#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240104.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_2240104
loop_
_publ_author_name
'Berger, Matthias'
'Auner, Norbert'
'Bolte, Michael'
_publ_section_title
;
 Crystal structure of
 1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium
 bromide dichloromethane disolvate
;
_journal_coeditor_code           HB7303
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1193
_journal_page_last               o1194
_journal_paper_doi               10.1107/S1600536814023150
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C29 H41 N2 + , Br - , 2C H2 Cl2 '
_chemical_formula_moiety         'C29 H41 N2, 2(C H2 Cl2), Br'
_chemical_formula_sum            'C31 H45 Br Cl4 N2'
_chemical_formula_weight         667.40
_chemical_name_systematic
;
1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide
dichloromethane disolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0644(11)
_cell_length_b                   16.6082(17)
_cell_length_c                   10.7107(15)
_cell_measurement_reflns_used    20226
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.2
_cell_volume                     1770.7(4)
_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
;
SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1564
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21288
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.195
_exptl_absorpt_coefficient_mu    1.484
_exptl_absorpt_correction_T_max  .756
_exptl_absorpt_correction_T_min  .756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.093
_refine_diff_density_min         -1.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1802
_refine_ls_R_factor_gt           0.1631
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1372P)²+27.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3826
_refine_ls_wR_factor_ref         0.3929
_reflns_number_gt                2618
_reflns_number_total             3229
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7303sup1.cif
_cod_data_source_block           I
_cod_database_code               2240104
_cod_database_fobs_code          2240104
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.756
_shelx_estimated_absorpt_t_max   0.756
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
N N1 0.7876(7) 0.1843(5) 0.4157(7) 0.0283(17) Uani d 1
C C1 0.7093(13) 0.2500 0.4193(12) 0.026(3) Uani d 1
H H1 0.6157 0.2500 0.4235 0.031 Uiso calc 1
C C2 0.9196(9) 0.2098(7) 0.4076(9) 0.035(2) Uani d 1
C C3 1.0285(10) 0.1493(7) 0.4038(12) 0.046(3) Uani d 1
H H3A 0.9910 0.0949 0.4060 0.069 Uiso calc 1
H H3B 1.0982 0.1569 0.4770 0.069 Uiso calc 1
H H3C 1.0678 0.1562 0.3261 0.069 Uiso calc 1
C C4 0.6880(14) 0.1029(8) 0.1817(11) 0.054(3) Uani d 1
H H4 0.7369 0.1553 0.1943 0.065 Uiso calc 1
C C5 0.5431(19) 0.1214(12) 0.1280(16) 0.092(6) Uani d 1
H H5A 0.5398 0.1470 0.0451 0.138 Uiso calc 1
H H5B 0.5049 0.1580 0.1852 0.138 Uiso calc 1
H H5C 0.4911 0.0714 0.1192 0.138 Uiso calc 1
C C6 0.7583(18) 0.0522(12) 0.0899(14) 0.081(5) Uani d 1
H H6A 0.8504 0.0401 0.1290 0.121 Uiso calc 1
H H6B 0.7602 0.0824 0.0117 0.121 Uiso calc 1
H H6C 0.7089 0.0017 0.0708 0.121 Uiso calc 1
C C7 0.7974(12) 0.1111(8) 0.6591(11) 0.048(3) Uani d 1
H H7 0.8410 0.1618 0.6351 0.057 Uiso calc 1
C C8 0.9077(15) 0.0617(10) 0.7486(13) 0.069(4) Uani d 1
H H8A 0.9385 0.0932 0.8247 0.103 Uiso calc 1
H H8B 0.9840 0.0504 0.7039 0.103 Uiso calc 1
H H8C 0.8689 0.0108 0.7723 0.103 Uiso calc 1
C C9 0.6840(16) 0.1355(10) 0.7316(13) 0.068(4) Uani d 1
H H9A 0.7215 0.1645 0.8085 0.102 Uiso calc 1
H H9B 0.6370 0.0873 0.7544 0.102 Uiso calc 1
H H9C 0.6206 0.1705 0.6785 0.102 Uiso calc 1
C C11 0.7393(10) 0.1030(7) 0.4224(10) 0.037(2) Uani d 1
C C12 0.6930(11) 0.0638(7) 0.3109(11) 0.045(3) Uani d 1
C C13 0.6476(13) -0.0157(8) 0.3211(13) 0.056(3) Uani d 1
H H13 0.6160 -0.0452 0.2467 0.067 Uiso calc 1
C C14 0.6482(13) -0.0516(8) 0.4379(13) 0.057(3) Uani d 1
H H14 0.6130 -0.1043 0.4434 0.068 Uiso calc 1
C C15 0.6993(12) -0.0112(8) 0.5450(12) 0.048(3) Uani d 1
H H15 0.7018 -0.0373 0.6242 0.058 Uiso calc 1
C C16 0.7483(10) 0.0679(7) 0.5420(10) 0.040(2) Uani d 1
Br Br1 0.36891(18) 0.2500 0.4011(2) 0.0582(7) Uani d 1
C C1L 0.250(3) 0.2500 0.711(3) 0.19(3) Uani d 1
H H1LA 0.2711 0.2180 0.6419 0.228 Uiso d 0.5
H H1LB 0.2390 0.3042 0.6806 0.228 Uiso d 0.5
Cl Cl1 0.3918(6) 0.2500 0.8208(6) 0.104(3) Uani d 1
Cl Cl2 0.1100(7) 0.2217(5) 0.7384(7) 0.074(2) Uani d 0.5
C C2L 1.165(2) 0.2500 0.089(2) 0.090(9) Uani d 1
H H2LA 1.1999 0.2798 0.0233 0.108 Uiso d 0.5
H H2LB 1.2084 0.2646 0.1703 0.108 Uiso d 0.5
Cl Cl3 1.1536(11) 0.1392(7) 0.0594(9) 0.100(3) Uani d 0.5
Cl Cl4 0.9934(12) 0.2500 0.0734(10) 0.253(11) 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'
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_site_symmetry_3
_geom_angle
C1 N1 C2 . . 108.6(8)
C1 N1 C11 . . 123.6(8)
C2 N1 C11 . . 127.8(8)
N1 C1 N1 4_565 . 107.9(11)
N1 C1 H1 4_565 . 126.1
N1 C1 H1 . . 126.1
C2 C2 N1 4_565 . 107.5(5)
C2 C2 C3 4_565 . 132.4(6)
N1 C2 C3 . . 120.2(10)
C2 C3 H3A . . 109.5
C2 C3 H3B . . 109.5
H3A C3 H3B . . 109.5
C2 C3 H3C . . 109.5
H3A C3 H3C . . 109.5
H3B C3 H3C . . 109.5
C5 C4 C12 . . 109.4(12)
C5 C4 C6 . . 112.0(12)
C12 C4 C6 . . 112.9(12)
C5 C4 H4 . . 107.4
C12 C4 H4 . . 107.4
C6 C4 H4 . . 107.4
C4 C5 H5A . . 109.5
C4 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C4 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C4 C6 H6A . . 109.5
C4 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C4 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C16 C7 C9 . . 112.5(11)
C16 C7 C8 . . 112.4(10)
C9 C7 C8 . . 109.9(11)
C16 C7 H7 . . 107.3
C9 C7 H7 . . 107.3
C8 C7 H7 . . 107.3
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C7 C9 H9A . . 109.5
C7 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C7 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C12 C11 C16 . . 124.3(11)
C12 C11 N1 . . 118.2(9)
C16 C11 N1 . . 117.4(9)
C11 C12 C13 . . 116.6(11)
C11 C12 C4 . . 123.2(11)
C13 C12 C4 . . 120.2(11)
C14 C13 C12 . . 121.1(12)
C14 C13 H13 . . 119.5
C12 C13 H13 . . 119.5
C15 C14 C13 . . 119.9(12)
C15 C14 H14 . . 120.0
C13 C14 H14 . . 120.0
C14 C15 C16 . . 122.1(11)
C14 C15 H15 . . 118.9
C16 C15 H15 . . 118.9
C11 C16 C15 . . 115.8(11)
C11 C16 C7 . . 123.2(10)
C15 C16 C7 . . 120.9(10)
Cl2 C1L Cl1 . . 123.9(16)
Cl2 C1L Cl1 4_565 . 123.9(16)
Cl2 C1L H1LA . . 106.5
Cl2 C1L H1LA 4_565 . 128.3
Cl1 C1L H1LA . . 106.1
Cl2 C1L H1LB . . 106.4
Cl1 C1L H1LB . . 106.2
H1LA C1L H1LB . . 106.8
Cl2 Cl2 C1L 4_565 . 72.4(5)
Cl4 C2L Cl3 . . 86.9(8)
Cl4 C2L Cl3 . 4_565 86.9(8)
Cl3 C2L Cl3 . 4_565 160.3(15)
Cl4 C2L H2LA . . 113.4
Cl3 C2L H2LA . . 113.8
Cl3 C2L H2LA 4_565 . 52.5
Cl4 C2L H2LB . . 114.0
Cl3 C2L H2LB . . 114.6
Cl3 C2L H2LB 4_565 . 85.0
H2LA C2L H2LB . . 112.0
Cl3 Cl4 Cl3 4_565 . 96.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.350(11)
N1 C2 . 1.409(12)
N1 C11 . 1.440(14)
C1 N1 4_565 1.350(11)
C1 H1 . 0.9500
C2 C2 4_565 1.34(2)
C2 C3 . 1.492(14)
C3 H3A . 0.9800
C3 H3B . 0.9800
C3 H3C . 0.9800
C4 C5 . 1.52(2)
C4 C12 . 1.523(17)
C4 C6 . 1.54(2)
C4 H4 . 1.0000
C5 H5A . 0.9800
C5 H5B . 0.9800
C5 H5C . 0.9800
C6 H6A . 0.9800
C6 H6B . 0.9800
C6 H6C . 0.9800
C7 C16 . 1.466(17)
C7 C9 . 1.527(17)
C7 C8 . 1.585(17)
C7 H7 . 1.0000
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C11 C12 . 1.380(16)
C11 C16 . 1.398(15)
C12 C13 . 1.406(18)
C13 C14 . 1.385(19)
C13 H13 . 0.9500
C14 C15 . 1.362(18)
C14 H14 . 0.9500
C15 C16 . 1.405(17)
C15 H15 . 0.9500
C1L Cl2 . 1.56(3)
C1L Cl2 4_565 1.56(3)
C1L Cl1 . 1.71(3)
C1L H1LA . 0.9592
C1L H1LB . 0.9585
Cl2 Cl2 4_565 0.941(16)
C2L Cl4 . 1.71(3)
C2L Cl3 . 1.867(12)
C2L Cl3 4_565 1.867(12)
C2L H2LA . 0.9648
C2L H2LB . 0.9468
Cl3 Cl4 . 2.465(14)
Cl4 Cl3 4_565 2.465(14)
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
C H Br1 0.95 2.46 3.403(13) 172
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_4
_geom_torsion
C2 N1 C1 N1 . 4_565 -1.0(13)
C11 N1 C1 N1 . 4_565 177.7(6)
C1 N1 C2 C2 . 4_565 0.6(8)
C11 N1 C2 C2 . 4_565 -178.0(8)
C1 N1 C2 C3 . . 179.2(10)
C11 N1 C2 C3 . . 0.6(15)
C1 N1 C11 C12 . . 91.6(12)
C2 N1 C11 C12 . . -89.9(12)
C1 N1 C11 C16 . . -91.3(12)
C2 N1 C11 C16 . . 87.2(12)
C16 C11 C12 C13 . . 2.6(16)
N1 C11 C12 C13 . . 179.5(9)
C16 C11 C12 C4 . . -178.2(10)
N1 C11 C12 C4 . . -1.3(16)
C5 C4 C12 C11 . . -107.1(14)
C6 C4 C12 C11 . . 127.4(13)
C5 C4 C12 C13 . . 72.0(15)
C6 C4 C12 C13 . . -53.5(16)
C11 C12 C13 C14 . . 0.8(17)
C4 C12 C13 C14 . . -178.3(12)
C12 C13 C14 C15 . . -3.1(19)
C13 C14 C15 C16 . . 2.1(19)
C12 C11 C16 C15 . . -3.6(15)
N1 C11 C16 C15 . . 179.5(9)
C12 C11 C16 C7 . . -179.8(10)
N1 C11 C16 C7 . . 3.3(15)
C14 C15 C16 C11 . . 1.1(17)
C14 C15 C16 C7 . . 177.4(11)
C9 C7 C16 C11 . . 104.4(13)
C8 C7 C16 C11 . . -130.9(12)
C9 C7 C16 C15 . . -71.5(14)
C8 C7 C16 C15 . . 53.1(15)
Cl1 C1L Cl2 Cl2 . 4_565 102.3(9)
Cl3 C2L Cl3 Cl4 4_565 . -72(4)
Cl3 C2L Cl4 Cl3 . 4_565 -161.3(14)
Cl3 C2L Cl4 Cl3 4_565 . 161.3(14)
