#------------------------------------------------------------------------------
#$Date: 2023-03-02 10:32:06 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106811.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106811
loop_
_publ_author_name
'Yao, Li-Ping'
'Zhao, Yan'
_publ_section_title
;
 Crystal structure of 4,4′-bipyridin-1-ium
 3,3′,5′-tricarboxy-[1,1′-biphenyl]-2-carboxylate,
 (C26H18N2O8)
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              153
_journal_page_last               155
_journal_paper_doi               10.1515/ncrs-2015-0065
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C26 H18 N2 O8'
_chemical_formula_weight         486.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                93.183(8)
_cell_angle_beta                 108.614(8)
_cell_angle_gamma                97.323(8)
_cell_formula_units_Z            2
_cell_length_a                   10.101(5)
_cell_length_b                   10.589(6)
_cell_length_c                   10.705(6)
_cell_measurement_reflns_used    3479
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.66
_cell_volume                     1070.6(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5700
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0399
_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)+(0.0545P)²+0.3391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3396
_reflns_number_total             3924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0065_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1070.5(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106811
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2130(2) 1.01801(17) -0.06998(16) 0.0613(5) Uani 1 1 d . . .
H1 H 0.1774 1.0429 -0.1471 0.074 Uiso 1 1 calc R . .
N2 N 0.47289(16) 0.78761(15) 0.54223(15) 0.0498(4) Uani 1 1 d . . .
O1 O 0.03299(14) 0.72075(13) 0.97909(13) 0.0535(3) Uani 1 1 d . . .
O2 O 0.11569(13) 0.65616(11) 1.17886(11) 0.0445(3) Uani 1 1 d . . .
H2 H 0.0639 0.7031 1.1961 0.067 Uiso 1 1 calc R . .
O3 O 0.41935(16) 0.34796(15) 1.26582(12) 0.0608(4) Uani 1 1 d . . .
H3 H 0.4611 0.2970 1.3125 0.091 Uiso 1 1 calc R . .
O4 O 0.49190(14) 0.25391(13) 1.11537(13) 0.0546(3) Uani 1 1 d . . .
O5 O 0.18850(12) 0.10968(10) 0.68101(11) 0.0382(3) Uani 1 1 d . . .
O6 O -0.06628(12) 0.11433(11) 0.44493(12) 0.0430(3) Uani 1 1 d . . .
H6 H -0.0985 0.0443 0.4020 0.064 Uiso 1 1 calc R . .
O7 O 0.0549(2) 0.13138(16) 0.30788(16) 0.0800(5) Uani 1 1 d . . .
O8 O 0.04291(13) 0.19439(11) 0.76259(11) 0.0402(3) Uani 1 1 d . . .
C1 C 0.10480(16) 0.29518(15) 0.48160(15) 0.0344(3) Uani 1 1 d . . .
C2 C 0.13861(15) 0.31113(14) 0.61868(14) 0.0312(3) Uani 1 1 d . . .
C3 C 0.19858(16) 0.43133(15) 0.68572(15) 0.0350(3) Uani 1 1 d . . .
C4 C 0.23179(16) 0.45599(14) 0.83071(15) 0.0337(3) Uani 1 1 d . . .
C5 C 0.31780(16) 0.38768(15) 0.92035(15) 0.0348(3) Uani 1 1 d . . .
H5 H 0.3625 0.3270 0.8901 0.042 Uiso 1 1 calc R . .
C6 C 0.33845(16) 0.40800(15) 1.05381(15) 0.0343(3) Uani 1 1 d . . .
C7 C 0.27127(16) 0.49676(15) 1.09925(15) 0.0351(3) Uani 1 1 d . . .
H7 H 0.2829 0.5091 1.1891 0.042 Uiso 1 1 calc R . .
C8 C 0.18703(16) 0.56697(14) 1.01140(15) 0.0332(3) Uani 1 1 d . . .
C9 C 0.16974(16) 0.54790(14) 0.87856(15) 0.0349(3) Uani 1 1 d . . .
H9 H 0.1153 0.5978 0.8200 0.042 Uiso 1 1 calc R . .
C10 C 0.22317(19) 0.53165(17) 0.61418(17) 0.0453(4) Uani 1 1 d . . .
H10 H 0.2609 0.6128 0.6585 0.054 Uiso 1 1 calc R . .
C11 C 0.1932(2) 0.51390(18) 0.47969(17) 0.0492(4) Uani 1 1 d . . .
H11 H 0.2122 0.5821 0.4337 0.059 Uiso 1 1 calc R . .
C12 C 0.13532(18) 0.39561(17) 0.41349(16) 0.0427(4) Uani 1 1 d . . .
H12 H 0.1164 0.3827 0.3224 0.051 Uiso 1 1 calc R . .
C13 C 0.10398(17) 0.65634(15) 1.05364(16) 0.0362(3) Uani 1 1 d . . .
C14 C 0.42577(17) 0.32871(16) 1.14682(16) 0.0396(4) Uani 1 1 d . . .
C15 C 0.11863(16) 0.19730(14) 0.69211(14) 0.0315(3) Uani 1 1 d . . .
C16 C 0.03106(18) 0.17234(16) 0.40313(15) 0.0388(4) Uani 1 1 d . . .
C17 C 0.3632(2) 0.84828(18) 0.51276(17) 0.0474(4) Uani 1 1 d . . .
H17 H 0.3179 0.8574 0.5753 0.057 Uiso 1 1 calc R . .
C18 C 0.31190(18) 0.89862(17) 0.39579(16) 0.0416(4) Uani 1 1 d . . .
H18 H 0.2334 0.9404 0.3797 0.050 Uiso 1 1 calc R . .
C19 C 0.37656(16) 0.88747(15) 0.30167(15) 0.0342(3) Uani 1 1 d . . .
C20 C 0.32183(16) 0.93664(15) 0.17173(16) 0.0363(4) Uani 1 1 d . . .
C21 C 0.2322(2) 1.02646(18) 0.15294(18) 0.0479(4) Uani 1 1 d . . .
H21 H 0.2085 1.0606 0.2235 0.057 Uiso 1 1 calc R . .
C22 C 0.1778(2) 1.06540(19) 0.0285(2) 0.0577(5) Uani 1 1 d . . .
H22 H 0.1162 1.1253 0.0145 0.069 Uiso 1 1 calc R . .
C23 C 0.3002(3) 0.9343(2) -0.05568(19) 0.0603(5) Uani 1 1 d . . .
H23 H 0.3236 0.9038 -0.1278 0.072 Uiso 1 1 calc R . .
C24 C 0.3560(2) 0.89243(18) 0.06372(17) 0.0476(4) Uani 1 1 d . . .
H24 H 0.4181 0.8331 0.0736 0.057 Uiso 1 1 calc R . .
C25 C 0.4927(2) 0.8262(2) 0.33314(19) 0.0548(5) Uani 1 1 d . . .
H25 H 0.5418 0.8178 0.2737 0.066 Uiso 1 1 calc R . .
C26 C 0.5356(2) 0.7777(2) 0.4527(2) 0.0623(6) Uani 1 1 d . . .
H26 H 0.6137 0.7351 0.4717 0.075 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C23 N1 C22 122.62(17) . .
C23 N1 H1 118.7 . .
C22 N1 H1 118.7 . .
C17 N2 C26 116.82(15) . .
C13 O2 H2 109.5 . .
C14 O3 H3 109.5 . .
C16 O6 H6 109.5 . .
C12 C1 C2 120.79(15) . .
C12 C1 C16 117.52(14) . .
C2 C1 C16 121.67(14) . .
C3 C2 C1 118.92(14) . .
C3 C2 C15 121.20(13) . .
C1 C2 C15 119.76(14) . .
C10 C3 C2 119.03(15) . .
C10 C3 C4 119.28(15) . .
C2 C3 C4 121.65(14) . .
C5 C4 C9 118.32(14) . .
C5 C4 C3 122.90(14) . .
C9 C4 C3 118.73(14) . .
C6 C5 C4 120.98(14) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C7 119.87(14) . .
C5 C6 C14 119.69(14) . .
C7 C6 C14 120.33(14) . .
C8 C7 C6 119.81(15) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C7 C8 C9 119.79(14) . .
C7 C8 C13 121.86(14) . .
C9 C8 C13 118.17(14) . .
C8 C9 C4 121.15(14) . .
C8 C9 H9 119.4 . .
C4 C9 H9 119.4 . .
C11 C10 C3 121.49(17) . .
C11 C10 H10 119.3 . .
C3 C10 H10 119.3 . .
C12 C11 C10 119.67(16) . .
C12 C11 H11 120.2 . .
C10 C11 H11 120.2 . .
C11 C12 C1 120.03(16) . .
C11 C12 H12 120.0 . .
C1 C12 H12 120.0 . .
O1 C13 O2 124.17(15) . .
O1 C13 C8 122.69(15) . .
O2 C13 C8 113.14(13) . .
O4 C14 O3 124.16(15) . .
O4 C14 C6 123.90(15) . .
O3 C14 C6 111.92(14) . .
O8 C15 O5 123.19(14) . .
O8 C15 C2 121.17(13) . .
O5 C15 C2 115.56(13) . .
O7 C16 O6 122.72(17) . .
O7 C16 C1 123.36(16) . .
O6 C16 C1 113.88(13) . .
N2 C17 C18 123.60(17) . .
N2 C17 H17 118.2 . .
C18 C17 H17 118.2 . .
C17 C18 C19 119.69(16) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
C25 C19 C18 116.82(15) . .
C25 C19 C20 121.59(15) . .
C18 C19 C20 121.58(14) . .
C21 C20 C24 117.49(16) . .
C21 C20 C19 121.02(15) . .
C24 C20 C19 121.48(15) . .
C20 C21 C22 119.29(18) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
N1 C22 C21 119.99(19) . .
N1 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
N1 C23 C24 119.9(2) . .
N1 C23 H23 120.1 . .
C24 C23 H23 120.1 . .
C23 C24 C20 120.69(19) . .
C23 C24 H24 119.7 . .
C20 C24 H24 119.7 . .
C26 C25 C19 119.34(17) . .
C26 C25 H25 120.3 . .
C19 C25 H25 120.3 . .
N2 C26 C25 123.72(17) . .
N2 C26 H26 118.1 . .
C25 C26 H26 118.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C23 1.308(3) .
N1 C22 1.310(3) .
N1 H1 0.8600 .
N2 C17 1.312(2) .
N2 C26 1.313(3) .
O1 C13 1.198(2) .
O2 C13 1.308(2) .
O2 H2 0.8200 .
O3 C14 1.302(2) .
O3 H3 0.8200 .
O4 C14 1.198(2) .
O5 C15 1.2574(18) .
O6 C16 1.304(2) .
O6 H6 0.8200 .
O7 C16 1.191(2) .
O8 C15 1.2330(19) .
C1 C12 1.380(2) .
C1 C2 1.391(2) .
C1 C16 1.478(2) .
C2 C3 1.388(2) .
C2 C15 1.502(2) .
C3 C10 1.386(2) .
C3 C4 1.480(2) .
C4 C5 1.380(2) .
C4 C9 1.381(2) .
C5 C6 1.377(2) .
C5 H5 0.9300 .
C6 C7 1.379(2) .
C6 C14 1.482(2) .
C7 C8 1.374(2) .
C7 H7 0.9300 .
C8 C9 1.376(2) .
C8 C13 1.483(2) .
C9 H9 0.9300 .
C10 C11 1.370(3) .
C10 H10 0.9300 .
C11 C12 1.365(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C17 C18 1.360(2) .
C17 H17 0.9300 .
C18 C19 1.372(2) .
C18 H18 0.9300 .
C19 C25 1.369(2) .
C19 C20 1.475(2) .
C20 C21 1.374(2) .
C20 C24 1.382(2) .
C21 C22 1.377(3) .
C21 H21 0.9300 .
C22 H22 0.9300 .
C23 C24 1.347(3) .
C23 H23 0.9300 .
C24 H24 0.9300 .
C25 C26 1.366(3) .
C25 H25 0.9300 .
C26 H26 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.86 2.04 2.835(2) 153.7 1_564
N1 H1 O8 0.86 2.29 2.979(2) 137.3 1_564
O2 H2 O8 0.82 1.76 2.5769(18) 178.3 2_567
O3 H3 N2 0.82 1.82 2.601(2) 158.9 2_667
O6 H6 O5 0.82 1.79 2.6084(19) 171.7 2_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C12 C1 C2 C3 2.6(2) . . . .
C16 C1 C2 C3 -175.36(14) . . . .
C12 C1 C2 C15 -173.48(14) . . . .
C16 C1 C2 C15 8.6(2) . . . .
C1 C2 C3 C10 -0.1(2) . . . .
C15 C2 C3 C10 175.87(14) . . . .
C1 C2 C3 C4 177.53(14) . . . .
C15 C2 C3 C4 -6.5(2) . . . .
C10 C3 C4 C5 -126.10(18) . . . .
C2 C3 C4 C5 56.3(2) . . . .
C10 C3 C4 C9 56.5(2) . . . .
C2 C3 C4 C9 -121.10(17) . . . .
C9 C4 C5 C6 1.7(2) . . . .
C3 C4 C5 C6 -175.67(15) . . . .
C4 C5 C6 C7 0.7(2) . . . .
C4 C5 C6 C14 177.01(14) . . . .
C5 C6 C7 C8 -1.8(2) . . . .
C14 C6 C7 C8 -177.99(15) . . . .
C6 C7 C8 C9 0.3(2) . . . .
C6 C7 C8 C13 175.27(14) . . . .
C7 C8 C9 C4 2.3(2) . . . .
C13 C8 C9 C4 -172.92(14) . . . .
C5 C4 C9 C8 -3.2(2) . . . .
C3 C4 C9 C8 174.27(14) . . . .
C2 C3 C10 C11 -1.8(3) . . . .
C4 C3 C10 C11 -179.51(17) . . . .
C3 C10 C11 C12 1.3(3) . . . .
C10 C11 C12 C1 1.2(3) . . . .
C2 C1 C12 C11 -3.2(2) . . . .
C16 C1 C12 C11 174.86(16) . . . .
C7 C8 C13 O1 177.97(16) . . . .
C9 C8 C13 O1 -7.0(2) . . . .
C7 C8 C13 O2 -2.6(2) . . . .
C9 C8 C13 O2 172.49(14) . . . .
C5 C6 C14 O4 7.1(3) . . . .
C7 C6 C14 O4 -176.63(17) . . . .
C5 C6 C14 O3 -171.40(16) . . . .
C7 C6 C14 O3 4.8(2) . . . .
C3 C2 C15 O8 61.3(2) . . . .
C1 C2 C15 O8 -122.74(16) . . . .
C3 C2 C15 O5 -115.73(16) . . . .
C1 C2 C15 O5 60.22(19) . . . .
C12 C1 C16 O7 38.2(3) . . . .
C2 C1 C16 O7 -143.85(19) . . . .
C12 C1 C16 O6 -139.67(15) . . . .
C2 C1 C16 O6 38.3(2) . . . .
C26 N2 C17 C18 0.8(3) . . . .
N2 C17 C18 C19 -0.3(3) . . . .
C17 C18 C19 C25 -0.8(3) . . . .
C17 C18 C19 C20 177.88(17) . . . .
C25 C19 C20 C21 -162.11(18) . . . .
C18 C19 C20 C21 19.2(3) . . . .
C25 C19 C20 C24 19.3(3) . . . .
C18 C19 C20 C24 -159.35(17) . . . .
C24 C20 C21 C22 1.8(3) . . . .
C19 C20 C21 C22 -176.84(17) . . . .
C23 N1 C22 C21 -0.6(3) . . . .
C20 C21 C22 N1 -0.8(3) . . . .
C22 N1 C23 C24 0.9(3) . . . .
N1 C23 C24 C20 0.2(3) . . . .
C21 C20 C24 C23 -1.5(3) . . . .
C19 C20 C24 C23 177.12(18) . . . .
C18 C19 C25 C26 1.5(3) . . . .
C20 C19 C25 C26 -177.24(19) . . . .
C17 N2 C26 C25 -0.1(3) . . . .
C19 C25 C26 N2 -1.1(4) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{053d63ed-064f-4711-90c8-72d204433cd7} ? ? ?
{17098b5a-86f8-4c84-8611-dfbf38734de3} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{053d63ed-064f-4711-90c8-72d204433cd7} '_publcif_info_datablock.publ_exptl'
{17098b5a-86f8-4c84-8611-dfbf38734de3} '_geom_hbond_atom_site_label_D'
loop_
_publcif_info_cif.paper_type
CB
