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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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 2.4.    #
#                                                                            #
# 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/  #
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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2009-08-13
_journal_date_accepted     2009-08-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     10
_journal_page_first     o2326
_journal_page_last     o2326
_journal_paper_category     QO
_journal_coeditor_code     BT5033
_publ_contact_author_name     'Professor Yun-Yu Liu'
_publ_contact_author_address
;
Department of Chemistry
Northeast Normal University
Changchun 130024,
People's Republic of China
;
_publ_contact_author_email     yunyuliu888@yahoo.com.cn
_publ_contact_author_fax     '?'
_publ_contact_author_phone     '?'
_publ_section_title
;
4,4'-Azinodibenzoic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Qun-Di Yu'
;
Food Science and Pharmacy College,
Zhejiang Ocean University,
Zhoushan 316000,
People's Republic of China
;
    'Yun-Yu Liu'
;
Department of Chemistry
Northeast Normal University
Changchun 130024,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,4'-Azinodibenzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 N2 O4'
_chemical_formula_sum     'C14 H10 N2 O4'
_chemical_formula_iupac     'C14 H10 N2 O4'
_chemical_formula_weight     270.16
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     3.772(2)
_cell_length_b     6.322(5)
_cell_length_c     12.692(3)
_cell_angle_alpha     79.323(5)
_cell_angle_beta     88.199(4)
_cell_angle_gamma     88.435(5)
_cell_volume     297.2(3)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     1351
_cell_measurement_theta_min     3.01
_cell_measurement_theta_max     28.96
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.509
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     140
_exptl_absorpt_coefficient_mu     0.113
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick 1996)'
_exptl_absorpt_correction_T_min     0.962
_exptl_absorpt_correction_T_max     0.971
_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 SMART APEX CCD area-detector'
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2173
_diffrn_reflns_av_R_equivalents     0.0170
_diffrn_reflns_av_sigmaI/netI     0.0467
_diffrn_reflns_theta_min     3.27
_diffrn_reflns_theta_max     28.96
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.858
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     1351
_reflns_number_gt     786
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0756
_refine_ls_R_factor_gt     0.0402
_refine_ls_wR_factor_gt     0.0917
_refine_ls_wR_factor_ref     0.1002
_refine_ls_goodness_of_fit_ref     0.855
_refine_ls_restrained_S_all     0.855
_refine_ls_number_reflns     1351
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^] where P=(Fo^2^+2Fc^2^)/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     0.194
_refine_diff_density_min     -0.186
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0030 0.0020
                         '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' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.0410(4) -0.0391(3) 0.23081(12) 0.0356(4) Uani d . 1 . .
    H H1 -0.0514 -0.1767 0.2450 0.043 Uiso calc R 1 . .
    C C2 0.1284(4) 0.0608(3) 0.31492(12) 0.0343(4) Uani d . 1 . .
    H H2 0.0924 -0.0090 0.3855 0.041 Uiso calc R 1 . .
    C C3 0.2692(4) 0.2646(2) 0.29319(11) 0.0292(4) Uani d . 1 . .
    C C4 0.3691(4) 0.3697(2) 0.38301(12) 0.0315(4) Uani d . 1 . .
    C C5 0.3203(4) 0.3700(2) 0.18790(12) 0.0337(4) Uani d . 1 . .
    H H5 0.4147 0.5070 0.1738 0.040 Uiso calc R 1 . .
    C C6 0.2312(4) 0.2720(3) 0.10404(12) 0.0355(4) Uani d . 1 . .
    H H6 0.2640 0.3426 0.0334 0.043 Uiso calc R 1 . .
    C C7 0.0913(4) 0.0659(2) 0.12647(12) 0.0315(4) Uani d . 1 . .
    N N1 -0.0103(4) -0.0518(2) 0.04644(9) 0.0372(4) Uani d . 1 . .
    O O1 0.2870(4) 0.2717(2) 0.47782(9) 0.0545(4) Uani d . 1 . .
    H H1A 0.3524 0.3417 0.5217 0.082 Uiso calc R 1 . .
    O O2 0.5255(3) 0.54435(18) 0.36449(9) 0.0453(4) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0452(10) 0.0306(9) 0.0329(9) -0.0099(7) -0.0026(7) -0.0095(7)
    C2 0.0438(10) 0.0360(9) 0.0243(8) -0.0081(8) -0.0014(7) -0.0072(7)
    C3 0.0321(9) 0.0322(8) 0.0261(8) -0.0037(7) -0.0030(6) -0.0115(7)
    C4 0.0377(9) 0.0334(9) 0.0253(8) -0.0060(7) -0.0040(6) -0.0092(7)
    C5 0.0436(10) 0.0295(8) 0.0299(9) -0.0082(7) -0.0009(7) -0.0092(7)
    C6 0.0465(10) 0.0376(9) 0.0240(8) -0.0067(7) -0.0030(7) -0.0084(7)
    C7 0.0333(9) 0.0349(9) 0.0299(9) -0.0023(7) -0.0048(7) -0.0144(7)
    N1 0.0471(8) 0.0382(8) 0.0300(7) -0.0081(7) -0.0058(7) -0.0143(6)
    O1 0.0875(10) 0.0544(8) 0.0254(6) -0.0314(7) -0.0023(6) -0.0128(6)
    O2 0.0674(8) 0.0397(7) 0.0321(7) -0.0215(6) -0.0027(6) -0.0119(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    C1 C7 . 1.377(2) ?
    C1 C2 . 1.389(2) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.384(2) ?
    C2 H2 . 0.9300 ?
    C3 C5 . 1.388(2) ?
    C3 C4 . 1.485(2) ?
    C4 O2 . 1.246(2) ?
    C4 O1 . 1.2800(18) ?
    C5 C6 . 1.381(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.396(2) ?
    C6 H6 . 0.9300 ?
    C7 N1 . 1.4327(19) ?
    N1 N1 2 1.239(2) ?
    O1 H1A . 0.8200 ?
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
    C7 C1 C2 . . 119.91(16) ?
    C7 C1 H1 . . 120.0 ?
    C2 C1 H1 . . 120.0 ?
    C3 C2 C1 . . 119.70(15) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    C2 C3 C5 . . 120.28(14) ?
    C2 C3 C4 . . 119.73(14) ?
    C5 C3 C4 . . 119.99(15) ?
    O2 C4 O1 . . 123.10(14) ?
    O2 C4 C3 . . 120.27(14) ?
    O1 C4 C3 . . 116.63(15) ?
    C6 C5 C3 . . 120.22(15) ?
    C6 C5 H5 . . 119.9 ?
    C3 C5 H5 . . 119.9 ?
    C5 C6 C7 . . 119.22(15) ?
    C5 C6 H6 . . 120.4 ?
    C7 C6 H6 . . 120.4 ?
    C1 C7 C6 . . 120.67(14) ?
    C1 C7 N1 . . 115.05(15) ?
    C6 C7 N1 . . 124.28(14) ?
    N1 N1 C7 2 . 114.04(17) ?
    C4 O1 H1A . . 109.5 ?
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
    O1 H1A O2 2_666 0.82 1.81 2.6181(17) 170.0