#------------------------------------------------------------------------------
#$Date: 2022-03-08 10:57:36 +0200 (Tue, 08 Mar 2022) $
#$Revision: 273521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104678.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_8104678
loop_
_publ_author_name
'Zhou, Yao-Hong'
'Nie, Xu-Liang'
'Xiong, Wan-Ming'
'Peng, Da-Yong'
'Zhang, Xiao-Hua'
_publ_section_title
;
 Crystal structure of
 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium)
 bis(hexafluoridophosphate), C32H56F24N8P4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1105
_journal_page_last               1107
_journal_paper_doi               10.1515/ncrs-2021-0237
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C32 H56 F24 N8 P4'
_chemical_formula_sum            'C32 H56 F24 N8 P4'
_chemical_formula_weight         1132.72
_chemical_name_systematic
'1,1'-(butane-1,4-diyl)bis(3-propyl-1H- imidazol-3-ium) bis(hexafluoridophosphate)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                81.710(2)
_cell_angle_beta                 89.406(2)
_cell_angle_gamma                89.446(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6769(13)
_cell_length_b                   9.8858(14)
_cell_length_c                   14.510(2)
_cell_measurement_reflns_used    1016
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.47
_cell_measurement_theta_min      2.34
_cell_volume                     1231.5(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9680
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.344
_exptl_absorpt_coefficient_mu    0.279
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         4556
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.0692
_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)+(0.1123P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.2245
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1874
_reflns_number_total             4556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0237_suppl.cif
_cod_data_source_block           5007_0m
_cod_database_code               8104678
_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   0.946
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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_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 -0.0033(11) 0.5243(9) -0.3639(5) 0.175(4) Uani 1 1 d . U . A 3
H1A H -0.0434 0.5299 -0.3026 0.263 Uiso 1 1 calc R U . A 3
H1B H -0.0871 0.5195 -0.4059 0.263 Uiso 1 1 calc R U . A 3
H1C H 0.0571 0.6039 -0.3848 0.263 Uiso 1 1 calc R U . A 3
C2 C 0.0946(10) 0.4007(8) -0.3612(4) 0.128(3) Uani 1 1 d . U . A 3
H2A H 0.1237 0.3909 -0.4246 0.153 Uiso 1 1 calc R U . A 3
H2B H 0.0328 0.3219 -0.3370 0.153 Uiso 1 1 calc R U . A 3
C3 C 0.2371(8) 0.3965(7) -0.3052(4) 0.107(2) Uani 1 1 d . . . A 3
H3A H 0.2950 0.3140 -0.3120 0.128 Uiso 1 1 calc R U . A 3
H3B H 0.3007 0.4742 -0.3289 0.128 Uiso 1 1 calc R U . A 3
C4 C 0.1599(6) 0.2916(5) -0.1464(4) 0.0668(13) Uani 1 1 d . . . A 3
H4 H 0.1440 0.2048 -0.1619 0.080 Uiso 1 1 calc R U . A 3
C5 C 0.2136(6) 0.5052(5) -0.1562(5) 0.0812(16) Uani 1 1 d . . . A 3
H5 H 0.2408 0.5944 -0.1796 0.097 Uiso 1 1 calc R U . A 3
C6 C 0.1777(6) 0.4582(6) -0.0680(4) 0.0800(16) Uani 1 1 d . . . A 3
H6 H 0.1770 0.5088 -0.0187 0.096 Uiso 1 1 calc R U . A 3
C7 C 0.0922(6) 0.2368(6) 0.0217(4) 0.0885(17) Uani 1 1 d . . . A 3
H7A H 0.0920 0.2894 0.0732 0.106 Uiso 1 1 calc R U . A 3
H7B H -0.0128 0.2086 0.0133 0.106 Uiso 1 1 calc R U . A 3
C8 C 0.1875(7) 0.1160(6) 0.0459(4) 0.0985(19) Uani 1 1 d . . . A 3
H8A H 0.1731 0.0576 -0.0016 0.118 Uiso 1 1 calc R U . A 3
H8B H 0.1475 0.0670 0.1039 0.118 Uiso 1 1 calc R U . A 3
C9 C 0.3559(8) 0.1316(7) 0.0572(4) 0.107(2) Uani 1 1 d . . . A 3
H9A H 0.4009 0.0406 0.0686 0.129 Uiso 1 1 calc R U . A 3
H9B H 0.3969 0.1754 -0.0020 0.129 Uiso 1 1 calc R U . A 3
C10 C 0.4120(8) 0.2080(6) 0.1298(5) 0.108(2) Uani 1 1 d . . . A 3
H10A H 0.3790 0.3026 0.1150 0.130 Uiso 1 1 calc R U . A 3
H10B H 0.5238 0.2064 0.1287 0.130 Uiso 1 1 calc R U . A 3
C11 C 0.3485(6) 0.0255(6) 0.2617(4) 0.0760(15) Uani 1 1 d . . . A 3
H11 H 0.3749 -0.0476 0.2307 0.091 Uiso 1 1 calc R U . A 3
C12 C 0.3122(8) 0.2264(7) 0.2933(6) 0.109(2) Uani 1 1 d . . . A 3
H12 H 0.3082 0.3212 0.2883 0.131 Uiso 1 1 calc R U . A 3
C13 C 0.2739(7) 0.1402(8) 0.3676(5) 0.102(2) Uani 1 1 d . . . A 3
H13 H 0.2377 0.1628 0.4241 0.122 Uiso 1 1 calc R U . A 3
C14 C 0.2674(8) -0.1125(7) 0.4078(4) 0.104(2) Uani 1 1 d . . . A 3
H14A H 0.2110 -0.1737 0.3740 0.124 Uiso 1 1 calc R U . A 3
H14B H 0.2034 -0.0936 0.4597 0.124 Uiso 1 1 calc R U . A 3
C15 C 0.4143(9) -0.1821(7) 0.4447(5) 0.133(3) Uani 1 1 d . . . A 3
H15A H 0.4800 -0.1952 0.3921 0.160 Uiso 1 1 calc R U . A 3
H15B H 0.4675 -0.1214 0.4803 0.160 Uiso 1 1 calc R U . A 3
C16 C 0.3954(11) -0.3119(8) 0.5023(5) 0.162(3) Uani 1 1 d . . . A 3
H16A H 0.3212 -0.3029 0.5506 0.243 Uiso 1 1 calc R U . A 3
H16B H 0.4924 -0.3416 0.5297 0.243 Uiso 1 1 calc R U . A 3
H16C H 0.3600 -0.3779 0.4650 0.243 Uiso 1 1 calc R U . A 3
N1 N 0.2033(5) 0.3992(5) -0.2056(3) 0.0695(11) Uani 1 1 d . . . A 3
N2 N 0.1424(4) 0.3249(4) -0.0625(3) 0.0620(10) Uani 1 1 d . . . A 3
N3 N 0.3582(5) 0.1546(5) 0.2257(3) 0.0798(13) Uani 1 1 d . . . A 3
N4 N 0.2967(5) 0.0140(5) 0.3467(3) 0.0759(12) Uani 1 1 d . . . A 3
P1 P 0.32433(16) 0.65806(14) 0.15320(10) 0.0685(5) Uani 1 1 d . . . B 3
P2 P 0.82607(18) 0.06239(16) 0.28031(11) 0.0802(5) Uani 1 1 d . . . C 3
F1 F 0.4619(19) 0.7628(16) 0.1611(8) 0.078(6) Uani 0.51(3) 1 d . . P D 1
F2 F 0.202(4) 0.541(3) 0.153(2) 0.091(7) Uani 0.51(3) 1 d . . P D 1
F3 F 0.219(2) 0.738(3) 0.2104(18) 0.143(10) Uani 0.51(3) 1 d . . P D 1
F4 F 0.428(3) 0.585(3) 0.091(2) 0.117(7) Uani 0.51(3) 1 d . . P D 1
F5 F 0.381(4) 0.566(3) 0.244(2) 0.148(11) Uani 0.51(3) 1 d . . P D 1
F6 F 0.273(2) 0.746(2) 0.0649(15) 0.119(6) Uani 0.51(3) 1 d . . P D 1
F7 F 0.7616(17) 0.0407(18) 0.1850(10) 0.162(6) Uani 0.569(13) 1 d . U P E 1
F8 F 0.9025(14) 0.0791(16) 0.3769(5) 0.130(5) Uani 0.569(13) 1 d . U P E 1
F9 F 0.7216(14) -0.0471(13) 0.3250(16) 0.199(7) Uani 0.569(13) 1 d . U P E 1
F10 F 0.9441(12) 0.1769(7) 0.2342(8) 0.118(4) Uani 0.569(13) 1 d . U P E 1
F11 F 0.709(2) 0.1842(14) 0.2836(11) 0.123(4) Uani 0.569(13) 1 d . U P E 1
F12 F 0.953(3) -0.051(2) 0.2736(14) 0.117(6) Uani 0.569(13) 1 d . U P E 1
F9A F 0.813(3) -0.039(2) 0.3742(9) 0.180(7) Uani 0.431(13) 1 d D U P E 2
F7A F 0.7079(12) -0.0393(13) 0.2466(12) 0.102(4) Uani 0.431(13) 1 d . U P E 2
F8A F 0.9232(17) 0.1530(17) 0.3268(19) 0.171(8) Uani 0.431(13) 1 d . U P E 2
F10A F 0.818(2) 0.1475(18) 0.1841(11) 0.165(7) Uani 0.431(13) 1 d D U P E 2
F11A F 0.678(2) 0.1379(19) 0.3133(12) 0.131(7) Uani 0.431(13) 1 d D U P E 2
F12A F 0.961(4) -0.020(3) 0.2426(18) 0.115(7) Uani 0.431(13) 1 d . U P E 2
F1A F 0.457(2) 0.757(2) 0.1666(15) 0.142(10) Uani 0.49(3) 1 d . . P D 2
F2A F 0.177(4) 0.567(3) 0.135(2) 0.079(6) Uani 0.49(3) 1 d . . P D 2
F3A F 0.204(2) 0.765(2) 0.174(3) 0.178(12) Uani 0.49(3) 1 d . . P D 2
F4A F 0.443(3) 0.546(3) 0.127(3) 0.162(13) Uani 0.49(3) 1 d . . P D 2
F5A F 0.336(5) 0.603(4) 0.255(2) 0.182(16) Uani 0.49(3) 1 d . . P D 2
F6A F 0.316(4) 0.709(4) 0.0441(12) 0.172(11) Uani 0.49(3) 1 d . . P D 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'
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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C1 C2 C3 116.6(7) . .
C1 C2 H2A 108.1 . .
C3 C2 H2A 108.1 . .
C1 C2 H2B 108.1 . .
C3 C2 H2B 108.1 . .
H2A C2 H2B 107.3 . .
N1 C3 C2 112.0(5) . .
N1 C3 H3A 109.2 . .
C2 C3 H3A 109.2 . .
N1 C3 H3B 109.2 . .
C2 C3 H3B 109.2 . .
H3A C3 H3B 107.9 . .
N2 C4 N1 110.2(4) . .
N2 C4 H4 124.9 . .
N1 C4 H4 124.9 . .
C6 C5 N1 107.6(5) . .
C6 C5 H5 126.2 . .
N1 C5 H5 126.2 . .
C5 C6 N2 108.2(5) . .
C5 C6 H6 125.9 . .
N2 C6 H6 125.9 . .
C8 C7 N2 114.1(4) . .
C8 C7 H7A 108.7 . .
N2 C7 H7A 108.7 . .
C8 C7 H7B 108.7 . .
N2 C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
C7 C8 C9 119.3(5) . .
C7 C8 H8A 107.5 . .
C9 C8 H8A 107.5 . .
C7 C8 H8B 107.5 . .
C9 C8 H8B 107.5 . .
H8A C8 H8B 107.0 . .
C10 C9 C8 119.3(6) . .
C10 C9 H9A 107.5 . .
C8 C9 H9A 107.5 . .
C10 C9 H9B 107.5 . .
C8 C9 H9B 107.5 . .
H9A C9 H9B 107.0 . .
C9 C10 N3 114.5(5) . .
C9 C10 H10A 108.6 . .
N3 C10 H10A 108.6 . .
C9 C10 H10B 108.6 . .
N3 C10 H10B 108.6 . .
H10A C10 H10B 107.6 . .
N4 C11 N3 110.4(5) . .
N4 C11 H11 124.8 . .
N3 C11 H11 124.8 . .
C13 C12 N3 108.7(6) . .
C13 C12 H12 125.6 . .
N3 C12 H12 125.6 . .
C12 C13 N4 107.1(6) . .
C12 C13 H13 126.4 . .
N4 C13 H13 126.4 . .
N4 C14 C15 112.1(5) . .
N4 C14 H14A 109.2 . .
C15 C14 H14A 109.2 . .
N4 C14 H14B 109.2 . .
C15 C14 H14B 109.2 . .
H14A C14 H14B 107.9 . .
C16 C15 C14 115.6(7) . .
C16 C15 H15A 108.4 . .
C14 C15 H15A 108.4 . .
C16 C15 H15B 108.4 . .
C14 C15 H15B 108.4 . .
H15A C15 H15B 107.5 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C4 N1 C5 106.8(4) . .
C4 N1 C3 124.3(5) . .
C5 N1 C3 128.9(5) . .
C4 N2 C6 107.2(4) . .
C4 N2 C7 127.4(5) . .
C6 N2 C7 125.4(5) . .
C11 N3 C12 106.0(5) . .
C11 N3 C10 126.0(5) . .
C12 N3 C10 128.0(6) . .
C11 N4 C13 107.7(5) . .
C11 N4 C14 126.2(5) . .
C13 N4 C14 126.1(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.478(9) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.483(8) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 N1 1.476(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 N2 1.312(5) .
C4 N1 1.323(5) .
C4 H4 0.9300 .
C5 C6 1.331(6) .
C5 N1 1.356(6) .
C5 H5 0.9300 .
C6 N2 1.347(6) .
C6 H6 0.9300 .
C7 C8 1.449(7) .
C7 N2 1.460(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.484(8) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.472(8) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N3 1.487(7) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 N4 1.299(6) .
C11 N3 1.311(6) .
C11 H11 0.9300 .
C12 C13 1.316(8) .
C12 N3 1.346(7) .
C12 H12 0.9300 .
C13 N4 1.338(7) .
C13 H13 0.9300 .
C14 N4 1.447(7) .
C14 C15 1.509(8) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.437(8) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 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
C1 C2 C3 N1 62.7(8) . . . .
N1 C5 C6 N2 -1.1(6) . . . .
N2 C7 C8 C9 54.9(8) . . . .
C7 C8 C9 C10 61.6(7) . . . .
C8 C9 C10 N3 56.9(8) . . . .
N3 C12 C13 N4 0.3(8) . . . .
N4 C14 C15 C16 -177.1(6) . . . .
N2 C4 N1 C5 0.1(5) . . . .
N2 C4 N1 C3 178.3(4) . . . .
C6 C5 N1 C4 0.7(6) . . . .
C6 C5 N1 C3 -177.5(5) . . . .
C2 C3 N1 C4 79.5(7) . . . .
C2 C3 N1 C5 -102.6(7) . . . .
N1 C4 N2 C6 -0.7(5) . . . .
N1 C4 N2 C7 178.4(4) . . . .
C5 C6 N2 C4 1.2(6) . . . .
C5 C6 N2 C7 -178.0(4) . . . .
C8 C7 N2 C4 57.5(7) . . . .
C8 C7 N2 C6 -123.5(6) . . . .
N4 C11 N3 C12 1.1(6) . . . .
N4 C11 N3 C10 -179.8(5) . . . .
C13 C12 N3 C11 -0.9(7) . . . .
C13 C12 N3 C10 -180.0(6) . . . .
C9 C10 N3 C11 41.3(8) . . . .
C9 C10 N3 C12 -139.8(6) . . . .
N3 C11 N4 C13 -0.9(6) . . . .
N3 C11 N4 C14 178.5(5) . . . .
C12 C13 N4 C11 0.4(7) . . . .
C12 C13 N4 C14 -179.1(5) . . . .
C15 C14 N4 C11 74.7(7) . . . .
C15 C14 N4 C13 -105.9(7) . . . .
