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#$Date: 2022-06-15 10:29:02 +0300 (Wed, 15 Jun 2022) $
#$Revision: 276045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105425.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_8105425
loop_
_publ_author_name
'Yao-Hong, Zhou'
'Ting, Huang'
'Xu-Liang, Nie'
'Jing, Chen'
'Wan-Ming, Xiong'
_publ_section_title
;
 Crystal structure of
 3,3′-(1,2-phenylenebis(methylene))bis(1-methyl-1H-imidazol-3-ium)
 bis(hexafluoridophosphate), C16H20F12N4P2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1217
_journal_page_last               1219
_journal_paper_doi               10.1515/ncrs-2020-0268
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C16 H20 F12 N4 P2'
_chemical_formula_sum            'C16 H20 F12 N4 P2'
_chemical_formula_weight         558.30
_chemical_name_systematic
;
3,3'-(1,2-phenylenebis(methylene))bis(1-methyl-
1H-imidazol-3-ium) bis(hexafluoro phosphate)(V)
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.500(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3086(15)
_cell_length_b                   12.174(3)
_cell_length_c                   26.355(6)
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.80
_cell_volume                     2337.7(9)
_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_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2,3]'
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.281
_exptl_absorpt_coefficient_mu    0.293
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Crystallogr. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1053P)²+3.6144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2262
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3316
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0268_suppl.cif
_cod_data_source_block           4062_0m
_cod_original_cell_volume        2337.6(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105425
_shelx_shelxl_version_number     2014/7
_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   0.944
_shelx_estimated_absorpt_t_max   0.957
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 0.1649(5) 0.3971(3) 0.66220(14) 0.0431(8) Uani 1 1 d . . . . .
C2 C 0.1323(5) 0.3453(3) 0.70776(15) 0.0512(10) Uani 1 1 d . . . . .
H2 H 0.2091 0.2889 0.7202 0.061 Uiso 1 1 calc R U . . .
C3 C -0.0137(6) 0.3775(4) 0.73465(15) 0.0541(10) Uani 1 1 d . . . . .
H3 H -0.0365 0.3420 0.7647 0.065 Uiso 1 1 calc R U . . .
C4 C -0.1249(6) 0.4623(4) 0.71665(16) 0.0550(10) Uani 1 1 d . . . . .
H4 H -0.2215 0.4852 0.7351 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0940(5) 0.5136(3) 0.67144(15) 0.0506(9) Uani 1 1 d . . . . .
H5 H -0.1704 0.5706 0.6595 0.061 Uiso 1 1 calc R U . . .
C6 C 0.0497(5) 0.4811(3) 0.64378(14) 0.0413(8) Uani 1 1 d . . . . .
C7 C 0.3283(6) 0.3650(4) 0.63315(18) 0.0583(11) Uani 1 1 d . . . . .
H7A H 0.2925 0.3679 0.5969 0.070 Uiso 1 1 calc R U . . .
H7B H 0.4258 0.4181 0.6404 0.070 Uiso 1 1 calc R U . . .
C8 C 0.0856(5) 0.5355(3) 0.59381(15) 0.0502(9) Uani 1 1 d . . . . .
H8A H 0.2012 0.5749 0.5982 0.060 Uiso 1 1 calc R U . . .
H8B H 0.0982 0.4789 0.5684 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5603(5) 0.2327(3) 0.66977(15) 0.0496(9) Uani 1 1 d . . . . .
H9 H 0.6471 0.2840 0.6821 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4231(7) 0.0776(4) 0.6510(2) 0.0699(13) Uani 1 1 d . . . . .
H10 H 0.3998 0.0026 0.6485 0.084 Uiso 1 1 calc R U . . .
C11 C 0.3106(7) 0.1585(4) 0.6337(2) 0.0695(13) Uani 1 1 d . . . . .
H11 H 0.1951 0.1504 0.6166 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7366(7) 0.0673(5) 0.6973(2) 0.0797(16) Uani 1 1 d . . . . .
H12A H 0.7875 0.0199 0.6730 0.120 Uiso 1 1 calc R U . . .
H12B H 0.6989 0.0242 0.7252 0.120 Uiso 1 1 calc R U . . .
H12C H 0.8275 0.1196 0.7098 0.120 Uiso 1 1 calc R U . . .
C13 C -0.0521(6) 0.7197(4) 0.57865(16) 0.0545(10) Uani 1 1 d . . . . .
H13 H 0.0442 0.7602 0.5944 0.065 Uiso 1 1 calc R U . . .
C14 C -0.2220(6) 0.5833(4) 0.54924(17) 0.0602(11) Uani 1 1 d . . . . .
H14 H -0.2623 0.5125 0.5412 0.072 Uiso 1 1 calc R U . . .
C15 C -0.3128(6) 0.6771(4) 0.53787(19) 0.0672(13) Uani 1 1 d . . . . .
H15 H -0.4283 0.6832 0.5206 0.081 Uiso 1 1 calc R U . . .
C16 C -0.2498(9) 0.8783(4) 0.5513(2) 0.0917(19) Uani 1 1 d . . . . .
H16A H -0.1424 0.9210 0.5612 0.138 Uiso 1 1 calc R U . . .
H16B H -0.3452 0.8962 0.5730 0.138 Uiso 1 1 calc R U . . .
H16C H -0.2908 0.8945 0.5166 0.138 Uiso 1 1 calc R U . . .
N1 N 0.3987(4) 0.2555(3) 0.64592(13) 0.0506(8) Uani 1 1 d . . . . .
N2 N 0.5776(5) 0.1254(3) 0.67302(13) 0.0554(9) Uani 1 1 d . . . . .
N3 N -0.0582(4) 0.6119(3) 0.57502(12) 0.0477(8) Uani 1 1 d . . . . .
N4 N -0.2057(5) 0.7611(3) 0.55623(14) 0.0600(10) Uani 1 1 d . . . . .
P1 P 0.53757(15) 0.23823(9) 0.82279(4) 0.0523(3) Uani 1 1 d . . . . .
P2 P 0.19576(15) 0.77518(10) 0.45696(4) 0.0531(3) Uani 1 1 d . . . . .
F1 F 0.6281(5) 0.3101(3) 0.86834(13) 0.1000(11) Uani 1 1 d . . . . .
F2 F 0.4456(5) 0.1675(3) 0.77745(12) 0.0878(9) Uani 1 1 d . . . . .
F3 F 0.5182(4) 0.1379(3) 0.86050(12) 0.0839(9) Uani 1 1 d . . . . .
F4 F 0.5557(4) 0.3382(2) 0.78450(11) 0.0794(8) Uani 1 1 d . . . . .
F5 F 0.7355(4) 0.1961(3) 0.81161(14) 0.0931(10) Uani 1 1 d . . . . .
F6 F 0.3417(4) 0.2803(3) 0.83457(12) 0.0913(10) Uani 1 1 d . . . . .
F7 F 0.2538(5) 0.7065(6) 0.50536(17) 0.169(3) Uani 1 1 d . . . . .
F8 F 0.1368(6) 0.8391(6) 0.40864(18) 0.180(3) Uani 1 1 d . . . . .
F9 F 0.1263(10) 0.8624(4) 0.4912(3) 0.205(3) Uani 1 1 d . . . . .
F10 F 0.2708(10) 0.6852(3) 0.4248(2) 0.198(3) Uani 1 1 d . . . . .
F11 F 0.3860(5) 0.8305(5) 0.45589(17) 0.1450(19) Uani 1 1 d . . . . .
F12 F 0.0058(5) 0.7173(4) 0.45793(15) 0.1268(16) 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'
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
C6 C1 C2 119.7(4) . .
C6 C1 C7 119.5(3) . .
C2 C1 C7 120.8(3) . .
C3 C2 C1 120.3(4) . .
C4 C3 C2 119.6(4) . .
C3 C4 C5 120.4(4) . .
C4 C5 C6 120.5(4) . .
C5 C6 C1 119.4(3) . .
C5 C6 C8 121.6(3) . .
C1 C6 C8 119.0(3) . .
N1 C7 C1 113.3(3) . .
N3 C8 C6 113.8(3) . .
N2 C9 N1 108.5(4) . .
C11 C10 N2 107.3(4) . .
C10 C11 N1 106.8(4) . .
N3 C13 N4 108.9(4) . .
C15 C14 N3 107.0(4) . .
C14 C15 N4 107.5(4) . .
C9 N1 C11 108.4(4) . .
C9 N1 C7 125.9(4) . .
C11 N1 C7 125.6(4) . .
C9 N2 C10 109.0(4) . .
C9 N2 C12 125.3(4) . .
C10 N2 C12 125.7(4) . .
C13 N3 C14 108.1(4) . .
C13 N3 C8 126.2(4) . .
C14 N3 C8 125.7(4) . .
C13 N4 C15 108.5(4) . .
C13 N4 C16 125.6(5) . .
C15 N4 C16 125.9(4) . .
F6 P1 F2 89.3(2) . .
F6 P1 F5 179.3(2) . .
F2 P1 F5 91.3(2) . .
F6 P1 F1 90.2(2) . .
F2 P1 F1 179.4(2) . .
F5 P1 F1 89.2(2) . .
F6 P1 F3 90.00(18) . .
F2 P1 F3 90.04(18) . .
F5 P1 F3 89.71(17) . .
F1 P1 F3 90.17(19) . .
F6 P1 F4 89.92(17) . .
F2 P1 F4 89.36(17) . .
F5 P1 F4 90.39(17) . .
F1 P1 F4 90.43(18) . .
F3 P1 F4 179.40(19) . .
F9 P2 F10 177.2(4) . .
F9 P2 F8 93.1(4) . .
F10 P2 F8 89.6(4) . .
F9 P2 F11 92.8(3) . .
F10 P2 F11 86.5(3) . .
F8 P2 F11 87.6(3) . .
F9 P2 F7 88.3(4) . .
F10 P2 F7 89.0(4) . .
F8 P2 F7 178.1(4) . .
F11 P2 F7 93.5(3) . .
F9 P2 F12 88.1(3) . .
F10 P2 F12 92.5(3) . .
F8 P2 F12 92.9(3) . .
F11 P2 F12 178.9(3) . .
F7 P2 F12 85.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(5) .
C1 C2 1.393(5) .
C1 C7 1.519(5) .
C2 C3 1.383(6) .
C3 C4 1.375(6) .
C4 C5 1.380(6) .
C5 C6 1.382(5) .
C6 C8 1.515(5) .
C7 N1 1.458(5) .
C8 N3 1.460(5) .
C9 N2 1.315(5) .
C9 N1 1.323(5) .
C10 C11 1.340(7) .
C10 N2 1.359(6) .
C11 N1 1.372(6) .
C12 N2 1.465(5) .
C13 N3 1.317(5) .
C13 N4 1.326(5) .
C14 C15 1.342(6) .
C14 N3 1.374(5) .
C15 N4 1.355(6) .
C16 N4 1.466(6) .
P1 F6 1.574(3) .
P1 F2 1.580(3) .
P1 F5 1.584(3) .
P1 F1 1.588(3) .
P1 F3 1.588(3) .
P1 F4 1.593(3) .
P2 F9 1.508(4) .
P2 F10 1.514(4) .
P2 F8 1.525(4) .
P2 F11 1.547(4) .
P2 F7 1.556(4) .
P2 F12 1.559(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 F7 0.93 2.34 3.235(6) 160.5 1_455
C14 H14 F10 0.93 2.57 3.364(6) 143.5 3_566
C13 H13 F1 0.93 2.59 3.477(6) 159.9 2_656
C11 H11 F8 0.93 2.47 3.371(6) 163.9 3_566
C10 H10 F1 0.93 2.39 3.313(6) 171.1 2_646
C8 H8B F12 0.97 2.58 3.410(6) 143.1 3_566
C8 H8A F3 0.97 2.37 3.292(5) 158.0 2_656
