#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235174.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_2235174
loop_
_publ_author_name
'Berger, Matthias'
'Auner, Norbert'
'Bolte, Michael'
_publ_section_title
;
 1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride
 dichloromethane disolvate
;
_journal_coeditor_code           NG5271
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1844
_journal_paper_doi               10.1107/S1600536812022234
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C27 H37 N2 +, Cl -, 2C H2 Cl2'
_chemical_formula_moiety         'C27 H37 N2 +, Cl -, 2(C H2 Cl2)'
_chemical_formula_sum            'C29 H41 Cl5 N2'
_chemical_formula_weight         594.89
_chemical_name_systematic
;
1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride
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                 101.068(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1117(4)
_cell_length_b                   16.4990(8)
_cell_length_c                   10.8875(6)
_cell_measurement_reflns_used    27732
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.3
_cell_volume                     1606.32(14)
_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 0.997
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            17793
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.8637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.360
_refine_diff_density_min         -1.601
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0746
_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)+(0.0696P)²+3.4645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1839
_reflns_number_gt                2648
_reflns_number_total             2934
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5271.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2235174
_cod_database_fobs_code          2235174
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
Cl Cl1 0.66661(12) 0.2500 0.57563(10) 0.0339(3) Uani d S 1 2 . .
N N1 0.2042(3) 0.31549(14) 0.5835(2) 0.0248(5) Uani d . 1 1 . .
C C1 0.2891(4) 0.2500 0.5788(3) 0.0245(8) Uani d S 1 2 . .
H H1 0.3918 0.2500 0.5730 0.029 Uiso calc SR 1 2 . .
C C2 0.0606(3) 0.29075(18) 0.5907(3) 0.0289(6) Uani d . 1 1 . .
H H2 -0.0222 0.3250 0.5948 0.035 Uiso calc R 1 1 . .
C C11 0.2556(3) 0.39874(17) 0.5807(3) 0.0298(6) Uani d . 1 1 . .
C C12 0.2225(4) 0.44066(19) 0.4672(3) 0.0356(7) Uani d . 1 1 B .
C C13 0.2757(4) 0.5201(2) 0.4671(3) 0.0484(9) Uani d . 1 1 . .
H H13 0.2547 0.5510 0.3921 0.058 Uiso calc R 1 1 . .
C C14 0.3582(5) 0.5546(2) 0.5738(4) 0.0571(10) Uani d . 1 1 . .
H H14 0.3955 0.6081 0.5711 0.068 Uiso calc R 1 1 . .
C C15 0.3866(5) 0.5115(2) 0.6843(4) 0.0503(9) Uani d . 1 1 . .
H H15 0.4419 0.5365 0.7574 0.060 Uiso calc R 1 1 . .
C C16 0.3359(4) 0.43202(18) 0.6913(3) 0.0358(7) Uani d . 1 1 . .
C C21 0.1357(4) 0.4026(2) 0.3483(3) 0.0386(7) Uani d . 1 1 . .
H H21 0.1064 0.3468 0.3703 0.046 Uiso calc R 1 1 A 1
C C22 0.2339(9) 0.3934(6) 0.2452(8) 0.054(2) Uiso d P 0.50 1 B 1
H H22A 0.3048 0.3487 0.2676 0.081 Uiso calc PR 0.50 1 B 1
H H22B 0.2890 0.4438 0.2393 0.081 Uiso calc PR 0.50 1 B 1
H H22C 0.1691 0.3820 0.1643 0.081 Uiso calc PR 0.50 1 B 1
C C23 -0.0049(9) 0.4473(5) 0.2962(8) 0.0508(18) Uiso d P 0.50 1 B 1
H H23A 0.0003 0.5021 0.3314 0.076 Uiso calc PR 0.50 1 B 1
H H23B -0.0905 0.4185 0.3180 0.076 Uiso calc PR 0.50 1 B 1
H H23C -0.0169 0.4505 0.2049 0.076 Uiso calc PR 0.50 1 B 1
C C22' 0.2392(8) 0.3593(5) 0.2818(7) 0.0421(16) Uiso d P 0.50 1 B 2
H H22D 0.1995 0.3606 0.1916 0.063 Uiso calc PR 0.50 1 B 2
H H22E 0.2495 0.3029 0.3105 0.063 Uiso calc PR 0.50 1 B 2
H H22F 0.3373 0.3858 0.2994 0.063 Uiso calc PR 0.50 1 B 2
C C23' 0.0432(10) 0.4686(5) 0.2642(8) 0.055(2) Uiso d P 0.50 1 B 2
H H23D -0.0477 0.4442 0.2157 0.082 Uiso calc PR 0.50 1 B 2
H H23E 0.1035 0.4912 0.2069 0.082 Uiso calc PR 0.50 1 B 2
H H23F 0.0159 0.5120 0.3171 0.082 Uiso calc PR 0.50 1 B 2
C C61 0.3705(4) 0.3863(2) 0.8146(3) 0.0405(8) Uani d . 1 1 . .
H H61 0.3160 0.3334 0.8034 0.049 Uiso calc R 1 1 . .
C C62 0.5383(5) 0.3685(3) 0.8486(3) 0.0561(10) Uani d . 1 1 . .
H H62A 0.5600 0.3388 0.9281 0.084 Uiso calc R 1 1 . .
H H62B 0.5941 0.4196 0.8571 0.084 Uiso calc R 1 1 . .
H H62C 0.5680 0.3356 0.7826 0.084 Uiso calc R 1 1 . .
C C63 0.3195(4) 0.4323(2) 0.9205(3) 0.0484(9) Uani d . 1 1 . .
H H63A 0.3446 0.4008 0.9981 0.073 Uiso calc R 1 1 . .
H H63B 0.2111 0.4406 0.8995 0.073 Uiso calc R 1 1 . .
H H63C 0.3701 0.4849 0.9321 0.073 Uiso calc R 1 1 . .
C C3 0.8708(8) 0.2675(6) 0.8843(7) 0.065(4) Uani d PD 0.50 1 . 1
H H3A 0.8224 0.2614 0.7953 0.078 Uiso calc PR 0.50 1 . 1
H H3B 0.7940 0.2572 0.9355 0.078 Uiso calc PR 0.50 1 . 1
Cl Cl31 0.9337(5) 0.3663(3) 0.9093(4) 0.1291(19) Uani d PD 0.50 1 . 1
Cl Cl32 1.0117(5) 0.1947(4) 0.9208(3) 0.149(2) Uani d PD 0.50 1 . 1
C C4 0.7100(8) 0.2771(5) 1.2652(7) 0.059(2) Uani d PD 0.50 1 . .
H H4A 0.7124 0.3367 1.2759 0.070 Uiso calc PR 0.50 1 . .
H H4B 0.7219 0.2526 1.3495 0.070 Uiso calc PR 0.50 1 . .
Cl Cl41 0.8547(2) 0.2500 1.20316(19) 0.1263(12) Uani d SD 1 2 . .
Cl Cl42 0.53459(19) 0.2500 1.18007(18) 0.0806(6) Uani d SD 1 2 . .
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'
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 . . 108.9(2)
C1 N1 C11 . . 124.9(2)
C2 N1 C11 . . 126.2(2)
N1 C1 N1 4_565 . 108.0(3)
N1 C1 H1 4_565 . 126.0
N1 C1 H1 . . 126.0
C2 C2 N1 4_565 . 107.11(15)
C2 C2 H2 4_565 . 126.4
N1 C2 H2 . . 126.4
C16 C11 C12 . . 123.8(3)
C16 C11 N1 . . 118.1(3)
C12 C11 N1 . . 118.1(3)
C11 C12 C13 . . 116.7(3)
C11 C12 C21 . . 122.6(3)
C13 C12 C21 . . 120.8(3)
C14 C13 C12 . . 121.2(3)
C14 C13 H13 . . 119.4
C12 C13 H13 . . 119.4
C15 C14 C13 . . 120.3(3)
C15 C14 H14 . . 119.9
C13 C14 H14 . . 119.9
C14 C15 C16 . . 121.5(3)
C14 C15 H15 . . 119.3
C16 C15 H15 . . 119.3
C11 C16 C15 . . 116.5(3)
C11 C16 C61 . . 123.6(3)
C15 C16 C61 . . 119.9(3)
C22' C21 C23 . . 129.3(5)
C22' C21 C12 . . 109.9(4)
C23 C21 C12 . . 112.9(4)
C22' C21 C23' . . 111.9(5)
C12 C21 C23' . . 110.2(4)
C23 C21 C22 . . 109.9(5)
C12 C21 C22 . . 112.0(4)
C23' C21 C22 . . 88.0(5)
C22' C21 H21 . . 84.1
C23 C21 H21 . . 107.2
C12 C21 H21 . . 107.2
C23' C21 H21 . . 130.0
C22 C21 H21 . . 107.2
C21 C22 H22A . . 109.5
C21 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C21 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C21 C23 H23A . . 109.5
C21 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C21 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C21 C22' H22D . . 109.5
C21 C22' H22E . . 109.5
H22D C22' H22E . . 109.5
C21 C22' H22F . . 109.5
H22D C22' H22F . . 109.5
H22E C22' H22F . . 109.5
C21 C23' H23D . . 109.5
C21 C23' H23E . . 109.5
H23D C23' H23E . . 109.5
C21 C23' H23F . . 109.5
H23D C23' H23F . . 109.5
H23E C23' H23F . . 109.5
C16 C61 C63 . . 112.3(3)
C16 C61 C62 . . 109.7(3)
C63 C61 C62 . . 110.4(3)
C16 C61 H61 . . 108.1
C63 C61 H61 . . 108.1
C62 C61 H61 . . 108.1
C61 C62 H62A . . 109.5
C61 C62 H62B . . 109.5
H62A C62 H62B . . 109.5
C61 C62 H62C . . 109.5
H62A C62 H62C . . 109.5
H62B C62 H62C . . 109.5
C61 C63 H63A . . 109.5
C61 C63 H63B . . 109.5
H63A C63 H63B . . 109.5
C61 C63 H63C . . 109.5
H63A C63 H63C . . 109.5
H63B C63 H63C . . 109.5
Cl31 C3 Cl32 . . 113.9(5)
Cl31 C3 H3A . . 108.8
Cl32 C3 H3A . . 108.8
Cl31 C3 H3B . . 108.8
Cl32 C3 H3B . . 108.8
H3A C3 H3B . . 107.7
Cl32 Cl31 C3 4_565 . 53.9(4)
Cl31 Cl32 C3 4_565 4_565 81.7(5)
Cl31 Cl32 C3 4_565 . 98.9(5)
Cl31 Cl32 Cl32 4_565 4_565 145.3(3)
Cl41 C4 Cl42 . . 115.8(4)
Cl41 C4 H4A . . 108.3
Cl42 C4 H4A . . 108.3
Cl41 C4 H4B . . 108.3
Cl42 C4 H4B . . 108.3
H4A C4 H4B . . 107.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.335(3)
N1 C2 . 1.388(4)
N1 C11 . 1.453(4)
C1 N1 4_565 1.335(3)
C1 H1 . 0.9500
C2 C2 4_565 1.345(6)
C2 H2 . 0.9500
C11 C16 . 1.395(4)
C11 C12 . 1.398(4)
C12 C13 . 1.398(5)
C12 C21 . 1.517(4)
C13 C14 . 1.379(5)
C13 H13 . 0.9500
C14 C15 . 1.378(5)
C14 H14 . 0.9500
C15 C16 . 1.398(5)
C15 H15 . 0.9500
C16 C61 . 1.519(4)
C21 C22' . 1.479(8)
C21 C23 . 1.493(8)
C21 C23' . 1.562(9)
C21 C22 . 1.572(9)
C21 H21 . 1.0000
C22 H22A . 0.9800
C22 H22B . 0.9800
C22 H22C . 0.9800
C23 H23A . 0.9800
C23 H23B . 0.9800
C23 H23C . 0.9800
C22' H22D . 0.9800
C22' H22E . 0.9800
C22' H22F . 0.9800
C23' H23D . 0.9800
C23' H23E . 0.9800
C23' H23F . 0.9800
C61 C63 . 1.525(5)
C61 C62 . 1.531(5)
C61 H61 . 1.0000
C62 H62A . 0.9800
C62 H62B . 0.9800
C62 H62C . 0.9800
C63 H63A . 0.9800
C63 H63B . 0.9800
C63 H63C . 0.9800
C3 Cl31 . 1.732(11)
C3 Cl32 . 1.748(9)
C3 H3A . 0.9900
C3 H3B . 0.9900
Cl31 Cl32 4_565 1.225(7)
Cl32 Cl31 4_565 1.225(7)
Cl32 C3 4_565 1.414(9)
Cl32 Cl32 4_565 1.825(13)
C4 Cl41 . 1.654(7)
C4 Cl42 . 1.744(7)
C4 H4A . 0.9900
C4 H4B . 0.9900
Cl41 C4 4_565 1.654(7)
Cl42 C4 4_565 1.744(7)
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 Cl1 0.95 2.50 3.447(4) 175.7
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 -0.4(4)
C11 N1 C1 N1 4_565 179.95(19)
C1 N1 C2 C2 4_565 0.3(2)
C11 N1 C2 C2 4_565 179.9(2)
C1 N1 C11 C16 . -79.7(4)
C2 N1 C11 C16 . 100.8(3)
C1 N1 C11 C12 . 100.0(4)
C2 N1 C11 C12 . -79.6(4)
C16 C11 C12 C13 . 0.7(5)
N1 C11 C12 C13 . -178.9(3)
C16 C11 C12 C21 . 179.6(3)
N1 C11 C12 C21 . 0.0(4)
C11 C12 C13 C14 . 0.7(5)
C21 C12 C13 C14 . -178.2(4)
C12 C13 C14 C15 . -1.7(7)
C13 C14 C15 C16 . 1.2(7)
C12 C11 C16 C15 . -1.1(5)
N1 C11 C16 C15 . 178.5(3)
C12 C11 C16 C61 . 179.5(3)
N1 C11 C16 C61 . -0.9(5)
C14 C15 C16 C11 . 0.1(6)
C14 C15 C16 C61 . 179.5(4)
C11 C12 C21 C22' . -87.2(5)
C13 C12 C21 C22' . 91.7(5)
C11 C12 C21 C23 . 120.6(5)
C13 C12 C21 C23 . -60.5(6)
C11 C12 C21 C23' . 149.1(5)
C13 C12 C21 C23' . -32.1(5)
C11 C12 C21 C22 . -114.7(5)
C13 C12 C21 C22 . 64.2(5)
C11 C16 C61 C63 . -125.9(3)
C15 C16 C61 C63 . 54.7(5)
C11 C16 C61 C62 . 110.9(4)
C15 C16 C61 C62 . -68.4(4)
Cl32 C3 Cl31 Cl32 4_565 4.6(3)
Cl31 C3 Cl32 Cl31 4_565 172.1(6)
Cl31 C3 Cl32 C3 4_565 176.6(3)
Cl31 C3 Cl32 Cl32 4_565 -3.4(3)
Cl42 C4 Cl41 C4 4_565 -64.5(5)
Cl41 C4 Cl42 C4 4_565 64.0(5)
