#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224884.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_2224884
loop_
_publ_author_name
'Ennajih, Hamid'
'Bouhfid, Rachid'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1,3-Dibenzyl-2-methylbenzimidazolium chloride
;
_journal_coeditor_code           BT5179
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o455
_journal_paper_doi               10.1107/S1600536810002588
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H21 N2 +, Cl -'
_chemical_formula_moiety         'C22 H21 N2 +, Cl -'
_chemical_formula_sum            'C22 H21 Cl N2'
_chemical_formula_weight         348.86
_chemical_name_systematic
;
1,3-Dibenzyl-2-methylbenzimidazolium chloride
;
_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                72.1390(10)
_cell_angle_beta                 81.3760(10)
_cell_angle_gamma                64.6050(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2539(2)
_cell_length_b                   9.4677(2)
_cell_length_c                   12.0984(3)
_cell_measurement_reflns_used    8258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      2.5
_cell_volume                     911.20(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24459
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9381
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                3336
_reflns_number_total             4175
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5179.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224884
_cod_database_fobs_code          2224884
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
Cl Cl1 0.29429(4) 0.33126(4) 0.00802(3) 0.04507(14) Uani d . 1 . .
N N1 0.77776(14) 0.02156(14) 0.14627(10) 0.0356(3) Uani d . 1 . .
N N2 0.91155(14) 0.15323(14) 0.16783(10) 0.0352(3) Uani d . 1 . .
C C1 0.61460(19) 0.30695(19) 0.16123(16) 0.0498(4) Uani d . 1 . .
H H1A 0.5794 0.3046 0.2403 0.075 Uiso calc R 1 . .
H H1B 0.5340 0.3064 0.1200 0.075 Uiso calc R 1 . .
H H1C 0.6328 0.4036 0.1249 0.075 Uiso calc R 1 . .
C C2 0.76494(17) 0.16248(17) 0.15880(12) 0.0360(3) Uani d . 1 . .
C C3 0.93932(17) -0.08252(17) 0.14577(12) 0.0349(3) Uani d . 1 . .
C C4 1.0170(2) -0.23710(18) 0.12901(14) 0.0434(4) Uani d . 1 . .
H H4 0.9608 -0.2928 0.1179 0.052 Uiso calc R 1 . .
C C5 1.1821(2) -0.3032(2) 0.12974(15) 0.0515(4) Uani d . 1 . .
H H5 1.2387 -0.4067 0.1194 0.062 Uiso calc R 1 . .
C C6 1.2669(2) -0.2194(2) 0.14549(16) 0.0541(4) Uani d . 1 . .
H H6 1.3781 -0.2688 0.1458 0.065 Uiso calc R 1 . .
C C7 1.18996(19) -0.0654(2) 0.16059(14) 0.0454(4) Uani d . 1 . .
H H7 1.2462 -0.0092 0.1704 0.054 Uiso calc R 1 . .
C C8 1.02401(17) 0.00110(17) 0.16028(12) 0.0350(3) Uani d . 1 . .
C C9 0.64487(18) -0.02047(18) 0.13464(14) 0.0416(3) Uani d . 1 . .
H H9 0.6788 -0.0902 0.0830 0.050 Uiso calc R 1 . .
H H9B 0.5545 0.0780 0.1000 0.050 Uiso calc R 1 . .
C C10 0.59317(18) -0.10561(18) 0.25015(14) 0.0411(3) Uani d . 1 . .
C C11 0.4779(2) -0.0170(2) 0.3180(2) 0.0646(5) Uani d . 1 . .
H H11 0.4329 0.0959 0.2926 0.078 Uiso calc R 1 . .
C C12 0.4288(3) -0.0946(3) 0.4233(2) 0.0821(7) Uani d . 1 . .
H H12 0.3506 -0.0341 0.4682 0.099 Uiso calc R 1 . .
C C13 0.4951(3) -0.2606(3) 0.4616(2) 0.0750(6) Uani d . 1 . .
H H13 0.4628 -0.3126 0.5329 0.090 Uiso calc R 1 . .
C C14 0.6089(3) -0.3505(3) 0.3951(2) 0.0668(5) Uani d . 1 . .
H H14 0.6539 -0.4633 0.4212 0.080 Uiso calc R 1 . .
C C15 0.6566(2) -0.2729(2) 0.28935(17) 0.0526(4) Uani d . 1 . .
H H15 0.7325 -0.3343 0.2438 0.063 Uiso calc R 1 . .
C C16 0.95196(19) 0.28401(18) 0.17480(13) 0.0405(3) Uani d . 1 . .
H H16 0.8649 0.3876 0.1434 0.049 Uiso calc R 1 . .
H H16B 1.0466 0.2809 0.1268 0.049 Uiso calc R 1 . .
C C17 0.98260(18) 0.27339(17) 0.29640(13) 0.0380(3) Uani d . 1 . .
C C18 0.9089(2) 0.2087(2) 0.39402(15) 0.0533(4) Uani d . 1 . .
H H18 0.8402 0.1638 0.3866 0.064 Uiso calc R 1 . .
C C19 0.9367(3) 0.2104(3) 0.50305(17) 0.0700(6) Uani d . 1 . .
H H19 0.8861 0.1670 0.5682 0.084 Uiso calc R 1 . .
C C20 1.0372(3) 0.2749(3) 0.5152(2) 0.0813(7) Uani d . 1 . .
H H20 1.0558 0.2754 0.5885 0.098 Uiso calc R 1 . .
C C21 1.1109(3) 0.3392(3) 0.4191(2) 0.0821(7) Uani d . 1 . .
H H21 1.1794 0.3838 0.4274 0.099 Uiso calc R 1 . .
C C22 1.0846(2) 0.3384(2) 0.31030(18) 0.0574(5) Uani d . 1 . .
H H22 1.1359 0.3820 0.2457 0.069 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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 N1 C3 . . 108.77(12) ?
C2 N1 C9 . . 126.81(12) ?
C3 N1 C9 . . 124.43(12) ?
C2 N2 C8 . . 108.89(12) ?
C2 N2 C16 . . 126.78(13) ?
C8 N2 C16 . . 124.15(12) ?
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 ?
N2 C2 N1 . . 109.12(13) ?
N2 C2 C1 . . 124.66(13) ?
N1 C2 C1 . . 126.21(13) ?
C8 C3 C4 . . 121.57(14) ?
C8 C3 N1 . . 106.52(12) ?
C4 C3 N1 . . 131.83(14) ?
C5 C4 C3 . . 116.23(15) ?
C5 C4 H4 . . 121.9 ?
C3 C4 H4 . . 121.9 ?
C4 C5 C6 . . 122.05(16) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C7 C6 C5 . . 121.71(16) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 116.38(15) ?
C6 C7 H7 . . 121.8 ?
C8 C7 H7 . . 121.8 ?
C7 C8 C3 . . 122.05(14) ?
C7 C8 N2 . . 131.20(14) ?
C3 C8 N2 . . 106.69(12) ?
N1 C9 C10 . . 111.98(12) ?
N1 C9 H9 . . 109.2 ?
C10 C9 H9 . . 109.2 ?
N1 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9 C9 H9B . . 107.9 ?
C15 C10 C11 . . 118.51(16) ?
C15 C10 C9 . . 121.09(15) ?
C11 C10 C9 . . 120.38(15) ?
C10 C11 C12 . . 120.55(19) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.2(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.71(19) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C10 C15 C14 . . 120.95(18) ?
C10 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
N2 C16 C17 . . 113.56(12) ?
N2 C16 H16 . . 108.9 ?
C17 C16 H16 . . 108.9 ?
N2 C16 H16B . . 108.9 ?
C17 C16 H16B . . 108.9 ?
H16 C16 H16B . . 107.7 ?
C22 C17 C18 . . 118.45(16) ?
C22 C17 C16 . . 117.98(14) ?
C18 C17 C16 . . 123.51(14) ?
C17 C18 C19 . . 120.39(18) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C20 C19 C18 . . 120.4(2) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C21 . . 119.68(19) ?
C19 C20 H20 . . 120.2 ?
C21 C20 H20 . . 120.2 ?
C20 C21 C22 . . 120.6(2) ?
C20 C21 H21 . . 119.7 ?
C22 C21 H21 . . 119.7 ?
C21 C22 C17 . . 120.4(2) ?
C21 C22 H22 . . 119.8 ?
C17 C22 H22 . . 119.8 ?
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 C2 . 1.3416(18) ?
N1 C3 . 1.3941(18) ?
N1 C9 . 1.4821(18) ?
N2 C2 . 1.3406(18) ?
N2 C8 . 1.3902(18) ?
N2 C16 . 1.4664(18) ?
C1 C2 . 1.479(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C8 . 1.389(2) ?
C3 C4 . 1.391(2) ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.397(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.378(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.388(2) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.507(2) ?
C9 H9 . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C15 . 1.380(2) ?
C10 C11 . 1.382(2) ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.368(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.370(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.380(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.505(2) ?
C16 H16 . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.381(2) ?
C17 C18 . 1.381(2) ?
C18 C19 . 1.387(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.358(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.368(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.377(3) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
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
C8 N2 C2 N1 . . . . 0.33(16) ?
C16 N2 C2 N1 . . . . 175.59(12) ?
C8 N2 C2 C1 . . . . -179.08(14) ?
C16 N2 C2 C1 . . . . -3.8(2) ?
C3 N1 C2 N2 . . . . -0.73(16) ?
C9 N1 C2 N2 . . . . 179.28(13) ?
C3 N1 C2 C1 . . . . 178.67(14) ?
C9 N1 C2 C1 . . . . -1.3(2) ?
C2 N1 C3 C8 . . . . 0.84(15) ?
C9 N1 C3 C8 . . . . -179.17(12) ?
C2 N1 C3 C4 . . . . -175.93(15) ?
C9 N1 C3 C4 . . . . 4.1(2) ?
C8 C3 C4 C5 . . . . 1.1(2) ?
N1 C3 C4 C5 . . . . 177.47(15) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . -0.3(3) ?
C5 C6 C7 C8 . . . . 0.5(3) ?
C6 C7 C8 C3 . . . . 0.1(2) ?
C6 C7 C8 N2 . . . . -176.73(15) ?
C4 C3 C8 C7 . . . . -1.0(2) ?
N1 C3 C8 C7 . . . . -178.13(13) ?
C4 C3 C8 N2 . . . . 176.55(13) ?
N1 C3 C8 N2 . . . . -0.62(14) ?
C2 N2 C8 C7 . . . . 177.39(15) ?
C16 N2 C8 C7 . . . . 2.0(2) ?
C2 N2 C8 C3 . . . . 0.20(15) ?
C16 N2 C8 C3 . . . . -175.22(12) ?
C2 N1 C9 C10 . . . . -93.34(17) ?
C3 N1 C9 C10 . . . . 86.67(17) ?
N1 C9 C10 C15 . . . . -93.28(17) ?
N1 C9 C10 C11 . . . . 88.23(18) ?
C15 C10 C11 C12 . . . . 0.7(3) ?
C9 C10 C11 C12 . . . . 179.22(19) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C11 C12 C13 C14 . . . . -0.8(4) ?
C12 C13 C14 C15 . . . . 0.0(4) ?
C11 C10 C15 C14 . . . . -1.5(3) ?
C9 C10 C15 C14 . . . . -179.97(16) ?
C13 C14 C15 C10 . . . . 1.1(3) ?
C2 N2 C16 C17 . . . . 100.24(17) ?
C8 N2 C16 C17 . . . . -85.18(17) ?
N2 C16 C17 C22 . . . . 152.21(15) ?
N2 C16 C17 C18 . . . . -30.7(2) ?
C22 C17 C18 C19 . . . . 0.4(3) ?
C16 C17 C18 C19 . . . . -176.69(16) ?
C17 C18 C19 C20 . . . . -0.3(3) ?
C18 C19 C20 C21 . . . . 0.3(4) ?
C19 C20 C21 C22 . . . . -0.3(4) ?
C20 C21 C22 C17 . . . . 0.3(3) ?
C18 C17 C22 C21 . . . . -0.4(3) ?
C16 C17 C22 C21 . . . . 176.83(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2118236
