#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222546.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_2222546
loop_
_publ_author_name
'Zhang, Ning'
'Shi, Xue-Min'
'Shao, Min'
'Li, Ming-Xing'
_publ_section_title
;
 Butane-1,2,3,4-tetracarboxylic acid--4,4'-bipyridine (1/2)
;
_journal_coeditor_code           AT2847
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2016
_journal_paper_doi               10.1107/S1600536809029237
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H10 O8, 2C10 H8 N2'
_chemical_formula_moiety         'C8 H10 O8, 2(C10 H8 N2)'
_chemical_formula_sum            'C28 H26 N4 O8'
_chemical_formula_weight         546.53
_chemical_name_systematic
;
Butane-1,2,3,4-tetracarboxylic acid--4,4'-bipyridine (1/2)
;
_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           SHELXL-97
_cell_angle_alpha                99.819(3)
_cell_angle_beta                 105.662(3)
_cell_angle_gamma                111.361(2)
_cell_formula_units_Z            1
_cell_length_a                   7.4435(11)
_cell_length_b                   8.6990(13)
_cell_length_c                   11.438(2)
_cell_measurement_reflns_used    1387
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.64
_cell_volume                     633.58(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD 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  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3287
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0606
_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)+(0.0797P)²+0.4629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1762
_reflns_number_gt                1721
_reflns_number_total             2196
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2847.cif
_cod_data_source_block           I
_cod_original_cell_volume        633.57(17)
_cod_database_code               2222546
_cod_database_fobs_code          2222546
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.1342(5) 0.6302(4) -0.0696(3) 0.0508(7) Uani d . 1 . .
C C2 -0.0232(5) 0.7892(4) 0.0456(3) 0.0597(9) Uani d . 1 . .
H H2A -0.1212 0.7939 0.0858 0.072 Uiso calc R 1 . .
H H2B 0.0844 0.7742 0.1058 0.072 Uiso calc R 1 . .
C C3 0.0728(5) 0.9587(3) 0.0242(3) 0.0548(8) Uani d . 1 . .
H H3 0.1316 0.9400 -0.0410 0.066 Uiso calc R 1 . .
C C4 0.2542(5) 1.0895(4) 0.1447(3) 0.0498(7) Uani d . 1 . .
C C5 -0.2914(4) 0.4885(4) 0.4266(3) 0.0479(7) Uani d . 1 . .
H H5 -0.3917 0.4111 0.4485 0.057 Uiso calc R 1 . .
C C6 -0.1373(4) 0.6347(4) 0.5207(3) 0.0449(7) Uani d . 1 . .
H H6 -0.1346 0.6548 0.6038 0.054 Uiso calc R 1 . .
C C7 0.0146(4) 0.7522(3) 0.4900(2) 0.0368(6) Uani d . 1 . .
C C8 -0.0007(4) 0.7138(4) 0.3640(3) 0.0490(7) Uani d . 1 . .
H H8 0.0963 0.7888 0.3387 0.059 Uiso calc R 1 . .
C C9 -0.1600(5) 0.5644(4) 0.2767(3) 0.0543(8) Uani d . 1 . .
H H9 -0.1671 0.5408 0.1928 0.065 Uiso calc R 1 . .
C C10 0.1856(4) 0.9112(3) 0.5876(2) 0.0373(6) Uani d . 1 . .
C C11 0.2302(4) 0.9316(4) 0.7163(3) 0.0467(7) Uani d . 1 . .
H H11 0.1531 0.8442 0.7436 0.056 Uiso calc R 1 . .
C C12 0.3888(4) 1.0814(4) 0.8037(3) 0.0515(7) Uani d . 1 . .
H H12 0.4160 1.0920 0.8897 0.062 Uiso calc R 1 . .
C C13 0.4643(4) 1.1920(4) 0.6489(3) 0.0500(7) Uani d . 1 . .
H H13 0.5455 1.2815 0.6249 0.060 Uiso calc R 1 . .
C C14 0.3093(4) 1.0477(4) 0.5543(3) 0.0452(7) Uani d . 1 . .
H H14 0.2869 1.0409 0.4692 0.054 Uiso calc R 1 . .
N N1 -0.3041(4) 0.4522(3) 0.3059(2) 0.0486(6) Uani d . 1 . .
N N2 0.5053(3) 1.2116(3) 0.7720(2) 0.0480(6) Uani d . 1 . .
O O1 -0.1175(4) 0.6219(3) -0.1724(2) 0.0646(6) Uani d . 1 . .
O O2 -0.2488(4) 0.5023(3) -0.0413(2) 0.0675(7) Uani d . 1 . .
H H2 -0.3115 0.4168 -0.1043 0.101 Uiso calc R 1 . .
O O3 0.4001(3) 1.1949(3) 0.11635(17) 0.0535(6) Uani d . 1 . .
H H3A 0.4895 1.2695 0.1816 0.080 Uiso calc R 1 . .
O O4 0.2601(3) 1.0897(3) 0.25184(19) 0.0617(6) Uani d . 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
O1 C1 O2 . . 124.5(3) ?
O1 C1 C2 . . 126.0(3) ?
O2 C1 C2 . . 109.5(3) ?
C3 C2 C1 . . 117.3(3) ?
C3 C2 H2A . . 108.0 ?
C1 C2 H2A . . 108.0 ?
C3 C2 H2B . . 108.0 ?
C1 C2 H2B . . 108.0 ?
H2A C2 H2B . . 107.2 ?
C2 C3 C4 . . 110.8(2) ?
C2 C3 C3 . 2_575 116.5(3) ?
C4 C3 C3 . 2_575 108.9(3) ?
C2 C3 H3 . . 106.7 ?
C4 C3 H3 . . 106.7 ?
C3 C3 H3 2_575 . 106.7 ?
O4 C4 O3 . . 125.2(2) ?
O4 C4 C3 . . 123.6(3) ?
O3 C4 C3 . . 111.2(3) ?
N1 C5 C6 . . 123.4(3) ?
N1 C5 H5 . . 118.3 ?
C6 C5 H5 . . 118.3 ?
C5 C6 C7 . . 119.2(2) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C8 C7 C6 . . 117.0(2) ?
C8 C7 C10 . . 121.3(2) ?
C6 C7 C10 . . 121.7(2) ?
C9 C8 C7 . . 119.6(3) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
N1 C9 C8 . . 123.5(3) ?
N1 C9 H9 . . 118.3 ?
C8 C9 H9 . . 118.3 ?
C11 C10 C14 . . 116.6(2) ?
C11 C10 C7 . . 121.5(2) ?
C14 C10 C7 . . 121.8(2) ?
C12 C11 C10 . . 119.8(3) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
N2 C12 C11 . . 123.5(3) ?
N2 C12 H12 . . 118.2 ?
C11 C12 H12 . . 118.2 ?
N2 C13 C14 . . 124.0(3) ?
N2 C13 H13 . . 118.0 ?
C14 C13 H13 . . 118.0 ?
C13 C14 C10 . . 119.2(3) ?
C13 C14 H14 . . 120.4 ?
C10 C14 H14 . . 120.4 ?
C9 N1 C5 . . 117.3(2) ?
C13 N2 C12 . . 116.9(2) ?
C1 O2 H2 . . 109.5 ?
C4 O3 H3A . . 109.5 ?
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
C1 O1 . 1.209(4) ?
C1 O2 . 1.285(4) ?
C1 C2 . 1.513(4) ?
C2 C3 . 1.482(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.536(4) ?
C3 C3 2_575 1.542(6) ?
C3 H3 . 0.9800 ?
C4 O4 . 1.214(3) ?
C4 O3 . 1.301(4) ?
C5 N1 . 1.332(4) ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.393(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.386(4) ?
C7 C10 . 1.484(4) ?
C8 C9 . 1.374(4) ?
C8 H8 . 0.9300 ?
C9 N1 . 1.325(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.383(4) ?
C10 C14 . 1.395(4) ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.327(4) ?
C12 H12 . 0.9300 ?
C13 N2 . 1.324(4) ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
O2 H2 . 0.8200 ?
O3 H3A . 0.8200 ?
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
C14 H14 O4 . 0.93 2.56 3.476(3) 168.3
C9 H9 O2 . 0.93 2.51 3.425(4) 166.8
O3 H3A N1 1_665 0.82 1.78 2.595(3) 170.4
O2 H2 N2 1_444 0.82 1.84 2.642(3) 167.1
