#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/71/2207162.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_2207162
loop_
_publ_author_name
'Fu, Yun-Long'
'Ren, Jia-Lin'
'Xu, Zhi-Wei'
'Ng, Seik Weng'
_publ_section_title
;
 Bis(4,4'-bipyridinium)
 tetrakis(oxalato-κ²O,O')zirconate(IV)
;
_journal_coeditor_code           BT6767
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2397
_journal_page_last               m2399
_journal_paper_doi               10.1107/S1600536805033829
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '(C10 H10 N2)2 [Zr (C2 O4)4]'
_chemical_formula_moiety         '2C10 H10 N2 2+, C8 O16 Zr 4-'
_chemical_formula_sum            'C28 H20 N4 O16 Zr'
_chemical_formula_weight         759.70
_chemical_name_systematic
;
Bis(4,4'-bipyridinium) tetrakis(oxalato-κ²O,O')zirconate(IV)
;
_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
_cell_angle_beta                 121.231(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.447(2)
_cell_length_b                   10.9860(10)
_cell_length_c                   15.084(2)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.1
_cell_measurement_theta_min      2.2
_cell_volume                     2755.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'Bruker APEX 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  0.045
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0564P)²+0.727P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.112
_reflns_number_gt                2340
_reflns_number_total             3097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6767.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2207162
_cod_database_fobs_code          2207162
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_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_type_symbol
Zr1 0.5000 0.29208(4) 0.2500 0.0219(2) Uani d S 1 Zr
O1 0.43200(10) 0.4489(2) 0.1533(2) 0.0355(6) Uani d . 1 O
O2 0.4563(2) 0.6300(2) 0.1042(2) 0.0495(7) Uani d . 1 O
O3 0.5534(2) 0.3521(2) 0.1605(2) 0.0369(6) Uani d . 1 O
O4 0.5859(2) 0.5189(2) 0.1072(2) 0.0387(6) Uani d . 1 O
O5 0.62560(10) 0.2302(2) 0.3295(2) 0.0364(6) Uani d . 1 O
O6 0.7017(2) 0.0629(2) 0.3810(2) 0.0440(7) Uani d . 1 O
O7 0.51520(10) 0.1318(2) 0.3486(2) 0.0304(6) Uani d . 1 O
O8 0.5773(2) -0.0502(2) 0.3870(2) 0.0425(7) Uani d . 1 O
N1 0.6068(2) 0.7576(3) 0.1035(3) 0.0353(7) Uani d D 1 N
N2 0.7780(2) 1.3220(3) 0.1246(2) 0.0352(7) Uani d D 1 N
C1 0.4708(2) 0.5230(3) 0.1276(3) 0.0323(8) Uani d . 1 C
C2 0.5430(2) 0.4623(3) 0.1305(3) 0.0295(8) Uani d . 1 C
C3 0.6403(2) 0.1196(3) 0.3590(3) 0.0283(8) Uani d . 1 C
C4 0.5721(2) 0.0581(3) 0.3659(3) 0.0292(8) Uani d . 1 C
C5 0.6767(2) 0.7619(3) 0.1059(3) 0.0395(9) Uani d . 1 C
C6 0.7129(2) 0.8711(3) 0.1152(3) 0.0342(8) Uani d . 1 C
C7 0.6780(2) 0.9789(3) 0.1208(2) 0.0265(7) Uani d . 1 C
C8 0.6058(2) 0.9689(3) 0.1186(3) 0.0328(8) Uani d . 1 C
C9 0.5709(2) 0.8578(4) 0.1097(3) 0.0381(9) Uani d . 1 C
C10 0.8195(2) 1.2217(3) 0.1338(3) 0.0381(9) Uani d . 1 C
C11 0.7889(2) 1.1096(3) 0.1342(3) 0.0343(9) Uani d . 1 C
C12 0.7147(2) 1.0997(3) 0.1258(3) 0.0270(8) Uani d . 1 C
C13 0.6742(2) 1.2072(3) 0.1184(3) 0.0368(9) Uani d . 1 C
C14 0.7072(2) 1.3172(3) 0.1168(3) 0.0391(9) Uani d . 1 C
H1 0.586(2) 0.688(2) 0.095(3) 0.040(10) Uiso d D 1 H
H2 0.797(2) 1.391(2) 0.122(3) 0.06(2) Uiso d D 1 H
H5 0.7003 0.6904 0.1013 0.047 Uiso calc R 1 H
H6 0.7617 0.8735 0.1177 0.041 Uiso calc R 1 H
H8 0.5808 1.0388 0.1233 0.039 Uiso calc R 1 H
H9 0.5225 0.8523 0.1080 0.046 Uiso calc R 1 H
H10 0.8695 1.2278 0.1399 0.046 Uiso calc R 1 H
H11 0.8181 1.0397 0.1402 0.041 Uiso calc R 1 H
H13 0.6249 1.2046 0.1146 0.044 Uiso calc R 1 H
H14 0.6794 1.3889 0.1102 0.047 Uiso calc R 1 H
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'
Zr Zr -2.9673 0.5597 '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
_geom_angle_publ_flag
O1 Zr1 O1 2_655 76.90(10) yes
O1 Zr1 O3 . 70.70(10) yes
O1 Zr1 O3 2_655 81.90(10) yes
O1 Zr1 O5 . 136.00(10) yes
O1 Zr1 O5 2_655 76.40(10) yes
O1 Zr1 O7 . 152.80(10) yes
O1 Zr1 O7 2_655 110.60(10) yes
O3 Zr1 O3 2_655 144.90(10) yes
O3 Zr1 O5 . 71.40(10) yes
O3 Zr1 O5 2_655 120.30(10) yes
O3 Zr1 O7 . 135.20(10) yes
O3 Zr1 O7 2_655 76.50(10) yes
O5 Zr1 O5 2_655 144.00(10) yes
O5 Zr1 O7 . 70.40(10) yes
O5 Zr1 O7 2_655 81.10(10) yes
O7 Zr1 O7 2_655 75.30(10) yes
C1 O1 Zr1 . 116.5(2) no
C2 O3 Zr1 . 117.9(2) no
C3 O5 Zr1 . 118.0(2) no
C4 O7 Zr1 . 116.0(2) no
C9 N1 C5 . 121.9(3) no
C14 N2 C10 . 121.7(3) no
O2 C1 O1 . 127.4(3) no
O2 C1 C2 . 120.0(3) no
O1 C1 C2 . 112.6(3) no
O4 C2 O3 . 125.3(3) no
O4 C2 C1 . 121.2(3) no
O3 C2 C1 . 113.4(3) no
O6 C3 O5 . 126.0(3) no
O6 C3 C4 . 120.6(3) no
O5 C3 C4 . 113.4(3) no
O8 C4 O7 . 127.8(3) no
O8 C4 C3 . 119.2(3) no
O7 C4 C3 . 113.0(3) no
N1 C5 C6 . 119.8(3) no
C5 C6 C7 . 120.9(3) no
C6 C7 C8 . 116.8(3) no
C6 C7 C12 . 121.8(3) no
C8 C7 C12 . 121.4(3) no
C9 C8 C7 . 121.0(3) no
N1 C9 C8 . 119.6(3) no
N2 C10 C11 . 120.3(3) no
C10 C11 C12 . 120.2(3) no
C11 C12 C13 . 117.4(3) no
C11 C12 C7 . 121.5(3) no
C13 C12 C7 . 121.1(3) no
C14 C13 C12 . 119.9(3) no
N2 C14 C13 . 120.5(3) no
C9 N1 H1 . 122(3) no
C5 N1 H1 . 116(3) no
C14 N2 H2 . 120(3) no
C10 N2 H2 . 119(3) no
N1 C5 H5 . 120.1 no
C6 C5 H5 . 120.1 no
C5 C6 H6 . 119.5 no
C7 C6 H6 . 119.5 no
C9 C8 H8 . 119.5 no
C7 C8 H8 . 119.5 no
N1 C9 H9 . 120.2 no
C8 C9 H9 . 120.2 no
N2 C10 H10 . 119.9 no
C11 C10 H10 . 119.9 no
C10 C11 H11 . 119.9 no
C12 C11 H11 . 119.9 no
C14 C13 H13 . 120.0 no
C12 C13 H13 . 120.0 no
N2 C14 H14 . 119.7 no
C13 C14 H14 . 119.7 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
Zr1 O1 . 2.201(2) yes
Zr1 O1 2_655 2.201(2) no
Zr1 O3 . 2.189(2) yes
Zr1 O3 2_655 2.189(2) no
Zr1 O5 . 2.197(2) yes
Zr1 O5 2_655 2.197(2) no
Zr1 O7 . 2.223(2) yes
Zr1 O7 2_655 2.223(2) no
O1 C1 . 1.299(4) no
O2 C1 . 1.218(4) no
O3 C2 . 1.271(4) no
O4 C2 . 1.228(4) no
O5 C3 . 1.275(4) no
O6 C3 . 1.229(4) no
O7 C4 . 1.284(4) no
O8 C4 . 1.222(4) no
N1 C9 . 1.333(5) no
N1 C5 . 1.340(5) no
N2 C14 . 1.322(5) no
N2 C10 . 1.330(5) no
C1 C2 . 1.535(5) no
C3 C4 . 1.539(5) no
C5 C6 . 1.361(5) no
C6 C7 . 1.390(5) no
C7 C8 . 1.392(5) no
C7 C12 . 1.490(5) no
C8 C9 . 1.368(5) no
C10 C11 . 1.370(5) no
C11 C12 . 1.387(5) no
C12 C13 . 1.391(5) no
C13 C14 . 1.374(5) no
N1 H1 . 0.850(10) no
N2 H2 . 0.860(10) no
C5 H5 . 0.93 no
C6 H6 . 0.93 no
C8 H8 . 0.93 no
C9 H9 . 0.93 no
C10 H10 . 0.93 no
C11 H11 . 0.93 no
C13 H13 . 0.93 no
C14 H14 . 0.93 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
N1 H1 O4 . 0.850(10) 1.86(2) 2.658(4) 155(4) yes
N2 H2 O6 4_665 0.860(10) 1.89(2) 2.683(4) 154(4) yes
C5 H5 O6 4_655 0.93 2.27 3.152(5) 159 yes
C6 H6 O5 4_655 0.93 2.47 3.199(4) 135 yes
C8 H8 O7 2_665 0.93 2.35 3.193(4) 150 yes
C9 H9 O8 2_665 0.93 2.25 3.078(4) 148 yes
C10 H10 O2 3 0.93 2.29 3.085(5) 144 yes
C11 H11 O1 3 0.93 2.34 3.179(4) 150 yes
C13 H13 O3 1_565 0.93 2.46 3.163(4) 133 yes
C14 H14 O4 1_565 0.93 2.29 3.184(4) 160 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
_geom_torsion_publ_flag
O3 Zr1 O1 C1 2_655 132.1(3) no
O3 Zr1 O1 C1 . -25.7(2) no
O5 Zr1 O1 C1 2_655 -155.2(3) no
O5 Zr1 O1 C1 . 6.1(3) no
O1 Zr1 O1 C1 2_655 60.1(2) no
O7 Zr1 O1 C1 2_655 -92.5(3) no
O7 Zr1 O1 C1 . 169.8(2) no
O3 Zr1 O3 C2 2_655 -15.7(2) no
O5 Zr1 O3 C2 2_655 85.3(3) no
O5 Zr1 O3 C2 . -132.4(3) no
O1 Zr1 O3 C2 2_655 -54.1(3) no
O1 Zr1 O3 C2 . 24.9(3) no
O7 Zr1 O3 C2 2_655 142.7(3) no
O7 Zr1 O3 C2 . -165.1(2) no
O3 Zr1 O5 C3 2_655 84.5(3) no
O3 Zr1 O5 C3 . -132.1(3) no
O5 Zr1 O5 C3 2_655 -15.7(2) no
O1 Zr1 O5 C3 2_655 142.1(3) no
O1 Zr1 O5 C3 . -163.8(2) no
O7 Zr1 O5 C3 2_655 -53.3(3) no
O7 Zr1 O5 C3 . 24.1(2) no
O3 Zr1 O7 C4 2_655 -156.3(2) no
O3 Zr1 O7 C4 . 6.2(3) no
O5 Zr1 O7 C4 2_655 130.8(2) no
O5 Zr1 O7 C4 . -26.8(2) no
O1 Zr1 O7 C4 2_655 -93.2(2) no
O1 Zr1 O7 C4 . 165.2(2) no
O7 Zr1 O7 C4 2_655 58.8(2) no
Zr1 O1 C1 O2 . -155.4(3) no
Zr1 O1 C1 C2 . 23.7(4) no
Zr1 O3 C2 O4 . 157.8(3) no
Zr1 O3 C2 C1 . -20.8(4) no
O2 C1 C2 O4 . -1.6(6) no
O1 C1 C2 O4 . 179.2(3) no
O2 C1 C2 O3 . 177.1(3) no
O1 C1 C2 O3 . -2.1(5) no
Zr1 O5 C3 O6 . 161.3(3) no
Zr1 O5 C3 C4 . -18.8(4) no
Zr1 O7 C4 O8 . -154.5(3) no
Zr1 O7 C4 C3 . 26.0(3) no
O6 C3 C4 O8 . -4.8(5) no
O5 C3 C4 O8 . 175.3(3) no
O6 C3 C4 O7 . 174.8(3) no
O5 C3 C4 O7 . -5.1(4) no
C9 N1 C5 C6 . 0.1(6) no
N1 C5 C6 C7 . -0.9(6) no
C5 C6 C7 C8 . 1.3(5) no
C5 C6 C7 C12 . -177.0(3) no
C6 C7 C8 C9 . -1.0(5) no
C12 C7 C8 C9 . 177.3(3) no
C5 N1 C9 C8 . 0.1(6) no
C7 C8 C9 N1 . 0.3(6) no
C14 N2 C10 C11 . 0.7(6) no
N2 C10 C11 C12 . -0.4(6) no
C10 C11 C12 C13 . -0.8(5) no
C10 C11 C12 C7 . 176.9(3) no
C6 C7 C12 C11 . -5.7(5) no
C8 C7 C12 C11 . 176.1(3) no
C6 C7 C12 C13 . 171.9(3) no
C8 C7 C12 C13 . -6.3(5) no
C11 C12 C13 C14 . 1.7(5) no
C7 C12 C13 C14 . -176.0(3) no
C10 N2 C14 C13 . 0.3(6) no
C12 C13 C14 N2 . -1.5(6) no
