#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239244.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_7239244
loop_
_publ_author_name
'Mukai, Tomohiro'
'Nishikawa, Keiko'
_publ_section_title
;
 4,5-Dihaloimidazolium-based ionic liquids: effects of halogen-bonding on
 crystal structures and ionic conductivity
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              19952
_journal_paper_doi               10.1039/c3ra43899f
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C6 H9 N2 I2, C2 F6 N1 O4 S2'
_chemical_formula_sum            'C8 H9 F6 I2 N3 O4 S2'
_chemical_formula_weight         643.10
_chemical_name_systematic
'4,5-diiodo-1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amide'
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2841(4)
_cell_length_b                   16.1160(8)
_cell_length_c                   26.3361(14)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.53
_cell_volume                     3516.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18783
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         1.55
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  0.8291
_exptl_absorpt_correction_T_min  0.5927
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.429
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0307
_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)+(0.0302P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0704
_reflns_number_gt                3156
_reflns_number_total             4197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra43899f.txt
_cod_data_source_block           i2emimtfsa
_cod_database_code               7239244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C8 C 0.1503(4) 0.9786(2) 0.18665(13) 0.0313(8) Uani 1 1 d .
N2 N 0.6108(3) 0.76508(15) 0.09565(10) 0.0234(6) Uani 1 1 d .
I1 I 0.73013(3) 0.698838(15) -0.006334(10) 0.03365(8) Uani 1 1 d .
I2 I 0.76588(3) 0.941231(14) -0.011993(9) 0.03118(8) Uani 1 1 d .
S2 S 0.10171(10) 0.92755(5) 0.12642(3) 0.02313(18) Uani 1 1 d .
O4 O 0.2563(3) 0.91067(14) 0.10401(9) 0.0300(6) Uani 1 1 d .
N3 N -0.0026(3) 0.85013(15) 0.13988(10) 0.0258(6) Uani 1 1 d .
S1 S 0.06633(10) 0.76144(5) 0.15526(3) 0.0265(2) Uani 1 1 d .
O3 O 0.0016(3) 0.98730(13) 0.10175(8) 0.0334(6) Uani 1 1 d .
O2 O 0.2355(3) 0.75775(14) 0.16488(9) 0.0348(6) Uani 1 1 d .
O1 O -0.0077(4) 0.69861(13) 0.12521(10) 0.0419(7) Uani 1 1 d .
F5 F 0.0179(3) 0.99518(13) 0.21293(8) 0.0491(6) Uani 1 1 d .
N1 N 0.6290(3) 0.89901(14) 0.09252(9) 0.0192(6) Uani 1 1 d .
C3 C 0.6857(4) 0.86852(19) 0.04657(11) 0.0206(7) Uani 1 1 d .
C1 C 0.5848(4) 0.83458(18) 0.12093(12) 0.0224(7) Uani 1 1 d .
H1 H 0.5414 0.8381 0.1542 0.027 Uiso 1 1 calc R
C5 C 0.6167(4) 0.98686(18) 0.10747(12) 0.0252(7) Uani 1 1 d .
H5A H 0.5131 1.0097 0.0950 0.030 Uiso 1 1 calc R
H5B H 0.7052 1.0185 0.0912 0.030 Uiso 1 1 calc R
C2 C 0.6751(4) 0.78415(19) 0.04864(12) 0.0223(7) Uani 1 1 d .
C7 C -0.0310(4) 0.7499(2) 0.21719(13) 0.0326(8) Uani 1 1 d .
F3 F 0.0086(3) 0.80965(12) 0.24914(7) 0.0414(6) Uani 1 1 d .
F1 F 0.0129(3) 0.67793(12) 0.23805(8) 0.0506(6) Uani 1 1 d .
C4 C 0.5748(5) 0.68108(17) 0.11523(14) 0.0325(9) Uani 1 1 d .
H4A H 0.5154 0.6856 0.1473 0.049 Uiso 1 1 calc R
H4B H 0.6760 0.6510 0.1210 0.049 Uiso 1 1 calc R
H4C H 0.5091 0.6509 0.0904 0.049 Uiso 1 1 calc R
F4 F 0.2456(2) 0.93168(12) 0.21542(8) 0.0392(5) Uani 1 1 d .
F6 F 0.2269(3) 1.04928(12) 0.17727(9) 0.0494(6) Uani 1 1 d .
F2 F -0.1902(3) 0.74922(16) 0.21196(8) 0.0554(7) Uani 1 1 d .
C6 C 0.6259(5) 0.9980(2) 0.16386(12) 0.0351(9) Uani 1 1 d .
H6A H 0.5338 0.9703 0.1799 0.053 Uiso 1 1 calc R
H6B H 0.6235 1.0573 0.1720 0.053 Uiso 1 1 calc R
H6C H 0.7266 0.9737 0.1765 0.053 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
F5 C8 F6 108.6(3)
F5 C8 F4 108.0(3)
F6 C8 F4 108.0(3)
F5 C8 S2 111.2(2)
F6 C8 S2 109.2(2)
F4 C8 S2 111.6(2)
C1 N2 C2 109.0(2)
C1 N2 C4 124.6(3)
C2 N2 C4 126.4(3)
O3 S2 O4 117.32(14)
O3 S2 N3 108.75(15)
O4 S2 N3 115.86(14)
O3 S2 C8 102.64(15)
O4 S2 C8 104.19(16)
N3 S2 C8 106.50(15)
S2 N3 S1 125.30(18)
O1 S1 O2 119.50(16)
O1 S1 N3 110.03(15)
O2 S1 N3 115.82(15)
O1 S1 C7 103.49(16)
O2 S1 C7 105.70(15)
N3 S1 C7 99.24(15)
C1 N1 C3 107.9(2)
C1 N1 C5 125.5(2)
C3 N1 C5 126.6(2)
C2 C3 N1 107.2(3)
C2 C3 I2 128.4(2)
N1 C3 I2 124.3(2)
N2 C1 N2 109.5(3)
N2 C1 H1 125.3
N1 C1 H1 125.3
N1 C5 C6 112.1(2)
N1 C5 H5A 109.2
C6 C5 H5A 109.2
N1 C5 H5B 109.2
C6 C5 H5B 109.2
H5A C5 H5B 107.9
C3 C2 N2 106.4(3)
C3 C2 I1 128.8(2)
N2 C2 I1 124.7(2)
F3 C7 F2 108.6(3)
F3 C7 F1 107.7(3)
F2 C7 F1 107.9(3)
F3 C7 S1 112.6(2)
F2 C7 S1 110.3(2)
F1 C7 S1 109.6(2)
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 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 F5 1.324(4)
C8 F6 1.328(4)
C8 F4 1.330(4)
C8 S2 1.831(4)
N2 C1 1.321(4)
N2 C2 1.382(4)
N2 C4 1.479(3)
I1 C2 2.048(3)
I2 C3 2.048(3)
S2 O3 1.427(2)
S2 O4 1.436(2)
S2 N3 1.559(3)
N3 S1 1.592(3)
S1 O1 1.424(2)
S1 O2 1.425(2)
S1 C7 1.829(4)
N1 C1 1.331(4)
N1 C3 1.388(4)
N1 C5 1.473(4)
C3 C2 1.364(4)
C1 H1 0.9500
C5 C6 1.498(4)
C5 H5A 0.9900
C5 H5B 0.9900
C7 F3 1.321(4)
C7 F2 1.327(4)
C7 F1 1.333(4)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 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
F5 C8 S2 O3 59.7(3)
F6 C8 S2 O3 -60.2(3)
F4 C8 S2 O3 -179.6(2)
F5 C8 S2 O4 -177.5(2)
F6 C8 S2 O4 62.6(3)
F4 C8 S2 O4 -56.8(3)
F5 C8 S2 N3 -54.5(3)
F6 C8 S2 N3 -174.4(2)
F4 C8 S2 N3 66.2(3)
O3 S2 N3 S1 164.43(19)
O4 S2 N3 S1 29.7(3)
C8 S2 N3 S1 -85.6(2)
S2 N3 S1 O1 -129.1(2)
S2 N3 S1 O2 10.3(3)
S2 N3 S1 C7 122.8(2)
C1 N1 C3 C2 -0.4(3)
C5 N1 C3 C2 -179.6(3)
C1 N1 C3 I2 178.9(2)
C5 N1 C3 I2 -0.3(4)
C2 N2 C1 N1 0.1(4)
C4 N2 C1 N1 -179.5(3)
C3 N1 C1 N2 0.2(4)
C5 N1 C1 N2 179.3(3)
C1 N1 C5 C6 27.6(4)
C3 N1 C5 C6 -153.4(3)
N1 C3 C2 N2 0.5(3)
I2 C3 C2 N2 -178.8(2)
N1 C3 C2 I1 177.8(2)
I2 C3 C2 I1 -1.5(4)
C1 N2 C2 C3 -0.4(4)
C4 N2 C2 C3 179.2(3)
C1 N2 C2 I1 -177.8(2)
C4 N2 C2 I1 1.8(5)
O1 S1 C7 F3 -172.6(2)
O2 S1 C7 F3 61.0(3)
N3 S1 C7 F3 -59.3(3)
O1 S1 C7 F2 -51.1(3)
O2 S1 C7 F2 -177.5(2)
N3 S1 C7 F2 62.2(3)
O1 S1 C7 F1 67.5(3)
O2 S1 C7 F1 -58.9(3)
N3 S1 C7 F1 -179.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340788
