#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225340.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_2225340
loop_
_publ_author_name
'Xia, Dao-Cheng'
'Yao, Ji-Huan'
_publ_section_title
;
 2-Phenylimidazolium chloride monohydrate
;
_journal_coeditor_code           OM2320
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o673
_journal_paper_doi               10.1107/S1600536810006136
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H9 N2 +, Cl -, H2 O'
_chemical_formula_moiety         'C9 H9 N2 +, Cl -, H2 O'
_chemical_formula_sum            'C9 H11 Cl N2 O'
_chemical_formula_weight         198.65
_chemical_name_systematic
;
2-Phenylimidazolium chloride 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                105.486(11)
_cell_angle_beta                 106.516(11)
_cell_angle_gamma                109.337(13)
_cell_formula_units_Z            2
_cell_length_a                   7.2751(10)
_cell_length_b                   8.8816(13)
_cell_length_c                   9.3228(10)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.49
_cell_volume                     499.65(15)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3460
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.49
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.808
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0343
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                1198
_reflns_number_total             2030
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2320.cif
_cod_data_source_block           I
_cod_database_code               2225340
_cod_database_fobs_code          2225340
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_disorder_assembly
_atom_site_disorder_group
C C1 0.4640(3) 0.2399(2) 0.3466(2) 0.0617(5) Uani d . 1 . .
H H1A 0.5140 0.2530 0.4549 0.074 Uiso calc R 1 . .
C C2 0.4744(3) 0.3668(2) 0.2929(2) 0.0653(6) Uani d . 1 . .
H H2A 0.5322 0.4849 0.3570 0.078 Uiso calc R 1 . .
C C3 0.3188(3) 0.1197(2) 0.0774(2) 0.0437(4) Uani d . 1 . .
C C4 0.2201(3) -0.0061(2) -0.0909(2) 0.0441(4) Uani d . 1 . .
C C5 0.1124(3) -0.1827(2) -0.1299(2) 0.0548(5) Uani d . 1 . .
H H5 0.1007 -0.2215 -0.0482 0.066 Uiso calc R 1 . .
C C6 0.0231(3) -0.3006(2) -0.2889(2) 0.0665(6) Uani d . 1 . .
H H6 -0.0509 -0.4186 -0.3146 0.080 Uiso calc R 1 . .
C C7 0.0428(3) -0.2445(3) -0.4101(3) 0.0693(6) Uani d . 1 . .
H H7 -0.0167 -0.3247 -0.5174 0.083 Uiso calc R 1 . .
C C8 0.1500(3) -0.0708(3) -0.3728(2) 0.0661(6) Uani d . 1 . .
H H8 0.1634 -0.0336 -0.4551 0.079 Uiso calc R 1 . .
C C9 0.2382(3) 0.0496(2) -0.2145(2) 0.0550(5) Uani d . 1 . .
H H9 0.3095 0.1676 -0.1903 0.066 Uiso calc R 1 . .
N N1 0.3844(2) 0.29054(16) 0.12684(18) 0.0543(4) Uani d . 1 . .
H H1 0.3719 0.3448 0.0635 0.065 Uiso calc R 1 . .
N N2 0.3658(2) 0.08756(17) 0.21156(17) 0.0504(4) Uani d . 1 . .
H H2 0.3385 -0.0138 0.2129 0.060 Uiso calc R 1 . .
O O1W 0.2454(3) 0.4594(2) -0.0598(3) 0.0680(4) Uani d . 1 . .
H HW11 0.249(4) 0.538(3) 0.019(3) 0.114(11) Uiso d . 1 . .
H HW12 0.107(5) 0.407(3) -0.117(3) 0.122(11) Uiso d . 1 . .
Cl Cl1 0.26211(8) 0.73220(5) 0.25005(5) 0.0634(2) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0669(14) 0.0637(12) 0.0518(12) 0.0312(10) 0.0177(10) 0.0234(10)
C2 0.0746(14) 0.0527(11) 0.0572(14) 0.0266(10) 0.0189(11) 0.0164(9)
C3 0.0437(10) 0.0496(10) 0.0537(11) 0.0267(8) 0.0245(8) 0.0305(8)
C4 0.0444(10) 0.0503(10) 0.0551(11) 0.0291(8) 0.0245(9) 0.0311(8)
C5 0.0648(13) 0.0558(11) 0.0580(12) 0.0308(10) 0.0284(10) 0.0340(9)
C6 0.0788(15) 0.0552(11) 0.0645(14) 0.0289(10) 0.0271(11) 0.0255(10)
C7 0.0787(15) 0.0748(14) 0.0579(13) 0.0407(12) 0.0277(11) 0.0229(10)
C8 0.0818(15) 0.0869(14) 0.0602(14) 0.0500(12) 0.0389(11) 0.0459(11)
C9 0.0628(12) 0.0587(11) 0.0663(13) 0.0335(10) 0.0350(10) 0.0397(10)
N1 0.0650(10) 0.0474(9) 0.0635(11) 0.0286(7) 0.0295(8) 0.0324(7)
N2 0.0566(10) 0.0501(8) 0.0560(10) 0.0293(7) 0.0218(8) 0.0316(7)
O1W 0.0656(12) 0.0655(9) 0.0919(12) 0.0366(8) 0.0345(9) 0.0460(9)
Cl1 0.0715(3) 0.0529(3) 0.0548(3) 0.0174(2) 0.0143(2) 0.0311(2)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_publ_flag
C2 C1 N2 . . 106.67(17) ?
C2 C1 H1A . . 126.7 ?
N2 C1 H1A . . 126.7 ?
C1 C2 N1 . . 107.20(16) ?
C1 C2 H2A . . 126.4 ?
N1 C2 H2A . . 126.4 ?
N1 C3 N2 . . 106.63(14) ?
N1 C3 C4 . . 126.29(15) ?
N2 C3 C4 . . 127.06(15) ?
C5 C4 C9 . . 119.14(16) ?
C5 C4 C3 . . 120.82(15) ?
C9 C4 C3 . . 120.01(15) ?
C6 C5 C4 . . 120.30(16) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 120.18(18) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 120.01(19) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.68(17) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C4 . . 119.67(16) ?
C8 C9 H9 . . 120.2 ?
C4 C9 H9 . . 120.2 ?
C3 N1 C2 . . 109.75(14) ?
C3 N1 H1 . . 125.1 ?
C2 N1 H1 . . 125.1 ?
C3 N2 C1 . . 109.74(14) ?
C3 N2 H2 . . 125.1 ?
C1 N2 H2 . . 125.1 ?
HW11 O1W HW12 . . 97(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.339(2) ?
C1 N2 . 1.366(2) ?
C1 H1A . 0.9300 ?
C2 N1 . 1.362(2) ?
C2 H2A . 0.9300 ?
C3 N1 . 1.3282(19) ?
C3 N2 . 1.332(2) ?
C3 C4 . 1.455(2) ?
C4 C5 . 1.388(2) ?
C4 C9 . 1.392(2) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.375(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.368(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.378(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
N1 H1 . 0.8600 ?
N2 H2 . 0.8600 ?
O1W HW11 . 0.86(3) ?
O1W HW12 . 0.88(3) ?
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
N1 H1 O1W . 0.86 1.96 2.774(2) 157.1
N2 H2 Cl1 1_545 0.86 2.28 3.1371(14) 172.0
O1W HW11 Cl1 . 0.86(3) 2.33(3) 3.177(2) 174(2)
O1W HW12 Cl1 2_565 0.88(3) 2.32(3) 3.190(2) 176(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656030
