#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235175.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_2235175
loop_
_publ_author_name
'Berger, Matthias'
'Auner, Norbert'
'Sinke, Tanja'
'Bolte, Michael'
_publ_section_title
;
 1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium bromide
 dichloromethane disolvate
;
_journal_coeditor_code           NG5272
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1845
_journal_paper_doi               10.1107/S1600536812022246
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C27 H37 N2 +, Br -, 2C H2 Cl2'
_chemical_formula_moiety         'C27 H37 N2 +, Br -, 2(C H2 Cl2)'
_chemical_formula_sum            'C29 H41 Br Cl4 N2'
_chemical_formula_weight         639.35
_chemical_name_systematic
;
1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium bromide
dichloromethane disolvate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 102.332(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1874(8)
_cell_length_b                   16.5165(12)
_cell_length_c                   11.0300(10)
_cell_measurement_reflns_used    19135
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.035
_cell_measurement_theta_min      3.345
_cell_volume                     1635.1(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20988
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.71
_diffrn_reflns_theta_min         3.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.604
_exptl_absorpt_correction_T_max  0.6995
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.362
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0377
_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)+(0.0410P)²+0.9357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                2867
_reflns_number_total             3200
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5272.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2235175
_cod_database_fobs_code          2235175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.29660(18) 0.18481(10) 0.41051(15) 0.0255(4) Uani d . 1 1 . .
C C1 0.2134(3) 0.2500 0.4158(3) 0.0241(6) Uani d S 1 2 . .
H H1 0.1119 0.2500 0.4222 0.029 Uiso calc SR 1 2 . .
C C2 0.4378(2) 0.20927(14) 0.4033(2) 0.0313(5) Uani d . 1 1 . .
H H2 0.5197 0.1751 0.3992 0.038 Uiso calc R 1 1 . .
C C3 0.1307(3) 0.11525(15) 0.1796(2) 0.0440(6) Uani d . 1 1 . .
H H3 0.1846 0.1682 0.1925 0.053 Uiso calc R 1 1 . .
C C4 -0.0359(4) 0.1327(2) 0.1415(3) 0.0594(8) Uani d . 1 1 . .
H H4A -0.0567 0.1626 0.0629 0.089 Uiso calc R 1 1 . .
H H4B -0.0669 0.1652 0.2059 0.089 Uiso calc R 1 1 . .
H H4C -0.0911 0.0815 0.1311 0.089 Uiso calc R 1 1 . .
C C5 0.1838(3) 0.0696(2) 0.0773(3) 0.0545(7) Uani d . 1 1 . .
H H5A 0.1607 0.1012 0.0004 0.082 Uiso calc R 1 1 . .
H H5B 0.1333 0.0171 0.0640 0.082 Uiso calc R 1 1 . .
H H5C 0.2917 0.0611 0.1017 0.082 Uiso calc R 1 1 . .
C C6 0.3631(3) 0.09778(16) 0.6435(2) 0.0394(5) Uani d . 1 1 . .
H H6 0.4138 0.1470 0.6197 0.047 Uiso calc R 1 1 . .
C C7 0.2619(4) 0.1250(3) 0.7253(4) 0.0934(15) Uani d . 1 1 . .
H H7A 0.1868 0.1621 0.6791 0.140 Uiso calc R 1 1 . .
H H7B 0.3203 0.1529 0.7980 0.140 Uiso calc R 1 1 . .
H H7C 0.2123 0.0779 0.7523 0.140 Uiso calc R 1 1 . .
C C8 0.4824(5) 0.0423(3) 0.7119(4) 0.1023(17) Uani d . 1 1 . .
H H8A 0.5472 0.0256 0.6565 0.153 Uiso calc R 1 1 . .
H H8B 0.4361 -0.0057 0.7401 0.153 Uiso calc R 1 1 . .
H H8C 0.5415 0.0707 0.7838 0.153 Uiso calc R 1 1 . .
C C11 0.2443(2) 0.10184(13) 0.4124(2) 0.0317(5) Uani d . 1 1 . .
C C12 0.1641(3) 0.06934(14) 0.3013(2) 0.0382(5) Uani d . 1 1 . .
C C13 0.1118(4) -0.00958(16) 0.3072(3) 0.0531(7) Uani d . 1 1 . .
H H13 0.0559 -0.0343 0.2342 0.064 Uiso calc R 1 1 . .
C C14 0.1396(4) -0.05222(16) 0.4166(3) 0.0578(8) Uani d . 1 1 . .
H H14 0.1019 -0.1057 0.4183 0.069 Uiso calc R 1 1 . .
C C15 0.2209(3) -0.01857(16) 0.5234(3) 0.0500(7) Uani d . 1 1 . .
H H15 0.2401 -0.0494 0.5978 0.060 Uiso calc R 1 1 . .
C C16 0.2761(3) 0.06008(14) 0.5248(2) 0.0366(5) Uani d . 1 1 . .
Br Br1 -0.17082(3) 0.2500 0.41902(3) 0.03239(11) Uani d S 1 2 . .
C C9 0.6207(8) 0.2781(5) 0.1008(6) 0.083(4) Uani d P 0.50 1 . .
H H9A 0.6687 0.2735 0.1899 0.100 Uiso calc PR 0.309(13) 1 A 1
H H9B 0.6987 0.2657 0.0540 0.100 Uiso calc PR 0.309(13) 1 A 1
H H9C 0.6825 0.2561 0.0452 0.100 Uiso calc PR 0.191(13) 1 A 2
H H9D 0.6666 0.2661 0.1886 0.100 Uiso calc PR 0.191(13) 1 A 2
Cl Cl1 0.5757(3) 0.3808(3) 0.0739(3) 0.1306(12) Uani d P 0.50 1 . .
Cl Cl2 0.4398(9) 0.2500 0.0600(7) 0.091(3) Uani d SP 0.38(3) 2 . 2
Cl Cl2' 0.4863(16) 0.1966(13) 0.0681(6) 0.129(7) Uani d P 0.309(13) 1 . 1
C C10 0.7893(8) 0.2231(4) 0.7366(6) 0.0643(18) Uani d P 0.50 1 . .
H H10A 0.7776 0.2363 0.6475 0.077 Uiso calc PR 0.50 1 . .
H H10B 0.7760 0.1639 0.7438 0.077 Uiso calc PR 0.50 1 . .
Cl Cl3 0.96814(15) 0.2500 0.81560(13) 0.0802(4) Uani d S 1 2 . .
Cl Cl4 0.6535(2) 0.27308(11) 0.79502(16) 0.0803(7) Uani d P 0.50 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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 '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
C1 N1 C2 . 108.82(18)
C1 N1 C11 . 124.62(18)
C2 N1 C11 . 126.56(18)
N1 C1 N1 4_565 108.2(3)
N1 C1 H1 4_565 125.9
N1 C1 H1 . 125.9
C2 C2 N1 4_565 107.06(12)
C2 C2 H2 4_565 126.5
N1 C2 H2 . 126.5
C12 C3 C5 . 111.9(2)
C12 C3 C4 . 109.9(2)
C5 C3 C4 . 110.6(2)
C12 C3 H3 . 108.1
C5 C3 H3 . 108.1
C4 C3 H3 . 108.1
C3 C4 H4A . 109.5
C3 C4 H4B . 109.5
H4A C4 H4B . 109.5
C3 C4 H4C . 109.5
H4A C4 H4C . 109.5
H4B C4 H4C . 109.5
C3 C5 H5A . 109.5
C3 C5 H5B . 109.5
H5A C5 H5B . 109.5
C3 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
C7 C6 C8 . 111.2(3)
C7 C6 C16 . 111.3(2)
C8 C6 C16 . 112.1(2)
C7 C6 H6 . 107.3
C8 C6 H6 . 107.3
C16 C6 H6 . 107.3
C6 C7 H7A . 109.5
C6 C7 H7B . 109.5
H7A C7 H7B . 109.5
C6 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C6 C8 H8A . 109.5
C6 C8 H8B . 109.5
H8A C8 H8B . 109.5
C6 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C16 C11 C12 . 124.2(2)
C16 C11 N1 . 118.2(2)
C12 C11 N1 . 117.7(2)
C11 C12 C13 . 116.2(2)
C11 C12 C3 . 123.7(2)
C13 C12 C3 . 120.1(2)
C14 C13 C12 . 121.2(3)
C14 C13 H13 . 119.4
C12 C13 H13 . 119.4
C15 C14 C13 . 120.8(2)
C15 C14 H14 . 119.6
C13 C14 H14 . 119.6
C14 C15 C16 . 121.2(2)
C14 C15 H15 . 119.4
C16 C15 H15 . 119.4
C15 C16 C11 . 116.4(2)
C15 C16 C6 . 121.1(2)
C11 C16 C6 . 122.5(2)
Cl2 C9 Cl1 . 92.2(4)
Cl2 C9 H9A . 116.6
Cl1 C9 H9A . 106.3
Cl2' C9 H9A . 106.3
Cl2 C9 H9B . 125.7
Cl1 C9 H9B . 106.3
Cl2' C9 H9B . 106.3
H9A C9 H9B . 106.4
Cl2 C9 H9C . 113.3
Cl1 C9 H9C . 113.3
Cl2 C9 H9D . 113.3
Cl1 C9 H9D . 113.3
Cl2' C9 H9D . 100.2
H9C C9 H9D . 110.6
Cl2' Cl1 C9 4_565 45.3(3)
Cl1 Cl2' C9 4_565 106.2(9)
Cl4 C10 Cl3 . 111.7(3)
Cl4 C10 H10A . 109.3
Cl3 C10 H10A . 109.3
Cl4 C10 H10B . 109.3
Cl3 C10 H10B . 109.3
H10A C10 H10B . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.329(2)
N1 C2 . 1.377(3)
N1 C11 . 1.454(3)
C1 N1 4_565 1.329(2)
C1 H1 . 0.9500
C2 C2 4_565 1.346(5)
C2 H2 . 0.9500
C3 C12 . 1.515(3)
C3 C5 . 1.521(4)
C3 C4 . 1.525(4)
C3 H3 . 1.0000
C4 H4A . 0.9800
C4 H4B . 0.9800
C4 H4C . 0.9800
C5 H5A . 0.9800
C5 H5B . 0.9800
C5 H5C . 0.9800
C6 C7 . 1.496(4)
C6 C8 . 1.503(4)
C6 C16 . 1.514(3)
C6 H6 . 1.0000
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 0.9800
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C11 C16 . 1.394(3)
C11 C12 . 1.395(3)
C12 C13 . 1.396(4)
C13 C14 . 1.373(4)
C13 H13 . 0.9500
C14 C15 . 1.371(4)
C14 H14 . 0.9500
C15 C16 . 1.393(4)
C15 H15 . 0.9500
C9 Cl2 . 1.691(10)
C9 Cl1 . 1.757(10)
C9 Cl2' . 1.810(11)
C9 H9A . 0.9900
C9 H9B . 0.9900
C9 H9C . 0.9900
C9 H9D . 0.9900
Cl1 Cl2' 4_565 1.51(3)
Cl2 C9 4_565 1.691(10)
Cl2' C9 4_565 1.280(11)
Cl2' Cl1 4_565 1.51(3)
Cl2' Cl2' 4_565 1.76(4)
C10 Cl4 . 1.731(6)
C10 Cl3 . 1.745(7)
C10 H10A . 0.9900
C10 H10B . 0.9900
Cl3 C10 4_565 1.745(7)
Cl4 Cl4 4_565 0.763(4)
Cl4 C10 4_565 1.523(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 Br1 0.95 2.59 3.538(3) 175.1
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_4
_geom_torsion
C2 N1 C1 N1 4_565 0.8(3)
C11 N1 C1 N1 4_565 -179.28(14)
C1 N1 C2 C2 4_565 -0.50(18)
C11 N1 C2 C2 4_565 179.60(16)
C1 N1 C11 C16 . -98.5(3)
C2 N1 C11 C16 . 81.4(3)
C1 N1 C11 C12 . 81.0(3)
C2 N1 C11 C12 . -99.1(3)
C16 C11 C12 C13 . 1.2(4)
N1 C11 C12 C13 . -178.1(2)
C16 C11 C12 C3 . -179.8(2)
N1 C11 C12 C3 . 0.8(4)
C5 C3 C12 C11 . 124.9(3)
C4 C3 C12 C11 . -111.8(3)
C5 C3 C12 C13 . -56.2(4)
C4 C3 C12 C13 . 67.1(3)
C11 C12 C13 C14 . -0.5(4)
C3 C12 C13 C14 . -179.5(3)
C12 C13 C14 C15 . -0.6(5)
C13 C14 C15 C16 . 0.9(5)
C14 C15 C16 C11 . -0.2(4)
C14 C15 C16 C6 . 178.7(3)
C12 C11 C16 C15 . -0.9(4)
N1 C11 C16 C15 . 178.5(2)
C12 C11 C16 C6 . -179.8(2)
N1 C11 C16 C6 . -0.4(3)
C7 C6 C16 C15 . -77.5(4)
C8 C6 C16 C15 . 47.7(4)
C7 C6 C16 C11 . 101.3(3)
C8 C6 C16 C11 . -133.5(3)
Cl2 C9 Cl1 Cl2' 4_565 2.7(5)
Cl2' C9 Cl1 Cl2' 4_565 7.6(4)
Cl1 C9 Cl2 C9 4_565 174.0(2)
Cl2' C9 Cl2 C9 4_565 1.6(6)
Cl2 C9 Cl2' C9 4_565 -177.7(8)
Cl1 C9 Cl2' C9 4_565 173.1(2)
Cl2 C9 Cl2' Cl1 4_565 175.3(9)
Cl1 C9 Cl2' Cl1 4_565 166.1(5)
Cl2 C9 Cl2' Cl2' 4_565 2.3(8)
Cl1 C9 Cl2' Cl2' 4_565 -6.9(2)
Cl4 C10 Cl3 C10 4_565 -50.6(3)
Cl3 C10 Cl4 Cl4 4_565 -121.8(4)
Cl3 C10 Cl4 C10 4_565 58.2(4)
