#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226261.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_2226261
loop_
_publ_author_name
'Liu, Jian-Feng'
'Zhao, Guo-Liang'
_publ_section_title
;
 2-(4-Hydroxyphenyl)acetic acid--4,4'-bipyridine (1/1)
;
_journal_coeditor_code           PV2281
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1455
_journal_paper_doi               10.1107/S1600536810018842
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H8 N2, C8 H8 O3'
_chemical_formula_moiety         'C10 H8 N2, C8 H8 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33
_chemical_name_systematic
;
2-(4-Hydroxyphenyl)acetic acid--4,4'-bipyridine (1/1)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.321(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.3578(6)
_cell_length_b                   10.2305(2)
_cell_length_c                   14.2546(4)
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      1.9
_cell_volume                     3125.03(15)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ & 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  0.043
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24334
_diffrn_reflns_theta_full        27.7
_diffrn_reflns_theta_max         27.7
_diffrn_reflns_theta_min         1.9
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.047
_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)+(0.0650P)²+0.2994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.120
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                2128
_reflns_number_total             3650
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2281.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226261
_cod_database_fobs_code          2226261
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'
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 . .
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
_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_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_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)
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656097
2 PubChem 139078994
