#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227380.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227380
loop_
_publ_author_name
'Baktır, Zeliha'
'Akkurt, Mehmet'
'Şireci, Nihat'
'Küçükbay, Hasan'
_publ_section_title
;
 1-(Prop-2-en-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide
 monohydrate
;
_journal_coeditor_code           DN2597
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2393
_journal_page_last               o2394
_journal_paper_doi               10.1107/S1600536810033015
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H21 N2 Si +, Br -, H2 O'
_chemical_formula_moiety         'C14 H21 N2 Si +, Br -, H2 O'
_chemical_formula_sum            'C14 H23 Br N2 O Si'
_chemical_formula_weight         343.33
_chemical_name_systematic
;
1-(Prop-2-en-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide
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                66.542(4)
_cell_angle_beta                 71.479(4)
_cell_angle_gamma                80.625(5)
_cell_formula_units_Z            2
_cell_length_a                   8.9063(2)
_cell_length_b                   10.4720(2)
_cell_length_c                   10.9439(3)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.3785
_cell_measurement_theta_min      2.4137
_cell_volume                     887.07(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18957
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0356P)²+0.3659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2202
_reflns_number_total             3618
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2597.cif
_cod_data_source_block           I
_cod_database_code               2227380
_cod_database_fobs_code          2227380
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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
Si Si1 0.53721(14) 0.18235(12) 0.70600(11) 0.0684(3) Uani d . 1 . .
N N1 0.6155(3) 0.3381(3) 0.8362(3) 0.0570(7) Uani d . 1 . .
N N2 0.7515(3) 0.3069(3) 0.9818(3) 0.0624(8) Uani d . 1 . .
C C1 0.5921(4) 0.3128(4) 1.0536(4) 0.0562(9) Uani d . 1 . .
C C2 0.5185(5) 0.3059(4) 1.1879(4) 0.0669(10) Uani d . 1 . .
H H2 0.5760 0.2927 1.2499 0.080 Uiso calc R 1 . .
C C3 0.3555(5) 0.3197(4) 1.2249(4) 0.0722(11) Uani d . 1 . .
H H3 0.3016 0.3143 1.3147 0.087 Uiso calc R 1 . .
C C4 0.2689(5) 0.3415(4) 1.1314(4) 0.0673(10) Uani d . 1 . .
H H4 0.1590 0.3509 1.1604 0.081 Uiso calc R 1 . .
C C5 0.3419(4) 0.3495(4) 0.9978(4) 0.0625(9) Uani d . 1 . .
H H5 0.2844 0.3649 0.9353 0.075 Uiso calc R 1 . .
C C6 0.5059(4) 0.3332(4) 0.9609(3) 0.0546(8) Uani d . 1 . .
C C7 0.7597(4) 0.3221(4) 0.8533(4) 0.0634(10) Uani d . 1 . .
H H7 0.8535 0.3216 0.7846 0.076 Uiso calc R 1 . .
C C8 0.5773(5) 0.3529(4) 0.7092(3) 0.0634(10) Uani d . 1 . .
H H8A 0.6649 0.3954 0.6294 0.076 Uiso calc R 1 . .
H H8B 0.4847 0.4153 0.7007 0.076 Uiso calc R 1 . .
C C9 0.7201(6) 0.0716(5) 0.7079(6) 0.1093(17) Uani d . 1 . .
H H9A 0.7050 -0.0136 0.7007 0.164 Uiso calc R 1 . .
H H9B 0.7453 0.0508 0.7931 0.164 Uiso calc R 1 . .
H H9C 0.8055 0.1197 0.6310 0.164 Uiso calc R 1 . .
C C10 0.4835(6) 0.2278(6) 0.5440(5) 0.1070(17) Uani d . 1 . .
H H10A 0.3868 0.2840 0.5472 0.160 Uiso calc R 1 . .
H H10B 0.4690 0.1442 0.5337 0.160 Uiso calc R 1 . .
H H10C 0.5666 0.2790 0.4667 0.160 Uiso calc R 1 . .
C C11 0.3721(6) 0.0963(5) 0.8586(5) 0.1049(16) Uani d . 1 . .
H H11A 0.3672 0.0022 0.8668 0.157 Uiso calc R 1 . .
H H11B 0.2741 0.1463 0.8470 0.157 Uiso calc R 1 . .
H H11C 0.3897 0.0958 0.9409 0.157 Uiso calc R 1 . .
C C12 0.8871(5) 0.2883(5) 1.0387(4) 0.0781(12) Uani d . 1 . .
H H12A 0.8701 0.3488 1.0902 0.094 Uiso calc R 1 . .
H H12B 0.9831 0.3152 0.9629 0.094 Uiso calc R 1 . .
C C13 0.9078(5) 0.1417(5) 1.1316(6) 0.0889(14) Uani d . 1 . .
H H13 0.9301 0.0731 1.0937 0.107 Uiso calc R 1 . .
C C14 0.8967(6) 0.1037(6) 1.2611(7) 0.1190(19) Uani d . 1 . .
H H14A 0.8744 0.1698 1.3021 0.143 Uiso calc R 1 . .
H H14B 0.9109 0.0101 1.3139 0.143 Uiso calc R 1 . .
O O1W 1.0389(5) 0.3039(4) 0.5704(4) 0.1283(12) Uani d D 1 . .
H H1W 1.0104 0.3435 0.4962 0.192 Uiso d RD 1 . .
H H2W 1.0969 0.3573 0.5761 0.192 Uiso d RD 1 . .
Br Br1 0.85464(5) 0.48204(5) 0.31301(5) 0.0895(2) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Si Si 0.0817 0.0704 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
C9 Si1 C10 . . 111.7(2) ?
C9 Si1 C11 . . 110.6(2) ?
C10 Si1 C11 . . 110.6(2) ?
C9 Si1 C8 . . 107.8(2) ?
C10 Si1 C8 . . 105.9(2) ?
C11 Si1 C8 . . 110.15(19) ?
C7 N1 C6 . . 108.0(3) ?
C7 N1 C8 . . 126.3(3) ?
C6 N1 C8 . . 125.7(3) ?
C7 N2 C1 . . 107.9(3) ?
C7 N2 C12 . . 126.3(3) ?
C1 N2 C12 . . 125.8(3) ?
C2 C1 C6 . . 121.7(3) ?
C2 C1 N2 . . 131.6(3) ?
C6 C1 N2 . . 106.7(3) ?
C3 C2 C1 . . 116.5(3) ?
C3 C2 H2 . . 121.8 ?
C1 C2 H2 . . 121.8 ?
C2 C3 C4 . . 121.9(4) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 121.7(4) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 116.6(3) ?
C4 C5 H5 . . 121.7 ?
C6 C5 H5 . . 121.7 ?
C5 C6 N1 . . 131.6(3) ?
C5 C6 C1 . . 121.7(3) ?
N1 C6 C1 . . 106.7(3) ?
N2 C7 N1 . . 110.8(3) ?
N2 C7 H7 . . 124.6 ?
N1 C7 H7 . . 124.6 ?
N1 C8 Si1 . . 113.9(2) ?
N1 C8 H8A . . 108.8 ?
Si1 C8 H8A . . 108.8 ?
N1 C8 H8B . . 108.8 ?
Si1 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
Si1 C9 H9A . . 109.5 ?
Si1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
Si1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
Si1 C10 H10A . . 109.5 ?
Si1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
Si1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
Si1 C11 H11A . . 109.5 ?
Si1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
Si1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N2 C12 C13 . . 111.7(3) ?
N2 C12 H12A . . 109.3 ?
C13 C12 H12A . . 109.3 ?
N2 C12 H12B . . 109.3 ?
C13 C12 H12B . . 109.3 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 124.1(5) ?
C14 C13 H13 . . 118.0 ?
C12 C13 H13 . . 118.0 ?
C13 C14 H14A . . 120.0 ?
C13 C14 H14B . . 120.0 ?
H14A C14 H14B . . 120.0 ?
H1W O1W H2W . . 109.9 ?
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
Si1 C9 . 1.840(5) ?
Si1 C10 . 1.842(4) ?
Si1 C11 . 1.854(5) ?
Si1 C8 . 1.893(4) ?
N1 C7 . 1.329(4) ?
N1 C6 . 1.390(4) ?
N1 C8 . 1.478(4) ?
N2 C7 . 1.330(4) ?
N2 C1 . 1.392(4) ?
N2 C12 . 1.480(5) ?
C1 C2 . 1.383(5) ?
C1 C6 . 1.390(5) ?
C2 C3 . 1.377(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.397(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.486(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.285(7) ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9300 ?
C14 H14B . 0.9300 ?
O1W H1W . 0.8512 ?
O1W H2W . 0.8513 ?
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
C7 H7 O1W . 0.93 2.46 3.351(5) 160.8
O1W H1W Br1 . 0.85 2.62 3.445(4) 164.7
O1W H2W Br1 2_766 0.85 2.59 3.360(4) 151.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656212
