#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/44/2234403.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_2234403
loop_
_publ_author_name
'Moon, Suk-Hee'
'Park, Ki-Min'
_publ_section_title
;
 4,4'-Bipyridine--trans,trans-hexa-2,4-dienedioic acid (1/1)
;
_journal_coeditor_code           SJ5219
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1201
_journal_paper_doi               10.1107/S1600536812012391
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H8 N2, C6 H6 O4'
_chemical_formula_moiety         'C10 H8 N2, C6 H6 O4'
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_chemical_name_systematic
;
4,4'-Bipyridine--trans,trans-hexa-2,4-dienedioic acid (1/1)
;
_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           SHELXTL
_cell_angle_alpha                91.837(5)
_cell_angle_beta                 92.584(5)
_cell_angle_gamma                111.907(4)
_cell_formula_units_Z            1
_cell_length_a                   5.8481(5)
_cell_length_b                   7.6348(6)
_cell_length_c                   8.4677(7)
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.41
_cell_volume                     349.93(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5973
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0398
_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)+(0.0688P)²+0.0753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                1336
_reflns_number_total             1517
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5219.cif
_cod_data_source_block           I
_cod_database_code               2234403
_cod_database_fobs_code          2234403
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_symmetry_multiplicity
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_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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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
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_4
_geom_torsion
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)
