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#$Date: 2022-03-31 09:59:00 +0200 (jue 31 de mar de 2022) $
#$Revision: 274168 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/49/8104974.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_8104974
loop_
_publ_author_name
'Huang-Xian, Zhang'
'Kun, Yuan'
'Qi-Long, Du'
'Xu-Liang, Nie'
'Wan-Ming, Xiong'
_publ_section_title
;
 Crystal structure of
 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium)
 bis(hexafluoridophosphate), C9H14F12N4P2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              109
_journal_page_last               111
_journal_paper_doi               10.1515/ncrs-2021-0400
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C9 H14 F12 N4 P2'
_chemical_formula_weight         468.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.577(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8968(9)
_cell_length_b                   11.5554(18)
_cell_length_c                   12.994(2)
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.36
_cell_volume                     882.6(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.362
_exptl_absorpt_coefficient_mu    0.369
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.067
_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       0.047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1095P)²+0.7484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2020
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1345
_reflns_number_total             1635
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0400_suppl.cif
_cod_data_source_block           3054_0m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               8104974
_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   0.930
_shelx_estimated_absorpt_t_max   0.947
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_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
P1 P 0.1006(2) 0.2500 0.61407(10) 0.0605(5) Uani 1 2 d S T P . .
F1 F 0.3674(7) 0.2500 0.6214(5) 0.1334(19) Uani 1 2 d S T P . .
F2 F 0.0933(7) 0.3455(4) 0.5280(3) 0.1516(16) Uani 1 1 d . . . . .
F3 F -0.1652(6) 0.2500 0.5999(4) 0.1196(17) Uani 1 2 d S T P . .
F4 F 0.1036(6) 0.1523(4) 0.6956(3) 0.1388(14) Uani 1 1 d . . . . .
P2 P 0.1201(2) 0.2500 0.04918(10) 0.0589(5) Uani 1 2 d S T P . .
F5 F -0.1333(11) 0.2204(15) 0.0491(6) 0.170(7) Uani 0.5 1 d . . P A -1
F6 F 0.050(2) 0.3636(7) 0.0950(9) 0.156(4) Uani 0.5 1 d . . P A -1
F7 F 0.3711(10) 0.2825(19) 0.0529(6) 0.179(10) Uani 0.5 1 d . . P A -1
F8 F 0.190(3) 0.1336(8) 0.0085(11) 0.190(5) Uani 0.5 1 d . . P A -1
F9 F 0.1523(16) 0.2038(12) 0.1611(5) 0.201(9) Uani 0.5 1 d . . P A -1
F10 F 0.0882(13) 0.2905(13) -0.0588(5) 0.179(9) Uani 0.5 1 d . . P A -1
N1 N 0.4653(6) 0.0018(2) 0.2353(3) 0.0657(9) Uani 1 1 d . . . . .
N2 N 0.6369(5) 0.1470(3) 0.3087(2) 0.0572(8) Uani 1 1 d . . . . .
C1 C 0.6139(6) 0.0828(3) 0.2237(3) 0.0586(9) Uani 1 1 d . . . . .
H1 H 0.6921 0.0940 0.1651 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3880(9) 0.0130(4) 0.3310(4) 0.0858(14) Uani 1 1 d . . . . .
H2 H 0.2806 -0.0340 0.3590 0.103 Uiso 1 1 calc R U . . .
C3 C 0.4935(9) 0.1032(4) 0.3773(3) 0.0825(13) Uani 1 1 d . . . . .
H3 H 0.4739 0.1310 0.4431 0.099 Uiso 1 1 calc R U . . .
C4 C 0.7751(9) 0.2500 0.3232(4) 0.0679(14) Uani 1 2 d S T P . .
H4A H 0.8911 0.2500 0.2743 0.081 Uiso 1 2 calc R U P . .
H4B H 0.8508 0.2500 0.3923 0.081 Uiso 1 2 calc R U P . .
C5 C 0.3919(10) -0.0859(4) 0.1587(4) 0.0988(16) Uani 1 1 d . . . . .
H5A H 0.2809 -0.1355 0.1862 0.148 Uiso 1 1 calc R U . . .
H5B H 0.3259 -0.0487 0.0974 0.148 Uiso 1 1 calc R U . . .
H5C H 0.5206 -0.1312 0.1421 0.148 Uiso 1 1 calc R U . . .
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
F4 P1 F4 93.7(3) . 4_565
F4 P1 F3 92.1(2) . .
F4 P1 F3 92.1(2) 4_565 .
F4 P1 F1 90.1(2) . .
F4 P1 F1 90.1(2) 4_565 .
F3 P1 F1 176.7(3) . .
F4 P1 F2 88.5(3) . 4_565
F4 P1 F2 177.7(2) 4_565 4_565
F3 P1 F2 86.9(2) . 4_565
F1 P1 F2 90.8(2) . 4_565
F4 P1 F2 177.7(2) . .
F4 P1 F2 88.5(3) 4_565 .
F3 P1 F2 86.9(2) . .
F1 P1 F2 90.8(2) . .
F2 P1 F2 89.4(4) 4_565 .
F10 P2 F6 94.6(7) . .
F10 P2 F8 88.1(9) . .
F6 P2 F8 177.2(7) . .
F10 P2 F7 90.1(5) . .
F6 P2 F7 93.9(8) . .
F8 P2 F7 86.6(10) . .
F10 P2 F5 91.1(5) . .
F6 P2 F5 84.2(8) . .
F8 P2 F5 95.3(8) . .
F7 P2 F5 177.8(7) . .
F10 P2 F9 178.3(8) . .
F6 P2 F9 86.9(8) . .
F8 P2 F9 90.3(7) . .
F7 P2 F9 90.5(6) . .
F5 P2 F9 88.3(5) . .
C1 N1 C2 108.3(4) . .
C1 N1 C5 125.9(4) . .
C2 N1 C5 125.8(4) . .
C1 N2 C3 107.9(3) . .
C1 N2 C4 126.0(4) . .
C3 N2 C4 126.0(4) . .
N1 C1 N2 109.3(3) . .
N1 C1 H1 125.3 . .
N2 C1 H1 125.3 . .
C3 C2 N1 107.9(4) . .
C3 C2 H2 126.0 . .
N1 C2 H2 126.0 . .
C2 C3 N2 106.5(4) . .
C2 C3 H3 126.7 . .
N2 C3 H3 126.7 . .
N2 C4 N2 110.7(4) . 4_565
N2 C4 H4A 109.5 . .
N2 C4 H4A 109.5 4_565 .
N2 C4 H4B 109.5 . .
N2 C4 H4B 109.5 4_565 .
H4A C4 H4B 108.1 . .
N1 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F4 1.547(3) .
P1 F4 1.547(3) 4_565
P1 F3 1.564(4) .
P1 F1 1.568(4) .
P1 F2 1.569(4) 4_565
P1 F2 1.569(4) .
P2 F10 1.477(6) .
P2 F6 1.512(7) .
P2 F8 1.514(8) .
P2 F7 1.524(7) .
P2 F5 1.533(6) .
P2 F9 1.547(6) .
N1 C1 1.299(5) .
N1 C2 1.364(6) .
N1 C5 1.462(5) .
N2 C1 1.328(4) .
N2 C3 1.373(5) .
N2 C4 1.447(4) .
C1 H1 0.9300 .
C2 C3 1.333(7) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C4 N2 1.447(4) 4_565
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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
C2 N1 C1 N2 0.0(4) . . . .
C5 N1 C1 N2 179.5(3) . . . .
C3 N2 C1 N1 0.0(4) . . . .
C4 N2 C1 N1 -175.7(3) . . . .
C1 N1 C2 C3 0.1(5) . . . .
C5 N1 C2 C3 -179.5(4) . . . .
N1 C2 C3 N2 -0.1(5) . . . .
C1 N2 C3 C2 0.1(5) . . . .
C4 N2 C3 C2 175.7(4) . . . .
C1 N2 C4 N2 99.4(5) . . . 4_565
C3 N2 C4 N2 -75.5(5) . . . 4_565
