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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/23/1542331.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_1542331
loop_
_publ_author_name
'Mukai, Tomohiro'
'Nishikawa, Keiko'
_publ_contact_author_address
;
Department of Chemistry, Faculty of Letters,
Keio University
Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan
;
_publ_contact_author_email       mukai-t@flet.keio.ac.jp
_publ_contact_author_fax         +81-45-566-1314
_publ_contact_author_name        'Tomohiro Mukai'
_publ_contact_author_phone       +81-45-566-1309
_publ_section_title
;
 Halogen Bonding and Hydrogen Bonding in
 4,5-Diiodo-3-methyl-1-propylimidazolium Hexafluorophosphate
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              39
_journal_page_last               40
_journal_paper_doi               10.2116/xraystruct.26.39
_journal_volume                  26
_journal_year                    2010
_chemical_formula_moiety         'C7 H11 I2 N2, F6 P'
_chemical_formula_sum            'C7 H11 F6 I2 N2 P'
_chemical_formula_weight         521.95
_chemical_name_systematic
'4,5-diiodo-3-methyl-1-propylimidazolium hexafluorophosphate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.1410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5373(6)
_cell_length_b                   8.6305(5)
_cell_length_c                   15.3770(8)
_cell_measurement_reflns_used    8754
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.77
_cell_volume                     1463.12(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24102
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.458
_exptl_absorpt_correction_T_max  0.6641
_exptl_absorpt_correction_T_min  0.3482
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0142P)²+9.3786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                3039
_reflns_number_total             3377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            26_39_1.cif
_cod_data_source_block           i2pmimpf6
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1542331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.32835(9) 0.11559(13) 0.15430(7) 0.0195(2) Uani 1 1 d . . .
I1 I 1.02799(2) 0.05063(3) 0.246674(19) 0.02492(8) Uani 1 1 d . . .
I2 I 0.99900(2) 0.23719(3) 0.474709(18) 0.02331(8) Uani 1 1 d . . .
F1 F 0.2659(3) 0.0767(4) 0.05008(19) 0.0484(8) Uani 1 1 d . . .
F2 F 0.2488(3) -0.0180(4) 0.1810(2) 0.0438(7) Uani 1 1 d . . .
F5 F 0.4314(2) -0.0090(4) 0.1567(2) 0.0444(8) Uani 1 1 d . . .
F3 F 0.3899(3) 0.1523(4) 0.25951(19) 0.0433(7) Uani 1 1 d . . .
F6 F 0.2231(3) 0.2383(3) 0.1518(2) 0.0404(7) Uani 1 1 d . . .
F4 F 0.4070(3) 0.2481(4) 0.1293(3) 0.0560(9) Uani 1 1 d . . .
N2 N 0.7627(3) 0.0270(4) 0.2413(2) 0.0204(7) Uani 1 1 d . . .
N1 N 0.7459(3) 0.1288(4) 0.3657(2) 0.0178(7) Uani 1 1 d . . .
C7 C 0.6516(5) 0.1192(7) 0.5829(3) 0.0429(13) Uani 1 1 d . . .
H7A H 0.6994 0.2074 0.6144 0.064 Uiso 1 1 calc R . .
H7B H 0.6529 0.0364 0.6269 0.064 Uiso 1 1 calc R . .
H7C H 0.5677 0.1522 0.5544 0.064 Uiso 1 1 calc R . .
C3 C 0.8671(3) 0.1395(5) 0.3687(3) 0.0167(7) Uani 1 1 d . . .
C1 C 0.6860(4) 0.0599(5) 0.2877(3) 0.0215(8) Uani 1 1 d . . .
H1 H 0.6016 0.0381 0.2685 0.026 Uiso 1 1 calc R . .
C2 C 0.8777(3) 0.0758(5) 0.2912(3) 0.0179(8) Uani 1 1 d . . .
C4 C 0.7305(4) -0.0553(6) 0.1536(3) 0.0283(9) Uani 1 1 d . . .
H4A H 0.7640 -0.1605 0.1627 0.042 Uiso 1 1 calc R . .
H4B H 0.7641 0.0004 0.1110 0.042 Uiso 1 1 calc R . .
H4C H 0.6420 -0.0607 0.1287 0.042 Uiso 1 1 calc R . .
C5 C 0.6900(4) 0.1789(5) 0.4356(3) 0.0230(8) Uani 1 1 d . . .
H5A H 0.6025 0.1978 0.4066 0.028 Uiso 1 1 calc R . .
H5B H 0.7274 0.2778 0.4624 0.028 Uiso 1 1 calc R . .
C6 C 0.7051(4) 0.0602(5) 0.5108(3) 0.0280(9) Uani 1 1 d . . .
H6A H 0.6642 -0.0374 0.4849 0.034 Uiso 1 1 calc R . .
H6B H 0.7923 0.0377 0.5386 0.034 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F4 P1 F1 91.7(2) . .
F4 P1 F5 90.94(18) . .
F1 P1 F5 89.70(17) . .
F4 P1 F3 89.2(2) . .
F1 P1 F3 179.0(2) . .
F5 P1 F3 90.24(17) . .
F4 P1 F2 179.2(2) . .
F1 P1 F2 89.00(19) . .
F5 P1 F2 89.31(18) . .
F3 P1 F2 90.05(18) . .
F4 P1 F6 90.08(18) . .
F1 P1 F6 90.02(17) . .
F5 P1 F6 178.95(18) . .
F3 P1 F6 90.03(17) . .
F2 P1 F6 89.67(17) . .
C1 N2 C2 108.6(3) . .
C1 N2 C4 124.8(4) . .
C2 N2 C4 126.5(3) . .
C1 N1 C3 107.9(3) . .
C1 N1 C5 124.5(3) . .
C3 N1 C5 127.6(3) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C2 C3 N1 107.2(3) . .
C2 C3 I2 129.0(3) . .
N1 C3 I2 123.8(3) . .
N2 C1 N1 109.3(4) . .
N2 C1 H1 125.4 . .
N1 C1 H1 125.4 . .
C3 C2 N2 106.9(3) . .
C3 C2 I1 129.9(3) . .
N2 C2 I1 123.1(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 . .
N1 C5 C6 112.5(3) . .
N1 C5 H5A 109.1 . .
C6 C5 H5A 109.1 . .
N1 C5 H5B 109.1 . .
C6 C5 H5B 109.1 . .
H5A C5 H5B 107.8 . .
C7 C6 C5 110.7(4) . .
C7 C6 H6A 109.5 . .
C5 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F4 1.576(3) .
P1 F1 1.587(3) .
P1 F5 1.595(3) .
P1 F3 1.595(3) .
P1 F2 1.601(3) .
P1 F6 1.603(3) .
I1 C2 2.055(4) .
I2 C3 2.055(4) .
N2 C1 1.320(5) .
N2 C2 1.387(5) .
N2 C4 1.472(5) .
N1 C1 1.335(5) .
N1 C3 1.389(5) .
N1 C5 1.471(5) .
C7 C6 1.508(6) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C3 C2 1.350(5) .
C1 H1 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.516(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C3 C2 0.0(5) . . . .
C5 N1 C3 C2 178.4(4) . . . .
C1 N1 C3 I2 179.8(3) . . . .
C5 N1 C3 I2 -1.8(6) . . . .
C2 N2 C1 N1 0.2(5) . . . .
C4 N2 C1 N1 177.3(4) . . . .
C3 N1 C1 N2 -0.1(5) . . . .
C5 N1 C1 N2 -178.6(4) . . . .
N1 C3 C2 N2 0.1(4) . . . .
I2 C3 C2 N2 -179.7(3) . . . .
N1 C3 C2 I1 179.5(3) . . . .
I2 C3 C2 I1 -0.3(6) . . . .
C1 N2 C2 C3 -0.2(5) . . . .
C4 N2 C2 C3 -177.3(4) . . . .
C1 N2 C2 I1 -179.7(3) . . . .
C4 N2 C2 I1 3.3(6) . . . .
C1 N1 C5 C6 96.1(5) . . . .
C3 N1 C5 C6 -82.1(5) . . . .
N1 C5 C6 C7 177.4(4) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139047949
