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#$Date: 2022-11-28 10:42:33 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106268.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_8106268
loop_
_publ_author_name
'Wan-Ming, Xiong'
'Long, Zhou'
'Shen-Ming, Lv'
'Xu-Liang, Nie'
'Jing, Chen'
'Chang-Gan, Huang'
_publ_section_title
;
 Crystal structure of
 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate),
 C13H22F12N4P2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              701
_journal_page_last               703
_journal_paper_doi               10.1515/ncrs-2018-0027
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C13 H22 F12 N4 P2'
_chemical_formula_weight         524.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 97.7660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9171(13)
_cell_length_b                   13.3953(13)
_cell_length_c                   12.5808(12)
_cell_measurement_reflns_used    4891
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.07
_cell_measurement_theta_min      2.23
_cell_volume                     2156.9(4)
_computing_cell_refinement       'Bruker SAINT[2]'
_computing_data_collection       'Bruker APEX2[1]'
_computing_data_reduction        'Bruker SAINT[2]'
_computing_molecular_graphics    'Bruker SHELXTL[2]'
_computing_publication_material  'Bruker SHELXTL[2]'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)[2]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)[2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16239
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.201
_exptl_absorpt_coefficient_mu    0.311
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0570P)²+2.6892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2890
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0027_suppl.cif
_cod_data_source_block           3268_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106268
_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   0.937
_shelx_estimated_absorpt_t_max   0.943
loop_
_space_group_symop_operation_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_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 -0.0707(3) 0.2384(2) 0.4278(3) 0.0645(8) Uani 1 1 d . . . . .
H1 H -0.041181 0.186915 0.392340 0.077 Uiso 1 1 calc R U . . .
C2 C -0.1801(3) 0.3470(3) 0.4727(3) 0.0782(10) Uani 1 1 d . . . . .
H2 H -0.240510 0.384554 0.473694 0.094 Uiso 1 1 calc R U . . .
C3 C -0.0921(3) 0.3568(3) 0.5389(3) 0.0747(10) Uani 1 1 d . . . . .
H3 H -0.079358 0.402278 0.595040 0.090 Uiso 1 1 calc R U . . .
C4 C -0.2423(3) 0.2406(4) 0.3117(3) 0.0999(14) Uani 1 1 d . . . . .
H4A H -0.248121 0.291045 0.257087 0.150 Uiso 1 1 calc R U . . .
H4B H -0.309208 0.230400 0.335190 0.150 Uiso 1 1 calc R U . . .
H4C H -0.219075 0.179265 0.283233 0.150 Uiso 1 1 calc R U . . .
C5 C 0.0838(3) 0.2752(3) 0.5611(3) 0.0737(10) Uani 1 1 d . . . . .
H5A H 0.105875 0.207134 0.550145 0.088 Uiso 1 1 calc R U . . .
H5B H 0.086822 0.285836 0.637739 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1583(3) 0.3466(3) 0.5171(3) 0.0739(10) Uani 1 1 d . . . . .
H6A H 0.129306 0.413406 0.516620 0.089 Uiso 1 1 calc R U . . .
H6B H 0.223874 0.347000 0.564912 0.089 Uiso 1 1 calc R U . . .
C7 C 0.1801(3) 0.3216(3) 0.4062(3) 0.0704(9) Uani 1 1 d . . . . .
H7A H 0.114245 0.317584 0.359115 0.085 Uiso 1 1 calc R U . . .
H7B H 0.212818 0.256411 0.407454 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2501(3) 0.3968(3) 0.3602(3) 0.0650(8) Uani 1 1 d . . . . .
H8A H 0.213024 0.459562 0.347692 0.078 Uiso 1 1 calc R U . . .
H8B H 0.311672 0.408674 0.411869 0.078 Uiso 1 1 calc R U . . .
C9 C 0.2822(4) 0.3611(3) 0.2589(4) 0.0971(14) Uani 1 1 d . . . . .
H9A H 0.318817 0.298191 0.272298 0.117 Uiso 1 1 calc R U . . .
H9B H 0.220072 0.348424 0.208327 0.117 Uiso 1 1 calc R U . . .
C10 C 0.4486(3) 0.4454(2) 0.2431(3) 0.0641(8) Uani 1 1 d . . . . .
H10 H 0.486480 0.415782 0.302964 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4081(4) 0.5357(3) 0.1021(3) 0.0852(12) Uani 1 1 d . . . . .
H11 H 0.412862 0.580438 0.046474 0.102 Uiso 1 1 calc R U . . .
C12 C 0.3230(4) 0.4863(3) 0.1200(3) 0.0849(12) Uani 1 1 d . . . . .
H12 H 0.257583 0.489575 0.078931 0.102 Uiso 1 1 calc R U . . .
C13 C 0.5941(4) 0.5428(4) 0.1882(4) 0.1133(17) Uani 1 1 d . . . . .
H13A H 0.632832 0.499230 0.147563 0.170 Uiso 1 1 calc R U . . .
H13B H 0.624474 0.541794 0.262166 0.170 Uiso 1 1 calc R U . . .
H13C H 0.596154 0.609555 0.160811 0.170 Uiso 1 1 calc R U . . .
F1 F 0.4346(2) 0.2733(2) 0.0285(3) 0.1443(12) Uani 1 1 d . . . . .
F2 F 0.61817(18) 0.13149(18) 0.1215(2) 0.0992(8) Uani 1 1 d . . . . .
F3 F 0.5080(2) 0.2244(2) 0.1927(2) 0.1141(9) Uani 1 1 d . . . . .
F4 F 0.44853(19) 0.11101(19) 0.0688(2) 0.1060(8) Uani 1 1 d . . . . .
F5 F 0.6052(2) 0.2914(2) 0.0786(2) 0.1276(11) Uani 1 1 d . . . . .
F6 F 0.5471(2) 0.1799(3) -0.04392(19) 0.1306(11) Uani 1 1 d . . . . .
F7 F 0.1675(11) 0.5845(8) 0.8689(11) 0.190(5) Uani 0.526(7) 1 d . . P A 1
F8 F 0.0986(13) 0.4094(5) 0.8066(12) 0.189(5) Uani 0.526(7) 1 d . . P A 1
F9 F 0.1122(9) 0.4474(10) 0.9202(10) 0.152(4) Uani 0.526(7) 1 d . . P A 1
F10 F -0.0404(5) 0.4992(14) 0.8311(12) 0.173(6) Uani 0.526(7) 1 d . . P A 1
F11 F 0.1830(7) 0.5365(10) 0.7795(16) 0.179(6) Uani 0.526(7) 1 d . . P A 1
F12 F 0.0365(11) 0.5282(6) 0.6908(5) 0.134(4) Uani 0.526(7) 1 d . . P A 1
F7' F 0.0548(10) 0.6326(6) 0.8133(8) 0.132(4) Uani 0.474(7) 1 d . . P A 2
F8' F 0.0027(13) 0.4322(12) 0.7749(6) 0.165(6) Uani 0.474(7) 1 d . . P A 2
F9' F 0.1056(12) 0.5216(16) 0.9296(7) 0.192(6) Uani 0.474(7) 1 d . . P A 2
F10' F -0.0001(12) 0.5584(13) 0.8789(12) 0.200(6) Uani 0.474(7) 1 d . . P A 2
F11' F 0.1527(12) 0.476(2) 0.7517(12) 0.272(11) Uani 0.474(7) 1 d . . P A 2
F12' F 0.0396(11) 0.590(3) 0.733(3) 0.337(14) Uani 0.474(7) 1 d . . P A 2
N1 N -0.1664(2) 0.2727(2) 0.4032(2) 0.0650(7) Uani 1 1 d . . . . .
N2 N -0.02379(19) 0.28810(19) 0.5099(2) 0.0575(7) Uani 1 1 d . . . . .
N3 N 0.3493(2) 0.4298(2) 0.2098(2) 0.0652(7) Uani 1 1 d . . . . .
N4 N 0.4863(2) 0.5092(2) 0.1792(2) 0.0686(8) Uani 1 1 d . . . . .
P1 P 0.52608(7) 0.20209(6) 0.07292(7) 0.0603(3) Uani 1 1 d . . . . .
P3 P 0.07664(8) 0.51739(8) 0.81503(8) 0.0724(3) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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'
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
N2 C1 N1 109.1(3) . .
N2 C1 H1 125.4 . .
N1 C1 H1 125.4 . .
C3 C2 N1 107.7(3) . .
C3 C2 H2 126.2 . .
N1 C2 H2 126.1 . .
C2 C3 N2 107.3(3) . .
C2 C3 H3 126.3 . .
N2 C3 H3 126.3 . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N2 C5 C6 112.2(3) . .
N2 C5 H5A 109.2 . .
C6 C5 H5A 109.2 . .
N2 C5 H5B 109.2 . .
C6 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
C7 C6 C5 114.1(3) . .
C7 C6 H6A 108.7 . .
C5 C6 H6A 108.7 . .
C7 C6 H6B 108.7 . .
C5 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C6 C7 C8 113.8(3) . .
C6 C7 H7A 108.8 . .
C8 C7 H7A 108.8 . .
C6 C7 H7B 108.8 . .
C8 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
C9 C8 C7 111.5(3) . .
C9 C8 H8A 109.3 . .
C7 C8 H8A 109.3 . .
C9 C8 H8B 109.3 . .
C7 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
N3 C9 C8 114.6(3) . .
N3 C9 H9A 108.6 . .
C8 C9 H9A 108.6 . .
N3 C9 H9B 108.6 . .
C8 C9 H9B 108.6 . .
H9A C9 H9B 107.6 . .
N3 C10 N4 109.6(3) . .
N3 C10 H10 125.2 . .
N4 C10 H10 125.2 . .
C12 C11 N4 107.7(4) . .
C12 C11 H11 126.2 . .
N4 C11 H11 126.2 . .
C11 C12 N3 107.3(4) . .
C11 C12 H12 126.3 . .
N3 C12 H12 126.3 . .
N4 C13 H13A 109.5 . .
N4 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N4 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C1 N1 C2 107.9(3) . .
C1 N1 C4 125.9(4) . .
C2 N1 C4 126.1(3) . .
C1 N2 C3 108.0(3) . .
C1 N2 C5 126.9(3) . .
C3 N2 C5 125.1(3) . .
C10 N3 C12 107.5(3) . .
C10 N3 C9 125.2(3) . .
C12 N3 C9 127.3(4) . .
C10 N4 C11 107.9(3) . .
C10 N4 C13 125.8(4) . .
C11 N4 C13 126.3(4) . .
F1 P1 F6 89.94(19) . .
F1 P1 F5 90.41(18) . .
F6 P1 F5 89.58(17) . .
F1 P1 F4 90.81(17) . .
F6 P1 F4 90.69(16) . .
F5 P1 F4 178.75(15) . .
F1 P1 F2 178.17(18) . .
F6 P1 F2 91.86(17) . .
F5 P1 F2 89.27(15) . .
F4 P1 F2 89.50(14) . .
F1 P1 F3 91.35(18) . .
F6 P1 F3 178.43(17) . .
F5 P1 F3 89.52(16) . .
F4 P1 F3 90.19(15) . .
F2 P1 F3 86.84(15) . .
F11' P3 F9' 117.3(10) . .
F11' P3 F12' 92.7(15) . .
F9' P3 F12' 135(2) . .
F11' P3 F10' 179.6(12) . .
F9' P3 F10' 62.6(8) . .
F12' P3 F10' 87.6(13) . .
F8 P3 F11 87.4(7) . .
F11' P3 F8' 88.4(10) . .
F9' P3 F8' 115.2(9) . .
F12' P3 F8' 97.6(16) . .
F10' P3 F8' 91.3(7) . .
F8 P3 F7 117.0(9) . .
F11 P3 F7 51.3(6) . .
F8 P3 F10 93.1(7) . .
F11 P3 F10 170.4(8) . .
F7 P3 F10 135.6(10) . .
F11' P3 F7' 120.0(11) . .
F9' P3 F7' 89.9(9) . .
F12' P3 F7' 44.8(17) . .
F10' P3 F7' 60.3(7) . .
F8' P3 F7' 128.8(9) . .
F8 P3 F12 93.4(7) . .
F11 P3 F12 83.3(8) . .
F7 P3 F12 120.2(6) . .
F10 P3 F12 87.1(7) . .
F8 P3 F9 57.5(6) . .
F11 P3 F9 99.6(7) . .
F7 P3 F9 82.3(5) . .
F10 P3 F9 88.7(5) . .
F12 P3 F9 150.3(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.307(4) .
C1 N1 1.315(4) .
C1 H1 0.9300 .
C2 C3 1.321(5) .
C2 N1 1.352(5) .
C2 H2 0.9300 .
C3 N2 1.359(4) .
C3 H3 0.9300 .
C4 N1 1.472(4) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 N2 1.462(4) .
C5 C6 1.514(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.497(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.518(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.473(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N3 1.457(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N3 1.311(4) .
C10 N4 1.312(4) .
C10 H10 0.9300 .
C11 C12 1.328(6) .
C11 N4 1.350(5) .
C11 H11 0.9300 .
C12 N3 1.363(5) .
C12 H12 0.9300 .
C13 N4 1.453(5) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
F1 P1 1.562(3) .
F2 P1 1.577(2) .
F3 P1 1.584(2) .
F4 P1 1.575(2) .
F5 P1 1.569(2) .
F6 P1 1.559(2) .
F7 P3 1.560(8) .
F8 P3 1.480(7) .
F9 P3 1.636(8) .
F10 P3 1.571(7) .
F11 P3 1.523(7) .
F12 P3 1.586(7) .
F7' P3 1.569(8) .
F8' P3 1.529(7) .
F9' P3 1.440(8) .
F10' P3 1.464(8) .
F11' P3 1.456(11) .
F12' P3 1.453(10) .
