#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:44:46 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/38/4033815.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_4033815
loop_
_publ_author_name
'Hu, Lei'
'Mahaut, Damien'
'Tumanov, Nikolay'
'Wouters, Johan'
'Robiette, Raphaël'
'Berionni, Guillaume'
_publ_section_title
;
 Complementary Synthetic Approaches toward 9-Phosphatriptycene and
 Structure-Reactivity Investigations of Its Association with Sterically
 Hindered Lewis Acids.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11268
_journal_page_last               11274
_journal_paper_doi               10.1021/acs.joc.9b01570
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C38 H28 P 1+, B F4 1-'
_chemical_formula_sum            'C38 H28 B F4 P'
_chemical_formula_weight         602.39
_chemical_name_common
'9-phosphatriptycene triphenylcarbenium tetrafluoroborate complex'
_chemical_name_systematic
'9-phosphatriptycene triphenylcarbenium tetrafluoroborate complex'
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   13.4876(2)
_cell_length_b                   13.4876(2)
_cell_length_c                   57.4638(16)
_cell_measurement_reflns_used    6752
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.9570
_cell_measurement_theta_min      4.0660
_cell_volume                     9053.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur, Ruby, Gemini Ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            24564
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.922
_diffrn_reflns_theta_max         66.922
_diffrn_reflns_theta_min         4.086
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.16b (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1415P)²+7.6459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2026
_refine_ls_wR_factor_ref         0.2122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1529
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01570_si_006.cif
_cod_data_source_block           nt0469_LH_Trip_CPh3
_cod_original_cell_volume        9053.0(4)
_cod_database_code               4033815
_shelx_shelxl_version_number     2018/3
_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   0.723
_shelx_estimated_absorpt_t_max   0.915
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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
P1 P 0.666667 0.333333 0.24610(2) 0.0522(4) Uani 1 3 d S T P
C1 C 0.7043(2) 0.4671(2) 0.23151(5) 0.0580(6) Uani 1 1 d . . .
C2 C 0.7373(2) 0.5745(2) 0.24066(5) 0.0669(7) Uani 1 1 d . . .
H2 H 0.743084 0.586206 0.256672 0.080 Uiso 1 1 calc R U .
C3 C 0.7614(3) 0.6642(2) 0.22553(6) 0.0783(9) Uani 1 1 d . . .
H3 H 0.784057 0.736527 0.231502 0.094 Uiso 1 1 calc R U .
C4 C 0.7523(3) 0.6474(3) 0.20191(7) 0.0832(9) Uani 1 1 d . . .
H4 H 0.767269 0.708150 0.192098 0.100 Uiso 1 1 calc R U .
C5 C 0.7211(3) 0.5417(3) 0.19246(5) 0.0730(8) Uani 1 1 d . . .
H5 H 0.716022 0.531307 0.176416 0.088 Uiso 1 1 calc R U .
C6 C 0.6975(2) 0.4507(2) 0.20728(5) 0.0627(7) Uani 1 1 d . . .
C7 C 0.666667 0.333333 0.19808(9) 0.0629(11) Uani 1 3 d S T P
H7 H 0.666667 0.333333 0.181025 0.075 Uiso 1 3 calc R U P
C8 C 0.666667 0.333333 0.27888(8) 0.0530(10) Uani 1 3 d S T P
C9 C 0.5499(2) 0.3161(2) 0.28696(4) 0.0554(6) Uani 1 1 d . . .
C10 C 0.5066(2) 0.3825(3) 0.27774(5) 0.0676(7) Uani 1 1 d . . .
H10 H 0.548466 0.437835 0.266600 0.081 Uiso 1 1 calc R U .
C11 C 0.4023(3) 0.3668(3) 0.28497(6) 0.0816(9) Uani 1 1 d . . .
H11 H 0.373779 0.410767 0.278531 0.098 Uiso 1 1 calc R U .
C12 C 0.3404(3) 0.2865(3) 0.30163(7) 0.0878(10) Uani 1 1 d . . .
H12 H 0.269690 0.275434 0.306387 0.105 Uiso 1 1 calc R U .
C13 C 0.3831(3) 0.2228(3) 0.31122(6) 0.0787(9) Uani 1 1 d . . .
H13 H 0.341829 0.169302 0.322703 0.094 Uiso 1 1 calc R U .
C14 C 0.4872(2) 0.2375(2) 0.30397(5) 0.0649(7) Uani 1 1 d . . .
H14 H 0.515385 0.193722 0.310652 0.078 Uiso 1 1 calc R U .
F1 F 0.8999(3) 0.9217(4) 0.19077(10) 0.1943(18) Uani 1 1 d . . .
F2 F 1.000000 1.000000 0.22181(14) 0.400(11) Uani 1 3 d S T P
B1 B 1.000000 1.000000 0.20061(19) 0.106(3) Uani 1 3 d S T P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C1 P1 C1 100.39(11) . 3_665
C1 P1 C1 100.39(11) . 2_655
C1 P1 C1 100.39(11) 3_665 2_655
C1 P1 C8 117.49(9) . .
C1 P1 C8 117.49(9) 3_665 .
C1 P1 C8 117.49(9) 2_655 .
C2 C1 C6 120.1(2) . .
C2 C1 P1 130.2(2) . .
C6 C1 P1 109.71(19) . .
C1 C2 C3 119.0(3) . .
C1 C2 H2 120.5 . .
C3 C2 H2 120.5 . .
C4 C3 C2 120.8(3) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 121.0(3) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C6 119.1(3) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
C5 C6 C1 119.9(3) . .
C5 C6 C7 121.9(3) . .
C1 C6 C7 118.1(3) . .
C6 C7 C6 108.5(2) 3_665 .
C6 C7 C6 108.5(2) 3_665 2_655
C6 C7 C6 108.5(2) . 2_655
C6 C7 H7 110.4 3_665 .
C6 C7 H7 110.4 . .
C6 C7 H7 110.4 2_655 .
C9 C8 C9 111.36(17) 2_655 3_665
C9 C8 C9 111.36(17) 2_655 .
C9 C8 C9 111.36(17) 3_665 .
C9 C8 P1 107.51(18) 2_655 .
C9 C8 P1 107.51(18) 3_665 .
C9 C8 P1 107.51(18) . .
C14 C9 C10 118.0(2) . .
C14 C9 C8 121.1(2) . .
C10 C9 C8 120.8(2) . .
C11 C10 C9 120.7(3) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C12 C11 C10 120.2(3) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 119.8(3) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C12 C13 C14 120.4(3) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C9 C14 C13 120.9(3) . .
C9 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
F2 B1 F1 114.7(5) . 3_675
F2 B1 F1 114.7(5) . .
F1 B1 F1 103.8(5) 3_675 .
F2 B1 F1 114.7(5) . 2_765
F1 B1 F1 103.8(5) 3_675 2_765
F1 B1 F1 103.8(5) . 2_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.816(3) .
P1 C1 1.816(3) 3_665
P1 C1 1.816(3) 2_655
P1 C8 1.884(5) .
C1 C2 1.389(4) .
C1 C6 1.405(4) .
C2 C3 1.390(4) .
C2 H2 0.9300 .
C3 C4 1.372(5) .
C3 H3 0.9300 .
C4 C5 1.380(5) .
C4 H4 0.9300 .
C5 C6 1.393(4) .
C5 H5 0.9300 .
C6 C7 1.517(3) .
C7 H7 0.9800 .
C8 C9 1.544(3) 2_655
C8 C9 1.544(3) 3_665
C8 C9 1.544(3) .
C9 C14 1.378(4) .
C9 C10 1.395(4) .
C10 C11 1.377(4) .
C10 H10 0.9300 .
C11 C12 1.372(5) .
C11 H11 0.9300 .
C12 C13 1.366(5) .
C12 H12 0.9300 .
C13 C14 1.381(4) .
C13 H13 0.9300 .
C14 H14 0.9300 .
F1 B1 1.353(6) .
F2 B1 1.218(14) .
