 1.000
C C2 0.8252(4) 0.25926(15) 0.18141(14) 0.0175(4) Uani 1.000
H H1N 0.754(6) 0.476(2) 0.693(2) 0.064(7) Uiso 1.000
H H3 0.54313 0.32866 0.44736 0.0227 Uiso 1.000
H H4 0.16446 0.08561 0.34271 0.0222 Uiso 1.000
H H6 0.16546 0.12985 0.74483 0.0240 Uiso 1.000
H H7 0.53261 0.37318 0.84102 0.0268 Uiso 1.000
H H1 0.675(5) 0.051(2) -0.066(2) 0.048(6) Uiso 1.000
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 O1 H1 . . 113.0(12) no
C3 N1 C7 . . 121.63(14) no
C3 N1 H1N . . 116.7(10) no
C7 N1 H1N . . 121.5(10) no
N1 C3 C4 . . 120.17(14) no
C3 C4 C5 . . 120.12(12) no
C4 C5 C5 . 2_556 121.78(12) no
C4 C5 C6 . . 117.55(14) no
C5 C5 C6 2_556 . 120.67(13) no
C5 C6 C7 . . 120.27(14) no
N1 C7 C6 . . 120.25(13) no
C4 C3 H3 . . 120.00 no
N1 C3 H3 . . 120.00 no
C3 C4 H4 . . 120.00 no
C5 C4 H4 . . 120.00 no
C7 C6 H6 . . 120.00 no
C5 C6 H6 . . 120.00 no
N1 C7 H7 . . 120.00 no
C6 C7 H7 . . 120.00 no
O1 C1 C2 . . 116.09(14) no
O2 C1 C2 . . 122.47(13) no
O1 C1 O2 . . 121.44(13) no
O3 C2 C1 . . 115.84(14) no
O4 C2 C1 . . 116.49(12) no
O3 C2 O4 . . 127.67(13) no
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 . 1.3166(18) no
O2 C1 . 1.208(2) no
O3 C2 . 1.2494(17) no
O4 C2 . 1.247(2) no
O1 H1 . 0.92(2) no
N1 C7 . 1.340(2) no
N1 C3 . 1.3412(17) no
N1 H1N . 1.05(2) no
C3 C4 . 1.381(2) no
C4 C5 . 1.396(2) no
C5 C5 2_556 1.492(2) no
C5 C6 . 1.3995(19) no
C6 C7 . 1.375(2) no
C3 H3 . 0.9300 no
C4 H4 . 0.9300 no
C6 H6 . 0.9300 no
C7 H7 . 0.9300 no
C1 C2 . 1.552(2) no
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
O1 H1 O4 . 0.92(2) 2.222(18) 2.6885(14) 110.8(14) yes
O1 H1 O4 2_655 0.92(2) 1.81(2) 2.5941(16) 142.5(16) yes
N1 H1N O2 2_766 1.05(2) 2.423(18) 3.0190(16) 114.8(14) yes
N1 H1N O3 2_766 1.05(2) 1.62(2) 2.6359(18) 162.1(16) yes
C3 H3 O3 . 0.93 2.47 3.3498(18) 157 yes
C6 H6 O1 1_456 0.93 2.37 3.2291(18) 153 yes
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C3 C4 . . . 0.4(2) no
C3 N1 C7 C6 . . . 0.3(2) no
N1 C3 C4 C5 . . . -0.7(2) no
C3 C4 C5 C6 . . . 0.3(2) no
C3 C4 C5 C5 . . 2_556 -179.42(14) no
C5 C5 C6 C7 2_556 . . -179.88(14) no
C4 C5 C5 C4 . 2_556 2_556 -179.98(16) no
C4 C5 C5 C6 . 2_556 2_556 -0.3(2) no
C6 C5 C5 C4 . 2_556 2_556 0.3(2) no
C6 C5 C5 C6 . 2_556 2_556 180.00(14) no
C4 C5 C6 C7 . . . 0.4(2) no
C5 C6 C7 N1 . . . -0.7(2) no
O1 C1 C2 O3 . . . 179.52(13) no
O1 C1 C2 O4 . . . -0.7(2) no
O2 C1 C2 O3 . . . -1.1(2) no
O2 C1 C2 O4 . . . 178.65(15) no
