##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(4-Hydroxyphenyl)acetic acid--4,4'-bipyridine (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H8 N2, C8 H8 O3'
_chemical_formula_sum     'C18 H16 N2 O3'
_chemical_formula_iupac     'C10 H8 N2, C8 H8 O3'
_chemical_formula_weight     308.33
_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     25.3578(6)
_cell_length_b     10.2305(2)
_cell_length_c     14.2546(4)
_cell_angle_alpha     90.00
_cell_angle_beta     122.321(2)
_cell_angle_gamma     90.00
_cell_volume     3125.03(15)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3274
_cell_measurement_theta_min     1.9
_cell_measurement_theta_max     27.7
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.245
_exptl_crystal_size_mid     0.144
_exptl_crystal_size_min     0.064
_exptl_crystal_density_diffrn     1.311
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1296
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.984
_exptl_absorpt_correction_T_max     0.994
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 area-detector'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     24334
_diffrn_reflns_av_R_equivalents     0.043
_diffrn_reflns_av_sigmaI/netI     0.029
_diffrn_reflns_theta_min     1.9
_diffrn_reflns_theta_max     27.7
_diffrn_reflns_theta_full     27.7
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -32
_diffrn_reflns_limit_h_max     32
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 >
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     3650
_reflns_number_gt     2128
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.085
_refine_ls_R_factor_gt     0.047
_refine_ls_wR_factor_gt     0.120
_refine_ls_wR_factor_ref     0.139
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.06
_refine_ls_number_reflns     3650
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0650P)²+0.2994P] 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     0.15
_refine_diff_density_min     -0.16
_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     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (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 0.54789(7) 0.32235(16) 0.04851(15) 0.0637(5) Uani d . 1 . .
    C C2 0.54036(7) 0.28856(15) 0.13430(17) 0.0674(5) Uani d . 1 . .
    H H2A 0.5211 0.2098 0.1308 0.081 Uiso calc R 1 . .
    C C3 0.56064(8) 0.36856(15) 0.22505(16) 0.0624(5) Uani d . 1 . .
    H H3A 0.5554 0.3431 0.2822 0.075 Uiso calc R 1 . .
    C C4 0.58890(7) 0.48680(14) 0.23132(14) 0.0540(4) Uani d . 1 . .
    C C5 0.59659(7) 0.52233(14) 0.14611(14) 0.0555(4) Uani d . 1 . .
    H H5A 0.6156 0.6014 0.1494 0.067 Uiso calc R 1 . .
    C C6 0.57611(8) 0.44072(16) 0.05596(15) 0.0618(4) Uani d . 1 . .
    H H6A 0.5814 0.4660 -0.0011 0.074 Uiso calc R 1 . .
    C C7 0.52498(9) 0.23409(19) -0.05088(17) 0.0888(7) Uani d . 1 . .
    H H7A 0.4826 0.2074 -0.0765 0.107 Uiso calc R 1 . .
    H H7B 0.5235 0.2843 -0.1100 0.107 Uiso calc R 1 . .
    C C8 0.56331(9) 0.11343(17) -0.03167(16) 0.0686(5) Uani d . 1 . .
    C C9 0.27818(7) 0.03470(14) 0.13722(13) 0.0531(4) Uani d . 1 . .
    C C10 0.24522(9) -0.08224(16) 0.10478(15) 0.0668(5) Uani d . 1 . .
    H H10A 0.2019 -0.0821 0.0680 0.080 Uiso calc R 1 . .
    C C11 0.27717(11) -0.19771(17) 0.12756(17) 0.0777(6) Uani d . 1 . .
    H H11A 0.2543 -0.2749 0.1067 0.093 Uiso calc R 1 . .
    C C12 0.37044(10) -0.09378(19) 0.20793(17) 0.0780(6) Uani d . 1 . .
    H H12A 0.4136 -0.0968 0.2423 0.094 Uiso calc R 1 . .
    C C13 0.34242(8) 0.02609(17) 0.19086(15) 0.0669(5) Uani d . 1 . .
    H H13A 0.3666 0.1015 0.2153 0.080 Uiso calc R 1 . .
    C C14 0.24634(7) 0.16282(14) 0.11616(13) 0.0510(4) Uani d . 1 . .
    C C15 0.18450(8) 0.17940(15) 0.03144(14) 0.0600(4) Uani d . 1 . .
    H H15A 0.1621 0.1097 -0.0147 0.072 Uiso calc R 1 . .
    C C16 0.15638(8) 0.29964(16) 0.01587(15) 0.0656(5) Uani d . 1 . .
    H H16A 0.1144 0.3078 -0.0394 0.079 Uiso calc R 1 . .
    C C17 0.24598(9) 0.38940(16) 0.15596(15) 0.0657(5) Uani d . 1 . .
    H H17A 0.2678 0.4619 0.1983 0.079 Uiso calc R 1 . .
    C C18 0.27730(8) 0.27190(15) 0.17954(14) 0.0616(4) Uani d . 1 . .
    H H18A 0.3188 0.2660 0.2375 0.074 Uiso calc R 1 . .
    N N1 0.33881(9) -0.20646(15) 0.17762(14) 0.0809(5) Uani d . 1 . .
    N N2 0.18645(7) 0.40479(13) 0.07623(12) 0.0636(4) Uani d . 1 . .
    O O1 0.54120(7) 0.01483(14) -0.08188(14) 0.1052(6) Uani d . 1 . .
    O O2 0.62304(6) 0.12757(12) 0.04163(12) 0.0847(5) Uani d . 1 . .
    H H2O 0.6456(10) 0.046(2) 0.0532(17) 0.102 Uiso d . 1 . .
    O O3 0.60808(6) 0.56199(12) 0.32305(11) 0.0733(4) Uani d . 1 . .
    H H3O 0.6234(10) 0.635(2) 0.3150(17) 0.088 Uiso d . 1 . .
_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
    C1 C2 . 1.379(3) ?
    C1 C6 . 1.382(2) ?
    C1 C7 . 1.510(2) ?
    C2 C3 . 1.377(2) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.384(2) ?
    C3 H3A . 0.9300 ?
    C4 O3 . 1.3631(19) ?
    C4 C5 . 1.378(2) ?
    C5 C6 . 1.380(2) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.503(2) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 O1 . 1.190(2) ?
    C8 O2 . 1.309(2) ?
    C9 C13 . 1.384(2) ?
    C9 C10 . 1.389(2) ?
    C9 C14 . 1.484(2) ?
    C10 C11 . 1.370(2) ?
    C10 H10A . 0.9300 ?
    C11 N1 . 1.330(2) ?
    C11 H11A . 0.9300 ?
    C12 N1 . 1.337(3) ?
    C12 C13 . 1.372(2) ?
    C12 H12A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C14 C18 . 1.385(2) ?
    C14 C15 . 1.386(2) ?
    C15 C16 . 1.379(2) ?
    C15 H15A . 0.9300 ?
    C16 N2 . 1.333(2) ?
    C16 H16A . 0.9300 ?
    C17 N2 . 1.327(2) ?
    C17 C18 . 1.380(2) ?
    C17 H17A . 0.9300 ?
    C18 H18A . 0.9300 ?
    O2 H2O . 0.97(2) ?
    O3 H3O . 0.87(2) ?
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
    C2 C1 C6 . . 117.60(16) ?
    C2 C1 C7 . . 121.07(18) ?
    C6 C1 C7 . . 121.33(19) ?
    C3 C2 C1 . . 121.66(16) ?
    C3 C2 H2A . . 119.2 ?
    C1 C2 H2A . . 119.2 ?
    C2 C3 C4 . . 120.03(17) ?
    C2 C3 H3A . . 120.0 ?
    C4 C3 H3A . . 120.0 ?
    O3 C4 C5 . . 123.41(14) ?
    O3 C4 C3 . . 117.52(16) ?
    C5 C4 C3 . . 119.07(15) ?
    C4 C5 C6 . . 120.07(14) ?
    C4 C5 H5A . . 120.0 ?
    C6 C5 H5A . . 120.0 ?
    C5 C6 C1 . . 121.56(17) ?
    C5 C6 H6A . . 119.2 ?
    C1 C6 H6A . . 119.2 ?
    C8 C7 C1 . . 115.68(15) ?
    C8 C7 H7A . . 108.4 ?
    C1 C7 H7A . . 108.4 ?
    C8 C7 H7B . . 108.4 ?
    C1 C7 H7B . . 108.4 ?
    H7A C7 H7B . . 107.4 ?
    O1 C8 O2 . . 123.08(17) ?
    O1 C8 C7 . . 122.41(17) ?
    O2 C8 C7 . . 114.47(15) ?
    C13 C9 C10 . . 116.75(15) ?
    C13 C9 C14 . . 121.38(14) ?
    C10 C9 C14 . . 121.87(15) ?
    C11 C10 C9 . . 119.30(18) ?
    C11 C10 H10A . . 120.3 ?
    C9 C10 H10A . . 120.3 ?
    N1 C11 C10 . . 124.19(18) ?
    N1 C11 H11A . . 117.9 ?
    C10 C11 H11A . . 117.9 ?
    N1 C12 C13 . . 123.29(19) ?
    N1 C12 H12A . . 118.4 ?
    C13 C12 H12A . . 118.4 ?
    C12 C13 C9 . . 119.99(17) ?
    C12 C13 H13A . . 120.0 ?
    C9 C13 H13A . . 120.0 ?
    C18 C14 C15 . . 116.89(14) ?
    C18 C14 C9 . . 121.49(14) ?
    C15 C14 C9 . . 121.61(14) ?
    C16 C15 C14 . . 119.74(16) ?
    C16 C15 H15A . . 120.1 ?
    C14 C15 H15A . . 120.1 ?
    N2 C16 C15 . . 123.21(16) ?
    N2 C16 H16A . . 118.4 ?
    C15 C16 H16A . . 118.4 ?
    N2 C17 C18 . . 123.72(16) ?
    N2 C17 H17A . . 118.1 ?
    C18 C17 H17A . . 118.1 ?
    C17 C18 C14 . . 119.42(16) ?
    C17 C18 H18A . . 120.3 ?
    C14 C18 H18A . . 120.3 ?
    C11 N1 C12 . . 116.44(15) ?
    C17 N2 C16 . . 116.96(14) ?
    C8 O2 H2O . . 111.5(12) ?
    C4 O3 H3O . . 108.1(14) ?
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
    C6 C1 C2 C3 . . . . -0.7(2) ?
    C7 C1 C2 C3 . . . . -179.55(15) ?
    C1 C2 C3 C4 . . . . 0.6(2) ?
    C2 C3 C4 O3 . . . . -179.97(15) ?
    C2 C3 C4 C5 . . . . -0.3(2) ?
    O3 C4 C5 C6 . . . . 179.78(14) ?
    C3 C4 C5 C6 . . . . 0.2(2) ?
    C4 C5 C6 C1 . . . . -0.2(2) ?
    C2 C1 C6 C5 . . . . 0.5(2) ?
    C7 C1 C6 C5 . . . . 179.37(15) ?
    C2 C1 C7 C8 . . . . -74.3(2) ?
    C6 C1 C7 C8 . . . . 106.8(2) ?
    C1 C7 C8 O1 . . . . 150.2(2) ?
    C1 C7 C8 O2 . . . . -32.1(3) ?
    C13 C9 C10 C11 . . . . 0.4(3) ?
    C14 C9 C10 C11 . . . . -179.26(16) ?
    C9 C10 C11 N1 . . . . -1.5(3) ?
    N1 C12 C13 C9 . . . . -1.8(3) ?
    C10 C9 C13 C12 . . . . 1.1(3) ?
    C14 C9 C13 C12 . . . . -179.22(16) ?
    C13 C9 C14 C18 . . . . -23.0(2) ?
    C10 C9 C14 C18 . . . . 156.71(16) ?
    C13 C9 C14 C15 . . . . 156.28(16) ?
    C10 C9 C14 C15 . . . . -24.1(2) ?
    C18 C14 C15 C16 . . . . -1.8(2) ?
    C9 C14 C15 C16 . . . . 178.93(15) ?
    C14 C15 C16 N2 . . . . 2.6(3) ?
    N2 C17 C18 C14 . . . . 1.4(3) ?
    C15 C14 C18 C17 . . . . -0.1(2) ?
    C9 C14 C18 C17 . . . . 179.18(15) ?
    C10 C11 N1 C12 . . . . 0.9(3) ?
    C13 C12 N1 C11 . . . . 0.8(3) ?
    C18 C17 N2 C16 . . . . -0.7(3) ?
    C15 C16 N2 C17 . . . . -1.3(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
    O2 H2O N2 3_545 0.97(2) 1.71(2) 2.679(2) 179(2)
    O3 H3O N1 2_665 0.87(2) 1.86(2) 2.728(2) 171(2)
data_global
_journal_date_recd_electronic     2010-05-10
_journal_date_accepted     2010-05-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1455
_journal_page_last     o1455
_journal_paper_category     QO
_journal_coeditor_code     PV2281
_publ_contact_author_name     'Guo-Liang Zhao'
_publ_contact_author_address
;
  College of Chemistry and Life Sciences,
  Zhejiang Normal University,
  Jinhua, Zhejiang 321004,
  People's Republic of China
  Zhejiang Normal University Xingzhi College,
  Jinhua, Zhejiang 321004,
  People's Republic of China
;
_publ_contact_author_email     'sky53@zjnu.cn'
_publ_contact_author_fax     '86-579-82282595'
_publ_contact_author_phone     '86-579-82283925'
_publ_section_title
;
2-(4-Hydroxyphenyl)acetic acid--4,4'-bipyridine (1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Jian-Feng Liu'
;
  College of Chemistry and Life Sciences,
  Zhejiang Normal University,
  Jinhua 321004, Zhejiang,
  People's Republic of China
;
    'Guo-Liang Zhao'
;
  College of Chemistry and Life Sciences,
  Zhejiang Normal University,
  Jinhua 321004, Zhejiang,
  People's Republic of China
;
