##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-08-24
_journal_date_accepted     2009-08-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     10
_journal_page_first     o2321
_journal_page_last     o2321
_journal_paper_category     QO
_journal_coeditor_code     SJ2636
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
1,3-Diallyl-2-methylbenzimidazolium bromide dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Ennajih, Hamid'
;
Institute of Nanomaterials and Nanotechnology
Avenue de l'Armée Royale
Madinat El Irfane
10100 Rabat
Morocco
;
    'Bouhfid, Rachid'
;
Institute of Nanomaterials and Nanotechnology
Avenue de l'Armée Royale
Madinat El Irfane
10100 Rabat
Morocco
;
    'Zouihri, Hafid'
;
CNRST Division of UATRS Angle Allal Fassi/FAR
BP 8027, Hay Riad
10000 Rabat
 Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique
Pôle de compétences Pharmacochimie
Université Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,3-Diallyl-2-methylbenzimidazolium bromide dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H17 N2 +, Br -, 2H2 O'
_chemical_formula_sum     'C14 H21 Br N2 O2'
_chemical_formula_iupac     'C14 H17 N2 +, Br -, 2H2 O'
_chemical_formula_weight     329.24
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/m'
_symmetry_space_group_name_Hall     '-C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
    '-x, -y, -z'
    'x, -y, z'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z'
_cell_length_a     13.2888(2)
_cell_length_b     16.8763(2)
_cell_length_c     7.38970(10)
_cell_angle_alpha     90.00
_cell_angle_beta     109.7730(10)
_cell_angle_gamma     90.00
_cell_volume     1559.54(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7035
_cell_measurement_theta_min     3.6
_cell_measurement_theta_max     24.3
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.402
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     2.636
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.403
_exptl_absorpt_correction_T_max     0.590
_diffrn_ambient_temperature     295(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     'Bruker APEXII'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11870
_diffrn_reflns_av_R_equivalents     0.0241
_diffrn_reflns_av_sigmaI/netI     0.0208
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     1851
_reflns_number_gt     1497
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0396
_refine_ls_R_factor_gt     0.0272
_refine_ls_wR_factor_gt     0.0771
_refine_ls_wR_factor_ref     0.0850
_refine_ls_goodness_of_fit_ref     0.950
_refine_ls_restrained_S_all     0.950
_refine_ls_number_reflns     1851
_refine_ls_number_parameters     103
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'calc w=1/[σ²(Fo²)+(0.06P)²+0.349P] 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     0.001
_refine_diff_density_max     0.310
_refine_diff_density_min     -0.182
_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'
    '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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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
    Br Br1 0.0000 0.691870(15) 0.5000 0.05502(14) Uani d S 1 . .
    O O1 0.07379(17) 0.58143(11) 0.9005(3) 0.0787(5) Uani d D 1 . .
    H H11 0.055(2) 0.6089(13) 0.796(2) 0.084(9) Uiso d D 1 . .
    H H12 0.086(3) 0.5342(9) 0.874(5) 0.075(18) Uiso d PD 0.50 . .
    H H13 0.021(2) 0.582(2) 0.942(5) 0.10(2) Uiso d PD 0.50 . .
    N N1 0.34476(11) 0.56471(8) 0.6215(2) 0.0381(3) Uani d . 1 . .
    C C1 0.1655(2) 0.5000 0.4821(5) 0.0557(7) Uani d S 1 . .
    H H1A 0.1386 0.4473 0.4841 0.083 Uiso calc PR 0.50 . .
    H H1B 0.1472 0.5176 0.3514 0.083 Uiso calc PR 0.50 . .
    H H1C 0.1343 0.5351 0.5507 0.083 Uiso calc PR 0.50 . .
    C C2 0.2831(2) 0.5000 0.5747(4) 0.0393(5) Uani d S 1 . .
    C C3 0.45113(13) 0.54109(10) 0.7010(2) 0.0375(4) Uani d . 1 . .
    C C4 0.54525(15) 0.58475(12) 0.7654(3) 0.0487(5) Uani d . 1 . .
    H H4 0.5454 0.6399 0.7646 0.058 Uiso calc R 1 . .
    C C5 0.63843(16) 0.54125(14) 0.8307(3) 0.0562(5) Uani d . 1 . .
    H H5 0.7034 0.5679 0.8762 0.067 Uiso calc R 1 . .
    C C6 0.30794(16) 0.64801(10) 0.5930(3) 0.0457(4) Uani d . 1 . .
    H H6A 0.2385 0.6504 0.4925 0.055 Uiso calc R 1 . .
    H H6B 0.3576 0.6791 0.5517 0.055 Uiso calc R 1 . .
    C C7 0.30000(19) 0.68243(11) 0.7729(3) 0.0509(5) Uani d . 1 . .
    H H7 0.2527 0.6592 0.8254 0.061 Uiso calc R 1 . .
    C C8 0.3551(2) 0.74283(14) 0.8607(3) 0.0640(6) Uani d . 1 . .
    H H8A 0.4031 0.7673 0.8115 0.077 Uiso calc R 1 . .
    H H8B 0.3468 0.7618 0.9729 0.077 Uiso calc R 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
    Br1 0.0512(2) 0.04358(19) 0.0763(2) 0.000 0.02951(16) 0.000
    O1 0.0922(14) 0.0556(11) 0.0888(13) -0.0055(9) 0.0312(12) 0.0044(9)
    N1 0.0389(8) 0.0313(7) 0.0430(8) 0.0003(6) 0.0122(6) 0.0006(6)
    C1 0.0375(14) 0.0427(15) 0.082(2) 0.000 0.0133(14) 0.000
    C2 0.0392(13) 0.0351(13) 0.0433(13) 0.000 0.0135(11) 0.000
    C3 0.0385(9) 0.0402(9) 0.0329(8) -0.0015(7) 0.0109(7) -0.0002(7)
    C4 0.0459(10) 0.0509(11) 0.0466(10) -0.0100(8) 0.0124(8) -0.0048(8)
    C5 0.0398(10) 0.0764(13) 0.0470(10) -0.0110(10) 0.0076(8) -0.0070(9)
    C6 0.0497(10) 0.0306(9) 0.0526(10) 0.0022(8) 0.0120(8) 0.0076(7)
    C7 0.0527(12) 0.0383(10) 0.0654(13) 0.0045(8) 0.0248(10) 0.0033(8)
    C8 0.0748(15) 0.0484(12) 0.0691(14) -0.0005(11) 0.0248(12) -0.0055(10)
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
    O1 H11 . 0.860(10)
                     ?
    O1 H12 . 0.850(10)
                     ?
    O1 H13 . 0.860(10)
                     ?
    N1 C2 . 1.339(2) ?
    N1 C3 . 1.393(2) ?
    N1 C6 . 1.480(2) ?
    C1 C2 . 1.479(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 N1 6_565 1.339(2) ?
    C3 C3 6_565 1.387(4) ?
    C3 C4 . 1.390(3) ?
    C4 C5 . 1.379(3) ?
    C4 H4 . 0.9300 ?
    C5 C5 6_565 1.392(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.487(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.294(3) ?
    C7 H7 . 0.9300 ?
    C8 H8A . 0.9300 ?
    C8 H8B . 0.9300 ?
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
    H11 O1 H12 . . 108.7(16) ?
    H11 O1 H13 . . 106.6(16) ?
    H12 O1 H13 . . 109.4(17) ?
    C2 N1 C3 . . 108.70(15) ?
    C2 N1 C6 . . 126.45(16) ?
    C3 N1 C6 . . 124.84(15) ?
    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 ?
    N1 C2 N1 . 6_565 109.3(2) ?
    N1 C2 C1 . . 125.33(11) ?
    N1 C2 C1 6_565 . 125.33(11) ?
    C3 C3 C4 6_565 . 122.02(12) ?
    C3 C3 N1 6_565 . 106.63(9) ?
    C4 C3 N1 . . 131.31(17) ?
    C5 C4 C3 . . 115.81(19) ?
    C5 C4 H4 . . 122.1 ?
    C3 C4 H4 . . 122.1 ?
    C4 C5 C5 . 6_565 122.17(12) ?
    C4 C5 H5 . . 118.9 ?
    C5 C5 H5 6_565 . 118.9 ?
    N1 C6 C7 . . 111.34(15) ?
    N1 C6 H6A . . 109.4 ?
    C7 C6 H6A . . 109.4 ?
    N1 C6 H6B . . 109.4 ?
    C7 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C8 C7 C6 . . 123.8(2) ?
    C8 C7 H7 . . 118.1 ?
    C6 C7 H7 . . 118.1 ?
    C7 C8 H8A . . 120.0 ?
    C7 C8 H8B . . 120.0 ?
    H8A C8 H8B . . 120.0 ?
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
    C3 N1 C2 N1 . . . 6_565 0.3(2) ?
    C6 N1 C2 N1 . . . 6_565 179.79(12) ?
    C3 N1 C2 C1 . . . . -178.4(2) ?
    C6 N1 C2 C1 . . . . 1.0(4) ?
    C2 N1 C3 C3 . . . 6_565 -0.20(15) ?
    C6 N1 C3 C3 . . . 6_565 -179.67(13) ?
    C2 N1 C3 C4 . . . . 177.40(19) ?
    C6 N1 C3 C4 . . . . -2.1(3) ?
    C3 C3 C4 C5 6_565 . . . -0.5(2) ?
    N1 C3 C4 C5 . . . . -177.78(17) ?
    C3 C4 C5 C5 . . . 6_565 0.5(2) ?
    C2 N1 C6 C7 . . . . 98.5(2) ?
    C3 N1 C6 C7 . . . . -82.1(2) ?
    N1 C6 C7 C8 . . . . 118.6(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
    _geom_hbond_publ_flag
    O1 H11 Br1 . 0.860(10)
                         2.490(10)
                                 3.351(2) 178(2) yes
    O1 H13 O1 2_557 0.860(10)
                            1.980(10)
                                    2.822(5) 166(4) yes
    O1 H12 O1 6_565 0.850(10)
                            1.97(2) 2.748(4) 152(3) yes
