#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:40:22 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105796.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_8105796
loop_
_publ_author_name
'Wen, Zhao'
'Jing, Chen'
'Wan-Ming, Xiong'
'Ying-Dong, Lan'
'Xu-Liang, Nie'
_publ_section_title
;
 Crystal structure of
 1,1′-(hexane-1,6-diyl)bis(3-ethyl-1H-imidazol-3-ium)
 bis(hexafluorido phosphate), C16H28F12N4P2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              609
_journal_page_last               611
_journal_paper_doi               10.1515/ncrs-2018-0527
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C16 H28 N4, 2(F6 P)'
_chemical_formula_sum            'C16 H28 F12 N4 P2'
_chemical_formula_weight         566.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 111.2360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7921(12)
_cell_length_b                   16.173(2)
_cell_length_c                   9.1376(12)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.31
_cell_measurement_theta_min      2.52
_cell_volume                     1211.1(3)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.519
_exptl_absorpt_coefficient_mu    0.284
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0601P)²+0.4622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1691
_reflns_number_total             2125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0527_suppl.cif
_cod_data_source_block           3687_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C16 H28 N4, 2(F6 P)'
_cod_database_code               8105796
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.922
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7923(3) 0.12721(14) 0.7499(3) 0.0575(6) Uani 1 1 d . . . A 4
H1 H 0.7552 0.1365 0.6422 0.069 Uiso 1 1 calc R U . A 4
C2 C 0.7987(3) 0.11004(16) 0.9873(3) 0.0672(7) Uani 1 1 d . . . A 4
H2 H 0.7661 0.1054 1.0730 0.081 Uiso 1 1 calc R U . A 4
C3 C 0.9506(3) 0.10413(17) 0.9903(3) 0.0677(7) Uani 1 1 d . . . A 4
H3 H 1.0435 0.0943 1.0785 0.081 Uiso 1 1 calc R U . A 4
C4 C 1.0899(3) 0.11948(17) 0.7957(3) 0.0705(7) Uani 1 1 d . . . A 4
H4A H 1.1727 0.0822 0.8619 0.085 Uiso 1 1 calc R U . A 4
H4B H 1.1340 0.1751 0.8149 0.085 Uiso 1 1 calc R U . A 4
C5 C 1.0557(3) 0.09795(17) 0.6285(3) 0.0692(7) Uani 1 1 d . . . A 4
H5A H 1.1514 0.1112 0.6041 0.083 Uiso 1 1 calc R U . A 4
H5B H 0.9672 0.1327 0.5632 0.083 Uiso 1 1 calc R U . A 4
C6 C 1.0109(3) 0.00919(17) 0.5847(3) 0.0653(7) Uani 1 1 d . . . A 4
H6A H 0.9103 -0.0035 0.6008 0.078 Uiso 1 1 calc R U . A 4
H6B H 1.0958 -0.0263 0.6533 0.078 Uiso 1 1 calc R U . A 4
C7 C 0.5235(3) 0.13844(18) 0.7799(3) 0.0698(7) Uani 1 1 d . . . A 4
H7A H 0.4757 0.1041 0.8391 0.084 Uiso 1 1 calc R U . A 4
H7B H 0.4751 0.1227 0.6703 0.084 Uiso 1 1 calc R U . A 4
C8 C 0.4863(4) 0.2258(2) 0.7974(5) 0.1031(12) Uani 1 1 d . . . A 4
H8A H 0.5316 0.2411 0.9062 0.155 Uiso 1 1 calc R U . A 4
H8B H 0.3701 0.2335 0.7589 0.155 Uiso 1 1 calc R U . A 4
H8C H 0.5328 0.2599 0.7383 0.155 Uiso 1 1 calc R U . A 4
N1 N 0.9453(2) 0.11507(11) 0.8413(2) 0.0543(5) Uani 1 1 d . . . A 4
N2 N 0.6998(2) 0.12405(11) 0.8359(2) 0.0530(5) Uani 1 1 d . . . A 4
P1 P 0.47114(8) 0.12475(4) 0.26721(7) 0.0611(3) Uani 1 1 d . . . B 4
F1A F 0.5814(5) 0.0605(3) 0.3840(5) 0.117(2) Uani 0.779(10) 1 d . . P C 1
F2A F 0.3524(7) 0.1910(4) 0.1550(8) 0.111(2) Uani 0.694(14) 1 d . . P D 1
F3A F 0.6207(8) 0.1665(3) 0.2408(10) 0.120(3) Uani 0.666(16) 1 d . . P E 1
F4A F 0.3188(4) 0.0808(3) 0.2762(8) 0.137(2) Uani 0.770(9) 1 d . . P F 1
F5A F 0.4945(8) 0.1866(2) 0.4046(3) 0.1095(17) Uani 0.770(9) 1 d . . P F 1
F6A F 0.4712(16) 0.0674(5) 0.1278(9) 0.128(3) Uani 0.62(2) 1 d . . P G 1
F1B F 0.609(2) 0.100(3) 0.235(3) 0.236(15) Uani 0.221(10) 1 d . . P C 2
F2B F 0.366(4) 0.1624(16) 0.344(3) 0.299(17) Uani 0.306(14) 1 d . . P D 2
F3B F 0.428(4) 0.1858(10) 0.1385(16) 0.193(13) Uani 0.334(16) 1 d . . P E 2
F4B F 0.502(4) 0.0617(12) 0.397(2) 0.195(17) Uani 0.230(9) 1 d . . P F 2
F5B F 0.631(2) 0.1746(11) 0.358(3) 0.165(12) Uani 0.230(9) 1 d . . P C 2
F6B F 0.389(4) 0.0635(7) 0.140(2) 0.179(10) Uani 0.38(2) 1 d . . P G 2
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_1
_geom_angle_site_symmetry_3
N1 C1 N2 109.0(2) . .
C3 C2 N2 107.5(2) . .
C2 C3 N1 107.5(2) . .
N1 C4 C5 113.8(2) . .
C4 C5 C6 115.7(2) . .
C5 C6 C6 112.5(3) . 3_756
N2 C7 C8 111.3(2) . .
C1 N1 C3 108.2(2) . .
C1 N1 C4 126.9(2) . .
C3 N1 C4 124.7(2) . .
C1 N2 C2 107.8(2) . .
C1 N2 C7 126.0(2) . .
C2 N2 C7 126.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.316(3) .
C1 N2 1.320(3) .
C2 C3 1.328(3) .
C2 N2 1.360(3) .
C3 N1 1.357(3) .
C4 N1 1.476(3) .
C4 C5 1.487(3) .
C5 C6 1.504(4) .
C6 C6 1.518(5) 3_756
C7 N2 1.464(3) .
C7 C8 1.472(4) .
F1B F5B 1.62(5) .
