#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/89/2218959.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_2218959
loop_
_publ_author_name
'Gao, Jin-Sheng'
'Yu, Ying-Hui'
'Hou, Guang-Feng'
_publ_section_title
;
 1,1'-(Butane-1,4-diyl)di-1H-imidazole--benzene-1,3,5-triol--water
 (1/1/1)
;
_journal_coeditor_code           CV2422
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1560
_journal_paper_doi               10.1107/S160053680802240X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H14 N4, C6 H6 O3, H2 O'
_chemical_formula_moiety         'C10 H14 N4, C6 H6 O3, H2 O'
_chemical_formula_sum            'C16 H22 N4 O4'
_chemical_formula_weight         334.38
_chemical_name_systematic
;1,1'-(Butane-1,4-diyl)di-1H-imidazole--benzene-1,3,5-triol--water
 (1/1/1)
;
_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                98.40(3)
_cell_angle_beta                 92.93(2)
_cell_angle_gamma                117.47(3)
_cell_formula_units_Z            2
_cell_length_a                   7.964(5)
_cell_length_b                   8.405(7)
_cell_length_c                   14.800(9)
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.05
_cell_volume                     861.6(11)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_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      291(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8527
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0568
_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)+(0.1078P)²+0.0441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.1950
_reflns_number_gt                2370
_reflns_number_total             3911
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2422.cif
_cod_data_source_block           I
_cod_original_cell_volume        861.5(10)
_cod_database_code               2218959
_cod_database_fobs_code          2218959
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
C C1 0.6082(3) 0.4322(3) 0.27525(15) 0.0495(5) Uani d . 1
H H1 0.5935 0.5359 0.2907 0.059 Uiso calc R 1
C C2 0.4512(3) 0.2634(3) 0.24735(14) 0.0463(5) Uani d . 1
C C3 0.4707(3) 0.1074(3) 0.22121(14) 0.0440(5) Uani d . 1
H H3 0.3639 -0.0060 0.2009 0.053 Uiso calc R 1
C C4 0.6534(3) 0.1248(3) 0.22616(14) 0.0431(5) Uani d . 1
C C5 0.8124(3) 0.2923(3) 0.25642(14) 0.0445(5) Uani d . 1
H H5 0.9340 0.3024 0.2609 0.053 Uiso calc R 1
C C6 0.7880(3) 0.4458(3) 0.28012(14) 0.0461(5) Uani d . 1
C C7 0.5669(4) 0.2164(4) 0.62310(17) 0.0599(6) Uani d . 1
H H7 0.5388 0.1550 0.6722 0.072 Uiso calc R 1
C C8 0.7113(4) 0.4008(4) 0.5372(2) 0.0807(9) Uani d . 1
H H8 0.8061 0.4952 0.5144 0.097 Uiso calc R 1
C C9 0.5333(4) 0.2938(5) 0.4948(2) 0.0814(9) Uani d . 1
H H9 0.4827 0.2997 0.4381 0.098 Uiso calc R 1
C C10 0.2441(4) 0.0249(4) 0.5326(2) 0.0770(8) Uani d . 1
H H10 0.2144 -0.0270 0.5878 0.092 Uiso calc R 1
H H11 0.2360 -0.0698 0.4837 0.092 Uiso calc R 1
C C11 0.0998(3) 0.0796(4) 0.50659(19) 0.0655(7) Uani d . 1
H H12 0.1248 0.1263 0.4498 0.079 Uiso calc R 1
H H13 0.1094 0.1768 0.5543 0.079 Uiso calc R 1
C C12 0.2720(3) 0.5418(3) 0.10952(16) 0.0561(6) Uani d . 1
H H16 0.2520 0.5172 0.1684 0.067 Uiso calc R 1
C C13 0.3851(4) 0.6740(4) -0.00145(17) 0.0606(6) Uani d . 1
H H14 0.4595 0.7618 -0.0344 0.073 Uiso calc R 1
C C14 0.2445(4) 0.5074(4) -0.03878(17) 0.0613(6) Uani d . 1
H H15 0.2052 0.4582 -0.1013 0.074 Uiso calc R 1
C C15 0.0159(3) 0.2379(3) 0.02391(18) 0.0572(6) Uani d . 1
H H17 -0.0806 0.2134 -0.0265 0.069 Uiso calc R 1
H H18 -0.0429 0.2277 0.0801 0.069 Uiso calc R 1
C C16 0.0830(3) 0.0959(3) 0.00706(15) 0.0502(6) Uani d . 1
H H19 0.1731 0.1147 0.0593 0.060 Uiso calc R 1
H H20 0.1485 0.1102 -0.0471 0.060 Uiso calc R 1
N N1 0.4412(3) 0.1758(3) 0.54990(13) 0.0574(5) Uani d . 1
N N2 0.7338(3) 0.3514(3) 0.61894(15) 0.0661(6) Uani d . 1
N N3 0.1703(3) 0.4238(2) 0.03210(12) 0.0497(5) Uani d . 1
N N4 0.4031(3) 0.6959(3) 0.09239(14) 0.0573(5) Uani d . 1
O O1 0.6793(2) -0.0244(2) 0.20167(12) 0.0587(5) Uani d . 1
H H4 0.5847 -0.1054 0.1677 0.088 Uiso calc R 1
O O2 0.9405(2) 0.6159(2) 0.30773(14) 0.0675(5) Uani d . 1
H H6 1.0348 0.6068 0.3247 0.101 Uiso calc R 1
O O3 0.2755(2) 0.2535(2) 0.24808(13) 0.0643(5) Uani d . 1
H H2 0.1939 0.1464 0.2426 0.096 Uiso calc R 1
O O4 0.9883(2) 0.9172(3) 0.23236(15) 0.0838(6) Uani d . 1
H H21 0.8952 0.9328 0.2485 0.101 Uiso d R 1
H H22 0.9716 0.8225 0.2530 0.101 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
C2 C1 C6 . . 119.1(2)
C2 C1 H1 . . 120.4
C6 C1 H1 . . 120.4
O3 C2 C1 . . 117.6(2)
O3 C2 C3 . . 121.2(2)
C1 C2 C3 . . 121.2(2)
C4 C3 C2 . . 118.5(2)
C4 C3 H3 . . 120.7
C2 C3 H3 . . 120.7
O1 C4 C5 . . 118.36(19)
O1 C4 C3 . . 120.58(19)
C5 C4 C3 . . 121.07(19)
C4 C5 C6 . . 118.88(19)
C4 C5 H5 . . 120.6
C6 C5 H5 . . 120.6
O2 C6 C1 . . 117.4(2)
O2 C6 C5 . . 121.5(2)
C1 C6 C5 . . 121.1(2)
N2 C7 N1 . . 112.9(2)
N2 C7 H7 . . 123.6
N1 C7 H7 . . 123.6
C9 C8 N2 . . 110.0(3)
C9 C8 H8 . . 125.0
N2 C8 H8 . . 125.0
C8 C9 N1 . . 106.8(3)
C8 C9 H9 . . 126.6
N1 C9 H9 . . 126.6
N1 C10 C11 . . 113.9(2)
N1 C10 H10 . . 108.8
C11 C10 H10 . . 108.8
N1 C10 H11 . . 108.8
C11 C10 H11 . . 108.8
H10 C10 H11 . . 107.7
C10 C11 C11 . 2_556 111.3(3)
C10 C11 H12 . . 109.4
C11 C11 H12 2_556 . 109.4
C10 C11 H13 . . 109.4
C11 C11 H13 2_556 . 109.4
H12 C11 H13 . . 108.0
N4 C12 N3 . . 111.8(2)
N4 C12 H16 . . 124.1
N3 C12 H16 . . 124.1
C14 C13 N4 . . 109.7(2)
C14 C13 H14 . . 125.1
N4 C13 H14 . . 125.1
C13 C14 N3 . . 106.8(2)
C13 C14 H15 . . 126.6
N3 C14 H15 . . 126.6
N3 C15 C16 . . 112.84(19)
N3 C15 H17 . . 109.0
C16 C15 H17 . . 109.0
N3 C15 H18 . . 109.0
C16 C15 H18 . . 109.0
H17 C15 H18 . . 107.8
C15 C16 C16 . 2 111.3(2)
C15 C16 H19 . . 109.4
C16 C16 H19 2 . 109.4
C15 C16 H20 . . 109.4
C16 C16 H20 2 . 109.4
H19 C16 H20 . . 108.0
C7 N1 C9 . . 106.2(2)
C7 N1 C10 . . 125.6(2)
C9 N1 C10 . . 128.2(2)
C7 N2 C8 . . 104.1(2)
C12 N3 C14 . . 106.6(2)
C12 N3 C15 . . 127.4(2)
C14 N3 C15 . . 126.0(2)
C12 N4 C13 . . 105.2(2)
C4 O1 H4 . . 109.5
C6 O2 H6 . . 109.5
C2 O3 H2 . . 109.5
H21 O4 H22 . . 102.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.373(3)
C1 C6 . 1.380(3)
C1 H1 . 0.9300
C2 O3 . 1.364(3)
C2 C3 . 1.392(3)
C3 C4 . 1.390(3)
C3 H3 . 0.9300
C4 O1 . 1.364(3)
C4 C5 . 1.378(3)
C5 C6 . 1.390(3)
C5 H5 . 0.9300
C6 O2 . 1.365(3)
C7 N2 . 1.302(3)
C7 N1 . 1.326(3)
C7 H7 . 0.9300
C8 C9 . 1.334(4)
C8 N2 . 1.364(4)
C8 H8 . 0.9300
C9 N1 . 1.347(4)
C9 H9 . 0.9300
C10 N1 . 1.471(3)
C10 C11 . 1.475(4)
C10 H10 . 0.9700
C10 H11 . 0.9700
C11 C11 2_556 1.512(5)
C11 H12 . 0.9700
C11 H13 . 0.9700
C12 N4 . 1.306(3)
C12 N3 . 1.336(3)
C12 H16 . 0.9300
C13 C14 . 1.335(4)
C13 N4 . 1.365(3)
C13 H14 . 0.9300
C14 N3 . 1.356(3)
C14 H15 . 0.9300
C15 N3 . 1.458(3)
C15 C16 . 1.512(3)
C15 H17 . 0.9700
C15 H18 . 0.9700
C16 C16 2 1.516(4)
C16 H19 . 0.9700
C16 H20 . 0.9700
O1 H4 . 0.8200
O2 H6 . 0.8200
O3 H2 . 0.8200
O4 H21 . 0.8501
O4 H22 . 0.8500
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
O4 H22 O2 . 0.85 1.94 2.789(3) 176.4
O4 H21 O1 1_565 0.85 2.02 2.751(3) 143.3
O3 H2 O4 1_445 0.82 1.84 2.658(3) 172.6
O2 H6 N2 2_766 0.82 1.84 2.636(3) 164.3
O1 H4 N4 1_545 0.82 1.79 2.596(3) 169.5
