#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502687.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_1502687
loop_
_publ_author_name
'Lee, Minjae'
'Niu, Zhenbin'
'Slebodnick, Carla'
'Gibson, Harry W.'
_publ_section_title
;
 Structure and properties of N,N-alkylene bis(N'-alkylimidazolium) salts.
;
_journal_issue                   21
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              7312
_journal_page_last               7319
_journal_paper_doi               10.1021/jp102370j
_journal_volume                  114
_journal_year                    2010
_chemical_formula_moiety         'C16 H28 N4, 2(F6 P)'
_chemical_formula_sum            'C16 H28 F12 N4 P2'
_chemical_formula_weight         566.36
_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           SHELXL-97
_cell_angle_alpha                97.336(4)
_cell_angle_beta                 97.674(4)
_cell_angle_gamma                99.448(4)
_cell_formula_units_Z            1
_cell_length_a                   6.5214(3)
_cell_length_b                   6.9156(3)
_cell_length_c                   13.8874(7)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4994
_cell_measurement_theta_min      2.9900
_cell_volume                     605.07(5)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_publication_material
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.2265
_diffrn_detector_type            'Oxford Diffraction Atlas CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.0866481571
_diffrn_orient_matrix_UB_12      0.0212595595
_diffrn_orient_matrix_UB_13      0.0226356502
_diffrn_orient_matrix_UB_21      0.0702848183
_diffrn_orient_matrix_UB_22      0.0568033088
_diffrn_orient_matrix_UB_23      0.0409788888
_diffrn_orient_matrix_UB_31      0.0000420523
_diffrn_orient_matrix_UB_32      0.0858536221
_diffrn_orient_matrix_UB_33      -0.0229920746
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6608
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38) Numerical absorption
correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0517
_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)+(0.0654P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1709
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp102370j_si_003.cif
_cod_data_source_block           cs1321
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1502687
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.26142(10) 0.38024(9) 0.29640(5) 0.0477(2) Uani 1 1 d D . .
F1 F 0.2199(3) 0.1473(2) 0.29979(14) 0.0784(6) Uani 1 1 d D A .
F2 F 0.3045(3) 0.6126(2) 0.29557(13) 0.0722(5) Uani 1 1 d D A .
F3 F 0.4495(6) 0.3989(7) 0.3858(4) 0.0791(14) Uani 0.761(9) 1 d PDU A 1
F4 F 0.4192(10) 0.3538(10) 0.2247(4) 0.0960(19) Uani 0.761(9) 1 d PDU A 1
F5 F 0.0689(7) 0.3670(5) 0.2156(4) 0.0886(14) Uani 0.761(9) 1 d PDU A 1
F6 F 0.1090(8) 0.4126(7) 0.3784(4) 0.0911(14) Uani 0.761(9) 1 d PDU A 1
F7 F 0.369(3) 0.433(3) 0.4005(9) 0.102(5) Uani 0.239(9) 1 d PDU A 2
F8 F 0.481(2) 0.373(3) 0.2611(15) 0.095(6) Uani 0.239(9) 1 d PDU A 2
F9 F 0.165(3) 0.3045(19) 0.1765(8) 0.097(4) Uani 0.239(9) 1 d PDU A 2
F10 F 0.0426(17) 0.3657(15) 0.3150(16) 0.085(4) Uani 0.239(9) 1 d PDU A 2
N1 N 0.7018(3) 0.9643(3) 0.41927(14) 0.0355(4) Uani 1 1 d . . .
N2 N 0.7795(3) 0.8934(3) 0.27455(14) 0.0411(5) Uani 1 1 d . . .
C1 C 0.6107(3) 1.0564(3) 0.50026(18) 0.0416(6) Uani 1 1 d . . .
H1A H 0.6055 1.1962 0.4931 0.050 Uiso 1 1 calc R . .
H1B H 0.6999 1.0551 0.5636 0.050 Uiso 1 1 calc R . .
C2 C 0.6958(3) 1.0181(3) 0.33070(18) 0.0395(6) Uani 1 1 d . . .
H2 H 0.6405 1.1282 0.3109 0.047 Uiso 1 1 calc R . .
C3 C 0.8404(4) 0.7555(4) 0.3290(2) 0.0484(6) Uani 1 1 d . . .
H3 H 0.9056 0.6485 0.3070 0.058 Uiso 1 1 calc R . .
C4 C 0.7916(3) 0.7983(3) 0.41892(19) 0.0442(6) Uani 1 1 d . . .
H4 H 0.8148 0.7272 0.4723 0.053 Uiso 1 1 calc R . .
C5 C 0.7999(4) 0.8985(4) 0.1705(2) 0.0586(7) Uani 1 1 d . . .
H5A H 0.9310 0.8526 0.1575 0.070 Uiso 1 1 calc R . .
H5B H 0.8118 1.0372 0.1577 0.070 Uiso 1 1 calc R . .
C6 C 0.6157(4) 0.7707(4) 0.1009(2) 0.0551(7) Uani 1 1 d . . .
H6A H 0.5933 0.6362 0.1195 0.066 Uiso 1 1 calc R . .
H6B H 0.6516 0.7583 0.0336 0.066 Uiso 1 1 calc R . .
C7 C 0.4120(4) 0.8493(4) 0.09952(19) 0.0537(7) Uani 1 1 d . . .
H7A H 0.3710 0.8554 0.1658 0.064 Uiso 1 1 calc R . .
H7B H 0.4346 0.9858 0.0834 0.064 Uiso 1 1 calc R . .
C8 C 0.2350(5) 0.7213(5) 0.0255(2) 0.0738(9) Uani 1 1 d . . .
H8A H 0.2791 0.7062 -0.0394 0.111 Uiso 1 1 calc R . .
H8B H 0.1107 0.7842 0.0223 0.111 Uiso 1 1 calc R . .
H8C H 0.2007 0.5905 0.0455 0.111 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'
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_3
F10 P1 F7 98.1(7) .
F10 P1 F4 149.9(8) .
F7 P1 F4 111.8(7) .
F7 P1 F5 151.5(7) .
F4 P1 F5 95.5(3) .
F10 P1 F8 171.0(8) .
F7 P1 F8 90.0(7) .
F10 P1 F2 96.1(4) .
F7 P1 F2 84.7(6) .
F4 P1 F2 90.3(3) .
F5 P1 F2 87.23(13) .
F8 P1 F2 88.4(7) .
F10 P1 F1 83.9(4) .
F7 P1 F1 94.0(6) .
F4 P1 F1 90.3(3) .
F5 P1 F1 93.80(13) .
F8 P1 F1 91.8(7) .
F2 P1 F1 178.73(10) .
F4 P1 F3 88.7(2) .
F5 P1 F3 175.7(2) .
F8 P1 F3 67.2(7) .
F2 P1 F3 92.05(18) .
F1 P1 F3 86.87(18) .
F4 P1 F6 175.9(2) .
F5 P1 F6 88.4(2) .
F2 P1 F6 89.08(17) .
F1 P1 F6 90.22(18) .
F3 P1 F6 87.3(2) .
F10 P1 F9 87.9(6) .
F7 P1 F9 172.8(7) .
F8 P1 F9 83.7(6) .
C2 N1 C4 108.29(19) .
C2 N1 C1 125.45(18) .
C4 N1 C1 126.05(18) .
C2 N2 C3 108.3(2) .
C2 N2 C5 126.1(2) .
C3 N2 C5 125.6(2) .
N1 C1 C1 109.8(2) 2_676
N2 C2 N1 108.79(19) .
C4 C3 N2 107.7(2) .
C3 C4 N1 107.0(2) .
N2 C5 C6 112.71(19) .
C5 C6 C7 114.2(2) .
C8 C7 C6 112.2(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F10 1.474(8) .
P1 F7 1.492(12) .
P1 F4 1.541(4) .
P1 F5 1.550(3) .
P1 F8 1.582(13) .
P1 F2 1.5870(15) .
P1 F1 1.5971(15) .
P1 F3 1.601(4) .
P1 F6 1.626(3) .
P1 F9 1.684(10) .
N1 C2 1.327(3) .
N1 C4 1.371(3) .
N1 C1 1.464(3) .
N2 C2 1.321(3) .
N2 C3 1.366(3) .
N2 C5 1.473(3) .
C1 C1 1.523(4) 2_676
C3 C4 1.338(3) .
C5 C6 1.511(4) .
C6 C7 1.514(3) .
C7 C8 1.513(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037583
