#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/54/2235417.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_2235417
loop_
_publ_author_name
'Ibrahim, Halliru'
'Bala, Muhammad D.'
'Omondi, Bernard'
_publ_section_title
;
 1-[4-(1H-imidazol-1-yl)phenyl]ethanone monohydrate
;
_journal_coeditor_code           FJ2569
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2305
_journal_paper_doi               10.1107/S1600536812029157
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H10 N2 O, H2 O'
_chemical_formula_moiety         'C11 H10 N2 O, H2 O'
_chemical_formula_sum            'C11 H12 N2 O2'
_chemical_formula_weight         204.23
_chemical_name_systematic
;
1-[4-(1H-imidazol-1-yl)phenyl]ethanone 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
_cell_angle_alpha                90.350(3)
_cell_angle_beta                 106.731(3)
_cell_angle_gamma                99.486(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7599(6)
_cell_length_b                   8.0885(8)
_cell_length_c                   9.7168(9)
_cell_measurement_reflns_used    7553
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.19
_cell_volume                     501.03(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6609
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.1639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1568
_reflns_number_total             1711
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2569.cif
_cod_data_source_block           I
_cod_database_code               2235417
_cod_database_fobs_code          2235417
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 0.3585(2) 0.18679(16) 0.96056(14) 0.0245(3) Uani d . 1 1
H H1A 0.3397 0.0859 1.0103 0.037 Uiso calc R 1 1
H H1B 0.2732 0.2621 0.9808 0.037 Uiso calc R 1 1
H H1C 0.5033 0.2395 0.9923 0.037 Uiso calc R 1 1
C C2 0.29495(19) 0.14436(15) 0.80160(14) 0.0195(3) Uani d . 1 1
C C3 0.28326(18) 0.28277(15) 0.70069(13) 0.0174(3) Uani d . 1 1
C C4 0.21354(19) 0.24258(15) 0.55292(14) 0.0184(3) Uani d . 1 1
H H4 0.1746 0.1304 0.5199 0.022 Uiso calc R 1 1
C C5 0.20107(19) 0.36543(15) 0.45475(13) 0.0182(3) Uani d . 1 1
H H5 0.1554 0.3361 0.3566 0.022 Uiso calc R 1 1
C C6 0.25730(17) 0.53395(14) 0.50336(13) 0.0160(3) Uani d . 1 1
C C7 0.32455(19) 0.57689(15) 0.65011(14) 0.0204(3) Uani d . 1 1
H H7 0.3611 0.6892 0.6829 0.024 Uiso calc R 1 1
C C8 0.3369(2) 0.45188(16) 0.74724(14) 0.0208(3) Uani d . 1 1
H H8 0.3818 0.4813 0.8454 0.025 Uiso calc R 1 1
C C9 0.17884(19) 0.63657(15) 0.25569(14) 0.0195(3) Uani d . 1 1
C C10 0.24881(19) 0.90217(15) 0.30220(14) 0.0206(3) Uani d . 1 1
C C11 0.28704(19) 0.83293(15) 0.43105(14) 0.0197(3) Uani d . 1 1
H H11 0.3339 0.8894 0.5213 0.024 Uiso calc R 1 1
N N1 0.24241(15) 0.66069(12) 0.40191(11) 0.0165(3) Uani d . 1 1
N N2 0.18116(16) 0.77885(13) 0.19181(11) 0.0210(3) Uani d . 1 1
O O1 0.25470(14) -0.00186(10) 0.75446(10) 0.0248(3) Uani d . 1 1
O O1S 0.04729(17) 0.73832(13) -0.11171(11) 0.0353(3) Uani d . 1 1
H H1D 0.115(3) 0.820(3) -0.147(2) 0.053(5) Uiso d . 1 1
H H1E 0.093(3) 0.762(2) -0.015(2) 0.047(5) Uiso d . 1 1
H H9 0.137(2) 0.5281(19) 0.2087(16) 0.024(4) Uiso d . 1 1
H H10 0.262(2) 1.0191(17) 0.2805(14) 0.017(3) Uiso d . 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 0 '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 0.006 '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 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
O1 C2 C3 . . 119.93(11)
O1 C2 C1 . . 120.84(11)
C3 C2 C1 . . 119.23(11)
C8 C3 C4 . . 118.11(11)
C8 C3 C2 . . 122.91(11)
C4 C3 C2 . . 118.98(11)
C5 C4 C3 . . 121.44(11)
C5 C4 H4 . . 119.3
C3 C4 H4 . . 119.3
C4 C5 C6 . . 119.63(11)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
C7 C6 C5 . . 119.90(11)
C7 C6 N1 . . 120.52(11)
C5 C6 N1 . . 119.58(11)
C8 C7 C6 . . 119.72(11)
C8 C7 H7 . . 120.1
C6 C7 H7 . . 120.1
C7 C8 C3 . . 121.20(12)
C7 C8 H8 . . 119.4
C3 C8 H8 . . 119.4
N2 C9 N1 1 . 112.07(11)
N2 C9 N1 . . 112.07(11)
N2 C9 H9 1 . 125.6(9)
N2 C9 H9 . . 125.6(9)
N1 C9 H9 . . 122.3(9)
C11 C10 N2 . 1 110.55(11)
C11 C10 N2 . . 110.55(11)
C11 C10 H10 . . 129.4(8)
N2 C10 H10 1 . 120.0(8)
N2 C10 H10 . . 120.0(8)
C10 C11 N1 . . 106.12(11)
C10 C11 H11 . . 126.9
N1 C11 H11 . . 126.9
C9 N1 C11 . . 106.12(10)
C9 N1 C6 . . 126.67(10)
C11 N1 C6 . . 127.20(10)
C9 N2 C10 . . 105.14(10)
H1D O1S H1E . . 104.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.5003(18)
C1 H1A . 0.96
C1 H1B . 0.96
C1 H1C . 0.96
C2 O1 . 1.2240(15)
C2 C3 . 1.4896(17)
C3 C8 . 1.3935(17)
C3 C4 . 1.3941(18)
C4 C5 . 1.3775(17)
C4 H4 . 0.93
C5 C6 . 1.3941(17)
C5 H5 . 0.93
C6 C7 . 1.3890(18)
C6 N1 . 1.4220(15)
C7 C8 . 1.3835(18)
C7 H7 . 0.93
C8 H8 . 0.93
C9 N2 1 1.3109(16)
C9 N2 . 1.3109(16)
C9 N1 . 1.3634(17)
C9 H9 . 0.948(15)
C10 C11 . 1.3483(19)
C10 N2 1 1.3816(17)
C10 N2 . 1.3816(17)
C10 H10 . 0.966(14)
C11 N1 . 1.3855(15)
C11 H11 . 0.93
O1S H1D . 0.87(2)
O1S H1E . 0.91(2)
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
O1S H1D O1 1_564 0.87(2) 2.00(2) 2.8610(14) 174.6(19)
O1S H1E N2 1 0.91(2) 1.92(2) 2.8246(15) 172.1(16)
C5 H5 O1S 2_565 0.93 2.39 3.3034(16) 166
C9 H9 O1S 2_565 0.948(15) 2.345(15) 3.2677(16) 164.5(12)
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
O1 C2 C3 C8 . . -176.76(11)
C1 C2 C3 C8 . . 2.59(18)
O1 C2 C3 C4 . . 3.98(18)
C1 C2 C3 C4 . . -176.67(11)
C8 C3 C4 C5 . . 1.18(18)
C2 C3 C4 C5 . . -179.52(10)
C3 C4 C5 C6 . . -0.60(18)
C4 C5 C6 C7 . . -0.27(18)
C4 C5 C6 N1 . . -179.39(10)
C5 C6 C7 C8 . . 0.51(18)
N1 C6 C7 C8 . . 179.62(11)
C6 C7 C8 C3 . . 0.10(19)
C4 C3 C8 C7 . . -0.93(19)
C2 C3 C8 C7 . . 179.80(11)
N2 C10 C11 N1 1 . -0.02(14)
N2 C10 C11 N1 . . -0.02(14)
N2 C9 N1 C11 1 . 0.29(14)
N2 C9 N1 C11 . . 0.29(14)
N2 C9 N1 C6 1 . 179.67(10)
N2 C9 N1 C6 . . 179.67(10)
C10 C11 N1 C9 . . -0.15(13)
C10 C11 N1 C6 . . -179.53(11)
C7 C6 N1 C9 . . -179.88(11)
C5 C6 N1 C9 . . -0.77(18)
C7 C6 N1 C11 . . -0.63(18)
C5 C6 N1 C11 . . 178.48(11)
N1 C9 N2 N2 . 1 0.0(3)
N2 C9 N2 C10 1 . 0E1(10)
N1 C9 N2 C10 . . -0.30(14)
C11 C10 N2 N2 . 1 0.00(19)
C11 C10 N2 C9 . . 0.20(14)
N2 C10 N2 C9 1 . 0E1(8)
