#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:24:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178563 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/72/4067210.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_4067210
loop_
_publ_author_name
'Dureen, Meghan A.'
'Brown, Christopher C.'
'Stephan, Douglas W.'
_publ_section_title
;
 Deprotonation and Addition Reactions of Frustrated Lewis Pairs with
 Alkynes
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6594
_journal_paper_doi               10.1021/om1009044
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C88 H64 B2 F28 P2'
_chemical_formula_weight         1821.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.190(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.9887(11)
_cell_length_b                   20.5295(11)
_cell_length_c                   18.5092(10)
_cell_measurement_temperature    150(2)
_cell_volume                     7928.9(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            66604
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3692
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.052
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         9158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0597
_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)+(0.0870P)²+22.5066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1742
_reflns_number_gt                7100
_reflns_number_total             9158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1009044_si_002.cif
_cod_data_source_block           '[(H)CC(Ph)Mes2PC6F4B(C6F5)2]2'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4067210
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.28242(3) 0.20867(3) 0.22399(3) 0.01775(14) Uani 1 1 d .
B1 B 0.23578(13) 0.08414(13) 0.03573(14) 0.0188(5) Uani 1 1 d .
F2 F 0.16710(6) 0.32490(7) 0.00767(7) 0.0221(3) Uani 1 1 d .
F4 F 0.39330(7) 0.29915(8) 0.17215(8) 0.0287(3) Uani 1 1 d .
F1 F 0.17450(7) 0.24575(7) 0.11525(8) 0.0240(3) Uani 1 1 d .
F14 F 0.21164(9) -0.06125(8) 0.01212(10) 0.0381(4) Uani 1 1 d .
F5 F 0.31644(8) -0.00361(8) 0.13212(8) 0.0330(4) Uani 1 1 d .
F3 F 0.38432(7) 0.38319(8) 0.07140(8) 0.0334(4) Uani 1 1 d .
F9 F 0.28098(10) 0.05883(8) -0.11393(8) 0.0423(5) Uani 1 1 d .
F12 F 0.00472(9) -0.05948(11) 0.08005(12) 0.0569(6) Uani 1 1 d .
F6 F 0.42558(9) -0.05857(9) 0.10738(11) 0.0486(5) Uani 1 1 d .
F7 F 0.46402(10) -0.05753(10) -0.02858(13) 0.0560(6) Uani 1 1 d .
F13 F 0.10455(10) -0.12271(9) 0.02939(10) 0.0481(5) Uani 1 1 d .
F8 F 0.38803(12) 0.00140(10) -0.13824(11) 0.0593(6) Uani 1 1 d .
F10 F 0.11619(8) 0.13682(8) 0.07328(9) 0.0317(4) Uiso 1 1 d .
F11 F 0.01141(10) 0.07178(10) 0.09944(11) 0.0484(5) Uiso 1 1 d .
C11 C 0.22564(11) 0.31901(11) 0.04531(12) 0.0179(4) Uani 1 1 d .
C13 C 0.33102(12) 0.34808(12) 0.07584(13) 0.0225(5) Uani 1 1 d .
C10 C 0.22868(11) 0.27603(11) 0.10261(12) 0.0185(4) Uani 1 1 d .
C2 C 0.24480(11) 0.13659(11) 0.17585(12) 0.0180(4) Uani 1 1 d .
C14 C 0.33585(12) 0.30376(12) 0.13304(13) 0.0211(5) Uani 1 1 d .
C27 C 0.23397(13) 0.23472(12) 0.29494(13) 0.0244(5) Uani 1 1 d .
C1 C 0.26214(11) 0.12689(11) 0.10881(12) 0.0171(4) Uani 1 1 d .
H1A H 0.2995 0.1510 0.1014 0.021 Uiso 1 1 calc R
C9 C 0.28398(11) 0.26678(11) 0.14988(12) 0.0182(4) Uani 1 1 d .
C3 C 0.19579(12) 0.09938(12) 0.21196(13) 0.0221(5) Uani 1 1 d .
C20 C 0.31615(14) 0.03345(12) -0.05538(14) 0.0287(6) Uani 1 1 d .
C38 C 0.45688(12) 0.14432(13) 0.32174(14) 0.0260(5) Uani 1 1 d .
H38A H 0.4820 0.1057 0.3240 0.031 Uiso 1 1 calc R
C12 C 0.27629(11) 0.35858(11) 0.02895(12) 0.0191(5) Uani 1 1 d .
C37 C 0.40159(12) 0.14664(12) 0.27363(13) 0.0217(5) Uani 1 1 d .
C22 C 0.11691(13) 0.07166(13) 0.06615(14) 0.0276(6) Uani 1 1 d .
C36 C 0.36316(12) 0.20319(12) 0.27182(12) 0.0209(5) Uani 1 1 d .
C28 C 0.23734(13) 0.19215(12) 0.35572(13) 0.0245(5) Uani 1 1 d .
C21 C 0.17121(12) 0.04187(12) 0.04513(13) 0.0235(5) Uani 1 1 d .
C16 C 0.33445(13) 0.00333(12) 0.06502(14) 0.0254(5) Uani 1 1 d .
C7 C 0.16134(15) -0.00167(15) 0.26229(16) 0.0358(6) Uani 1 1 d .
H7A H 0.1683 -0.0467 0.2720 0.043 Uiso 1 1 calc R
C4 C 0.14101(13) 0.12902(14) 0.23267(15) 0.0303(6) Uani 1 1 d .
H4A H 0.1334 0.1738 0.2223 0.036 Uiso 1 1 calc R
C42 C 0.38601(12) 0.08765(12) 0.22734(14) 0.0248(5) Uani 1 1 d .
H42A H 0.4194 0.0547 0.2382 0.037 Uiso 1 1 calc R
H42B H 0.3838 0.0998 0.1759 0.037 Uiso 1 1 calc R
H42C H 0.3446 0.0699 0.2376 0.037 Uiso 1 1 calc R
C15 C 0.29595(12) 0.03861(11) 0.01327(13) 0.0218(5) Uani 1 1 d .
C8 C 0.20520(13) 0.03326(13) 0.22662(14) 0.0261(5) Uani 1 1 d .
H8A H 0.2419 0.0119 0.2121 0.031 Uiso 1 1 calc R
C41 C 0.38442(14) 0.25731(12) 0.31532(13) 0.0257(5) Uani 1 1 d .
C23 C 0.06180(13) 0.03917(16) 0.07881(16) 0.0356(7) Uani 1 1 d .
C39 C 0.47720(13) 0.19591(14) 0.36677(14) 0.0284(6) Uani 1 1 d .
C17 C 0.39031(14) -0.02774(13) 0.05290(17) 0.0325(6) Uani 1 1 d .
C25 C 0.10865(15) -0.05843(14) 0.04395(15) 0.0357(7) Uani 1 1 d .
C33 C 0.27641(14) 0.13044(13) 0.36450(14) 0.0269(5) Uani 1 1 d .
H33A H 0.2706 0.1102 0.4113 0.040 Uiso 1 1 calc R
H33B H 0.3218 0.1408 0.3628 0.040 Uiso 1 1 calc R
H33C H 0.2622 0.1002 0.3251 0.040 Uiso 1 1 calc R
C18 C 0.40951(15) -0.02768(14) -0.01541(19) 0.0378(7) Uani 1 1 d .
C26 C 0.16404(14) -0.02469(13) 0.03411(14) 0.0288(6) Uani 1 1 d .
C40 C 0.44125(14) 0.25227(14) 0.36089(14) 0.0300(6) Uani 1 1 d .
H40A H 0.4559 0.2890 0.3891 0.036 Uiso 1 1 calc R
C44 C 0.35062(17) 0.32208(13) 0.31632(15) 0.0364(7) Uani 1 1 d .
H44A H 0.3751 0.3513 0.3507 0.055 Uiso 1 1 calc R
H44B H 0.3077 0.3157 0.3313 0.055 Uiso 1 1 calc R
H44C H 0.3471 0.3413 0.2676 0.055 Uiso 1 1 calc R
C29 C 0.20274(14) 0.20741(14) 0.41344(14) 0.0304(6) Uani 1 1 d .
H29A H 0.2050 0.1788 0.4540 0.036 Uiso 1 1 calc R
C30 C 0.16532(15) 0.26254(15) 0.41382(15) 0.0337(6) Uani 1 1 d .
C19 C 0.37169(16) 0.00245(14) -0.07017(16) 0.0363(7) Uani 1 1 d .
C34 C 0.12739(18) 0.27705(18) 0.47682(17) 0.0456(8) Uani 1 1 d .
H34A H 0.1037 0.3178 0.4675 0.068 Uiso 1 1 calc R
H34B H 0.1567 0.2813 0.5215 0.068 Uiso 1 1 calc R
H34C H 0.0972 0.2414 0.4823 0.068 Uiso 1 1 calc R
C31 C 0.16313(16) 0.30362(15) 0.35491(15) 0.0378(7) Uani 1 1 d .
H31A H 0.1374 0.3417 0.3549 0.045 Uiso 1 1 calc R
C32 C 0.19680(15) 0.29214(14) 0.29508(14) 0.0328(6) Uani 1 1 d .
C35 C 0.18933(19) 0.34445(15) 0.23748(16) 0.0443(8) Uani 1 1 d .
H35A H 0.1604 0.3784 0.2519 0.066 Uiso 1 1 calc R
H35B H 0.1714 0.3253 0.1912 0.066 Uiso 1 1 calc R
H35C H 0.2313 0.3636 0.2319 0.066 Uiso 1 1 calc R
C5 C 0.09739(15) 0.09386(17) 0.26837(18) 0.0412(7) Uani 1 1 d .
H5A H 0.0602 0.1147 0.2824 0.049 Uiso 1 1 calc R
C6 C 0.10786(16) 0.02850(17) 0.28362(19) 0.0443(8) Uani 1 1 d .
H6A H 0.0783 0.0046 0.3087 0.053 Uiso 1 1 calc R
C43 C 0.53662(15) 0.19074(17) 0.41980(17) 0.0400(7) Uani 1 1 d .
H43A H 0.5431 0.2316 0.4469 0.060 Uiso 1 1 calc R
H43B H 0.5737 0.1823 0.3933 0.060 Uiso 1 1 calc R
H43C H 0.5317 0.1549 0.4538 0.060 Uiso 1 1 calc R
C24 C 0.05808(15) -0.02678(16) 0.06815(16) 0.0393(8) Uani 1 1 d .
C52 C 0.0000 0.2843(3) 0.2500 0.0684(16) Uiso 1 2 d S
C51 C 0.0000 0.3538(4) 0.2500 0.089(2) Uiso 1 2 d S
C54 C 0.0328(4) 0.2864(4) 0.1316(5) 0.061(2) Uiso 0.50 1 d P
C55 C 0.0387(4) 0.3497(4) 0.1318(5) 0.063(2) Uiso 0.50 1 d P
C56 C 0.0275(4) 0.3866(5) 0.1944(5) 0.065(2) Uiso 0.50 1 d P
C53 C 0.0134(3) 0.2547(3) 0.1901(4) 0.0290(14) Uiso 0.50 1 d P
C57 C 0.0125(8) 0.2464(8) 0.1709(9) 0.102(6) Uiso 0.50 1 d 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'
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
C9 P1 C27 113.99(11) . .
C9 P1 C36 108.30(11) . .
C27 P1 C36 103.22(11) . .
C9 P1 C2 101.63(10) . .
C27 P1 C2 109.71(12) . .
C36 P1 C2 120.44(11) . .
C21 B1 C1 113.72(19) . .
C21 B1 C15 112.9(2) . .
C1 B1 C15 107.86(19) . .
C21 B1 C12 112.64(19) . 7
C1 B1 C12 102.87(18) . 7
C15 B1 C12 106.05(18) . 7
F2 C11 C10 114.8(2) . .
F2 C11 C12 120.5(2) . .
C10 C11 C12 124.5(2) . .
F3 C13 C12 121.4(2) . .
F3 C13 C14 113.9(2) . .
C12 C13 C14 124.6(2) . .
F1 C10 C11 117.6(2) . .
F1 C10 C9 119.6(2) . .
C11 C10 C9 122.6(2) . .
C1 C2 C3 127.2(2) . .
C1 C2 P1 114.64(17) . .
C3 C2 P1 118.00(17) . .
F4 C14 C9 121.4(2) . .
F4 C14 C13 116.4(2) . .
C9 C14 C13 122.2(2) . .
C32 C27 C28 119.5(2) . .
C32 C27 P1 126.57(19) . .
C28 C27 P1 113.92(18) . .
C2 C1 B1 137.0(2) . .
C10 C9 C14 113.9(2) . .
C10 C9 P1 118.84(18) . .
C14 C9 P1 127.22(18) . .
C4 C3 C8 118.4(2) . .
C4 C3 C2 121.9(2) . .
C8 C3 C2 119.6(2) . .
F9 C20 C19 114.8(2) . .
F9 C20 C15 120.8(3) . .
C19 C20 C15 124.4(3) . .
C37 C38 C39 122.8(2) . .
C13 C12 C11 112.0(2) . .
C13 C12 B1 127.6(2) . 7
C11 C12 B1 120.2(2) . 7
C38 C37 C36 118.7(2) . .
C38 C37 C42 117.1(2) . .
C36 C37 C42 124.2(2) . .
F10 C22 C23 116.5(3) . .
F10 C22 C21 119.0(2) . .
C23 C22 C21 124.4(3) . .
C37 C36 C41 119.2(2) . .
C37 C36 P1 124.00(18) . .
C41 C36 P1 116.48(19) . .
C29 C28 C27 119.0(2) . .
C29 C28 C33 115.4(2) . .
C27 C28 C33 125.6(2) . .
C22 C21 C26 113.4(2) . .
C22 C21 B1 120.8(2) . .
C26 C21 B1 125.8(2) . .
F5 C16 C17 115.6(2) . .
F5 C16 C15 119.5(2) . .
C17 C16 C15 124.9(2) . .
C6 C7 C8 120.4(3) . .
C5 C4 C3 120.7(3) . .
C20 C15 C16 112.3(2) . .
C20 C15 B1 126.1(2) . .
C16 C15 B1 121.5(2) . .
C7 C8 C3 120.5(3) . .
C40 C41 C36 119.0(2) . .
C40 C41 C44 115.6(2) . .
C36 C41 C44 125.4(2) . .
F11 C23 C24 120.0(3) . .
F11 C23 C22 120.6(3) . .
C24 C23 C22 119.4(3) . .
C40 C39 C38 117.6(2) . .
C40 C39 C43 121.2(3) . .
C38 C39 C43 121.2(3) . .
F6 C17 C18 120.1(3) . .
F6 C17 C16 120.5(3) . .
C18 C17 C16 119.5(3) . .
F13 C25 C24 119.9(3) . .
F13 C25 C26 120.1(3) . .
C24 C25 C26 120.1(3) . .
F7 C18 C19 120.7(3) . .
F7 C18 C17 120.6(3) . .
C19 C18 C17 118.7(3) . .
F14 C26 C25 115.0(2) . .
F14 C26 C21 121.4(2) . .
C25 C26 C21 123.6(3) . .
C39 C40 C41 122.5(2) . .
C30 C29 C28 122.3(2) . .
C31 C30 C29 118.0(2) . .
C31 C30 C34 121.0(3) . .
C29 C30 C34 120.9(3) . .
F8 C19 C18 120.2(3) . .
F8 C19 C20 120.0(3) . .
C18 C19 C20 119.8(3) . .
C30 C31 C32 123.3(3) . .
C31 C32 C27 117.9(2) . .
C31 C32 C35 114.7(2) . .
C27 C32 C35 127.4(2) . .
C6 C5 C4 120.2(3) . .
C7 C6 C5 119.6(3) . .
F12 C24 C25 120.6(3) . .
F12 C24 C23 120.4(3) . .
C25 C24 C23 119.0(3) . .
C53 C52 C53 125.1(8) . 2
C53 C52 C51 117.4(4) . .
C53 C52 C51 117.4(4) 2 .
C53 C52 C57 125.2(7) . 2
C53 C52 C57 3.5(8) 2 2
C51 C52 C57 117.2(6) . 2
C53 C52 C57 3.5(8) . .
C53 C52 C57 125.2(7) 2 .
C51 C52 C57 117.2(6) . .
C57 C52 C57 125.6(12) 2 .
C56 C51 C56 122.8(10) 2 .
C56 C51 C52 118.6(5) 2 .
C56 C51 C52 118.6(5) . .
C57 C54 C55 135.8(12) . .
C57 C54 C53 16.1(9) . .
C55 C54 C53 120.6(8) . .
C54 C55 C56 120.6(9) . .
C51 C56 C55 117.2(8) . .
C52 C53 C54 123.7(7) . .
C54 C57 C52 107.7(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C9 1.821(2) .
P1 C27 1.826(2) .
P1 C36 1.829(2) .
P1 C2 1.859(2) .
B1 C21 1.634(4) .
B1 C1 1.657(3) .
B1 C15 1.660(4) .
B1 C12 1.678(3) 7
F2 C11 1.351(3) .
F4 C14 1.341(3) .
F1 C10 1.339(3) .
F14 C26 1.347(4) .
F5 C16 1.344(3) .
F3 C13 1.341(3) .
F9 C20 1.349(3) .
F12 C24 1.344(3) .
F6 C17 1.343(3) .
F7 C18 1.343(3) .
F13 C25 1.348(3) .
F8 C19 1.341(3) .
F10 C22 1.345(3) .
F11 C23 1.341(4) .
C11 C10 1.376(3) .
C11 C12 1.397(3) .
C13 C12 1.380(3) .
C13 C14 1.391(3) .
C10 C9 1.389(3) .
C2 C1 1.345(3) .
C2 C3 1.496(3) .
C14 C9 1.390(3) .
C27 C32 1.414(4) .
C27 C28 1.420(3) .
C3 C4 1.391(4) .
C3 C8 1.394(4) .
C20 C19 1.381(4) .
C20 C15 1.386(4) .
C38 C37 1.385(3) .
C38 C39 1.386(4) .
C12 B1 1.678(3) 7
C37 C36 1.412(3) .
C37 C42 1.499(3) .
C22 C23 1.377(4) .
C22 C21 1.386(4) .
C36 C41 1.416(3) .
C28 C29 1.391(4) .
C28 C33 1.508(3) .
C21 C26 1.387(4) .
C16 C17 1.374(4) .
C16 C15 1.389(4) .
C7 C6 1.377(5) .
C7 C8 1.389(4) .
C4 C5 1.388(4) .
C41 C40 1.389(4) .
C41 C44 1.508(4) .
C23 C24 1.369(5) .
C39 C40 1.379(4) .
C39 C43 1.505(4) .
C17 C18 1.368(4) .
C25 C24 1.361(5) .
C25 C26 1.382(4) .
C18 C19 1.366(5) .
C29 C30 1.378(4) .
C30 C31 1.375(4) .
C30 C34 1.511(4) .
C31 C32 1.396(4) .
C32 C35 1.509(4) .
C5 C6 1.384(5) .
C52 C53 1.321(8) .
C52 C53 1.321(8) 2
C52 C51 1.427(10) .
C52 C57 1.703(16) 2
C52 C57 1.703(16) .
C51 C56 1.404(10) 2
C51 C56 1.404(10) .
C54 C57 1.205(18) .
C54 C55 1.304(12) .
C54 C53 1.363(12) .
C55 C56 1.425(13) .
