#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225821.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_2225821
loop_
_publ_author_name
'Bu, Feng-Quan'
'Wu, Ying'
'Ye, Ling'
'Yan, Peng'
_publ_section_title
;
 4,4'-Bipyridine--2,2'-(1,2-phenylenedioxy)diacetic acid--water (1/1/1)
;
_journal_coeditor_code           DN2556
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1129
_journal_paper_doi               10.1107/S1600536810013905
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H8 N2, C10 H10 O6, H2 O'
_chemical_formula_moiety         'C10 H8 N2, C10 H10 O6, H2 O'
_chemical_formula_sum            'C20 H20 N2 O7'
_chemical_formula_weight         400.38
_chemical_name_systematic
;
4,4'-Bipyridine--2,2'-(1,2-phenylenedioxy)diacetic acid--water (1/1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.81(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.566(5)
_cell_length_b                   9.712(5)
_cell_length_c                   16.810(7)
_cell_measurement_reflns_used    11161
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.00
_cell_volume                     1888.1(15)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996),  ORTEP-3 for Windows (Farrugia,
1997)
and SHELXTL (Sheldrick, 2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18105
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0389
_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)+(0.0647P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2654
_reflns_number_total             4306
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2556.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_cell_volume        1888.2(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225821
_cod_database_fobs_code          2225821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N1 0.60888(10) 0.06435(13) 0.44070(7) 0.0574(3) Uani d . 1 . .
C C1 0.59235(13) -0.04189(17) 0.39244(9) 0.0616(4) Uani d . 1 . .
H H1 0.5467 -0.0293 0.3470 0.074 Uiso calc R 1 . .
C C2 0.63933(12) -0.16976(16) 0.40627(8) 0.0588(4) Uani d . 1 . .
H H2 0.6265 -0.2406 0.3700 0.071 Uiso calc R 1 . .
C C3 0.70588(11) -0.19349(14) 0.47429(8) 0.0462(3) Uani d . 1 . .
C C4 0.72238(12) -0.08127(15) 0.52468(9) 0.0574(4) Uani d . 1 . .
H H4 0.7662 -0.0910 0.5712 0.069 Uiso calc R 1 . .
C C5 0.67402(13) 0.04364(16) 0.50574(9) 0.0613(4) Uani d . 1 . .
H H5 0.6873 0.1175 0.5399 0.074 Uiso calc R 1 . .
C C6 0.75714(11) -0.33068(14) 0.49263(8) 0.0460(3) Uani d . 1 . .
C C7 0.72463(14) -0.44768(16) 0.45093(9) 0.0662(4) Uani d . 1 . .
H H7 0.6697 -0.4416 0.4101 0.079 Uiso calc R 1 . .
C C8 0.77316(14) -0.57246(17) 0.46966(10) 0.0672(4) Uani d . 1 . .
H H8 0.7498 -0.6493 0.4406 0.081 Uiso calc R 1 . .
C C9 0.88302(13) -0.47824(16) 0.56821(9) 0.0609(4) Uani d . 1 . .
H H9 0.9375 -0.4879 0.6091 0.073 Uiso calc R 1 . .
C C10 0.83819(12) -0.34962(15) 0.55282(9) 0.0579(4) Uani d . 1 . .
H H10 0.8626 -0.2748 0.5832 0.069 Uiso calc R 1 . .
C C11 0.27722(11) 0.59624(14) 0.26783(7) 0.0458(3) Uani d . 1 . .
C C12 0.32396(13) 0.71838(15) 0.29545(8) 0.0554(4) Uani d . 1 . .
H H12 0.3895 0.7167 0.3282 0.066 Uiso calc R 1 . .
C C13 0.27396(13) 0.84376(16) 0.27477(9) 0.0597(4) Uani d . 1 . .
H H13 0.3061 0.9256 0.2935 0.072 Uiso calc R 1 . .
C C14 0.17787(14) 0.84657(15) 0.22704(9) 0.0594(4) Uani d . 1 . .
H H14 0.1442 0.9305 0.2135 0.071 Uiso calc R 1 . .
C C15 0.12991(12) 0.72505(14) 0.19859(9) 0.0561(4) Uani d . 1 . .
H H15 0.0644 0.7282 0.1659 0.067 Uiso calc R 1 . .
C C16 0.17855(11) 0.59898(13) 0.21839(8) 0.0460(3) Uani d . 1 . .
C C17 0.04541(11) 0.47710(14) 0.13642(8) 0.0495(3) Uani d . 1 . .
H H17A 0.0694 0.5276 0.0897 0.059 Uiso calc R 1 . .
H H17B -0.0208 0.5239 0.1587 0.059 Uiso calc R 1 . .
C C18 0.01249(11) 0.33352(14) 0.11347(8) 0.0479(3) Uani d . 1 . .
C C19 0.41863(12) 0.46231(15) 0.33609(8) 0.0542(4) Uani d . 1 . .
H H19A 0.4001 0.5044 0.3867 0.065 Uiso calc R 1 . .
H H19B 0.4818 0.5135 0.3130 0.065 Uiso calc R 1 . .
C C20 0.45447(12) 0.31491(16) 0.34906(9) 0.0548(4) Uani d . 1 . .
N N2 0.85154(10) -0.58951(13) 0.52696(7) 0.0564(3) Uani d . 1 . .
O O1 0.13736(8) 0.47386(9) 0.19334(6) 0.0545(3) Uani d . 1 . .
O O2 0.05129(9) 0.23016(10) 0.14397(6) 0.0597(3) Uani d . 1 . .
O O3 -0.06491(9) 0.33379(10) 0.05595(6) 0.0651(3) Uani d . 1 . .
H H23 -0.0867 0.2512 0.0481 0.098 Uiso d R 1 . .
O O4 0.32100(8) 0.46709(9) 0.28462(6) 0.0531(3) Uani d . 1 . .
O O5 0.42135(9) 0.21927(11) 0.30849(7) 0.0710(3) Uani d . 1 . .
O O6 0.52702(9) 0.30628(11) 0.40864(6) 0.0709(3) Uani d . 1 . .
H H24 0.5506 0.2251 0.4185 0.106 Uiso d R 1 . .
O O7 0.17765(9) 0.17334(11) 0.28219(6) 0.0712(3) Uani d . 1 . .
H H21 0.2472 0.2012 0.2804 0.107 Uiso d R 1 . .
H H22 0.1466 0.2093 0.2410 0.107 Uiso d R 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
C1 N1 C5 . . 117.34(13) ?
N1 C1 C2 . . 123.17(12) ?
N1 C1 H1 . . 118.4 ?
C2 C1 H1 . . 118.4 ?
C1 C2 C3 . . 120.17(14) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 116.16(13) ?
C2 C3 C6 . . 122.24(13) ?
C4 C3 C6 . . 121.60(11) ?
C5 C4 C3 . . 119.96(12) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
N1 C5 C4 . . 123.18(14) ?
N1 C5 H5 . . 118.4 ?
C4 C5 H5 . . 118.4 ?
C10 C6 C7 . . 115.98(13) ?
C10 C6 C3 . . 122.33(12) ?
C7 C6 C3 . . 121.68(12) ?
C8 C7 C6 . . 120.14(13) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
N2 C8 C7 . . 123.49(14) ?
N2 C8 H8 . . 118.3 ?
C7 C8 H8 . . 118.3 ?
N2 C9 C10 . . 122.64(12) ?
N2 C9 H9 . . 118.7 ?
C10 C9 H9 . . 118.7 ?
C9 C10 C6 . . 120.57(13) ?
C9 C10 H10 . . 119.7 ?
C6 C10 H10 . . 119.7 ?
O4 C11 C12 . . 124.82(11) ?
O4 C11 C16 . . 115.56(11) ?
C12 C11 C16 . . 119.61(11) ?
C11 C12 C13 . . 120.59(12) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C14 C13 C12 . . 119.87(13) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C15 . . 120.36(13) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C16 C15 C14 . . 120.67(13) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
O1 C16 C15 . . 124.87(11) ?
O1 C16 C11 . . 116.23(11) ?
C15 C16 C11 . . 118.90(12) ?
O1 C17 C18 . . 109.80(10) ?
O1 C17 H17A . . 109.7 ?
C18 C17 H17A . . 109.7 ?
O1 C17 H17B . . 109.7 ?
C18 C17 H17B . . 109.7 ?
H17A C17 H17B . . 108.2 ?
O2 C18 O3 . . 124.09(13) ?
O2 C18 C17 . . 124.94(12) ?
O3 C18 C17 . . 110.98(11) ?
O4 C19 C20 . . 109.62(11) ?
O4 C19 H19A . . 109.7 ?
C20 C19 H19A . . 109.7 ?
O4 C19 H19B . . 109.7 ?
C20 C19 H19B . . 109.7 ?
H19A C19 H19B . . 108.2 ?
O5 C20 O6 . . 125.43(14) ?
O5 C20 C19 . . 124.30(12) ?
O6 C20 C19 . . 110.26(13) ?
C8 N2 C9 . . 117.18(13) ?
C16 O1 C17 . . 116.18(10) ?
C18 O3 H23 . . 108.1 ?
C11 O4 C19 . . 116.26(10) ?
C20 O6 H24 . . 114.3 ?
H21 O7 H22 . . 103.2 ?
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
N1 C1 . 1.325(2) ?
N1 C5 . 1.3342(18) ?
C1 C2 . 1.374(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.3885(18) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.392(2) ?
C3 C6 . 1.489(2) ?
C4 C5 . 1.371(2) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C10 . 1.3818(18) ?
C6 C7 . 1.384(2) ?
C7 C8 . 1.370(2) ?
C7 H7 . 0.9300 ?
C8 N2 . 1.3237(18) ?
C8 H8 . 0.9300 ?
C9 N2 . 1.3320(19) ?
C9 C10 . 1.376(2) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 O4 . 1.3803(17) ?
C11 C12 . 1.3812(19) ?
C11 C16 . 1.4025(18) ?
C12 C13 . 1.390(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.362(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.386(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.3861(19) ?
C15 H15 . 0.9300 ?
C16 O1 . 1.3695(16) ?
C17 O1 . 1.4208(15) ?
C17 C18 . 1.495(2) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 O2 . 1.2105(16) ?
C18 O3 . 1.3083(16) ?
C19 O4 . 1.4136(15) ?
C19 C20 . 1.505(2) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 O5 . 1.2113(18) ?
C20 O6 . 1.3002(16) ?
O3 H23 . 0.8499 ?
O6 H24 . 0.8500 ?
O7 H21 . 0.8499 ?
O7 H22 . 0.8501 ?
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
O3 H23 N2 4_455 0.85 1.76 2.6051(19) 172.6
O6 H24 N1 . 0.85 1.74 2.5871(19) 175.7
O7 H21 O5 . 0.85 2.07 2.8817(19) 159.7
O7 H22 O2 . 0.85 1.97 2.7826(17) 160.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656067
2 PubChem 139078769
