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###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
benzene-1,2,3-tricarboxylic acid--4,4'-bipyridine (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H6 O6, C10 H8 N2'
_chemical_formula_sum     'C19 H14 N2 O6'
_chemical_formula_iupac     'C9 H6 O6, C10 H8 N2'
_chemical_formula_weight     366.32
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
_cell_length_a     26.118(3)
_cell_length_b     7.8131(9)
_cell_length_c     19.881(2)
_cell_angle_alpha     90.00
_cell_angle_beta     127.0050(10)
_cell_angle_gamma     90.00
_cell_volume     3239.8(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2052
_cell_measurement_theta_min     2.57
_cell_measurement_theta_max     23.11
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.502
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1520
_exptl_absorpt_coefficient_mu     0.114
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.829393
_exptl_absorpt_correction_T_max     1.000000
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX-II CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8469
_diffrn_reflns_av_R_equivalents     0.0241
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -29
_diffrn_reflns_limit_h_max     30
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2845
_reflns_number_gt     2212
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0549
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.1232
_refine_ls_wR_factor_ref     0.1329
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     2845
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0824P)²+0.8334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.562
_refine_diff_density_min     -0.325
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     none
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'Apex II (Bruker, 2003)'
_computing_cell_refinement     'Apex II and SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
               'SHELXTL (Bruker, 2001) and Diamond (Brandenburg & Berndt, 1999)'
_computing_publication_material     'SHELXTL'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.00470(8) 0.62634(18) 0.04046(8) 0.0471(4) Uani d . 1 . . O
    H1 -0.0106 0.5398 0.0114 0.071 Uiso calc R 1 . . H
    O2 0.03844(8) 0.44554(17) 0.14488(9) 0.0487(4) Uani d . 1 . . O
    O3 0.15311(6) 0.50974(18) 0.33856(8) 0.0389(4) Uani d . 1 . . O
    O4 0.05817(6) 0.45596(16) 0.30515(7) 0.0325(3) Uani d . 1 . . O
    H4 0.0216 0.4686 0.2619 0.049 Uiso calc R 1 . . H
    O5 0.16515(9) 0.9775(2) 0.44631(10) 0.0710(6) Uani d . 1 . . O
    O6 0.11423(7) 0.73634(19) 0.42988(8) 0.0457(4) Uani d . 1 . . O
    H6 0.1337 0.7460 0.4809 0.069 Uiso calc R 1 . . H
    N1 0.36332(9) 0.1491(2) 0.52918(10) 0.0450(5) Uani d . 1 . . N
    N2 0.17152(8) 0.2477(2) 0.09181(10) 0.0423(5) Uani d . 1 . . N
    C1 0.35244(10) 0.2406(3) 0.40921(13) 0.0452(5) Uani d . 1 . . C
    H1A 0.3711 0.2827 0.3849 0.054 Uiso calc R 1 . . H
    C2 0.38955(11) 0.2067(3) 0.49364(13) 0.0490(6) Uani d . 1 . . C
    H2 0.4336 0.2243 0.5264 0.059 Uiso calc R 1 . . H
    C3 0.30044(12) 0.1255(3) 0.48483(13) 0.0492(6) Uani d . 1 . . C
    H3 0.2832 0.0880 0.5117 0.059 Uiso calc R 1 . . H
    C4 0.26064(11) 0.1560(3) 0.39964(12) 0.0449(5) Uani d . 1 . . C
    H4A 0.2167 0.1394 0.3690 0.054 Uiso calc R 1 . . H
    C5 0.28653(10) 0.2118(3) 0.35963(11) 0.0365(5) Uani d . 1 . . C
    C6 0.24615(9) 0.2301(3) 0.26644(11) 0.0347(5) Uani d . 1 . . C
    C7 0.18193(10) 0.2711(3) 0.21904(12) 0.0404(5) Uani d . 1 . . C
    H7 0.1627 0.2931 0.2451 0.049 Uiso calc R 1 . . H
    C8 0.14659(10) 0.2792(3) 0.13253(12) 0.0436(5) Uani d . 1 . . C
    H8 0.1034 0.3080 0.1012 0.052 Uiso calc R 1 . . H
    C9 0.23335(11) 0.2080(3) 0.13773(13) 0.0488(6) Uani d . 1 . . C
    H9 0.2514 0.1861 0.1101 0.059 Uiso calc R 1 . . H
    C10 0.27185(10) 0.1976(3) 0.22373(12) 0.0448(5) Uani d . 1 . . C
    H10 0.3149 0.1690 0.2533 0.054 Uiso calc R 1 . . H
    C11 0.04310(8) 0.7420(2) 0.17188(11) 0.0281(4) Uani d . 1 . . C
    C12 0.07494(8) 0.7225(2) 0.25857(11) 0.0264(4) Uani d . 1 . . C
    C13 0.09214(8) 0.8693(2) 0.30836(11) 0.0321(4) Uani d . 1 . . C
    C14 0.07660(10) 1.0304(3) 0.27098(13) 0.0418(5) Uani d . 1 . . C
    H14 0.0885 1.1276 0.3043 0.050 Uiso calc R 1 . . H
    C15 0.04401(10) 1.0477(3) 0.18589(13) 0.0438(5) Uani d . 1 . . C
    H15 0.0330 1.1560 0.1615 0.053 Uiso calc R 1 . . H
    C16 0.02758(9) 0.9049(2) 0.13653(12) 0.0364(5) Uani d . 1 . . C
    H16 0.0058 0.9172 0.0788 0.044 Uiso calc R 1 . . H
    C17 0.02755(9) 0.5900(2) 0.11672(10) 0.0295(4) Uani d . 1 . . C
    C18 0.09726(8) 0.5502(2) 0.30177(10) 0.0271(4) Uani d . 1 . . C
    C19 0.12770(9) 0.8660(3) 0.40173(12) 0.0383(5) Uani d . 1 . . C
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C17 . 1.283(2) yes
    O1 H1 . 0.8200 ?
    O2 C17 . 1.215(2) yes
    O3 C18 . 1.216(2) yes
    O4 C18 . 1.293(2) yes
    O4 H4 . 0.8200 ?
    O5 C19 . 1.207(2) yes
    O6 C19 . 1.304(2) yes
    O6 H6 . 0.8200 ?
    N1 C2 . 1.324(3) yes
    N1 C3 . 1.329(3) yes
    N2 C9 . 1.328(3) yes
    N2 C8 . 1.332(3) yes
    C1 C2 . 1.367(3) ?
    C1 C5 . 1.394(3) ?
    C1 H1A . 0.9300 ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.373(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.388(3) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.488(2) ?
    C6 C7 . 1.379(3) ?
    C6 C10 . 1.386(3) ?
    C7 C8 . 1.380(3) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.368(3) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C16 . 1.391(3) ?
    C11 C12 . 1.400(2) ?
    C11 C17 . 1.497(2) ?
    C12 C13 . 1.401(3) ?
    C12 C18 . 1.513(2) ?
    C13 C14 . 1.392(3) ?
    C13 C19 . 1.494(3) ?
    C14 C15 . 1.368(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.373(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C17 O1 H1 . . 109.5 ?
    C18 O4 H4 . . 109.5 ?
    C19 O6 H6 . . 109.5 ?
    C2 N1 C3 . . 121.52(17) yes
    C9 N2 C8 . . 117.55(16) yes
    C2 C1 C5 . . 119.9(2) ?
    C2 C1 H1A . . 120.1 ?
    C5 C1 H1A . . 120.1 ?
    N1 C2 C1 . . 120.6(2) ?
    N1 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    N1 C3 C4 . . 120.7(2) ?
    N1 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 119.5(2) ?
    C3 C4 H4A . . 120.2 ?
    C5 C4 H4A . . 120.2 ?
    C4 C5 C1 . . 117.74(18) ?
    C4 C5 C6 . . 121.27(18) ?
    C1 C5 C6 . . 120.88(18) ?
    C7 C6 C10 . . 117.54(17) ?
    C7 C6 C5 . . 122.16(17) ?
    C10 C6 C5 . . 120.23(17) ?
    C6 C7 C8 . . 119.23(18) ?
    C6 C7 H7 . . 120.4 ?
    C8 C7 H7 . . 120.4 ?
    N2 C8 C7 . . 122.98(19) ?
    N2 C8 H8 . . 118.5 ?
    C7 C8 H8 . . 118.5 ?
    N2 C9 C10 . . 123.22(19) ?
    N2 C9 H9 . . 118.4 ?
    C10 C9 H9 . . 118.4 ?
    C9 C10 C6 . . 119.48(19) ?
    C9 C10 H10 . . 120.3 ?
    C6 C10 H10 . . 120.3 ?
    C16 C11 C12 . . 119.87(16) ?
    C16 C11 C17 . . 119.18(15) ?
    C12 C11 C17 . . 120.91(15) ?
    C11 C12 C13 . . 118.77(16) ?
    C11 C12 C18 . . 122.43(15) ?
    C13 C12 C18 . . 118.52(15) ?
    C14 C13 C12 . . 119.77(16) ?
    C14 C13 C19 . . 116.25(16) ?
    C12 C13 C19 . . 123.98(17) ?
    C15 C14 C13 . . 120.94(18) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C14 C15 C16 . . 119.84(18) ?
    C14 C15 H15 . . 120.1 ?
    C16 C15 H15 . . 120.1 ?
    C15 C16 C11 . . 120.78(17) ?
    C15 C16 H16 . . 119.6 ?
    C11 C16 H16 . . 119.6 ?
    O2 C17 O1 . . 124.27(17) yes
    O2 C17 C11 . . 120.95(15) ?
    O1 C17 C11 . . 114.73(15) ?
    O3 C18 O4 . . 121.32(16) yes
    O3 C18 C12 . . 119.05(16) ?
    O4 C18 C12 . . 119.34(15) ?
    O5 C19 O6 . . 123.64(18) yes
    O5 C19 C13 . . 121.52(19) ?
    O6 C19 C13 . . 114.83(16) ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 C2 C1 . . . . -1.4(3) ?
    C5 C1 C2 N1 . . . . -1.0(3) ?
    C2 N1 C3 C4 . . . . 1.8(3) ?
    N1 C3 C4 C5 . . . . 0.1(3) ?
    C3 C4 C5 C1 . . . . -2.4(3) ?
    C3 C4 C5 C6 . . . . 174.0(2) ?
    C2 C1 C5 C4 . . . . 2.8(3) ?
    C2 C1 C5 C6 . . . . -173.5(2) ?
    C4 C5 C6 C7 . . . . 30.5(3) ?
    C1 C5 C6 C7 . . . . -153.3(2) ?
    C4 C5 C6 C10 . . . . -146.3(2) ?
    C1 C5 C6 C10 . . . . 29.9(3) ?
    C10 C6 C7 C8 . . . . -0.5(3) ?
    C5 C6 C7 C8 . . . . -177.3(2) ?
    C9 N2 C8 C7 . . . . -0.4(3) ?
    C6 C7 C8 N2 . . . . 0.5(3) ?
    C8 N2 C9 C10 . . . . 0.2(3) ?
    N2 C9 C10 C6 . . . . -0.2(4) ?
    C7 C6 C10 C9 . . . . 0.3(3) ?
    C5 C6 C10 C9 . . . . 177.2(2) ?
    C16 C11 C12 C13 . . . . -1.8(3) ?
    C17 C11 C12 C13 . . . . 175.89(16) ?
    C16 C11 C12 C18 . . . . -175.62(17) ?
    C17 C11 C12 C18 . . . . 2.1(3) ?
    C11 C12 C13 C14 . . . . 0.9(3) ?
    C18 C12 C13 C14 . . . . 174.98(17) ?
    C11 C12 C13 C19 . . . . -178.33(17) ?
    C18 C12 C13 C19 . . . . -4.3(3) ?
    C12 C13 C14 C15 . . . . 0.8(3) ?
    C19 C13 C14 C15 . . . . -179.93(19) ?
    C13 C14 C15 C16 . . . . -1.6(3) ?
    C14 C15 C16 C11 . . . . 0.7(3) ?
    C12 C11 C16 C15 . . . . 1.0(3) ?
    C17 C11 C16 C15 . . . . -176.70(18) ?
    C16 C11 C17 O2 . . . . -177.48(18) ?
    C12 C11 C17 O2 . . . . 4.8(3) ?
    C16 C11 C17 O1 . . . . 4.9(3) ?
    C12 C11 C17 O1 . . . . -172.78(17) ?
    C11 C12 C18 O3 . . . . 99.1(2) ?
    C13 C12 C18 O3 . . . . -74.7(2) ?
    C11 C12 C18 O4 . . . . -86.9(2) ?
    C13 C12 C18 O4 . . . . 99.23(19) ?
    C14 C13 C19 O5 . . . . -32.6(3) ?
    C12 C13 C19 O5 . . . . 146.7(2) ?
    C14 C13 C19 O6 . . . . 146.48(19) ?
    C12 C13 C19 O6 . . . . -34.2(3) ?
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
    O6 H6 N2 6_566 0.82 1.79 2.612(2) 175 yes
    O1 H1 O1 5_565 0.82 1.72 2.464(2) 150 yes
    O4 H4 O4 2_555 0.82 1.67 2.454(2) 159 yes
    C15 H15 O2 1_565 0.93 2.30 3.194(3) 160 yes
    C3 H3 O3 7_556 0.93 2.50 3.129(3) 125 yes
    C8 H8 O2 ? 0.93 2.56 3.250(4) 131 yes
    C8 H8 O1 5_565 0.93 2.57 3.410(3) 151 yes
    C9 H9 O3 4_545 0.93 2.47 3.120(4) 127 yes
data_global
_journal_date_recd_electronic     2005-08-12
_journal_date_accepted     2005-08-18
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     o574
_journal_page_last     o576
_journal_paper_category     FO
_journal_coeditor_code     JZ1752
_publ_contact_author_name     ' Prof. Dr Miao Du'
_publ_contact_author_address
; College of Chemistry and Life Sciences
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
_publ_contact_author_email     dumiao@public.tpt.tj.cn
_publ_section_title
;
Cocrystallization of hemimellitic acid with 4,4'-bipyridine forming a
pillar-layered hydrogen-bonded network
;
loop_
    _publ_author_name
    _publ_author_address
    'Miao Du'
;
College of Chemistry and Life Sciences
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
    'Zhi-Hui Zhang'
;
College of Chemistry and Life Sciences
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
    'Yan-Ping You'
;
College of Chemistry and Life Sciences
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
