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#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/41/4324164.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_4324164
loop_
_publ_author_name
'Stephen J. Geier'
'Thomas M. Gilbert'
'Douglas W. Stephan'
_publ_section_title
;
 Synthesis and Reactivity of the Phosphinoboranes R2PB(C6F5)2
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              336
_journal_page_last               344
_journal_paper_doi               10.1021/ic102003x
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C24 H12 B F10 P'
_chemical_formula_weight         532.12
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.381(3)
_cell_angle_beta                 94.690(3)
_cell_angle_gamma                96.226(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9820(6)
_cell_length_b                   10.3690(6)
_cell_length_c                   12.4150(6)
_cell_measurement_reflns_used    4947
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.70
_cell_volume                     1095.11(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9937
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.6725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                3199
_reflns_number_total             4947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic102003x_si_002_6.cif
_cod_data_source_block           (Ph2PH)(BH(C6F5)2)
_cod_database_code               4324164
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 0.04476(9) 0.15722(7) 0.22988(6) 0.0274(2) Uani 1 1 d . . .
B1 B -0.0525(4) 0.3226(3) 0.2620(2) 0.0254(6) Uani 1 1 d . . .
H1 H -0.053(3) 0.337(3) 0.355(2) 0.027(7) Uiso 1 1 d . . .
H2 H 0.064(3) 0.104(3) 0.124(3) 0.041(9) Uiso 1 1 d . . .
C1 C 0.0501(3) 0.4441(3) 0.2343(2) 0.0256(6) Uani 1 1 d . . .
C2 C 0.0994(3) 0.5684(3) 0.3140(2) 0.0296(6) Uani 1 1 d . . .
C3 C 0.1786(3) 0.6766(3) 0.2900(2) 0.0333(7) Uani 1 1 d . . .
C4 C 0.2146(3) 0.6618(3) 0.1819(2) 0.0311(6) Uani 1 1 d . . .
C5 C 0.1698(3) 0.5414(3) 0.0992(2) 0.0280(6) Uani 1 1 d . . .
C6 C 0.0875(3) 0.4369(3) 0.1270(2) 0.0245(6) Uani 1 1 d . . .
C7 C -0.2220(3) 0.2979(3) 0.1983(2) 0.0249(6) Uani 1 1 d . . .
C8 C -0.3176(3) 0.3900(3) 0.2450(2) 0.0287(6) Uani 1 1 d . . .
C9 C -0.4622(3) 0.3881(3) 0.1978(2) 0.0325(7) Uani 1 1 d . . .
C10 C -0.5187(3) 0.2889(3) 0.0989(2) 0.0318(6) Uani 1 1 d . . .
C11 C -0.4302(3) 0.1949(3) 0.0482(2) 0.0270(6) Uani 1 1 d . . .
C12 C -0.2853(3) 0.2010(3) 0.0984(2) 0.0265(6) Uani 1 1 d . . .
C13 C -0.0639(3) 0.0233(3) 0.2680(2) 0.0285(6) Uani 1 1 d . . .
C14 C -0.1014(4) -0.1039(3) 0.1908(3) 0.0441(8) Uani 1 1 d . . .
H14A H -0.0715 -0.1204 0.1187 0.053 Uiso 1 1 calc R . .
C15 C -0.1838(5) -0.2072(3) 0.2211(3) 0.0529(10) Uani 1 1 d . . .
H15A H -0.2086 -0.2930 0.1693 0.063 Uiso 1 1 calc R . .
C16 C -0.2287(4) -0.1826(3) 0.3275(3) 0.0455(8) Uani 1 1 d . . .
H16A H -0.2839 -0.2519 0.3474 0.055 Uiso 1 1 calc R . .
C17 C -0.1923(4) -0.0559(3) 0.4048(3) 0.0384(7) Uani 1 1 d . . .
H17A H -0.2230 -0.0396 0.4766 0.046 Uiso 1 1 calc R . .
C18 C -0.1096(3) 0.0475(3) 0.3752(2) 0.0338(7) Uani 1 1 d . . .
H18A H -0.0848 0.1331 0.4274 0.041 Uiso 1 1 calc R . .
C19 C 0.2326(3) 0.1841(3) 0.3033(2) 0.0282(6) Uani 1 1 d . . .
C20 C 0.3311(3) 0.0939(3) 0.2602(2) 0.0336(7) Uani 1 1 d . . .
H20A H 0.3004 0.0231 0.1943 0.040 Uiso 1 1 calc R . .
C21 C 0.4747(4) 0.1089(3) 0.3150(3) 0.0385(7) Uani 1 1 d . . .
H21A H 0.5404 0.0478 0.2863 0.046 Uiso 1 1 calc R . .
C22 C 0.5211(4) 0.2147(3) 0.4123(3) 0.0383(7) Uani 1 1 d . . .
H22A H 0.6181 0.2245 0.4489 0.046 Uiso 1 1 calc R . .
C23 C 0.4246(4) 0.3059(3) 0.4556(2) 0.0365(7) Uani 1 1 d . . .
H23A H 0.4566 0.3771 0.5210 0.044 Uiso 1 1 calc R . .
C24 C 0.2793(3) 0.2911(3) 0.4012(2) 0.0322(7) Uani 1 1 d . . .
H24A H 0.2138 0.3523 0.4300 0.039 Uiso 1 1 calc R . .
F2 F 0.0702(2) 0.58977(17) 0.42257(13) 0.0430(5) Uani 1 1 d . . .
F3 F 0.2208(2) 0.79594(17) 0.37018(14) 0.0482(5) Uani 1 1 d . . .
F4 F 0.2943(2) 0.76479(17) 0.15744(15) 0.0474(5) Uani 1 1 d . . .
F5 F 0.2077(2) 0.52460(17) -0.00600(13) 0.0369(4) Uani 1 1 d . . .
F6 F 0.04138(18) 0.32025(15) 0.04197(12) 0.0310(4) Uani 1 1 d . . .
F8 F -0.26783(19) 0.48953(16) 0.34193(13) 0.0378(4) Uani 1 1 d . . .
F9 F -0.5478(2) 0.48092(19) 0.24780(15) 0.0460(5) Uani 1 1 d . . .
F10 F -0.66043(19) 0.28334(19) 0.05186(15) 0.0454(5) Uani 1 1 d . . .
F11 F -0.48472(18) 0.10041(16) -0.04995(13) 0.0342(4) Uani 1 1 d . . .
F12 F -0.20344(18) 0.10579(16) 0.04382(13) 0.0339(4) Uani 1 1 d . . .
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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
C19 P1 C13 107.72(12) . . ?
C19 P1 B1 112.96(13) . . ?
C13 P1 B1 111.46(13) . . ?
C19 P1 H2 103.5(14) . . ?
C13 P1 H2 105.1(13) . . ?
B1 P1 H2 115.5(13) . . ?
C1 B1 C7 111.3(2) . . ?
C1 B1 P1 111.06(19) . . ?
C7 B1 P1 112.98(19) . . ?
C1 B1 H1 113.4(14) . . ?
C7 B1 H1 111.2(14) . . ?
P1 B1 H1 96.1(14) . . ?
C2 C1 C6 114.1(2) . . ?
C2 C1 B1 122.9(2) . . ?
C6 C1 B1 122.9(2) . . ?
F2 C2 C3 115.9(2) . . ?
F2 C2 C1 120.4(2) . . ?
C3 C2 C1 123.7(2) . . ?
F3 C3 C4 119.6(3) . . ?
F3 C3 C2 121.2(2) . . ?
C4 C3 C2 119.3(3) . . ?
F4 C4 C3 120.2(3) . . ?
F4 C4 C5 119.9(2) . . ?
C3 C4 C5 120.0(3) . . ?
F5 C5 C4 120.5(2) . . ?
F5 C5 C6 121.0(2) . . ?
C4 C5 C6 118.5(2) . . ?
F6 C6 C5 116.8(2) . . ?
F6 C6 C1 118.8(2) . . ?
C5 C6 C1 124.4(2) . . ?
C12 C7 C8 114.0(2) . . ?
C12 C7 B1 129.1(2) . . ?
C8 C7 B1 116.7(2) . . ?
F8 C8 C9 116.6(2) . . ?
F8 C8 C7 119.3(3) . . ?
C9 C8 C7 124.0(3) . . ?
F9 C9 C8 120.6(3) . . ?
F9 C9 C10 120.3(3) . . ?
C8 C9 C10 119.1(2) . . ?
F10 C10 C11 119.8(3) . . ?
F10 C10 C9 120.4(2) . . ?
C11 C10 C9 119.9(3) . . ?
F11 C11 C10 119.5(3) . . ?
F11 C11 C12 121.4(2) . . ?
C10 C11 C12 119.0(3) . . ?
F12 C12 C11 116.1(2) . . ?
F12 C12 C7 119.9(2) . . ?
C11 C12 C7 123.9(2) . . ?
C14 C13 C18 119.7(3) . . ?
C14 C13 P1 120.1(2) . . ?
C18 C13 P1 120.1(2) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C13 C18 C17 120.0(3) . . ?
C13 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C20 C19 C24 119.9(3) . . ?
C20 C19 P1 118.2(2) . . ?
C24 C19 P1 121.9(2) . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23A 120.1 . . ?
C24 C23 H23A 120.1 . . ?
C19 C24 C23 119.6(3) . . ?
C19 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C19 1.805(3) . ?
P1 C13 1.805(3) . ?
P1 B1 1.964(3) . ?
P1 H2 1.31(3) . ?
B1 C1 1.612(4) . ?
B1 C7 1.617(4) . ?
B1 H1 1.12(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.384(4) . ?
C2 F2 1.356(3) . ?
C2 C3 1.380(4) . ?
C3 F3 1.345(3) . ?
C3 C4 1.376(4) . ?
C4 F4 1.341(3) . ?
C4 C5 1.370(4) . ?
C5 F5 1.345(3) . ?
C5 C6 1.385(4) . ?
C6 F6 1.360(3) . ?
C7 C12 1.389(4) . ?
C7 C8 1.390(4) . ?
C8 F8 1.351(3) . ?
C8 C9 1.376(4) . ?
C9 F9 1.344(3) . ?
C9 C10 1.377(4) . ?
C10 F10 1.345(3) . ?
C10 C11 1.372(4) . ?
C11 F11 1.345(3) . ?
C11 C12 1.383(4) . ?
C12 F12 1.355(3) . ?
C13 C14 1.382(4) . ?
C13 C18 1.388(4) . ?
C14 C15 1.392(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.384(4) . ?
C19 C24 1.393(4) . ?
C20 C21 1.380(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.392(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139135313
