#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227866.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_2227866
loop_
_publ_author_name
'Lee, Hon Man'
'Cheng, Pi-Yun'
_publ_section_title
;
 3,3'-Dibenzyl-1,1'-ethylenediimidazolium dibromide
;
_journal_coeditor_code           OM2353
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2308
_journal_paper_doi               10.1107/S1600536810031934
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H24 N4 2+, 2Br -'
_chemical_formula_moiety         'C22 H24 N4 2+, 2(Br -)'
_chemical_formula_sum            'C22 H24 Br2 N4'
_chemical_formula_weight         504.27
_chemical_name_systematic
;
3,3'-Dibenzyl-1,1'-ethylenediimidazolium dibromide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.495(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.4674(8)
_cell_length_b                   5.2099(2)
_cell_length_c                   12.3736(6)
_cell_measurement_reflns_used    2242
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1054.76(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10232
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.858
_exptl_absorpt_correction_T_max  0.5125
_exptl_absorpt_correction_T_min  0.4455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.458
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1915
_reflns_number_total             2542
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om2353.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227866
_cod_database_fobs_code          2227866
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'
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 0.326856(16) 0.58076(5) 0.570787(19) 0.02456(10) Uani d . 1 . .
C C1 0.34814(15) 0.0860(5) 0.37001(19) 0.0191(5) Uani d . 1 . .
H H1 0.3171 -0.0415 0.4018 0.023 Uiso calc R 1 . .
C C2 0.45155(15) 0.3145(5) 0.32355(19) 0.0186(5) Uani d . 1 . .
H H2 0.5056 0.3725 0.3176 0.022 Uiso calc R 1 . .
C C3 0.38199(15) 0.4239(5) 0.27857(19) 0.0196(5) Uani d . 1 . .
H H3 0.3777 0.5737 0.2345 0.024 Uiso calc R 1 . .
C C4 0.48543(14) -0.0683(4) 0.44729(18) 0.0173(5) Uani d . 1 . .
H H4A 0.5327 -0.1128 0.4082 0.021 Uiso calc R 1 . .
H H4B 0.4569 -0.2290 0.4628 0.021 Uiso calc R 1 . .
C C5 0.23178(16) 0.3432(5) 0.2752(2) 0.0300(7) Uani d . 1 . .
H H5A 0.2227 0.3566 0.1949 0.036 Uiso calc R 1 . .
H H5B 0.2199 0.5131 0.3056 0.036 Uiso calc R 1 . .
C C6 0.17344(15) 0.1494(5) 0.3122(2) 0.0230(6) Uani d . 1 . .
C C7 0.15780(16) 0.1430(6) 0.4197(2) 0.0324(7) Uani d . 1 . .
H H7 0.1842 0.2621 0.4701 0.039 Uiso calc R 1 . .
C C8 0.10409(18) -0.0349(6) 0.4545(3) 0.0381(8) Uani d . 1 . .
H H8 0.0944 -0.0402 0.5287 0.046 Uiso calc R 1 . .
C C9 0.06422(16) -0.2064(6) 0.3799(3) 0.0380(8) Uani d . 1 . .
H H9 0.0271 -0.3289 0.4031 0.046 Uiso calc R 1 . .
C C10 0.07858(17) -0.1982(6) 0.2731(3) 0.0350(7) Uani d . 1 . .
H H10 0.0508 -0.3134 0.2221 0.042 Uiso calc R 1 . .
C C11 0.13354(16) -0.0224(5) 0.2392(2) 0.0281(6) Uani d . 1 . .
H H11 0.1439 -0.0199 0.1652 0.034 Uiso calc R 1 . .
N N1 0.42965(12) 0.1019(4) 0.37997(15) 0.0166(4) Uani d . 1 . .
N N2 0.31810(11) 0.2793(4) 0.30799(15) 0.0178(4) Uani d . 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'
Br Br -0.2901 2.4595 '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
N2 C1 N1 . . 108.1(2) ?
N2 C1 H1 . . 125.9 ?
N1 C1 H1 . . 125.9 ?
C3 C2 N1 . . 106.9(2) ?
C3 C2 H2 . . 126.5 ?
N1 C2 H2 . . 126.5 ?
C2 C3 N2 . . 107.5(2) ?
C2 C3 H3 . . 126.3 ?
N2 C3 H3 . . 126.3 ?
N1 C4 C4 . 3_656 108.8(2) ?
N1 C4 H4A . . 109.9 ?
C4 C4 H4A 3_656 . 109.9 ?
N1 C4 H4B . . 109.9 ?
C4 C4 H4B 3_656 . 109.9 ?
H4A C4 H4B . . 108.3 ?
N2 C5 C6 . . 113.3(2) ?
N2 C5 H5A . . 108.9 ?
C6 C5 H5A . . 108.9 ?
N2 C5 H5B . . 108.9 ?
C6 C5 H5B . . 108.9 ?
H5A C5 H5B . . 107.7 ?
C7 C6 C11 . . 119.1(3) ?
C7 C6 C5 . . 120.3(2) ?
C11 C6 C5 . . 120.6(3) ?
C6 C7 C8 . . 120.7(3) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C7 C8 C9 . . 119.6(3) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C10 C9 C8 . . 119.9(3) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 120.2(3) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C6 C11 C10 . . 120.6(3) ?
C6 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C1 N1 C2 . . 108.7(2) ?
C1 N1 C4 . . 125.0(2) ?
C2 N1 C4 . . 126.2(2) ?
C1 N2 C3 . . 108.8(2) ?
C1 N2 C5 . . 128.0(2) ?
C3 N2 C5 . . 123.1(2) ?
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
C1 N2 . 1.328(3) ?
C1 N1 . 1.336(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.343(3) ?
C2 N1 . 1.379(3) ?
C2 H2 . 0.9500 ?
C3 N2 . 1.376(3) ?
C3 H3 . 0.9500 ?
C4 N1 . 1.467(3) ?
C4 C4 3_656 1.515(4) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 N2 . 1.472(3) ?
C5 C6 . 1.501(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.384(4) ?
C6 C11 . 1.384(4) ?
C7 C8 . 1.383(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.394(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.369(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.386(4) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
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
C1 H1 Br1 1_545 0.95 2.86 3.663(2) 142.6
C3 H3 Br1 4_575 0.95 2.77 3.683(2) 162.0
C4 H4B Br1 1_545 0.99 2.83 3.661(3) 142.2
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
N1 C2 C3 N2 . . . . 0.3(3) ?
N2 C5 C6 C7 . . . . 76.1(3) ?
N2 C5 C6 C11 . . . . -105.0(3) ?
C11 C6 C7 C8 . . . . 1.0(4) ?
C5 C6 C7 C8 . . . . 180.0(3) ?
C6 C7 C8 C9 . . . . -1.2(4) ?
C7 C8 C9 C10 . . . . 0.2(4) ?
C8 C9 C10 C11 . . . . 1.0(4) ?
C7 C6 C11 C10 . . . . 0.1(4) ?
C5 C6 C11 C10 . . . . -178.8(2) ?
C9 C10 C11 C6 . . . . -1.1(4) ?
N2 C1 N1 C2 . . . . 0.9(3) ?
N2 C1 N1 C4 . . . . 176.4(2) ?
C3 C2 N1 C1 . . . . -0.7(3) ?
C3 C2 N1 C4 . . . . -176.2(2) ?
C4 C4 N1 C1 3_656 . . . -100.5(3) ?
C4 C4 N1 C2 3_656 . . . 74.3(3) ?
N1 C1 N2 C3 . . . . -0.7(3) ?
N1 C1 N2 C5 . . . . -179.3(2) ?
C2 C3 N2 C1 . . . . 0.2(3) ?
C2 C3 N2 C5 . . . . 178.9(2) ?
C6 C5 N2 C1 . . . . -4.6(4) ?
C6 C5 N2 C3 . . . . 176.9(2) ?
