#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/81/2208144.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_2208144
loop_
_publ_author_name
'Zhou, Yun-Shu'
'Shen, Hong'
'Xu, Gang'
'Huang, Wei'
'Gou, Shao-Hua'
_publ_section_title
;
 2,6-Bis(imidazol-1-ylmethyl)-4-methylphenol monohydrate
;
_journal_coeditor_code           RN6077
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o573
_journal_page_last               o575
_journal_paper_doi               10.1107/S1600536806000791
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H16 N4 O, H2 O'
_chemical_formula_moiety         'C15 H16 N4 O, H2 O'
_chemical_formula_sum            'C15 H18 N4 O2'
_chemical_formula_weight         286.33
_chemical_name_systematic
;
2,6-Bis(imidazol-1-ylmethyl)-4-methylphenol monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.460(10)
_cell_angle_beta                 105.340(10)
_cell_angle_gamma                112.330(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8020(10)
_cell_length_b                   9.606(2)
_cell_length_c                   10.648(2)
_cell_measurement_reflns_used    1249
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.52
_cell_volume                     732.0(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'π 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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3699
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0521
_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)+(0.0874P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                1791
_reflns_number_total             2544
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn6077.cif
_cod_data_source_block           I
_cod_database_code               2208144
_cod_database_fobs_code          2208144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.1418(4) 1.0633(3) 0.1661(3) 0.0553(7) Uani d . 1 C
H1 0.2343 1.1477 0.1613 0.066 Uiso calc R 1 H
C2 -0.0868(4) 0.9299(4) 0.1990(3) 0.0675(8) Uani d . 1 C
H2 -0.1861 0.9036 0.2219 0.081 Uiso calc R 1 H
C3 -0.0281(3) 0.8234(3) 0.1521(3) 0.0569(7) Uani d . 1 C
H3 -0.0780 0.7128 0.1371 0.068 Uiso calc R 1 H
C4 0.2336(3) 0.8519(3) 0.0858(2) 0.0524(6) Uani d . 1 C
H4A 0.2876 0.9149 0.0370 0.063 Uiso calc R 1 H
H4B 0.1606 0.7370 0.0183 0.063 Uiso calc R 1 H
C5 0.3812(3) 0.8678(3) 0.2097(2) 0.0415(6) Uani d . 1 C
C6 0.3616(3) 0.7336(3) 0.2435(2) 0.0380(5) Uani d . 1 C
C7 0.5019(3) 0.7511(3) 0.3565(2) 0.0365(5) Uani d . 1 C
C8 0.6535(3) 0.9044(3) 0.4373(2) 0.0420(6) Uani d . 1 C
H8 0.7443 0.9166 0.5150 0.050 Uiso calc R 1 H
C9 0.6755(3) 1.0402(3) 0.4070(2) 0.0430(6) Uani d . 1 C
C10 0.5373(3) 1.0177(3) 0.2908(2) 0.0462(6) Uani d . 1 C
H10 0.5499 1.1064 0.2666 0.055 Uiso calc R 1 H
C11 0.4961(3) 0.6061(3) 0.3888(2) 0.0412(5) Uani d . 1 C
H11A 0.5690 0.6449 0.4895 0.049 Uiso calc R 1 H
H11B 0.3731 0.5311 0.3691 0.049 Uiso calc R 1 H
C12 0.4938(3) 0.4427(3) 0.1580(3) 0.0577(7) Uani d . 1 C
H12 0.3927 0.4346 0.0936 0.069 Uiso calc R 1 H
C13 0.6016(4) 0.3834(3) 0.1266(3) 0.0635(7) Uani d . 1 C
H13 0.5863 0.3267 0.0346 0.076 Uiso calc R 1 H
C14 0.7067(3) 0.4982(3) 0.3523(3) 0.0467(6) Uani d . 1 C
H14 0.7781 0.5372 0.4488 0.056 Uiso calc R 1 H
C15 0.8446(3) 1.2040(3) 0.4950(3) 0.0625(7) Uani d . 1 C
H15A 0.8214 1.2766 0.5590 0.094 Uiso calc R 1 H
H15B 0.8826 1.2518 0.4329 0.094 Uiso calc R 1 H
H15C 0.9378 1.1879 0.5491 0.094 Uiso calc R 1 H
N1 0.1180(3) 0.9103(2) 0.13137(19) 0.0453(5) Uani d . 1 N
N2 0.0210(3) 1.0818(3) 0.2076(2) 0.0643(6) Uani d . 1 N
N3 0.5627(2) 0.5170(2) 0.30337(19) 0.0391(5) Uani d . 1 N
N4 0.7359(3) 0.4184(3) 0.2485(2) 0.0578(6) Uani d . 1 N
O1 0.20765(19) 0.58623(19) 0.15792(17) 0.0523(5) Uani d . 1 O
H1B 0.1484 0.5488 0.2155 0.078 Uiso d R 1 H
O2 0.05322(19) 0.39584(18) 0.27827(18) 0.0531(5) Uani d . 1 O
H2A -0.0409 0.3089 0.2138 0.080 Uiso d R 1 H
H2C 0.0247 0.4484 0.3372 0.080 Uiso d R 1 H
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_publ_flag
N2 C1 N1 112.6(3) ?
N2 C1 H1 123.7 ?
N1 C1 H1 123.7 ?
C3 C2 N2 110.1(3) ?
C3 C2 H2 125.0 ?
N2 C2 H2 125.0 ?
C2 C3 N1 106.1(2) ?
C2 C3 H3 126.9 ?
N1 C3 H3 126.9 ?
N1 C4 C5 112.41(18) y
N1 C4 H4A 109.1 ?
C5 C4 H4A 109.1 ?
N1 C4 H4B 109.1 ?
C5 C4 H4B 109.1 ?
H4A C4 H4B 107.9 ?
C10 C5 C6 119.5(2) ?
C10 C5 C4 119.7(2) ?
C6 C5 C4 120.8(2) ?
O1 C6 C5 117.72(19) ?
O1 C6 C7 122.72(19) ?
C5 C6 C7 119.45(19) ?
C8 C7 C6 118.99(19) ?
C8 C7 C11 119.15(19) ?
C6 C7 C11 121.80(19) ?
C9 C8 C7 122.6(2) ?
C9 C8 H8 118.7 ?
C7 C8 H8 118.7 ?
C8 C9 C10 117.1(2) ?
C8 C9 C15 121.1(2) ?
C10 C9 C15 121.8(2) ?
C5 C10 C9 122.2(2) ?
C5 C10 H10 118.9 ?
C9 C10 H10 118.9 ?
N3 C11 C7 111.71(18) y
N3 C11 H11A 109.3 ?
C7 C11 H11A 109.3 ?
N3 C11 H11B 109.3 ?
C7 C11 H11B 109.3 ?
H11A C11 H11B 107.9 ?
C13 C12 N3 106.2(2) ?
C13 C12 H12 126.9 ?
N3 C12 H12 126.9 ?
C12 C13 N4 110.3(2) ?
C12 C13 H13 124.8 ?
N4 C13 H13 124.8 ?
N4 C14 N3 112.3(2) ?
N4 C14 H14 123.9 ?
N3 C14 H14 123.9 ?
C9 C15 H15A 109.5 ?
C9 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C9 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C1 N1 C3 106.8(2) ?
C1 N1 C4 125.9(2) ?
C3 N1 C4 127.3(2) ?
C1 N2 C2 104.4(2) ?
C14 N3 C12 106.46(19) ?
C14 N3 C11 126.86(19) ?
C12 N3 C11 126.64(18) ?
C14 N4 C13 104.75(19) ?
C6 O1 H1B 109.1 ?
H2A O2 H2C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.308(3) ?
C1 N1 1.332(3) ?
C1 H1 0.9300 ?
C2 C3 1.353(3) ?
C2 N2 1.367(4) ?
C2 H2 0.9300 ?
C3 N1 1.353(3) ?
C3 H3 0.9300 ?
C4 N1 1.462(3) y
C4 C5 1.512(3) y
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C10 1.383(3) ?
C5 C6 1.390(3) ?
C6 O1 1.368(2) ?
C6 C7 1.397(3) ?
C7 C8 1.384(3) ?
C7 C11 1.507(3) y
C8 C9 1.381(3) ?
C8 H8 0.9300 ?
C9 C10 1.385(3) ?
C9 C15 1.505(3) ?
C10 H10 0.9300 ?
C11 N3 1.466(3) y
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.347(3) ?
C12 N3 1.363(3) ?
C12 H12 0.9300 ?
C13 N4 1.361(3) ?
C13 H13 0.9300 ?
C14 N4 1.313(3) ?
C14 N3 1.337(3) ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
O1 H1B 0.9599 ?
O2 H2A 0.8499 ?
O2 H2C 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
C11 H11B O2 . 0.97 2.38 3.314(3) 162
C4 H4B O1 . 0.97 2.40 2.802(3) 104
O2 H2C N4 1_455 0.85 2.34 2.824(2) 117
O2 H2A N2 1_545 0.85 2.43 2.788(3) 106
O1 H1B O2 . 0.96 1.79 2.668(2) 151
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126500
