#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:07:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208187.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_7208187
loop_
_publ_author_name
'Tadesse, Haregewine'
'Blake, Alexander J.'
'Champness, Neil R.'
'Warren, John E.'
'Rizkallah, Pierre J.'
'Licence, Peter'
_publ_section_title
;
 Supramolecular architectures of symmetrical dicationic ionic liquid based
 systems
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              4886
_journal_paper_doi               10.1039/c2ce25106j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H36 N4 2+, 2(Br-), 1.2(C7 H8)'
_chemical_formula_sum            'C28.4 H45.6 Br2 N4'
_chemical_formula_weight         602.91
_chemical_name_systematic
;
?
;
_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           'enCIFer eding of SHELXL97 CIF output'
_cell_angle_alpha                79.880(2)
_cell_angle_beta                 86.970(2)
_cell_angle_gamma                63.148(2)
_cell_formula_units_Z            2
_cell_length_a                   8.402(2)
_cell_length_b                   8.826(2)
_cell_length_c                   23.752(5)
_cell_measurement_reflns_used    4410
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1546.3(6)
_computing_cell_refinement       'Bruker SAINT version 7.23A (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 version 2.0-1 (Bruker, 2006)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'MERCURY (Bruno et al., 2006)'
_computing_publication_material
'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS Station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6703
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17642
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS version 2004/1; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.016
_platon_squeeze_details
;
?
;
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.66
_refine_diff_density_rms         0.07
_refine_ls_extinction_coef       0.0252(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.86
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         9183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.86
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                5377
_reflns_number_total             9183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce25106j.txt
_cod_data_source_block           4.1.2(C7H8)
_cod_database_code               7208187
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.59941(3) 0.58258(3) 0.063430(11) 0.04195(9) Uani 1 1 d .
Br2 Br 0.04248(4) 1.03745(4) 0.177506(13) 0.05234(10) Uani 1 1 d .
N1 N 0.6682(3) 1.0838(3) 0.07767(9) 0.0360(4) Uani 1 1 d .
N2 N 0.5011(3) 1.1194(2) 0.15073(8) 0.0332(4) Uani 1 1 d .
N1' N 0.1015(3) 0.4316(2) 0.08716(8) 0.0318(4) Uani 1 1 d .
N2' N 0.0090(3) 0.5944(2) 0.15156(8) 0.0316(4) Uani 1 1 d .
C2 C 0.6043(3) 1.1759(3) 0.11873(11) 0.0371(5) Uani 1 1 d .
H2A H 0.6279 1.2677 0.1246 0.045 Uiso 1 1 calc R
C4 C 0.6063(3) 0.9621(3) 0.08347(11) 0.0403(6) Uani 1 1 d .
H4A H 0.6325 0.8784 0.0596 0.048 Uiso 1 1 calc R
C5 C 0.5022(3) 0.9835(3) 0.12907(10) 0.0368(5) Uani 1 1 d .
H5A H 0.4410 0.9177 0.1437 0.044 Uiso 1 1 calc R
C1" C 0.4134(3) 1.1803(3) 0.20267(10) 0.0385(5) Uani 1 1 d .
H1"A H 0.2936 1.1844 0.2036 0.046 Uiso 1 1 calc R
H1"B H 0.3975 1.2988 0.2020 0.046 Uiso 1 1 calc R
C1'A C 0.1165(4) 0.3077(3) 0.05118(11) 0.0407(6) Uani 1 1 d .
H1'A H 0.1451 0.1959 0.0752 0.061 Uiso 1 1 calc R
H1'B H 0.2113 0.2952 0.0238 0.061 Uiso 1 1 calc R
H1'C H 0.0029 0.3490 0.0303 0.061 Uiso 1 1 calc R
C1"A C -0.0822(3) 0.6660(3) 0.20201(10) 0.0351(5) Uani 1 1 d .
H1"C H -0.2030 0.6726 0.2030 0.042 Uiso 1 1 calc R
H1"D H -0.0953 0.7844 0.1993 0.042 Uiso 1 1 calc R
C2"A C 0.0212(3) 0.5560(3) 0.25657(10) 0.0367(5) Uani 1 1 d .
H2"A H 0.1430 0.5473 0.2550 0.044 Uiso 1 1 calc R
H2"B H 0.0323 0.4383 0.2595 0.044 Uiso 1 1 calc R
C3"A C -0.0687(3) 0.6298(3) 0.30935(10) 0.0385(5) Uani 1 1 d .
H3"A H -0.1926 0.6440 0.3099 0.046 Uiso 1 1 calc R
H3"B H -0.0743 0.7451 0.3074 0.046 Uiso 1 1 calc R
C4"A C 0.0307(3) 0.5142(3) 0.36438(10) 0.0411(6) Uani 1 1 d .
H4"A H 0.0370 0.3987 0.3659 0.049 Uiso 1 1 calc R
H4"B H 0.1544 0.5004 0.3635 0.049 Uiso 1 1 calc R
C5"A C -0.0555(4) 0.5828(3) 0.41824(10) 0.0435(6) Uani 1 1 d .
H5"A H -0.1792 0.5967 0.4191 0.052 Uiso 1 1 calc R
H5"B H -0.0617 0.6982 0.4168 0.052 Uiso 1 1 calc R
C6"A C 0.0440(4) 0.4669(3) 0.47321(10) 0.0439(6) Uani 1 1 d .
H6"A H 0.0529 0.3508 0.4742 0.053 Uiso 1 1 calc R
H6"B H 0.1669 0.4554 0.4728 0.053 Uiso 1 1 calc R
C1' C 0.7910(4) 1.1055(4) 0.03435(12) 0.0504(7) Uani 1 1 d .
H1'D H 0.7729 1.2251 0.0281 0.076 Uiso 1 1 calc R
H1'E H 0.7678 1.0780 -0.0016 0.076 Uiso 1 1 calc R
H1'F H 0.9144 1.0280 0.0476 0.076 Uiso 1 1 calc R
C2" C 0.5199(3) 1.0650(3) 0.25603(11) 0.0393(5) Uani 1 1 d .
H2"C H 0.6405 1.0592 0.2548 0.047 Uiso 1 1 calc R
H2"D H 0.5338 0.9470 0.2572 0.047 Uiso 1 1 calc R
C3" C 0.4291(4) 1.1313(3) 0.30985(10) 0.0423(6) Uani 1 1 d .
H3"C H 0.3075 1.1395 0.3104 0.051 Uiso 1 1 calc R
H3"D H 0.4171 1.2486 0.3088 0.051 Uiso 1 1 calc R
C4" C 0.5317(4) 1.0157(3) 0.36431(11) 0.0442(6) Uani 1 1 d .
H4"C H 0.5420 0.8989 0.3655 0.053 Uiso 1 1 calc R
H4"D H 0.6539 1.0059 0.3633 0.053 Uiso 1 1 calc R
C5" C 0.4442(4) 1.0819(3) 0.41831(11) 0.0434(6) Uani 1 1 d .
H5"C H 0.3207 1.0953 0.4186 0.052 Uiso 1 1 calc R
H5"D H 0.4373 1.1972 0.4175 0.052 Uiso 1 1 calc R
C6" C 0.5425(4) 0.9646(3) 0.47338(11) 0.0444(6) Uani 1 1 d .
H6"C H 0.5454 0.8505 0.4750 0.053 Uiso 1 1 calc R
H6"D H 0.6673 0.9476 0.4726 0.053 Uiso 1 1 calc R
C2A C -0.0070(3) 0.4724(3) 0.13041(10) 0.0337(5) Uani 1 1 d .
H2AA H -0.0838 0.4223 0.1441 0.040 Uiso 1 1 calc R
C4A C 0.1349(3) 0.6314(3) 0.12099(10) 0.0362(5) Uani 1 1 d .
H4AA H 0.1737 0.7129 0.1273 0.043 Uiso 1 1 calc R
C5A C 0.1927(3) 0.5306(3) 0.08049(10) 0.0357(5) Uani 1 1 d .
H5AA H 0.2791 0.5279 0.0527 0.043 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
C2 N1 C4 108.9(2) .
C2 N1 C1' 124.7(2) .
C4 N1 C1' 126.3(2) .
C2 N2 C5 108.3(2) .
C2 N2 C1" 126.1(2) .
C5 N2 C1" 125.49(19) .
C2A N1' C5A 108.61(19) .
C2A N1' C1'A 125.36(19) .
C5A N1' C1'A 126.0(2) .
C2A N2' C4A 108.4(2) .
C2A N2' C1"A 125.03(19) .
C4A N2' C1"A 126.40(19) .
N1 C2 N2 108.7(2) .
N1 C2 H2A 125.6 .
N2 C2 H2A 125.6 .
C5 C4 N1 107.2(2) .
C5 C4 H4A 126.4 .
N1 C4 H4A 126.4 .
C4 C5 N2 106.9(2) .
C4 C5 H5A 126.6 .
N2 C5 H5A 126.6 .
N2 C1" C2" 111.8(2) .
N2 C1" H1"A 109.3 .
C2" C1" H1"A 109.3 .
N2 C1" H1"B 109.3 .
C2" C1" H1"B 109.3 .
H1"A C1" H1"B 107.9 .
N1' C1'A H1'A 109.5 .
N1' C1'A H1'B 109.5 .
H1'A C1'A H1'B 109.5 .
N1' C1'A H1'C 109.5 .
H1'A C1'A H1'C 109.5 .
H1'B C1'A H1'C 109.5 .
N2' C1"A C2"A 111.11(19) .
N2' C1"A H1"C 109.4 .
C2"A C1"A H1"C 109.4 .
N2' C1"A H1"D 109.4 .
C2"A C1"A H1"D 109.4 .
H1"C C1"A H1"D 108.0 .
C1"A C2"A C3"A 112.0(2) .
C1"A C2"A H2"A 109.2 .
C3"A C2"A H2"A 109.2 .
C1"A C2"A H2"B 109.2 .
C3"A C2"A H2"B 109.2 .
H2"A C2"A H2"B 107.9 .
C2"A C3"A C4"A 111.9(2) .
C2"A C3"A H3"A 109.2 .
C4"A C3"A H3"A 109.2 .
C2"A C3"A H3"B 109.2 .
C4"A C3"A H3"B 109.2 .
H3"A C3"A H3"B 107.9 .
C5"A C4"A C3"A 113.6(2) .
C5"A C4"A H4"A 108.8 .
C3"A C4"A H4"A 108.8 .
C5"A C4"A H4"B 108.8 .
C3"A C4"A H4"B 108.8 .
H4"A C4"A H4"B 107.7 .
C4"A C5"A C6"A 113.5(2) .
C4"A C5"A H5"A 108.9 .
C6"A C5"A H5"A 108.9 .
C4"A C5"A H5"B 108.9 .
C6"A C5"A H5"B 108.9 .
H5"A C5"A H5"B 107.7 .
C6"A C6"A C5"A 113.5(3) 2_566
C6"A C6"A H6"A 108.9 2_566
C5"A C6"A H6"A 108.9 .
C6"A C6"A H6"B 108.9 2_566
C5"A C6"A H6"B 108.9 .
H6"A C6"A H6"B 107.7 .
N1 C1' H1'D 109.5 .
N1 C1' H1'E 109.5 .
H1'D C1' H1'E 109.5 .
N1 C1' H1'F 109.5 .
H1'D C1' H1'F 109.5 .
H1'E C1' H1'F 109.5 .
C1" C2" C3" 111.4(2) .
C1" C2" H2"C 109.3 .
C3" C2" H2"C 109.3 .
C1" C2" H2"D 109.3 .
C3" C2" H2"D 109.3 .
H2"C C2" H2"D 108.0 .
C2" C3" C4" 112.5(2) .
C2" C3" H3"C 109.1 .
C4" C3" H3"C 109.1 .
C2" C3" H3"D 109.1 .
C4" C3" H3"D 109.1 .
H3"C C3" H3"D 107.8 .
C5" C4" C3" 113.1(2) .
C5" C4" H4"C 109.0 .
C3" C4" H4"C 109.0 .
C5" C4" H4"D 109.0 .
C3" C4" H4"D 109.0 .
H4"C C4" H4"D 107.8 .
C4" C5" C6" 113.8(2) .
C4" C5" H5"C 108.8 .
C6" C5" H5"C 108.8 .
C4" C5" H5"D 108.8 .
C6" C5" H5"D 108.8 .
H5"C C5" H5"D 107.7 .
C6" C6" C5" 113.1(3) 2_676
C6" C6" H6"C 109.0 2_676
C5" C6" H6"C 109.0 .
C6" C6" H6"D 109.0 2_676
C5" C6" H6"D 109.0 .
H6"C C6" H6"D 107.8 .
N1' C2A N2' 108.94(19) .
N1' C2A H2AA 125.5 .
N2' C2A H2AA 125.5 .
C5A C4A N2' 107.4(2) .
C5A C4A H4AA 126.3 .
N2' C4A H4AA 126.3 .
C4A C5A N1' 106.7(2) .
C4A C5A H5AA 126.7 .
N1' C5A H5AA 126.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.315(3) .
N1 C4 1.374(3) .
N1 C1' 1.469(3) .
N2 C2 1.328(3) .
N2 C5 1.382(3) .
N2 C1" 1.461(3) .
N1' C2A 1.323(3) .
N1' C5A 1.385(3) .
N1' C1'A 1.461(3) .
N2' C2A 1.326(3) .
N2' C4A 1.378(3) .
N2' C1"A 1.468(3) .
C2 H2A 0.9500 .
C4 C5 1.340(3) .
C4 H4A 0.9500 .
C5 H5A 0.9500 .
C1" C2" 1.512(3) .
C1" H1"A 0.9900 .
C1" H1"B 0.9900 .
C1'A H1'A 0.9800 .
C1'A H1'B 0.9800 .
C1'A H1'C 0.9800 .
C1"A C2"A 1.514(3) .
C1"A H1"C 0.9900 .
C1"A H1"D 0.9900 .
C2"A C3"A 1.520(3) .
C2"A H2"A 0.9900 .
C2"A H2"B 0.9900 .
C3"A C4"A 1.525(3) .
C3"A H3"A 0.9900 .
C3"A H3"B 0.9900 .
C4"A C5"A 1.518(3) .
C4"A H4"A 0.9900 .
C4"A H4"B 0.9900 .
C5"A C6"A 1.524(3) .
C5"A H5"A 0.9900 .
C5"A H5"B 0.9900 .
C6"A C6"A 1.510(5) 2_566
C6"A H6"A 0.9900 .
C6"A H6"B 0.9900 .
C1' H1'D 0.9800 .
C1' H1'E 0.9800 .
C1' H1'F 0.9800 .
C2" C3" 1.522(3) .
C2" H2"C 0.9900 .
C2" H2"D 0.9900 .
C3" C4" 1.523(3) .
C3" H3"C 0.9900 .
C3" H3"D 0.9900 .
C4" C5" 1.517(4) .
C4" H4"C 0.9900 .
C4" H4"D 0.9900 .
C5" C6" 1.527(3) .
C5" H5"C 0.9900 .
C5" H5"D 0.9900 .
C6" C6" 1.510(5) 2_676
C6" H6"C 0.9900 .
C6" H6"D 0.9900 .
C2A H2AA 0.9500 .
C4A C5A 1.347(3) .
C4A H4AA 0.9500 .
C5A H5AA 0.9500 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.023 -0.024 0.500 571 121 ' '
