#------------------------------------------------------------------------------
#$Date: 2019-11-17 10:46:43 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/70/7047085.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_7047085
loop_
_publ_author_name
'LaFortune, James H. W.'
'Szkop, Kevin M.'
'Farinha, Farah E.'
'Johnstone, Timothy C.'
'Postle, Shawn'
'Stephan, Douglas W.'
_publ_section_title
;
 Probing steric influences on electrophilic phosphonium cations: a
 comparison of
 [(3,5-(CF₃)₂C₆H₃)₃PF]⁺
 and [(C₆F₅)₃PF]<sup/>.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11411
_journal_page_last               11419
_journal_paper_doi               10.1039/c8dt02594k
_journal_volume                  47
_journal_year                    2018
_chemical_formula_sum            'C24 H9 F20 P'
_chemical_formula_weight         708.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-25 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.447(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.911(4)
_cell_length_b                   9.461(4)
_cell_length_c                   14.845(6)
_cell_measurement_reflns_used    5268
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      3.29
_cell_volume                     1230.8(9)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10846
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.767
_diffrn_reflns_theta_min         2.153
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1109P)²+1.0186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2496
_reflns_number_total             2899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt02594k2.cif
_cod_data_source_block           pre
_cod_depositor_comments
'Adding full bibliography for 7047085--7047086.cif.'
_cod_database_code               7047085
_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   0.936
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
P1 P 0.2500 0.44828(8) 0.2500 0.0170(2) Uani 1 2 d S T P . .
F1 F 0.42220(14) 0.44781(13) 0.22461(9) 0.0211(3) Uani 1 1 d . . . . .
F2 F 0.3067(3) 0.5049(3) -0.11023(17) 0.0751(8) Uani 1 1 d . . . . .
F3 F 0.4314(2) 0.6807(3) -0.05426(14) 0.0586(6) Uani 1 1 d . . . . .
F4 F 0.2276(3) 0.7107(4) -0.14861(14) 0.0810(9) Uani 1 1 d . . . . .
C8 C -0.1334(3) 0.8102(3) 0.0645(2) 0.0384(6) Uani 1 1 d D U . . .
F5 F -0.1031(9) 0.9430(5) 0.0657(7) 0.076(2) Uani 0.712(14) 1 d D U P A 1
F6 F -0.2426(5) 0.7804(6) -0.0056(3) 0.0579(15) Uani 0.712(14) 1 d D U P A 1
F7 F -0.2022(9) 0.7919(10) 0.1378(4) 0.065(2) Uani 0.712(14) 1 d D U P A 1
F5B F -0.181(2) 0.856(2) -0.0203(6) 0.085(5) Uani 0.288(14) 1 d D U P A 2
F6B F -0.2253(19) 0.7732(17) 0.1155(12) 0.049(3) Uani 0.288(14) 1 d D U P A 2
F7B F -0.073(2) 0.9366(14) 0.0997(11) 0.064(3) Uani 0.288(14) 1 d D U P A 2
C13 C 0.4618(4) -0.0422(3) 0.1618(2) 0.0361(6) Uani 1 1 d D U . . .
F8 F 0.4442(16) -0.0201(12) 0.0771(5) 0.076(3) Uani 0.57(2) 1 d D U P B 1
F9 F 0.6085(6) 0.0049(8) 0.1991(10) 0.068(2) Uani 0.57(2) 1 d D U P B 1
F10 F 0.4673(17) -0.1784(7) 0.1788(8) 0.0405(16) Uani 0.57(2) 1 d D U P B 1
F8B F 0.3842(11) -0.0713(12) 0.0714(5) 0.056(2) Uani 0.43(2) 1 d D U P B 2
F9B F 0.5786(11) 0.0247(7) 0.1487(10) 0.052(3) Uani 0.43(2) 1 d D U P B 2
F10B F 0.498(2) -0.1645(13) 0.1965(13) 0.061(4) Uani 0.43(2) 1 d D U P B 2
C1 C 0.1801(2) 0.5501(2) 0.14739(15) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.2578(3) 0.5516(2) 0.07429(16) 0.0232(5) Uani 1 1 d . . . . .
H2 H 0.3471 0.4960 0.0765 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2050(3) 0.6342(3) -0.00179(16) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.0791(3) 0.7181(3) -0.00573(17) 0.0287(5) Uani 1 1 d . . . . .
H4 H 0.0446 0.7758 -0.0577 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0028(3) 0.7173(3) 0.06759(17) 0.0269(5) Uani 1 1 d . . . . .
C6 C 0.0501(3) 0.6333(2) 0.14283(15) 0.0224(5) Uani 1 1 d . . . . .
H6 H -0.0057 0.6320 0.1916 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2913(3) 0.6330(3) -0.07932(18) 0.0355(6) Uani 1 1 d . . . . .
C9 C 0.2500 0.2557(3) 0.2500 0.0189(6) Uani 1 2 d S T P . .
C10 C 0.3554(2) 0.1807(2) 0.21012(14) 0.0204(4) Uani 1 1 d . . . . .
H10 H 0.4294 0.2300 0.1835 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3526(3) 0.0350(2) 0.20916(16) 0.0231(5) Uani 1 1 d . . . . .
C12 C 0.2500 -0.0384(3) 0.2500 0.0230(6) Uani 1 2 d S T P . .
H12 H 0.2500 -0.1388 0.2500 0.028 Uiso 1 2 calc R U P . .
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'
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
F1 P1 F1 179.69(10) 2 .
F1 P1 C1 90.06(8) 2 .
F1 P1 C1 90.10(8) . .
F1 P1 C1 90.10(8) 2 2
F1 P1 C1 90.07(9) . 2
C1 P1 C1 115.87(14) . 2
F1 P1 C9 89.85(5) 2 .
F1 P1 C9 89.85(5) . .
C1 P1 C9 122.07(7) . .
C1 P1 C9 122.06(7) 2 .
F5 C8 F6 110.0(4) . .
F6B C8 F5B 121.8(11) . .
F5 C8 F7 103.8(6) . .
F6 C8 F7 103.3(4) . .
F6B C8 F7B 105.3(12) . .
F5B C8 F7B 96.4(10) . .
F6B C8 C5 115.5(9) . .
F5 C8 C5 114.1(4) . .
F6 C8 C5 112.2(3) . .
F5B C8 C5 110.0(5) . .
F7 C8 C5 112.6(4) . .
F7B C8 C5 104.0(8) . .
F9B C13 F10B 111.2(10) . .
F8 C13 F10 110.4(7) . .
F8 C13 F9 106.4(5) . .
F10 C13 F9 103.7(6) . .
F9B C13 F8B 103.0(5) . .
F10B C13 F8B 104.3(8) . .
F8 C13 C11 114.7(4) . .
F9B C13 C11 117.0(4) . .
F10B C13 C11 112.8(10) . .
F10 C13 C11 113.3(8) . .
F9 C13 C11 107.5(4) . .
F8B C13 C11 107.1(4) . .
C2 C1 C6 119.0(2) . .
C2 C1 P1 121.15(17) . .
C6 C1 P1 119.81(17) . .
C3 C2 C1 120.0(2) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C4 C3 C2 121.2(2) . .
C4 C3 C7 120.3(2) . .
C2 C3 C7 118.5(2) . .
C3 C4 C5 118.6(2) . .
C3 C4 H4 120.7 . .
C5 C4 H4 120.7 . .
C6 C5 C4 121.4(2) . .
C6 C5 C8 119.6(2) . .
C4 C5 C8 119.0(2) . .
C5 C6 C1 119.8(2) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
F4 C7 F2 107.6(3) . .
F4 C7 F3 106.5(3) . .
F2 C7 F3 105.1(3) . .
F4 C7 C3 113.0(3) . .
F2 C7 C3 112.2(2) . .
F3 C7 C3 112.0(2) . .
C10 C9 C10 118.7(3) 2 .
C10 C9 P1 120.62(14) 2 .
C10 C9 P1 120.63(14) . .
C11 C10 C9 120.1(2) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C12 C11 C10 120.9(2) . .
C12 C11 C13 120.3(2) . .
C10 C11 C13 118.9(2) . .
C11 C12 C11 119.3(3) 2 .
C11 C12 H12 120.4 2 .
C11 C12 H12 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F1 1.6451(14) 2
P1 F1 1.6452(14) .
P1 C1 1.815(2) .
P1 C1 1.815(2) 2
P1 C9 1.822(3) .
F2 C7 1.312(4) .
F3 C7 1.316(4) .
F4 C7 1.307(3) .
C8 F6B 1.261(12) .
C8 F5 1.285(6) .
C8 F6 1.320(4) .
C8 F5B 1.327(9) .
C8 F7 1.353(7) .
C8 F7B 1.374(13) .
C8 C5 1.493(3) .
C13 F8 1.256(6) .
C13 F9B 1.263(6) .
C13 F10B 1.283(10) .
C13 F10 1.313(7) .
C13 F9 1.397(7) .
C13 F8B 1.420(7) .
C13 C11 1.491(3) .
C1 C2 1.389(3) .
C1 C6 1.392(3) .
C2 C3 1.384(3) .
C2 H2 0.9500 .
C3 C4 1.367(4) .
C3 C7 1.496(4) .
C4 C5 1.384(4) .
C4 H4 0.9500 .
C5 C6 1.373(3) .
C6 H6 0.9500 .
C9 C10 1.392(3) 2
C9 C10 1.392(3) .
C10 C11 1.379(3) .
C10 H10 0.9500 .
C11 C12 1.374(3) .
C12 C11 1.374(3) 2
C12 H12 0.9500 .
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_4
F1 P1 C1 C2 -158.49(18) 2 .
F1 P1 C1 C2 21.25(19) . .
C1 P1 C1 C2 111.37(19) 2 .
C9 P1 C1 C2 -68.63(19) . .
F1 P1 C1 C6 24.36(18) 2 .
F1 P1 C1 C6 -155.90(18) . .
C1 P1 C1 C6 -65.78(16) 2 .
C9 P1 C1 C6 114.22(16) . .
C6 C1 C2 C3 -0.5(3) . .
P1 C1 C2 C3 -177.65(17) . .
C1 C2 C3 C4 1.7(4) . .
C1 C2 C3 C7 -179.9(2) . .
C2 C3 C4 C5 -1.1(4) . .
C7 C3 C4 C5 -179.5(2) . .
C3 C4 C5 C6 -0.7(4) . .
C3 C4 C5 C8 179.1(2) . .
F6B C8 C5 C6 -22.6(10) . .
F5 C8 C5 C6 113.8(6) . .
F6 C8 C5 C6 -120.2(4) . .
F5B C8 C5 C6 -165.4(12) . .
F7 C8 C5 C6 -4.2(5) . .
F7B C8 C5 C6 92.3(8) . .
F6B C8 C5 C4 157.6(9) . .
F5 C8 C5 C4 -66.0(6) . .
F6 C8 C5 C4 60.0(5) . .
F5B C8 C5 C4 14.8(12) . .
F7 C8 C5 C4 176.0(5) . .
F7B C8 C5 C4 -87.5(8) . .
C4 C5 C6 C1 2.0(4) . .
C8 C5 C6 C1 -177.8(2) . .
C2 C1 C6 C5 -1.4(3) . .
P1 C1 C6 C5 175.86(17) . .
C4 C3 C7 F4 -4.0(4) . .
C2 C3 C7 F4 177.6(3) . .
C4 C3 C7 F2 -125.9(3) . .
C2 C3 C7 F2 55.7(4) . .
C4 C3 C7 F3 116.2(3) . .
C2 C3 C7 F3 -62.2(3) . .
F1 P1 C9 C10 -16.06(11) 2 2
F1 P1 C9 C10 163.94(11) . 2
C1 P1 C9 C10 -106.04(13) . 2
C1 P1 C9 C10 73.96(13) 2 2
F1 P1 C9 C10 163.94(11) 2 .
F1 P1 C9 C10 -16.06(11) . .
C1 P1 C9 C10 73.96(13) . .
C1 P1 C9 C10 -106.04(13) 2 .
C10 C9 C10 C11 1.11(16) 2 .
P1 C9 C10 C11 -178.89(16) . .
C9 C10 C11 C12 -2.3(3) . .
C9 C10 C11 C13 176.9(2) . .
F8 C13 C11 C12 116.0(9) . .
F9B C13 C11 C12 -160.5(8) . .
F10B C13 C11 C12 -29.6(10) . .
F10 C13 C11 C12 -12.1(6) . .
F9 C13 C11 C12 -126.0(6) . .
F8B C13 C11 C12 84.6(6) . .
F8 C13 C11 C10 -63.2(9) . .
F9B C13 C11 C10 20.3(9) . .
F10B C13 C11 C10 151.2(10) . .
F10 C13 C11 C10 168.7(6) . .
F9 C13 C11 C10 54.8(7) . .
F8B C13 C11 C10 -94.6(6) . .
C10 C11 C12 C11 1.14(16) . 2
C13 C11 C12 C11 -178.0(3) . 2
