#------------------------------------------------------------------------------
#$Date: 2015-09-27 04:13:45 +0300 (Sun, 27 Sep 2015) $
#$Revision: 158428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241160.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_2241160
loop_
_publ_author_name
'Paul, Rima'
'Bora, Sanchay Jyoti'
_publ_section_title
;
 Redetermined structure of 4,4'-bipyridine--1,4-phenylenediacetic acid
 (1:1) co-crystal
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o799
_journal_page_last               o800
_journal_paper_doi               10.1107/S2056989015017569
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H8 N2 , C10 H10 O4'
_chemical_formula_moiety         'C10 H8 N2 , C10 H10 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_name_systematic
;
4,4'-Bipyridine--1,4-phenylenediacetic 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           SHELXL-97
_cell_angle_alpha                99.508(6)
_cell_angle_beta                 94.297(6)
_cell_angle_gamma                97.643(7)
_cell_formula_units_Z            1
_cell_length_a                   4.5577(5)
_cell_length_b                   6.9806(8)
_cell_length_c                   13.7995(15)
_cell_measurement_temperature    296(2)
_cell_volume                     427.05(8)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
SMART (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8581
_diffrn_reflns_theta_full        29.84
_diffrn_reflns_theta_max         29.84
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.156
_refine_ls_extinction_coef       0.061(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.0515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                1876
_reflns_number_total             2405
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7506sup1.cif
_cod_data_source_block           I
_cod_database_code               2241160
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_occupancy
_atom_site_symmetry_multiplicity
O O1 0.8197(2) 0.45294(13) -0.18830(6) 0.0541(3) Uani d 1 1
C C1 0.7209(2) 0.60720(15) -0.21279(8) 0.0408(3) Uani d 1 1
C C2 0.5619(3) 0.71533(19) -0.13310(10) 0.0490(3) Uani d 1 1
C C3 0.7850(2) 0.86342(15) -0.06291(8) 0.0400(3) Uani d 1 1
C C4 0.9459(3) 0.80852(16) 0.01476(9) 0.0454(3) Uani d 1 1
C C5 0.8422(3) 1.05717(17) -0.07687(8) 0.0446(3) Uani d 1 1
O O2 0.7616(3) 0.66207(15) -0.28973(7) 0.0675(3) Uani d 1 1
N N1 0.8832(2) 0.73182(15) 0.32203(7) 0.0476(3) Uani d 1 1
C C6 0.8316(3) 0.67172(18) 0.40629(9) 0.0517(3) Uani d 1 1
C C7 0.6844(3) 0.77149(18) 0.47798(9) 0.0487(3) Uani d 1 1
C C8 0.5796(2) 0.94340(15) 0.46266(7) 0.0376(2) Uani d 1 1
C C10 0.7840(3) 0.8964(2) 0.30711(10) 0.0566(3) Uani d 1 1
C C9 0.6326(3) 1.00451(19) 0.37423(9) 0.0532(3) Uani d 1 1
H H9 0.927(5) 0.382(3) -0.2421(15) 0.104(7) Uiso d 1 1
H H3 0.908(3) 0.676(2) 0.0263(11) 0.061(4) Uiso d 1 1
H H4 0.731(3) 1.100(2) -0.1302(11) 0.055(4) Uiso d 1 1
H H6 0.660(3) 0.722(2) 0.5378(12) 0.067(4) Uiso d 1 1
H H1 0.462(4) 0.621(2) -0.0977(12) 0.065(4) Uiso d 1 1
H H8 0.822(4) 0.935(2) 0.2459(13) 0.073(5) Uiso d 1 1
H H7 0.560(4) 1.122(3) 0.3533(13) 0.081(5) Uiso d 1 1
H H2 0.412(4) 0.787(3) -0.1669(12) 0.071(5) Uiso d 1 1
H H5 0.902(4) 0.551(3) 0.4159(12) 0.071(4) Uiso d 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 H9 . . 112.6(12)
O2 C1 O1 . . 123.26(10)
O2 C1 C2 . . 123.39(11)
O1 C1 C2 . . 113.30(10)
C3 C2 C1 . . 109.58(9)
C3 C2 H1 . . 110.0(9)
C1 C2 H1 . . 108.9(10)
C3 C2 H2 . . 109.4(9)
C1 C2 H2 . . 107.7(9)
H1 C2 H2 . . 111.2(13)
C4 C3 C5 . . 118.28(11)
C4 C3 C2 . . 121.06(10)
C5 C3 C2 . . 120.61(10)
C5 C4 C3 2_775 . 120.99(10)
C5 C4 H3 2_775 . 119.3(9)
C3 C4 H3 . . 119.7(9)
C4 C5 C3 2_775 . 120.73(11)
C4 C5 H4 2_775 . 119.2(8)
C3 C5 H4 . . 120.1(8)
C6 N1 C10 . . 117.10(10)
N1 C6 C7 . . 123.47(11)
N1 C6 H5 . . 116.3(10)
C7 C6 H5 . . 120.2(10)
C6 C7 C8 . . 119.66(11)
C6 C7 H6 . . 119.0(10)
C8 C7 H6 . . 121.4(10)
C9 C8 C7 . . 116.53(10)
C9 C8 C8 . 2_676 121.59(12)
C7 C8 C8 . 2_676 121.88(12)
N1 C10 C9 . . 123.35(12)
N1 C10 H8 . . 115.3(10)
C9 C10 H8 . . 121.3(10)
C10 C9 C8 . . 119.89(11)
C10 C9 H7 . . 116.0(11)
C8 C9 H7 . . 124.1(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3051(13)
O1 H9 . 1.02(2)
C1 O2 . 1.2056(14)
C1 C2 . 1.5147(16)
C2 C3 . 1.5108(17)
C2 H1 . 0.970(16)
C2 H2 . 1.027(17)
C3 C4 . 1.3877(16)
C3 C5 . 1.3908(15)
C4 C5 2_775 1.3844(18)
C4 H3 . 0.961(15)
C5 C4 2_775 1.3844(18)
C5 H4 . 0.972(14)
N1 C6 . 1.3264(16)
N1 C10 . 1.3301(16)
C6 C7 . 1.3820(17)
C6 H5 . 0.964(17)
C7 C8 . 1.3906(15)
C7 H6 . 0.955(16)
C8 C9 . 1.3850(16)
C8 C8 2_676 1.486(2)
C10 C9 . 1.3810(17)
C10 H8 . 0.950(18)
C9 H7 . 0.998(19)
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 H9 N1 2_765 1.02(2) 1.62(2) 2.6373(13) 176(2)
C7 H6 O2 1_556 0.954(16) 2.504(16) 3.4196(16) 160.8(11)
C9 H7 O2 2_675 1.00(2) 2.45(2) 3.4205(18) 162.2(16)

_cod_database_fobs_code 2241160
