##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Allyl-1-(3-cyanophenylmethylene)-2-methyl-1H-benzoimidazol-3-ium bromide
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H18 N3 +, Br -, H2 O1'
_chemical_formula_sum     'C19 H20 Br N3 O'
_chemical_formula_iupac     'C19 H18 N3 +, Br -, H2 O1'
_chemical_formula_weight     386.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     P21/c
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.4291(18)
_cell_length_b     15.6490(17)
_cell_length_c     9.0335(14)
_cell_angle_alpha     90.000(10)
_cell_angle_beta     104.048(8)
_cell_angle_gamma     90.000(3)
_cell_volume     1841.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4089
_cell_measurement_theta_min     3.0337
_cell_measurement_theta_max     28.2730
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.2200
_exptl_crystal_size_mid     0.1500
_exptl_crystal_size_min     0.0800
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     2.242
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.8396
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury2'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     14149
_diffrn_reflns_av_R_equivalents     0.0361
_diffrn_reflns_av_sigmaI/netI     0.0335
_diffrn_reflns_theta_min     2.66
_diffrn_reflns_theta_max     27.89
_diffrn_reflns_theta_full     27.89
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4366
_reflns_number_gt     3365
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0602
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.1008
_refine_ls_wR_factor_ref     0.1113
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     4366
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0552P)²+0.1803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.322
_refine_diff_density_min     -0.330
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1999)'
_computing_publication_material     'SHELXTL (Sheldrick, 1999)'
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
    N N1 0.21740(14) 0.01484(13) 0.0889(2) 0.0399(4) Uani d . 1 . .
    N N2 0.13955(16) 0.06050(14) -0.1380(2) 0.0467(5) Uani d . 1 . .
    N N3 0.4739(2) 0.12165(17) 0.8335(3) 0.0710(8) Uani d . 1 . .
    C C13 0.5074(2) 0.1603(2) 0.4691(3) 0.0578(7) Uani d . 1 . .
    H H13A 0.5544 0.1990 0.5246 0.069 Uiso calc R 1 . .
    C C16 0.4615(2) 0.11908(17) 0.7045(4) 0.0553(7) Uani d . 1 . .
    C C2 0.08324(19) 0.09107(16) -0.0375(3) 0.0441(6) Uani d . 1 . .
    C C11 0.37725(18) 0.05370(16) 0.4585(3) 0.0452(6) Uani d . 1 . .
    H H11A 0.3372 0.0213 0.5081 0.054 Uiso calc R 1 . .
    C C7 0.13222(18) 0.06166(15) 0.1066(3) 0.0419(5) Uani d . 1 . .
    C C9 0.29401(19) -0.02289(16) 0.2168(3) 0.0441(6) Uani d . 1 . .
    H H9A 0.3330 -0.0660 0.1779 0.053 Uiso calc R 1 . .
    H H9B 0.2591 -0.0507 0.2858 0.053 Uiso calc R 1 . .
    C C10 0.36673(18) 0.04385(15) 0.3033(3) 0.0411(5) Uani d . 1 . .
    C C6 0.0942(2) 0.07708(18) 0.2331(3) 0.0513(6) Uani d . 1 . .
    H H6A 0.1267 0.0566 0.3293 0.062 Uiso calc R 1 . .
    C C1 0.21926(18) 0.01478(16) -0.0588(3) 0.0432(6) Uani d . 1 . .
    C C12 0.4477(2) 0.11203(16) 0.5407(3) 0.0478(6) Uani d . 1 . .
    C C3 -0.0059(2) 0.13911(17) -0.0624(4) 0.0560(7) Uani d . 1 . .
    H H3A -0.0386 0.1593 -0.1588 0.067 Uiso calc R 1 . .
    C C5 0.0052(2) 0.12465(17) 0.2082(4) 0.0612(8) Uani d . 1 . .
    H H5A -0.0233 0.1367 0.2900 0.073 Uiso calc R 1 . .
    C C15 0.4277(2) 0.09288(18) 0.2320(3) 0.0508(6) Uani d . 1 . .
    H H15A 0.4216 0.0866 0.1279 0.061 Uiso calc R 1 . .
    C C8 0.2952(2) -0.0302(2) -0.1243(3) 0.0585(7) Uani d . 1 . .
    H H8A 0.2728 -0.0296 -0.2336 0.088 Uiso calc R 1 . .
    H H8B 0.3017 -0.0882 -0.0888 0.088 Uiso calc R 1 . .
    H H8C 0.3604 -0.0020 -0.0931 0.088 Uiso calc R 1 . .
    C C14 0.4973(2) 0.1509(2) 0.3143(4) 0.0612(8) Uani d . 1 . .
    H H14A 0.5374 0.1836 0.2652 0.073 Uiso calc R 1 . .
    C C4 -0.0434(2) 0.15524(19) 0.0631(4) 0.0624(8) Uani d . 1 . .
    H H4A -0.1029 0.1875 0.0515 0.075 Uiso calc R 1 . .
    C C17 0.1160(2) 0.0806(2) -0.3020(3) 0.0597(8) Uani d . 1 . .
    H H17A 0.0422 0.0852 -0.3401 0.072 Uiso calc R 1 . .
    H H17B 0.1394 0.0339 -0.3555 0.072 Uiso calc R 1 . .
    C C18 0.1641(3) 0.1606(3) -0.3359(4) 0.0743(9) Uani d . 1 . .
    H H18A 0.1468 0.1784 -0.4372 0.089 Uiso calc R 1 . .
    C C19 0.2281(3) 0.2095(3) -0.2405(5) 0.0915(12) Uani d . 1 . .
    H H19A 0.2481 0.1949 -0.1377 0.110 Uiso calc R 1 . .
    H H19B 0.2536 0.2588 -0.2753 0.110 Uiso calc R 1 . .
    O O1W 0.7083(2) 0.25974(19) 0.2290(4) 0.1174(12) Uani d . 1 . .
    H H1 0.7192 0.2206 0.2963 0.176 Uiso d R 1 . .
    H H2 0.7528 0.2564 0.1764 0.176 Uiso d R 1 . .
    Br Br1 0.83295(2) 0.126019(17) 0.50549(3) 0.04996(12) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C1 . 1.340(3) ?
    N1 C7 . 1.400(3) ?
    N1 C9 . 1.472(3) ?
    N2 C1 . 1.341(3) ?
    N2 C2 . 1.400(3) ?
    N2 C17 . 1.471(3) ?
    N3 C16 . 1.137(4) ?
    C13 C12 . 1.372(4) ?
    C13 C14 . 1.379(4) ?
    C13 H13A . 0.9300 ?
    C16 C12 . 1.450(4) ?
    C2 C7 . 1.387(4) ?
    C2 C3 . 1.385(4) ?
    C11 C10 . 1.383(3) ?
    C11 C12 . 1.392(4) ?
    C11 H11A . 0.9300 ?
    C7 C6 . 1.381(3) ?
    C9 C10 . 1.512(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C15 . 1.389(4) ?
    C6 C5 . 1.380(4) ?
    C6 H6A . 0.9300 ?
    C1 C8 . 1.476(4) ?
    C3 C4 . 1.371(4) ?
    C3 H3A . 0.9300 ?
    C5 C4 . 1.399(5) ?
    C5 H5A . 0.9300 ?
    C15 C14 . 1.383(4) ?
    C15 H15A . 0.9300 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C14 H14A . 0.9300 ?
    C4 H4A . 0.9300 ?
    C17 C18 . 1.475(5) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 C19 . 1.306(5) ?
    C18 H18A . 0.9300 ?
    C19 H19A . 0.9300 ?
    C19 H19B . 0.9300 ?
    O1W H1 . 0.8499 ?
    O1W H2 . 0.8502 ?
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
    C1 N1 C7 . . 109.1(2) ?
    C1 N1 C9 . . 127.1(2) ?
    C7 N1 C9 . . 123.7(2) ?
    C1 N2 C2 . . 108.8(2) ?
    C1 N2 C17 . . 126.9(2) ?
    C2 N2 C17 . . 124.2(2) ?
    C12 C13 C14 . . 119.6(3) ?
    C12 C13 H13A . . 120.2 ?
    C14 C13 H13A . . 120.2 ?
    N3 C16 C12 . . 177.5(3) ?
    C7 C2 C3 . . 121.8(2) ?
    C7 C2 N2 . . 106.7(2) ?
    C3 C2 N2 . . 131.5(2) ?
    C10 C11 C12 . . 120.2(2) ?
    C10 C11 H11A . . 119.9 ?
    C12 C11 H11A . . 119.9 ?
    C2 C7 C6 . . 122.2(2) ?
    C2 C7 N1 . . 106.3(2) ?
    C6 C7 N1 . . 131.5(2) ?
    N1 C9 C10 . . 111.70(19) ?
    N1 C9 H9A . . 109.3 ?
    C10 C9 H9A . . 109.3 ?
    N1 C9 H9B . . 109.3 ?
    C10 C9 H9B . . 109.3 ?
    H9A C9 H9B . . 107.9 ?
    C11 C10 C15 . . 118.8(2) ?
    C11 C10 C9 . . 119.7(2) ?
    C15 C10 C9 . . 121.4(2) ?
    C7 C6 C5 . . 116.0(3) ?
    C7 C6 H6A . . 122.0 ?
    C5 C6 H6A . . 122.0 ?
    N2 C1 N1 . . 109.0(2) ?
    N2 C1 C8 . . 125.4(2) ?
    N1 C1 C8 . . 125.5(2) ?
    C13 C12 C11 . . 120.5(3) ?
    C13 C12 C16 . . 119.6(3) ?
    C11 C12 C16 . . 119.8(3) ?
    C4 C3 C2 . . 116.2(3) ?
    C4 C3 H3A . . 121.9 ?
    C2 C3 H3A . . 121.9 ?
    C6 C5 C4 . . 121.7(3) ?
    C6 C5 H5A . . 119.1 ?
    C4 C5 H5A . . 119.1 ?
    C14 C15 C10 . . 120.7(3) ?
    C14 C15 H15A . . 119.6 ?
    C10 C15 H15A . . 119.6 ?
    C1 C8 H8A . . 109.5 ?
    C1 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C1 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C15 C14 C13 . . 120.1(3) ?
    C15 C14 H14A . . 119.9 ?
    C13 C14 H14A . . 119.9 ?
    C3 C4 C5 . . 122.1(3) ?
    C3 C4 H4A . . 119.0 ?
    C5 C4 H4A . . 119.0 ?
    N2 C17 C18 . . 113.1(3) ?
    N2 C17 H17A . . 109.0 ?
    C18 C17 H17A . . 109.0 ?
    N2 C17 H17B . . 109.0 ?
    C18 C17 H17B . . 109.0 ?
    H17A C17 H17B . . 107.8 ?
    C19 C18 C17 . . 127.6(3) ?
    C19 C18 H18A . . 116.2 ?
    C17 C18 H18A . . 116.2 ?
    C18 C19 H19A . . 120.0 ?
    C18 C19 H19B . . 120.0 ?
    H19A C19 H19B . . 120.0 ?
    H1 O1W H2 . . 109.5 ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 N2 C2 C7 . . . . -0.1(3) ?
    C17 N2 C2 C7 . . . . -177.1(2) ?
    C1 N2 C2 C3 . . . . -178.3(3) ?
    C17 N2 C2 C3 . . . . 4.8(4) ?
    C3 C2 C7 C6 . . . . 1.2(4) ?
    N2 C2 C7 C6 . . . . -177.2(2) ?
    C3 C2 C7 N1 . . . . 178.9(2) ?
    N2 C2 C7 N1 . . . . 0.6(3) ?
    C1 N1 C7 C2 . . . . -0.8(3) ?
    C9 N1 C7 C2 . . . . 175.9(2) ?
    C1 N1 C7 C6 . . . . 176.6(3) ?
    C9 N1 C7 C6 . . . . -6.6(4) ?
    C1 N1 C9 C10 . . . . 99.8(3) ?
    C7 N1 C9 C10 . . . . -76.3(3) ?
    C12 C11 C10 C15 . . . . 0.2(4) ?
    C12 C11 C10 C9 . . . . 176.8(2) ?
    N1 C9 C10 C11 . . . . 123.7(2) ?
    N1 C9 C10 C15 . . . . -59.7(3) ?
    C2 C7 C6 C5 . . . . -0.9(4) ?
    N1 C7 C6 C5 . . . . -178.0(3) ?
    C2 N2 C1 N1 . . . . -0.4(3) ?
    C17 N2 C1 N1 . . . . 176.5(2) ?
    C2 N2 C1 C8 . . . . 178.2(3) ?
    C17 N2 C1 C8 . . . . -5.0(4) ?
    C7 N1 C1 N2 . . . . 0.8(3) ?
    C9 N1 C1 N2 . . . . -175.9(2) ?
    C7 N1 C1 C8 . . . . -177.8(2) ?
    C9 N1 C1 C8 . . . . 5.6(4) ?
    C14 C13 C12 C11 . . . . 0.1(4) ?
    C14 C13 C12 C16 . . . . 177.2(3) ?
    C10 C11 C12 C13 . . . . 0.0(4) ?
    C10 C11 C12 C16 . . . . -177.2(2) ?
    C7 C2 C3 C4 . . . . -0.5(4) ?
    N2 C2 C3 C4 . . . . 177.4(3) ?
    C7 C6 C5 C4 . . . . 0.0(4) ?
    C11 C10 C15 C14 . . . . -0.3(4) ?
    C9 C10 C15 C14 . . . . -177.0(3) ?
    C10 C15 C14 C13 . . . . 0.4(5) ?
    C12 C13 C14 C15 . . . . -0.3(5) ?
    C2 C3 C4 C5 . . . . -0.4(4) ?
    C6 C5 C4 C3 . . . . 0.6(5) ?
    C1 N2 C17 C18 . . . . -89.6(3) ?
    C2 N2 C17 C18 . . . . 86.7(3) ?
    N2 C17 C18 C19 . . . . 5.1(5) ?
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
    O1W H1 Br1 . 0.85 2.59 3.375(2) 154.5
    O1W H2 Br1 4_565 0.85 2.78 3.422(3) 133.5
    C6 H6A Br1 3_656 0.93 3.21 3.939(3) 136.8
    C8 H8A Br1 3_655 0.96 2.94 3.767(3) 145.3
    C8 H8C N3 1_554 0.96 2.64 3.463(4) 143.4
    C13 H13A O1W 4_566 0.93 2.50 3.359(4) 153.9
    C17 H17A Br1 1_454 0.97 2.89 3.843(3) 168.0
    C17 H17B Br1 3_655 0.97 2.91 3.862(3) 166.6
data_global
_journal_date_recd_electronic     2007-10-09
_journal_date_accepted     2007-11-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o109
_journal_page_last     o109
_journal_paper_category     QO
_journal_coeditor_code     KJ2074
_publ_contact_author_name     'Qiong Ye*'
_publ_contact_author_address
;
Ordered Matter Science Research Center, Southeast UniVersity,
Nanjing 210096, People's Republic of China
;
_publ_contact_author_email     yeqiong@seu.edu.cn
_publ_contact_author_fax     '86-25-52090626'
_publ_contact_author_phone     '86-25-52090626'
_publ_section_title
;
3-Allyl-1-(3-cyanophenylmethylene)-2-methyl-1H-benzoimidazol-3-ium
bromide monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xu, Xiong-Bin' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 210096, People's Republic of China
;
    'Fu, Rong' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 210096, People's Republic of China
;
    'Ye, Qiong' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 210096, People's Republic of China
;
