##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXTL
_chemical_name_systematic
;
4,4'-Bipyridine--trans,trans-hexa-2,4-dienedioic acid (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H8 N2, C6 H6 O4'
_chemical_formula_sum     'C16 H14 N2 O4'
_chemical_formula_iupac     'C10 H8 N2, C6 H6 O4'
_chemical_formula_weight     298.29
_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     5.8481(5)
_cell_length_b     7.6348(6)
_cell_length_c     8.4677(7)
_cell_angle_alpha     91.837(5)
_cell_angle_beta     92.584(5)
_cell_angle_gamma     111.907(4)
_cell_volume     349.93(5)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     4151
_cell_measurement_theta_min     2.41
_cell_measurement_theta_max     28.39
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.415
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     156
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9598
_exptl_absorpt_correction_T_max     0.9756
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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 APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5973
_diffrn_reflns_av_R_equivalents     0.0313
_diffrn_reflns_av_sigmaI/netI     0.0261
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_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 >
σ(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     1517
_reflns_number_gt     1336
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0438
_refine_ls_R_factor_gt     0.0398
_refine_ls_wR_factor_gt     0.1122
_refine_ls_wR_factor_ref     0.1164
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     1517
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0688P)²+0.0753P] 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     0.238
_refine_diff_density_min     -0.250
_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' 0.0033 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     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL and DIAMOND (Brandenburg, 1998)'
_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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.05949(18) 1.05053(14) 0.23387(13) 0.0414(3) Uani d . 1 1 . .
    H H1 0.184(4) 0.987(3) 0.271(3) 0.084(7) Uiso d . 1 1 . .
    O O2 0.37461(17) 1.23144(14) 0.09959(12) 0.0394(3) Uani d . 1 1 . .
    C C1 0.1653(2) 1.18769(18) 0.13952(14) 0.0285(3) Uani d . 1 1 . .
    C C2 -0.0033(2) 1.28402(18) 0.09016(15) 0.0299(3) Uani d . 1 1 . .
    H H2 -0.1740 1.2262 0.1077 0.036 Uiso calc R 1 1 . .
    C C3 0.0786(2) 1.44912(17) 0.02208(14) 0.0288(3) Uani d . 1 1 . .
    H H3 0.2485 1.5031 0.0013 0.035 Uiso calc R 1 1 . .
    N N1 0.3031(2) 0.85144(15) 0.34658(13) 0.0331(3) Uani d . 1 1 . .
    C C4 0.2266(3) 0.7745(2) 0.48325(17) 0.0374(3) Uani d . 1 1 . .
    H H4 0.1161 0.8150 0.5389 0.045 Uiso calc R 1 1 . .
    C C5 0.3007(3) 0.6385(2) 0.54775(16) 0.0350(3) Uani d . 1 1 . .
    H H5 0.2419 0.5882 0.6458 0.042 Uiso calc R 1 1 . .
    C C6 0.4615(2) 0.57572(16) 0.46878(14) 0.0262(3) Uani d . 1 1 . .
    C C7 0.5464(3) 0.6613(2) 0.32875(16) 0.0351(3) Uani d . 1 1 . .
    H H7 0.6611 0.6270 0.2719 0.042 Uiso calc R 1 1 . .
    C C8 0.4627(3) 0.79683(19) 0.27252(16) 0.0362(3) Uani d . 1 1 . .
    H H8 0.5224 0.8532 0.1766 0.043 Uiso calc R 1 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
    O1 0.0346(5) 0.0401(6) 0.0593(7) 0.0222(4) 0.0127(5) 0.0259(5)
    O2 0.0314(5) 0.0469(6) 0.0488(6) 0.0229(4) 0.0109(4) 0.0174(5)
    C1 0.0283(6) 0.0293(6) 0.0319(6) 0.0148(5) 0.0032(5) 0.0056(5)
    C2 0.0260(6) 0.0327(7) 0.0355(6) 0.0156(5) 0.0037(5) 0.0077(5)
    C3 0.0270(6) 0.0324(6) 0.0316(6) 0.0156(5) 0.0042(5) 0.0067(5)
    N1 0.0322(6) 0.0287(6) 0.0407(6) 0.0141(5) -0.0015(5) 0.0074(4)
    C4 0.0397(7) 0.0387(7) 0.0434(7) 0.0248(6) 0.0073(6) 0.0078(6)
    C5 0.0406(7) 0.0390(7) 0.0339(7) 0.0234(6) 0.0080(5) 0.0106(5)
    C6 0.0253(6) 0.0255(6) 0.0291(6) 0.0110(5) -0.0015(5) 0.0030(5)
    C7 0.0372(7) 0.0377(7) 0.0373(7) 0.0205(6) 0.0084(5) 0.0114(6)
    C8 0.0395(7) 0.0351(7) 0.0382(7) 0.0176(6) 0.0055(6) 0.0135(6)
_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
    O1 C1 . 1.3162(15) ?
    O1 H1 . 1.06(2) ?
    O2 C1 . 1.2096(16) ?
    C1 C2 . 1.4873(16) ?
    C2 C3 . 1.3310(18) ?
    C2 H2 . 0.9500 ?
    C3 C3 2_585 1.452(2) ?
    C3 H3 . 0.9500 ?
    N1 C8 . 1.3286(17) ?
    N1 C4 . 1.3337(18) ?
    C4 C5 . 1.3839(18) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3907(17) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.3929(18) ?
    C6 C6 2_666 1.492(2) ?
    C7 C8 . 1.3872(17) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
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
    C1 O1 H1 . . 110.3(13) ?
    O2 C1 O1 . . 124.23(11) ?
    O2 C1 C2 . . 124.24(11) ?
    O1 C1 C2 . . 111.52(10) ?
    C3 C2 C1 . . 121.76(12) ?
    C3 C2 H2 . . 119.1 ?
    C1 C2 H2 . . 119.1 ?
    C2 C3 C3 . 2_585 123.31(15) ?
    C2 C3 H3 . . 118.3 ?
    C3 C3 H3 2_585 . 118.3 ?
    C8 N1 C4 . . 117.62(11) ?
    N1 C4 C5 . . 123.05(12) ?
    N1 C4 H4 . . 118.5 ?
    C5 C4 H4 . . 118.5 ?
    C4 C5 C6 . . 119.86(12) ?
    C4 C5 H5 . . 120.1 ?
    C6 C5 H5 . . 120.1 ?
    C5 C6 C7 . . 116.57(11) ?
    C5 C6 C6 . 2_666 121.53(14) ?
    C7 C6 C6 . 2_666 121.90(14) ?
    C8 C7 C6 . . 119.78(12) ?
    C8 C7 H7 . . 120.1 ?
    C6 C7 H7 . . 120.1 ?
    N1 C8 C7 . . 123.05(12) ?
    N1 C8 H8 . . 118.5 ?
    C7 C8 H8 . . 118.5 ?
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
    O2 C1 C2 C3 . . . . -13.0(2) ?
    O1 C1 C2 C3 . . . . 166.14(12) ?
    C1 C2 C3 C3 . . . 2_585 -177.53(14) ?
    C8 N1 C4 C5 . . . . -1.8(2) ?
    N1 C4 C5 C6 . . . . -0.3(2) ?
    C4 C5 C6 C7 . . . . 2.3(2) ?
    C4 C5 C6 C6 . . . 2_666 -177.69(14) ?
    C5 C6 C7 C8 . . . . -2.2(2) ?
    C6 C6 C7 C8 2_666 . . . 177.72(14) ?
    C4 N1 C8 C7 . . . . 1.8(2) ?
    C6 C7 C8 N1 . . . . 0.2(2) ?
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
    O1 H1 N1 . 1.06(2) 1.58(2) 2.6148(14) 164(2) y
    C2 H2 O2 1_455 0.95 2.65 3.5130(15) 150.9 y
    C3 H3 O2 2_685 0.95 2.58 3.4457(16) 152.1 y
    C4 H4 O1 2_576 0.95 2.58 3.4848(17) 159.7 y
    C8 H8 O2 2_675 0.95 2.56 3.3555(17) 141.0 y
_iucr_refine_instructions_details
;
TITL BDDCAbpy in P-1
CELL 0.71073   5.8481   7.6348   8.4677  91.837  92.584 111.907
ZERR    1.00   0.0005   0.0006   0.0007   0.005   0.005   0.004
LATT 1
SFAC C  H  N  O
UNIT 16  14  2  4
SIZE 0.24 0.26 0.40
TEMP -100
omit -4 54
L.S. 4
ACTA
mpla 5 o1 o2 c1 c2 c3
mpla 6 n1 c4 c5 c6 c7 c8
eqiv $1 -1+x, y, z
eqiv $2 1-x, 3-y, -z
eqiv $3 -x, 2-y, 1-z
eqiv $4 1-x, 2-y, -z
HTAB O1 N1
HTAB C2 O2_$1
HTAB C3 O2_$2
HTAB C4 O1_$3
HTAB C8 O2_$4
BOND $H
CONF
FMAP 2
PLAN 20
WGHT    0.068800    0.075300
FVAR       0.42064
O1    4    0.059489    1.050533    0.233873    11.00000    0.03455    0.04009 =
         0.05931    0.02594    0.01270    0.02216
H1    2    0.184324    0.987159    0.270801    11.00000    0.08359
O2    4    0.374611    1.231443    0.099588    11.00000    0.03139    0.04690 =
         0.04876    0.01739    0.01093    0.02286
C1    1    0.165337    1.187687    0.139523    11.00000    0.02830    0.02932 =
         0.03187    0.00563    0.00324    0.01476
C2    1   -0.003297    1.284024    0.090161    11.00000    0.02596    0.03270 =
         0.03548    0.00769    0.00366    0.01560
AFIX  43
H2    2   -0.174028    1.226177    0.107689    11.00000   -1.20000
AFIX   0
C3    1    0.078617    1.449124    0.022083    11.00000    0.02698    0.03237 =
         0.03159    0.00668    0.00419    0.01561
AFIX  43
H3    2    0.248488    1.503131    0.001333    11.00000   -1.20000
AFIX   0
N1    3    0.303100    0.851443    0.346576    11.00000    0.03221    0.02867 =
         0.04073    0.00740   -0.00148    0.01410
C4    1    0.226598    0.774534    0.483255    11.00000    0.03973    0.03874 =
         0.04342    0.00785    0.00729    0.02475
AFIX  43
H4    2    0.116071    0.814983    0.538927    11.00000   -1.20000
AFIX   0
C5    1    0.300740    0.638541    0.547755    11.00000    0.04059    0.03898 =
         0.03387    0.01057    0.00803    0.02335
AFIX  43
H5    2    0.241918    0.588202    0.645775    11.00000   -1.20000
AFIX   0
C6    1    0.461533    0.575724    0.468782    11.00000    0.02527    0.02547 =
         0.02909    0.00305   -0.00155    0.01103
C7    1    0.546358    0.661324    0.328746    11.00000    0.03716    0.03774 =
         0.03733    0.01141    0.00838    0.02052
AFIX  43
H7    2    0.661103    0.627022    0.271930    11.00000   -1.20000
AFIX   0
C8    1    0.462733    0.796830    0.272519    11.00000    0.03945    0.03509 =
         0.03820    0.01351    0.00547    0.01759
AFIX  43
H8    2    0.522380    0.853197    0.176600    11.00000   -1.20000
HKLF 4
REM  BDDCAbpy in P-1
REM R1 =  0.0398 for   1336 Fo > 4sig(Fo)  and  0.0438 for all   1517 data
REM    104 parameters refined using      0 restraints
END
;
data_global
_journal_date_recd_electronic     2012-03-20
_journal_date_accepted     2012-03-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1201
_journal_page_last     o1201
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812012391
_journal_coeditor_code     SJ5219
_publ_contact_author_name     'Ki-Min Park'
_publ_contact_author_address
;
Department of Chemistry
Gyeongsang National University
Jinju 660-701
Republic of Korea
;
_publ_contact_author_email     kmpark@gnu.ac.kr
_publ_contact_author_fax     +82-55-753-7614
_publ_contact_author_phone     +82-55-772-1483
_publ_section_title
;
4,4'-Bipyridine--trans,trans-hexa-2,4-dienedioic acid (1/1)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Moon, Suk-Hee' .
;
Department of Food and Nutrition, Kyungnam College of Information and
 Technology,
Busan 617-701, Republic of Korea
;
    'Park, Ki-Min' .
;
Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang
 National University,
 Jinju 660-701, Republic of Korea
;
