#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/25/2232519.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_2232519
loop_
_publ_author_name
'Jiang, Yan-Ke'
'Hou, Gui-Ge'
_publ_section_title
;
 Benzene-1,4-diol--5-(1H-imidazol-1-yl)pyrimidine (1/1)
;
_journal_coeditor_code           XU5356
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3073
_journal_paper_doi               10.1107/S1600536811043819
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H6 N4, C6 H6 O2'
_chemical_formula_moiety         'C7 H6 N4, C6 H6 O2'
_chemical_formula_sum            'C13 H12 N4 O2'
_chemical_formula_weight         256.27
_chemical_name_systematic
;
Benzene-1,4-diol--5-(1H-imidazol-1-yl)pyrimidine (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
_cell_angle_alpha                108.177(3)
_cell_angle_beta                 102.381(4)
_cell_angle_gamma                98.602(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8219(18)
_cell_length_b                   9.550(3)
_cell_length_c                   10.449(3)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.779
_cell_measurement_theta_min      2.308
_cell_volume                     614.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'φ and ω'
_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  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3103
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1791
_reflns_number_total             2176
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5356.cif
_cod_data_source_block           I
_cod_database_code               2232519
_cod_database_fobs_code          2232519
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.3093(3) 0.5951(2) 0.03876(18) 0.0443(4) Uani d . 1 1
H H1 0.3309 0.6809 0.0146 0.053 Uiso calc R 1 1
C C2 0.2073(3) 0.3702(2) 0.02839(19) 0.0489(5) Uani d . 1 1
H H2 0.1427 0.2677 -0.0065 0.059 Uiso calc R 1 1
C C3 0.3175(3) 0.4481(2) 0.16172(19) 0.0479(5) Uani d . 1 1
H H3 0.3432 0.4109 0.2345 0.058 Uiso calc R 1 1
C C4 0.6323(3) 0.83862(19) 0.27343(19) 0.0468(5) Uani d . 1 1
H H4 0.6347 0.8351 0.1838 0.056 Uiso calc R 1 1
C C5 0.5094(2) 0.71929(18) 0.28759(17) 0.0379(4) Uani d . 1 1
C C6 0.5138(3) 0.7279(2) 0.42203(18) 0.0470(5) Uani d . 1 1
H H6 0.4334 0.6490 0.4355 0.056 Uiso calc R 1 1
C C7 0.7401(3) 0.9551(2) 0.5069(2) 0.0511(5) Uani d . 1 1
H H7 0.8208 1.0382 0.5843 0.061 Uiso calc R 1 1
C C8 -0.0026(3) 0.41667(18) 0.58820(17) 0.0396(4) Uani d . 1 1
C C9 -0.0960(3) 0.34868(19) 0.44598(18) 0.0465(5) Uani d . 1 1
H H9 -0.1616 0.2463 0.4087 0.056 Uiso calc R 1 1
C C10 0.0931(3) 0.56915(19) 0.64137(18) 0.0459(5) Uani d . 1 1
H H10 0.1561 0.6168 0.7371 0.055 Uiso calc R 1 1
C C11 0.1916(3) 0.0311(2) 0.09527(17) 0.0416(4) Uani d . 1 1
C C12 0.0237(3) 0.06699(19) 0.14148(17) 0.0425(4) Uani d . 1 1
H H12 0.0393 0.1122 0.2370 0.051 Uiso calc R 1 1
C C13 -0.1671(3) 0.03627(19) 0.04686(17) 0.0415(4) Uani d . 1 1
H H13 -0.2791 0.0609 0.0788 0.050 Uiso calc R 1 1
N N1 0.2027(2) 0.46188(16) -0.04935(15) 0.0475(4) Uani d . 1 1
N N2 0.3850(2) 0.59439(15) 0.16903(14) 0.0397(4) Uani d . 1 1
N N3 0.7474(2) 0.95816(17) 0.38243(17) 0.0525(4) Uani d . 1 1
N N4 0.6296(2) 0.84580(19) 0.53321(15) 0.0515(4) Uani d . 1 1
O O1 -0.0130(2) 0.33007(14) 0.67005(13) 0.0547(4) Uani d . 1 1
H H1A 0.0532 0.3808 0.7513 0.082 Uiso calc R 1 1
O O2 0.3846(2) 0.0619(2) 0.18407(13) 0.0668(4) Uani d . 1 1
H H2A 0.3794 0.0945 0.2655 0.100 Uiso calc R 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
N1 C1 N2 . . 112.37(16)
N1 C1 H1 . . 123.8
N2 C1 H1 . . 123.8
C3 C2 N1 . . 110.82(15)
C3 C2 H2 . . 124.6
N1 C2 H2 . . 124.6
C2 C3 N2 . . 105.99(16)
C2 C3 H3 . . 127.0
N2 C3 H3 . . 127.0
N3 C4 C5 . . 122.56(17)
N3 C4 H4 . . 118.7
C5 C4 H4 . . 118.7
C6 C5 C4 . . 116.74(16)
C6 C5 N2 . . 121.95(15)
C4 C5 N2 . . 121.31(15)
N4 C6 C5 . . 121.87(17)
N4 C6 H6 . . 119.1
C5 C6 H6 . . 119.1
N3 C7 N4 . . 126.88(17)
N3 C7 H7 . . 116.6
N4 C7 H7 . . 116.6
O1 C8 C9 . . 118.15(15)
O1 C8 C10 . . 123.22(15)
C9 C8 C10 . . 118.61(16)
C10 C9 C8 2_566 . 120.72(16)
C10 C9 H9 2_566 . 119.6
C8 C9 H9 . . 119.6
C9 C10 C8 2_566 . 120.67(16)
C9 C10 H10 2_566 . 119.7
C8 C10 H10 . . 119.7
O2 C11 C13 . 2 117.69(16)
O2 C11 C12 . . 122.90(15)
C13 C11 C12 2 . 119.40(16)
C13 C12 C11 . . 120.52(16)
C13 C12 H12 . . 119.7
C11 C12 H12 . . 119.7
C12 C13 C11 . 2 120.08(17)
C12 C13 H13 . . 120.0
C11 C13 H13 2 . 120.0
C1 N1 C2 . . 104.87(15)
C1 N2 C3 . . 105.95(14)
C1 N2 C5 . . 126.48(14)
C3 N2 C5 . . 127.57(15)
C7 N3 C4 . . 115.79(16)
C7 N4 C6 . . 116.16(16)
C8 O1 H1A . . 109.5
C11 O2 H2A . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.304(2)
C1 N2 . 1.351(2)
C1 H1 . 0.9300
C2 C3 . 1.340(3)
C2 N1 . 1.367(2)
C2 H2 . 0.9300
C3 N2 . 1.377(2)
C3 H3 . 0.9300
C4 N3 . 1.324(2)
C4 C5 . 1.377(2)
C4 H4 . 0.9300
C5 C6 . 1.375(2)
C5 N2 . 1.415(2)
C6 N4 . 1.329(2)
C6 H6 . 0.9300
C7 N3 . 1.321(2)
C7 N4 . 1.329(2)
C7 H7 . 0.9300
C8 O1 . 1.368(2)
C8 C9 . 1.380(2)
C8 C10 . 1.382(2)
C9 C10 2_566 1.378(2)
C9 H9 . 0.9300
C10 C9 2_566 1.378(2)
C10 H10 . 0.9300
C11 O2 . 1.368(2)
C11 C13 2 1.383(2)
C11 C12 . 1.383(3)
C12 C13 . 1.382(2)
C12 H12 . 0.9300
C13 C11 2 1.383(2)
C13 H13 . 0.9300
O1 H1A . 0.8200
O2 H2A . 0.8200
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 H1A N1 1_556 0.82 1.96 2.764(2) 168.2
O2 H2A N4 2_666 0.82 2.02 2.835(2) 174.2
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_4
_geom_torsion
N1 C2 C3 N2 . . 0.1(2)
N3 C4 C5 C6 . . -1.2(3)
N3 C4 C5 N2 . . 178.71(17)
C4 C5 C6 N4 . . 0.4(3)
N2 C5 C6 N4 . . -179.50(16)
O1 C8 C9 C10 . 2_566 179.04(17)
C10 C8 C9 C10 . 2_566 0.3(3)
O1 C8 C10 C9 . 2_566 -178.97(17)
C9 C8 C10 C9 . 2_566 -0.3(3)
O2 C11 C12 C13 . . 178.57(16)
C13 C11 C12 C13 2 . -0.1(3)
C11 C12 C13 C11 . 2 0.1(3)
N2 C1 N1 C2 . . 0.7(2)
C3 C2 N1 C1 . . -0.5(2)
N1 C1 N2 C3 . . -0.7(2)
N1 C1 N2 C5 . . 178.84(15)
C2 C3 N2 C1 . . 0.3(2)
C2 C3 N2 C5 . . -179.20(16)
C6 C5 N2 C1 . . 154.15(18)
C4 C5 N2 C1 . . -25.8(3)
C6 C5 N2 C3 . . -26.4(3)
C4 C5 N2 C3 . . 153.65(18)
N4 C7 N3 C4 . . -0.3(3)
C5 C4 N3 C7 . . 1.2(3)
N3 C7 N4 C6 . . -0.4(3)
C5 C6 N4 C7 . . 0.3(3)
