#------------------------------------------------------------------------------
#$Date: 2023-01-11 10:38:23 +0200 (Wed, 11 Jan 2023) $
#$Revision: 280273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106436.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_8106436
loop_
_publ_author_name
'Xu-Liang, Nie'
'Juan-Hua, Kong'
'Jing, Chen'
'Jin-Zhu, Chen'
'Wan-Ming, Xiong'
_publ_section_title
;
 Crystal structure of
 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium)
 bis(hexafluoro phosphate), C14H24F12N4P2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              73
_journal_page_last               74
_journal_paper_doi               10.1515/ncrs-2016-0153
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C14 H24 F12 N4 P2'
_chemical_formula_sum            'C14 H24 F12 N4 P2'
_chemical_formula_weight         538.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                62.2060(10)
_cell_angle_beta                 64.2980(10)
_cell_angle_gamma                89.661(2)
_cell_formula_units_Z            1
_cell_length_a                   8.8173(12)
_cell_length_b                   8.8845(12)
_cell_length_c                   9.1494(12)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.12
_cell_measurement_theta_min      2.65
_cell_volume                     553.72(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4276
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.9040
_exptl_absorpt_correction_T_min  0.8820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1218P)²+0.4937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2038
_refine_ls_wR_factor_ref         0.2114
_reflns_number_gt                1821
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0153_suppl.cif
_cod_data_source_block           3071_0m
_cod_database_code               8106436
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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 0.25471(11) 0.26293(11) 0.41180(12) 0.0581(8) Uani 1 1 d . A 1
C5 C 0.1407(4) 0.7015(4) 0.9532(4) 0.0522(10) Uani 1 1 d . B 1
H5A H 0.2499 0.6673 0.9211 0.063 Uiso 1 1 calc R B 1
H5B H 0.1439 0.7877 0.8364 0.063 Uiso 1 1 calc R B 1
C1 C 0.4002(4) 1.0051(4) 0.8052(4) 0.0506(10) Uani 1 1 d . B 1
H1 H 0.4322 0.9530 0.7320 0.061 Uiso 1 1 calc R B 1
C6 C -0.0073(4) 0.5416(4) 1.0578(4) 0.0528(10) Uani 1 1 d . . 1
H6A H -0.0092 0.4552 1.1737 0.063 Uiso 1 1 calc R . 1
H6B H -0.1165 0.5759 1.0921 0.063 Uiso 1 1 calc R . 1
C4 C 0.1204(4) 0.7822(4) 1.0702(5) 0.0584(11) Uani 1 1 d . B 1
H4A H 0.0085 0.8108 1.1071 0.070 Uiso 1 1 calc R B 1
H4B H 0.1215 0.6967 1.1847 0.070 Uiso 1 1 calc R B 1
C3 C 0.2583(4) 1.0552(4) 1.0348(5) 0.0559(10) Uani 1 1 d . B 1
H3 H 0.1742 1.0429 1.1481 0.067 Uiso 1 1 calc R B 1
C2 C 0.4023(4) 1.1861(4) 0.9037(5) 0.0562(11) Uani 1 1 d . B 1
H2 H 0.4364 1.2814 0.9091 0.067 Uiso 1 1 calc R B 1
C7 C 0.6532(5) 1.2621(5) 0.5837(6) 0.0733(13) Uani 1 1 d . B 1
H7A H 0.6289 1.3534 0.4926 0.110 Uiso 1 1 calc R B 1
H7B H 0.7099 1.1906 0.5348 0.110 Uiso 1 1 calc R B 1
H7C H 0.7275 1.3136 0.6087 0.110 Uiso 1 1 calc R B 1
N1 N 0.2577(3) 0.9423(3) 0.9708(3) 0.0462(9) Uani 1 1 d . B 1
N2 N 0.4901(3) 1.1531(3) 0.7598(4) 0.0505(10) Uani 1 1 d . B 1
F2 F 0.2620(5) 0.3025(6) 0.5617(5) 0.1278(15) Uani 1 1 d . A 1
F1 F 0.2518(7) 0.2274(6) 0.2650(6) 0.1673(19) Uani 1 1 d . A 1
F3A F 0.4232(16) 0.193(3) 0.403(2) 0.131(7) Uani 0.50(3) 1 d P A 1
F5A F 0.147(2) 0.0888(11) 0.6038(12) 0.144(5) Uani 0.55(3) 1 d P A 1
F4A F 0.0800(18) 0.320(3) 0.4532(18) 0.126(8) Uani 0.49(3) 1 d P A 1
F6A F 0.365(3) 0.4384(15) 0.2440(11) 0.182(11) Uani 0.57(3) 1 d P A 1
F3B F 0.305(4) 0.0866(16) 0.4778(19) 0.171(10) Uani 0.50(3) 1 d P A 2
F6B F 0.4493(14) 0.344(4) 0.310(3) 0.181(8) Uani 0.43(3) 1 d P A 2
F5B F 0.0673(14) 0.173(5) 0.525(4) 0.212(17) Uani 0.45(3) 1 d P A 2
F4B F 0.217(5) 0.443(2) 0.333(4) 0.181(13) Uani 0.51(3) 1 d P A 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'
O O 0.0106 0.0060 '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
F6A P1 F1 83.9(5) . .
F6A P1 F5A 171.4(7) . .
F1 P1 F5A 104.6(6) . .
F6A P1 F4A 95.1(13) . .
F1 P1 F4A 92.6(5) . .
F5A P1 F4A 85.9(9) . .
F6A P1 F2 95.0(5) . .
F1 P1 F2 178.7(2) . .
F5A P1 F2 76.4(5) . .
F4A P1 F2 88.2(5) . .
F6A P1 F3A 90.6(13) . .
F1 P1 F3A 94.8(4) . .
F5A P1 F3A 87.4(10) . .
F4A P1 F3A 171.1(6) . .
F2 P1 F3A 84.5(3) . .
C4 C5 C6 111.5(2) . .
N2 C1 N1 109.6(3) . .
C6 C6 C5 113.0(3) 2_567 .
N1 C4 C5 113.3(3) . .
C2 C3 N1 107.5(3) . .
C3 C2 N2 107.3(3) . .
C1 N1 C3 107.7(3) . .
C1 N1 C4 127.0(2) . .
C3 N1 C4 125.3(3) . .
C1 N2 C2 108.0(3) . .
C1 N2 C7 124.9(3) . .
C2 N2 C7 127.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F6A 1.492(6) .
P1 F1 1.527(3) .
P1 F5A 1.555(7) .
P1 F4A 1.561(7) .
P1 F2 1.592(3) .
P1 F3A 1.593(8) .
C5 C4 1.497(4) .
C5 C6 1.519(4) .
C1 N2 1.322(4) .
C1 N1 1.325(4) .
C6 C6 1.513(6) 2_567
C4 N1 1.475(4) .
C3 C2 1.341(5) .
C3 N1 1.379(4) .
C2 N2 1.375(4) .
C7 N2 1.467(4) .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{3ac30dfa-75c4-4a45-9f18-af898ed6a3da} ? ? ?
{9b9d3ac3-4952-44fb-b7be-69c9f02b4251} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{3ac30dfa-75c4-4a45-9f18-af898ed6a3da} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EX
