#------------------------------------------------------------------------------
#$Date: 2019-06-20 15:03:23 +0200 (jue 20 de jun de 2019) $
#$Revision: 216372 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/17/1551760.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_1551760
loop_
_publ_author_name
'MUKAI, Tomohiro'
'NISHIKAWA, Keiko'
_publ_section_title
;
 Zigzag Sheet Crystal Packing in a Halogen-bonding Imidazolium Salt:
 1-Butyl-4,5-dibromo-3-methylimidazolium Iodide
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              31
_journal_paper_doi               10.2116/xraystruct.26.31
_journal_volume                  26
_journal_year                    2010
_chemical_formula_moiety         'C8 H13 Br2 N2, I'
_chemical_formula_sum            'C8 H13 Br2 I N2'
_chemical_formula_weight         423.92
_chemical_name_systematic
'1-butyl-4,5-dibromo-3-methylimidazolium iodide'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.5950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8471(6)
_cell_length_b                   14.8581(11)
_cell_length_c                   10.9176(8)
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.74
_cell_volume                     1258.62(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7060
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    8.857
_exptl_absorpt_correction_T_max  0.4712
_exptl_absorpt_correction_T_min  0.3501
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0253
_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)+(0.0295P)²+0.0681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0582
_reflns_number_gt                2463
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            26_31_1.cif
_cod_data_source_block           br2bmimi
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1551760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
I1 I 0.56811(3) 0.204945(14) 0.41937(2) 0.02641(8) Uani 1 1 d .
Br1 Br 0.84338(4) 0.63510(2) 0.37983(3) 0.02748(9) Uani 1 1 d .
Br2 Br 0.69446(4) 0.42412(2) 0.52909(3) 0.02565(9) Uani 1 1 d .
C5 C 0.7280(4) 0.4949(2) 0.8205(3) 0.0267(7) Uani 1 1 d .
H5A H 0.7830 0.5163 0.9029 0.032 Uiso 1 1 calc R
H5B H 0.7666 0.4323 0.8098 0.032 Uiso 1 1 calc R
C1 C 0.8420(4) 0.6357(2) 0.7432(3) 0.0234(7) Uani 1 1 d .
H1 H 0.8611 0.6650 0.8213 0.028 Uiso 1 1 calc R
C3 C 0.7706(4) 0.5352(2) 0.5976(3) 0.0218(7) Uani 1 1 d .
C2 C 0.8250(4) 0.6097(2) 0.5443(3) 0.0214(7) Uani 1 1 d .
N1 N 0.7827(3) 0.55247(17) 0.7235(2) 0.0215(6) Uani 1 1 d .
N2 N 0.8704(3) 0.67136(17) 0.6376(3) 0.0218(6) Uani 1 1 d .
C4 C 0.9364(4) 0.7632(2) 0.6233(3) 0.0300(8) Uani 1 1 d .
H4A H 0.9612 0.7921 0.7048 0.045 Uiso 1 1 calc R
H4B H 0.8496 0.7985 0.5698 0.045 Uiso 1 1 calc R
H4C H 1.0423 0.7602 0.5859 0.045 Uiso 1 1 calc R
C6 C 0.5327(4) 0.4964(2) 0.8147(3) 0.0255(7) Uani 1 1 d .
H6A H 0.5001 0.4544 0.8778 0.031 Uiso 1 1 calc R
H6B H 0.4786 0.4745 0.7324 0.031 Uiso 1 1 calc R
C7 C 0.4618(4) 0.5900(2) 0.8368(3) 0.0290(8) Uani 1 1 d .
H7A H 0.4912 0.6318 0.7726 0.035 Uiso 1 1 calc R
H7B H 0.5168 0.6126 0.9185 0.035 Uiso 1 1 calc R
C8 C 0.2653(4) 0.5885(3) 0.8330(4) 0.0359(9) Uani 1 1 d .
H8A H 0.2101 0.5691 0.7508 0.054 Uiso 1 1 calc R
H8B H 0.2250 0.6489 0.8503 0.054 Uiso 1 1 calc R
H8C H 0.2356 0.5464 0.8957 0.054 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02740(13) 0.03021(14) 0.02117(12) 0.00150(9) 0.00219(9) -0.00366(9)
Br1 0.02692(18) 0.0347(2) 0.02076(17) 0.00207(14) 0.00338(14) -0.00078(14)
Br2 0.02581(18) 0.02193(18) 0.02833(19) -0.00421(13) 0.00116(14) 0.00087(12)
C5 0.0345(19) 0.0258(18) 0.0195(17) 0.0056(14) 0.0025(15) 0.0013(14)
C1 0.0194(16) 0.0254(17) 0.0242(18) -0.0023(14) -0.0003(14) -0.0009(13)
C3 0.0212(16) 0.0237(17) 0.0197(16) -0.0037(13) 0.0009(13) 0.0020(12)
C2 0.0202(15) 0.0256(17) 0.0178(16) -0.0005(13) 0.0007(13) 0.0019(13)
N1 0.0214(13) 0.0241(14) 0.0181(14) 0.0027(11) 0.0001(11) 0.0021(11)
N2 0.0186(13) 0.0221(14) 0.0236(15) -0.0021(12) 0.0001(11) -0.0027(10)
C4 0.0293(18) 0.0254(18) 0.036(2) 0.0018(16) 0.0066(16) -0.0111(14)
C6 0.0276(17) 0.0250(18) 0.0252(17) 0.0025(14) 0.0080(14) -0.0016(13)
C7 0.0341(19) 0.0254(18) 0.0281(19) 0.0025(15) 0.0069(16) -0.0014(14)
C8 0.0322(19) 0.046(2) 0.031(2) -0.0005(18) 0.0088(16) 0.0063(17)
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'
I I -0.4742 1.8119 '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
N1 C5 C6 111.2(3)
N1 C5 H5A 109.4
C6 C5 H5A 109.4
N1 C5 H5B 109.4
C6 C5 H5B 109.4
H5A C5 H5B 108.0
N2 C1 N1 109.6(3)
N2 C1 H1 125.2
N1 C1 H1 125.2
C2 C3 N1 107.2(3)
C2 C3 Br2 130.8(3)
N1 C3 Br2 121.9(2)
C3 C2 N2 106.9(3)
C3 C2 Br1 131.1(3)
N2 C2 Br1 122.0(2)
C1 N1 C3 107.6(3)
C1 N1 C5 123.9(3)
C3 N1 C5 128.3(3)
C1 N2 C2 108.7(3)
C1 N2 C4 124.9(3)
C2 N2 C4 126.4(3)
N2 C4 H4A 109.5
N2 C4 H4B 109.5
H4A C4 H4B 109.5
N2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C5 C6 C7 113.2(3)
C5 C6 H6A 108.9
C7 C6 H6A 108.9
C5 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.8
C6 C7 C8 111.7(3)
C6 C7 H7A 109.3
C8 C7 H7A 109.3
C6 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 107.9
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.862(3)
Br2 C3 1.872(3)
C5 N1 1.475(4)
C5 C6 1.524(4)
C5 H5A 0.9900
C5 H5B 0.9900
C1 N2 1.317(4)
C1 N1 1.327(4)
C1 H1 0.9500
C3 C2 1.349(4)
C3 N1 1.388(4)
C2 N2 1.377(4)
N2 C4 1.477(4)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C6 C7 1.531(5)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.536(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
N1 C3 C2 N2 0.2(3)
Br2 C3 C2 N2 -178.4(2)
N1 C3 C2 Br1 -179.8(2)
Br2 C3 C2 Br1 1.6(5)
N2 C1 N1 C3 -0.9(3)
N2 C1 N1 C5 -176.3(3)
C2 C3 N1 C1 0.4(4)
Br2 C3 N1 C1 179.2(2)
C2 C3 N1 C5 175.5(3)
Br2 C3 N1 C5 -5.7(4)
C6 C5 N1 C1 98.8(3)
C6 C5 N1 C3 -75.6(4)
N1 C1 N2 C2 1.1(3)
N1 C1 N2 C4 179.9(3)
C3 C2 N2 C1 -0.8(4)
Br1 C2 N2 C1 179.2(2)
C3 C2 N2 C4 -179.5(3)
Br1 C2 N2 C4 0.4(4)
N1 C5 C6 C7 -61.9(4)
C5 C6 C7 C8 -178.8(3)
