#------------------------------------------------------------------------------
#$Date: 2023-03-02 12:23:29 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281255 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106823.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106823
loop_
_publ_author_name
'Xu, Wen-Jun'
'Qi, De-Qiang'
'You, Jin-Zong'
'Wang, Xue-Jie'
'Zhang, Yi-Ping'
'Hu, Fei-Fei'
'Bian, Jia-Ying'
'Yang, Chun-Xia'
'Huang, Juan'
_publ_section_title
;
 Crystal structure of
 5-(4-pyridyl)pyrimidine--4,4′-bipyridine--1,3,5-benzenetriol--water
 (1:1:1:1), C25H23N5O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              195
_journal_page_last               197
_journal_paper_doi               10.1515/ncrs-2015-0083
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety
;
C9 H7 N3, C10 H8 N2, C6 H6 O3, H2 O
;
_chemical_formula_sum            'C25 H23 N5 O4'
_chemical_formula_weight         457.48
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                87.887(4)
_cell_angle_beta                 89.803(4)
_cell_angle_gamma                72.727(4)
_cell_formula_units_Z            2
_cell_length_a                   8.157(2)
_cell_length_b                   9.262(2)
_cell_length_c                   15.465(4)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.250
_cell_measurement_theta_min      2.611
_cell_volume                     1114.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5757
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plan
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0755
_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)+(0.0609P)²+0.8312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1840
_reflns_number_gt                2479
_reflns_number_total             3973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0083_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8106823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.0799(4) 0.6427(4) 0.10908(18) 0.1071(12) Uani 1 1 d . . .
H4B H 0.1234 0.6989 0.0776 0.161 Uiso 1 1 d R . .
H4A H 0.1045 0.5524 0.0882 0.161 Uiso 1 1 d R . .
C1 C 1.1497(5) 0.1962(7) 0.0888(2) 0.0828(14) Uani 1 1 d . . .
H1 H 1.2067 0.1957 0.0366 0.099 Uiso 1 1 calc R . .
C2 C 1.0065(5) 0.3257(5) 0.1981(2) 0.0620(10) Uani 1 1 d . . .
H2 H 0.9613 0.4169 0.2252 0.074 Uiso 1 1 calc R . .
C3 C 0.9845(4) 0.1975(4) 0.2377(2) 0.0501(8) Uani 1 1 d . . .
C4 C 1.0563(6) 0.0676(5) 0.1934(2) 0.0827(13) Uani 1 1 d . . .
H4 H 1.0456 -0.0232 0.2165 0.099 Uiso 1 1 calc R . .
C5 C 0.8976(4) 0.1988(4) 0.3214(2) 0.0486(8) Uani 1 1 d . . .
C6 C 0.8101(5) 0.3335(4) 0.3594(2) 0.0626(10) Uani 1 1 d . . .
H6 H 0.7999 0.4258 0.3307 0.075 Uiso 1 1 calc R . .
C7 C 0.7391(5) 0.3292(5) 0.4396(2) 0.0680(11) Uani 1 1 d . . .
H7 H 0.6836 0.4210 0.4641 0.082 Uiso 1 1 calc R . .
C8 C 0.9001(5) 0.0687(4) 0.3676(2) 0.0656(10) Uani 1 1 d . . .
H8 H 0.9549 -0.0249 0.3450 0.079 Uiso 1 1 calc R . .
C9 C 0.8228(5) 0.0754(5) 0.4467(3) 0.0752(12) Uani 1 1 d . . .
H9 H 0.8255 -0.0152 0.4755 0.090 Uiso 1 1 calc R . .
C10 C 0.3526(5) 0.1815(5) 0.3797(2) 0.0640(10) Uani 1 1 d . . .
H10 H 0.3607 0.0932 0.4123 0.077 Uiso 1 1 calc R . .
C11 C 0.4435(5) 0.1705(4) 0.3052(2) 0.0577(9) Uani 1 1 d . . .
H11 H 0.5127 0.0768 0.2883 0.069 Uiso 1 1 calc R . .
C12 C 0.4326(4) 0.2995(4) 0.25480(19) 0.0483(8) Uani 1 1 d . . .
C13 C 0.3280(5) 0.4338(4) 0.2853(2) 0.0601(9) Uani 1 1 d . . .
H13 H 0.3173 0.5237 0.2540 0.072 Uiso 1 1 calc R . .
C14 C 0.5278(4) 0.2946(4) 0.1732(2) 0.0521(9) Uani 1 1 d . . .
C15 C 0.2405(5) 0.4365(5) 0.3604(2) 0.0658(10) Uani 1 1 d . . .
H15 H 0.1696 0.5282 0.3791 0.079 Uiso 1 1 calc R . .
C16 C 0.5708(5) 0.4209(5) 0.1410(2) 0.0698(11) Uani 1 1 d . . .
H16 H 0.5379 0.5105 0.1705 0.084 Uiso 1 1 calc R . .
C17 C 0.6607(5) 0.4131(6) 0.0666(3) 0.0840(13) Uani 1 1 d . . .
H17 H 0.6869 0.4994 0.0463 0.101 Uiso 1 1 calc R . .
C18 C 0.6707(6) 0.1708(6) 0.0492(3) 0.0882(13) Uani 1 1 d U . .
H18 H 0.7039 0.0852 0.0162 0.106 Uiso 1 1 calc R . .
C19 C 0.5781(5) 0.1673(5) 0.1265(2) 0.0739(12) Uani 1 1 d . . .
H19 H 0.5523 0.0799 0.1450 0.089 Uiso 1 1 calc R . .
C20 C 0.3961(5) 0.2500(4) 0.6165(2) 0.0541(9) Uani 1 1 d . . .
H20 H 0.4284 0.2523 0.5589 0.065 Uiso 1 1 calc R . .
C21 C 0.5190(5) 0.2211(4) 0.6811(2) 0.0517(9) Uani 1 1 d . . .
C22 C 0.4717(5) 0.2166(4) 0.7670(2) 0.0587(9) Uani 1 1 d . . .
H22 H 0.5543 0.1959 0.8108 0.070 Uiso 1 1 calc R . .
C23 C 0.2999(5) 0.2434(4) 0.7870(2) 0.0576(9) Uani 1 1 d . . .
C24 C 0.1767(5) 0.2719(4) 0.7222(2) 0.0562(9) Uani 1 1 d . . .
H24 H 0.0617 0.2886 0.7361 0.067 Uiso 1 1 calc R . .
C25 C 0.2258(5) 0.2755(4) 0.6371(2) 0.0545(9) Uani 1 1 d . . .
N1 N 1.0878(4) 0.3287(4) 0.12386(19) 0.0749(10) Uani 1 1 d . . .
N2 N 1.1402(5) 0.0654(5) 0.1191(2) 0.0974(13) Uani 1 1 d . . .
N3 N 0.7440(4) 0.2038(4) 0.48464(19) 0.0662(9) Uani 1 1 d . . .
N4 N 0.7112(5) 0.2949(5) 0.0230(2) 0.0815(10) Uani 1 1 d U . .
N5 N 0.2544(4) 0.3090(5) 0.40813(19) 0.0746(10) Uani 1 1 d . . .
O1 O 0.6876(3) 0.1958(3) 0.66328(15) 0.0685(7) Uani 1 1 d . . .
H1A H 0.6991 0.2104 0.6113 0.103 Uiso 1 1 calc R . .
O2 O 0.1019(3) 0.3037(3) 0.57521(15) 0.0716(8) Uani 1 1 d . . .
H2A H 0.1445 0.3097 0.5276 0.107 Uiso 1 1 calc R . .
O3 O 0.2587(4) 0.2395(4) 0.87244(14) 0.0819(9) Uani 1 1 d . . .
H3 H 0.1541 0.2698 0.8776 0.123 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
H4B O4 H4A 110.1 . .
N2 C1 N1 127.4(4) . .
N2 C1 H1 116.3 . .
N1 C1 H1 116.3 . .
N1 C2 C3 124.6(4) . .
N1 C2 H2 117.7 . .
C3 C2 H2 117.7 . .
C2 C3 C4 113.8(3) . .
C2 C3 C5 122.8(3) . .
C4 C3 C5 123.3(3) . .
N2 C4 C3 123.5(4) . .
N2 C4 H4 118.3 . .
C3 C4 H4 118.3 . .
C8 C5 C6 115.8(3) . .
C8 C5 C3 122.7(3) . .
C6 C5 C3 121.6(3) . .
C7 C6 C5 119.5(4) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
N3 C7 C6 124.6(3) . .
N3 C7 H7 117.7 . .
C6 C7 H7 117.7 . .
C9 C8 C5 120.7(3) . .
C9 C8 H8 119.7 . .
C5 C8 H8 119.7 . .
N3 C9 C8 123.8(4) . .
N3 C9 H9 118.1 . .
C8 C9 H9 118.1 . .
N5 C10 C11 123.7(4) . .
N5 C10 H10 118.1 . .
C11 C10 H10 118.1 . .
C10 C11 C12 119.6(3) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C13 C12 C11 116.3(3) . .
C13 C12 C14 121.7(3) . .
C11 C12 C14 122.0(3) . .
C15 C13 C12 121.1(4) . .
C15 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C19 C14 C16 117.3(3) . .
C19 C14 C12 121.8(3) . .
C16 C14 C12 121.0(3) . .
N5 C15 C13 121.2(4) . .
N5 C15 H15 119.4 . .
C13 C15 H15 119.4 . .
C17 C16 C14 119.9(4) . .
C17 C16 H16 120.0 . .
C14 C16 H16 120.0 . .
N4 C17 C16 123.8(4) . .
N4 C17 H17 118.1 . .
C16 C17 H17 118.1 . .
N4 C18 C19 121.2(4) . .
N4 C18 H18 119.4 . .
C19 C18 H18 119.4 . .
C14 C19 C18 118.5(4) . .
C14 C19 H19 120.7 . .
C18 C19 H19 120.7 . .
C25 C20 C21 120.2(3) . .
C25 C20 H20 119.9 . .
C21 C20 H20 119.9 . .
O1 C21 C20 121.8(3) . .
O1 C21 C22 118.1(3) . .
C20 C21 C22 120.1(3) . .
C23 C22 C21 119.2(3) . .
C23 C22 H22 120.4 . .
C21 C22 H22 120.4 . .
O3 C23 C24 122.0(3) . .
O3 C23 C22 117.3(3) . .
C24 C23 C22 120.7(3) . .
C25 C24 C23 119.4(3) . .
C25 C24 H24 120.3 . .
C23 C24 H24 120.3 . .
O2 C25 C20 121.7(3) . .
O2 C25 C24 117.9(3) . .
C20 C25 C24 120.4(3) . .
C1 N1 C2 114.8(4) . .
C1 N2 C4 115.8(4) . .
C7 N3 C9 115.6(3) . .
C17 N4 C18 119.3(4) . .
C10 N5 C15 118.2(3) . .
C21 O1 H1A 109.5 . .
C25 O2 H2A 109.5 . .
C23 O3 H3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 H4B 0.8503 .
O4 H4A 0.8740 .
C1 N2 1.307(6) .
C1 N1 1.316(6) .
C1 H1 0.9300 .
C2 N1 1.327(4) .
C2 C3 1.375(5) .
C2 H2 0.9300 .
C3 C4 1.378(5) .
C3 C5 1.473(4) .
C4 N2 1.332(5) .
C4 H4 0.9300 .
C5 C8 1.373(5) .
C5 C6 1.391(4) .
C6 C7 1.372(5) .
C6 H6 0.9300 .
C7 N3 1.322(5) .
C7 H7 0.9300 .
C8 C9 1.369(5) .
C8 H8 0.9300 .
C9 N3 1.329(5) .
C9 H9 0.9300 .
C10 N5 1.305(5) .
C10 C11 1.359(4) .
C10 H10 0.9300 .
C11 C12 1.383(5) .
C11 H11 0.9300 .
C12 C13 1.381(5) .
C12 C14 1.475(4) .
C13 C15 1.357(5) .
C13 H13 0.9300 .
C14 C19 1.361(5) .
C14 C16 1.392(5) .
C15 N5 1.345(5) .
C15 H15 0.9300 .
C16 C17 1.355(5) .
C16 H16 0.9300 .
C17 N4 1.267(5) .
C17 H17 0.9300 .
C18 N4 1.336(6) .
C18 C19 1.417(5) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C25 1.376(5) .
C20 C21 1.379(5) .
C20 H20 0.9300 .
C21 O1 1.354(4) .
C21 C22 1.385(4) .
C22 C23 1.384(5) .
C22 H22 0.9300 .
C23 O3 1.364(4) .
C23 C24 1.383(5) .
C24 C25 1.377(4) .
C24 H24 0.9300 .
C25 O2 1.356(4) .
O1 H1A 0.8200 .
O2 H2A 0.8200 .
O3 H3 0.8200 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N3 0.82 1.99 2.801(4) 169.2 .
O2 H2A N5 0.82 2.05 2.869(4) 176.1 .
C18 H18 N2 0.93 2.66 3.512(5) 152.3 2_755
C15 H15 O2 0.93 2.42 3.279(5) 153.7 2_566
O3 H3 O4 0.82 1.85 2.670(4) 174.3 2_566
O4 H4A N1 0.87 2.17 2.891(5) 139.8 1_455
O4 H4B N4 0.85 2.07 2.808(4) 145.4 2_665
C1 H1 O3 0.93 2.61 3.499(5) 160.3 1_654
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C2 C3 C4 0.4(6) . . . .
N1 C2 C3 C5 178.2(3) . . . .
C2 C3 C4 N2 0.3(6) . . . .
C5 C3 C4 N2 -177.6(4) . . . .
C2 C3 C5 C8 -169.0(4) . . . .
C4 C3 C5 C8 8.6(6) . . . .
C2 C3 C5 C6 9.6(5) . . . .
C4 C3 C5 C6 -172.7(4) . . . .
C8 C5 C6 C7 2.3(5) . . . .
C3 C5 C6 C7 -176.5(3) . . . .
C5 C6 C7 N3 -1.4(6) . . . .
C6 C5 C8 C9 -1.1(6) . . . .
C3 C5 C8 C9 177.6(4) . . . .
C5 C8 C9 N3 -1.2(7) . . . .
N5 C10 C11 C12 -0.7(6) . . . .
C10 C11 C12 C13 0.5(5) . . . .
C10 C11 C12 C14 -179.8(3) . . . .
C11 C12 C13 C15 -0.6(5) . . . .
C14 C12 C13 C15 179.7(3) . . . .
C13 C12 C14 C19 -155.5(4) . . . .
C11 C12 C14 C19 24.8(5) . . . .
C13 C12 C14 C16 24.9(5) . . . .
C11 C12 C14 C16 -154.8(3) . . . .
C12 C13 C15 N5 0.9(6) . . . .
C19 C14 C16 C17 -0.6(6) . . . .
C12 C14 C16 C17 178.9(3) . . . .
C14 C16 C17 N4 -0.5(7) . . . .
C16 C14 C19 C18 0.2(6) . . . .
C12 C14 C19 C18 -179.3(3) . . . .
N4 C18 C19 C14 1.2(7) . . . .
C25 C20 C21 O1 -179.9(3) . . . .
C25 C20 C21 C22 0.4(5) . . . .
O1 C21 C22 C23 179.5(3) . . . .
C20 C21 C22 C23 -0.8(5) . . . .
C21 C22 C23 O3 -179.3(3) . . . .
C21 C22 C23 C24 1.0(5) . . . .
O3 C23 C24 C25 179.6(3) . . . .
C22 C23 C24 C25 -0.8(5) . . . .
C21 C20 C25 O2 -179.7(3) . . . .
C21 C20 C25 C24 -0.2(5) . . . .
C23 C24 C25 O2 180.0(3) . . . .
C23 C24 C25 C20 0.4(5) . . . .
N2 C1 N1 C2 -0.3(7) . . . .
C3 C2 N1 C1 -0.4(6) . . . .
N1 C1 N2 C4 0.9(8) . . . .
C3 C4 N2 C1 -0.8(7) . . . .
C6 C7 N3 C9 -0.8(6) . . . .
C8 C9 N3 C7 2.1(6) . . . .
C16 C17 N4 C18 2.0(7) . . . .
C19 C18 N4 C17 -2.4(7) . . . .
C11 C10 N5 C15 1.0(6) . . . .
C13 C15 N5 C10 -1.0(6) . . . .
