#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226414.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_2226414
loop_
_publ_author_name
'Akkurt, Mehmet'
'Çelik, Ísmail'
'Küçükbay, Hasan'
'Şireci, Nihat'
'Büyükgüngör, Orhan'
_publ_section_title
;
 1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride
 monohydrate
;
_journal_coeditor_code           DN2582
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1770
_journal_page_last               o1771
_journal_paper_doi               10.1107/S1600536810024128
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H23 N2 Si +, Cl -, H2 O'
_chemical_formula_moiety         'C18 H23 N2 Si +, Cl -, H2 O'
_chemical_formula_sum            'C18 H25 Cl N2 O Si'
_chemical_formula_weight         348.94
_chemical_name_systematic
;
1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium 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
_cell_angle_alpha                117.594(6)
_cell_angle_beta                 103.295(6)
_cell_angle_gamma                92.094(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3592(7)
_cell_length_b                   10.9500(9)
_cell_length_c                   11.0522(8)
_cell_measurement_reflns_used    28124
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.13
_cell_volume                     963.39(15)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), 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      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12149
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.497
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0485
_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)+(0.0637P)²+0.2683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                3241
_reflns_number_total             3987
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2582.cif
_cod_data_source_block           I
_cod_database_code               2226414
_cod_database_fobs_code          2226414
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 0.53328(7) 0.20172(7) 0.79168(6) 0.05705(19) Uani d . 1 . .
N N1 0.72385(17) 0.36741(17) 0.52896(17) 0.0466(4) Uani d . 1 . .
N N2 0.59349(17) 0.36730(17) 0.66907(17) 0.0466(4) Uani d . 1 . .
C C1 0.4923(2) 0.33506(19) 0.54087(19) 0.0428(4) Uani d . 1 . .
C C2 0.3377(2) 0.3101(2) 0.4971(2) 0.0521(5) Uani d . 1 . .
H H2 0.2816 0.3104 0.5566 0.063 Uiso calc R 1 . .
C C3 0.2721(2) 0.2847(2) 0.3611(2) 0.0587(5) Uani d . 1 . .
H H3 0.1688 0.2667 0.3276 0.070 Uiso calc R 1 . .
C C4 0.3560(2) 0.2853(3) 0.2717(2) 0.0592(5) Uani d . 1 . .
H H4 0.3071 0.2682 0.1806 0.071 Uiso calc R 1 . .
C C5 0.5084(2) 0.3104(2) 0.3150(2) 0.0532(5) Uani d . 1 . .
H H5 0.5641 0.3111 0.2555 0.064 Uiso calc R 1 . .
C C6 0.57570(19) 0.33479(19) 0.4512(2) 0.0432(4) Uani d . 1 . .
C C7 0.7293(2) 0.3855(2) 0.6574(2) 0.0505(5) Uani d . 1 . .
H H7 0.8165 0.4079 0.7293 0.061 Uiso calc R 1 . .
C C8 0.8534(2) 0.3833(2) 0.4794(2) 0.0547(5) Uani d . 1 . .
H H8A 0.9413 0.4273 0.5602 0.066 Uiso calc R 1 . .
H H8B 0.8371 0.4442 0.4377 0.066 Uiso calc R 1 . .
C C9 0.8803(2) 0.2461(2) 0.3720(2) 0.0510(5) Uani d . 1 . .
C C10 0.8520(3) 0.2111(3) 0.2308(3) 0.0717(7) Uani d . 1 . .
H H10 0.8171 0.2741 0.2014 0.086 Uiso calc R 1 . .
C C11 0.8748(3) 0.0831(4) 0.1329(3) 0.0935(10) Uani d . 1 . .
H H11 0.8546 0.0600 0.0377 0.112 Uiso calc R 1 . .
C C12 0.9272(3) -0.0100(3) 0.1753(4) 0.0947(10) Uani d . 1 . .
H H12 0.9404 -0.0970 0.1089 0.114 Uiso calc R 1 . .
C C13 0.9600(3) 0.0255(3) 0.3158(4) 0.0909(10) Uani d . 1 . .
H H13 0.9980 -0.0367 0.3451 0.109 Uiso calc R 1 . .
C C14 0.9372(3) 0.1527(3) 0.4141(3) 0.0700(7) Uani d . 1 . .
H H14 0.9602 0.1760 0.5095 0.084 Uiso calc R 1 . .
C C15 0.5549(3) 0.3754(2) 0.7947(2) 0.0549(5) Uani d . 1 . .
H H15A 0.4625 0.4122 0.8003 0.066 Uiso calc R 1 . .
H H15B 0.6320 0.4406 0.8796 0.066 Uiso calc R 1 . .
C C16 0.3837(3) 0.0757(3) 0.6328(3) 0.0812(8) Uani d . 1 . .
H H16A 0.4063 0.0662 0.5487 0.122 Uiso calc R 1 . .
H H16B 0.2907 0.1090 0.6377 0.122 Uiso calc R 1 . .
H H16C 0.3767 -0.0135 0.6297 0.122 Uiso calc R 1 . .
C C17 0.4849(4) 0.2374(4) 0.9569(3) 0.1001(10) Uani d . 1 . .
H H17A 0.4744 0.1524 0.9619 0.150 Uiso calc R 1 . .
H H17B 0.3928 0.2732 0.9569 0.150 Uiso calc R 1 . .
H H17C 0.5624 0.3050 1.0376 0.150 Uiso calc R 1 . .
C C18 0.7121(3) 0.1391(3) 0.7877(3) 0.0899(9) Uani d . 1 . .
H H18A 0.7028 0.0478 0.7796 0.135 Uiso calc R 1 . .
H H18B 0.7869 0.2023 0.8737 0.135 Uiso calc R 1 . .
H H18C 0.7403 0.1344 0.7076 0.135 Uiso calc R 1 . .
O O1 0.9113(3) 0.6314(2) 0.9603(2) 0.1024(7) Uani d . 1 . .
H H1A 0.9910 0.6000 0.9420 0.154 Uiso d R 1 . .
H H1B 0.9090 0.6350 1.0380 0.154 Uiso d R 1 . .
Cl Cl1 1.14370(9) 0.44812(10) 0.80296(8) 0.0961(3) 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'
Cl Cl 0.1484 0.1585 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1370
0 0 1 0.2040
0 1 0 0.2010
5 -3 2 0.2680
-11 3 1 0.3240
-1 -2 2 0.3970
-3 6 2 0.2400
-1 -3 6 0.3100
-3 1 4 0.3290
-7 5 1 0.3170
-1 -9 4 0.2960
-4 -5 2 0.3510
1 -3 1 0.3070
1 3 -4 0.3050
2 0 -1 0.3570
3 2 -2 0.3740
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
C18 Si1 C17 . . 111.82(16) ?
C18 Si1 C16 . . 110.58(15) ?
C17 Si1 C16 . . 110.93(16) ?
C18 Si1 C15 . . 107.44(14) ?
C17 Si1 C15 . . 105.86(13) ?
C16 Si1 C15 . . 110.04(12) ?
C7 N1 C6 . . 108.20(15) ?
C7 N1 C8 . . 125.70(17) ?
C6 N1 C8 . . 126.08(16) ?
C7 N2 C1 . . 108.16(15) ?
C7 N2 C15 . . 126.39(17) ?
C1 N2 C15 . . 125.43(16) ?
N2 C1 C2 . . 131.97(17) ?
N2 C1 C6 . . 106.56(16) ?
C2 C1 C6 . . 121.45(18) ?
C3 C2 C1 . . 116.40(18) ?
C3 C2 H2 . . 121.8 ?
C1 C2 H2 . . 121.8 ?
C2 C3 C4 . . 122.03(19) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 121.6(2) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 116.92(18) ?
C4 C5 H5 . . 121.5 ?
C6 C5 H5 . . 121.5 ?
C5 C6 N1 . . 131.92(17) ?
C5 C6 C1 . . 121.62(17) ?
N1 C6 C1 . . 106.41(16) ?
N2 C7 N1 . . 110.68(17) ?
N2 C7 H7 . . 124.7 ?
N1 C7 H7 . . 124.7 ?
N1 C8 C9 . . 112.22(16) ?
N1 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
N1 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C10 C9 C14 . . 118.7(2) ?
C10 C9 C8 . . 121.3(2) ?
C14 C9 C8 . . 120.0(2) ?
C9 C10 C11 . . 120.5(3) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.2(3) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.7(3) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.4(3) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
N2 C15 Si1 . . 113.64(13) ?
N2 C15 H15A . . 108.8 ?
Si1 C15 H15A . . 108.8 ?
N2 C15 H15B . . 108.8 ?
Si1 C15 H15B . . 108.8 ?
H15A C15 H15B . . 107.7 ?
Si1 C16 H16A . . 109.5 ?
Si1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
Si1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
Si1 C17 H17A . . 109.5 ?
Si1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
Si1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
Si1 C18 H18A . . 109.5 ?
Si1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
Si1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
H1A O1 H1B . . 107.0 ?
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 C18 . 1.834(3) ?
Si1 C17 . 1.850(3) ?
Si1 C16 . 1.852(3) ?
Si1 C15 . 1.890(2) ?
N1 C7 . 1.328(3) ?
N1 C6 . 1.386(2) ?
N1 C8 . 1.476(2) ?
N2 C7 . 1.324(2) ?
N2 C1 . 1.387(2) ?
N2 C15 . 1.478(2) ?
C1 C2 . 1.389(3) ?
C1 C6 . 1.394(2) ?
C2 C3 . 1.374(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.398(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.497(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.378(3) ?
C9 C14 . 1.383(3) ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.368(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
O1 H1A . 0.8598 ?
O1 H1B . 0.8466 ?
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
O1 H1A Cl1 . 0.86 2.45 3.257(2) 157.4
O1 H1B Cl1 2_767 0.85 2.45 3.250(3) 157.7
C7 H7 O1 . 0.93 2.51 3.170(3) 128.1
C8 H8A Cl1 . 0.97 2.81 3.703(2) 153.2
C3 H3 Cg3 1_455 0.93 2.69 3.526(2) 151.0
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
C7 N2 C1 C2 . . . . -178.0(2) ?
C15 N2 C1 C2 . . . . 3.6(3) ?
C7 N2 C1 C6 . . . . 0.1(2) ?
C15 N2 C1 C6 . . . . -178.27(17) ?
N2 C1 C2 C3 . . . . 178.1(2) ?
C6 C1 C2 C3 . . . . 0.2(3) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . 0.4(4) ?
C3 C4 C5 C6 . . . . 0.2(3) ?
C4 C5 C6 N1 . . . . -177.7(2) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C7 N1 C6 C5 . . . . 177.7(2) ?
C8 N1 C6 C5 . . . . -0.7(3) ?
C7 N1 C6 C1 . . . . 0.3(2) ?
C8 N1 C6 C1 . . . . -178.13(17) ?
N2 C1 C6 C5 . . . . -177.97(18) ?
C2 C1 C6 C5 . . . . 0.4(3) ?
N2 C1 C6 N1 . . . . -0.2(2) ?
C2 C1 C6 N1 . . . . 178.10(18) ?
C1 N2 C7 N1 . . . . 0.1(2) ?
C15 N2 C7 N1 . . . . 178.44(17) ?
C6 N1 C7 N2 . . . . -0.3(2) ?
C8 N1 C7 N2 . . . . 178.18(18) ?
C7 N1 C8 C9 . . . . 109.6(2) ?
C6 N1 C8 C9 . . . . -72.2(2) ?
N1 C8 C9 C10 . . . . 108.7(2) ?
N1 C8 C9 C14 . . . . -72.5(2) ?
C14 C9 C10 C11 . . . . 2.3(4) ?
C8 C9 C10 C11 . . . . -178.8(2) ?
C9 C10 C11 C12 . . . . -0.5(4) ?
C10 C11 C12 C13 . . . . -1.5(5) ?
C11 C12 C13 C14 . . . . 1.7(5) ?
C12 C13 C14 C9 . . . . 0.2(4) ?
C10 C9 C14 C13 . . . . -2.2(3) ?
C8 C9 C14 C13 . . . . 179.0(2) ?
C7 N2 C15 Si1 . . . . -91.7(2) ?
C1 N2 C15 Si1 . . . . 86.4(2) ?
C18 Si1 C15 N2 . . . . 60.61(19) ?
C17 Si1 C15 N2 . . . . -179.77(18) ?
C16 Si1 C15 N2 . . . . -59.84(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656111
