organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1549

Tri-tert-butyl­phospho­nium hy­dr­oxy­tris­­(penta­fluoro­phen­yl)borate

aLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: marcus.klahn@catalysis.de

(Received 20 April 2012; accepted 23 April 2012; online 28 April 2012)

The ionic title compound, C12H28P+·C18HBF15O, was obtained by the stoichiometric reaction of tBu3P, B(C6F5)3 and water in toluene. A weak P—H⋯O hydrogen bond is observed in the crystal structure.

Related literature

For general aspects of related compounds, see: Welch et al. (2007[Welch, G. C., Cabrera, L., Chase, P. A., Hollink, E., Masuda, J. D., Wei, P. & Stephan, D. W. (2007). Dalton Trans. pp. 3407-3414.]); Stephan & Erker (2010[Stephan, D. W. & Erker, G. (2010). Angew. Chem. Int. Ed. 49, 46-76.]). For related structures, see: Roesler et al. (2003[Roesler, R., Piers, W. E. & Parvez, M. (2003). J. Organomet. Chem. 680, 218-222.]); Di Saverio et al. (2005[Di Saverio, A., Focante, F., Camurati, I., Resconi, L., Beringhelli, T., D'Alfonso, G., Donghi, D., Maggioni, D., Mercandelli, P. & Sironi, A. (2005). Inorg. Chem. 44, 5030-5041.]); Welch & Stephan (2007[Welch, G. C. & Stephan, D. W. (2007). J. Am. Chem. Soc. 129, 1880-1881.]).

[Scheme 1]

Experimental

Crystal data
  • C12H28P+·C18HBF15O

  • Mr = 732.31

  • Triclinic, [P \overline 1]

  • a = 9.798 (2) Å

  • b = 12.042 (2) Å

  • c = 15.389 (3) Å

  • α = 112.31 (3)°

  • β = 94.51 (3)°

  • γ = 108.93 (3)°

  • V = 1546.2 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 200 K

  • 0.30 × 0.23 × 0.15 mm

Data collection
  • Stoe IPDS II diffractometer

  • 24084 measured reflections

  • 6557 independent reflections

  • 4256 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.069

  • S = 0.84

  • 6557 reflections

  • 450 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
P1—H2⋯O1i 1.288 (14) 2.276 (14) 3.4080 (13) 144.6 (9)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The concept of "frustrated Lewis pairs" has been explored in depth and coined by Welch et al. (2007). The key issue is the sterical hindrance between the Lewis acids and bases preventing a classical adduct formation which gives rise to a unique reactivity due to the interaction of the basic and acidic centres. During the last years, this feature has been shown in reactions with a wide variety of reagents, these can be either small molecules like H2, CO2, and N2O, or larger ones like terminal olefins, alkynes, dienes, B–H bonds, disulfides and the C–O bonds of cyclic ethers (Stephan & Erker 2010). The reaction of tri-tert-butylphosphine, tris(pentafluorophenyl)borane and water proceeds in a similar way to the conversion of tris(pentafluorophenyl)borane with water in the presence of triethylamine (Di Saverio et al., 2005). Roesler et al. (2003) obtained an intramolecular salt of the type 1-[N(H)Ph2]-2-[B(OH)(C6F5)2]C6H4 with a phenyl bridge between nitrogen and boron. The title compound consists of the phosphonium cation [tBu3PH]+ and the boranate anion [HOB(C6F5)3]- (Figure 1), which are probably generated via subsequent protonation of the phosphine by the formed borane water adduct. The phosphonium cation is comparable to that in the compound [tBu3PH][HB(C6F5)3], which is the product of dihydrogen activation (Welch & Stephan 2007). Besides the unexceptional metric parameters both ions exhibit a geometry of a distorted tetrahedron at the phosphorous and the boron centre, respectively. Noteworthy, a weak P—H···O hydrogen bond was obtained with following geometric parameters: P1—H2 1.288 (14), H2···O1 2.276 (14), P1···O1 3.4080 (13) Å, P1—H2···O1 144.6 (9)°.

Related literature top

For general aspects of related compounds, see: Welch et al. (2007); Stephan & Erker (2010). For related structures, see: Roesler et al. (2003); Di Saverio et al. (2005); Welch & Stephan (2007).

Experimental top

Solid tris(pentafluorophenyl)borane (0.256 g, 0.5 mmol) and tri-tert-butylphosphine (0.101 g, 0.5 mmol) were dissolved in 20 ml of toluene resulting in a pale yellow solution. After stirring this mixture for 30 minutes 9 µL of water (0.5 mmol) was added. The reaction mixture was allowed to stir for 12 h at 40 °C during which the solution turned colorless. The reaction was concentrated until the first precipitate was formed, which was resolved by gentle heating. Leaving the solution at -78 °C gave colorless prisms in an isolated yield of 0.127 g (35%) The colorless compound was fully characterized by standard analytical methods, NMR (295 K, CDCl3): 1H: d = 5.96 (d, 1H, 1JHP = 451 Hz, PH), 2.05 (br s, 1H, HOB), 1.58 (d, 27H, 3JHP = 15.3 Hz, {(CH3)3C}3). 11B: d = -3.74 (s). 31P{1H}: d = 54.8 (s). 31P: d = 54.8 (dm, 1JPH = 452 Hz, 3JHP = 15.4 Hz). 19F: d = -135.0 (d, 6 F, 3JFF = 21.6 Hz, o-F), -161.8 (t, 3 F, 3JFF = 20.1 Hz, p-F), -165.5 (m, 6 F, m-F).

Refinement top

H1 and H2 were found in a difference Fourier map and refined isotropically. All other H atoms were placed in idealized positions with d(C—H) = 0.98 Å and refined using a riding model with Uiso(H) fixed at 1.5 Ueq(C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 30% displacement ellipsoids. Hydrogen atoms at carbon atoms are omitted for clarity.
Tri-tert-butylphosphonium hydroxytris(pentafluorophenyl)borate top
Crystal data top
C12H28P+·C18HBF15OZ = 2
Mr = 732.31F(000) = 744
Triclinic, P1Dx = 1.573 Mg m3
a = 9.798 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.042 (2) ÅCell parameters from 5729 reflections
c = 15.389 (3) Åθ = 1.5–27.2°
α = 112.31 (3)°µ = 0.21 mm1
β = 94.51 (3)°T = 200 K
γ = 108.93 (3)°Prism, colourless
V = 1546.2 (8) Å30.30 × 0.23 × 0.15 mm
Data collection top
Stoe IPDS II
diffractometer
4256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.7°, θmin = 1.5°
ω scansh = 1212
24084 measured reflectionsk = 1515
6557 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 0.84 w = 1/[σ2(Fo2) + (0.0383P)2]
where P = (Fo2 + 2Fc2)/3
6557 reflections(Δ/σ)max = 0.001
450 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C12H28P+·C18HBF15Oγ = 108.93 (3)°
Mr = 732.31V = 1546.2 (8) Å3
Triclinic, P1Z = 2
a = 9.798 (2) ÅMo Kα radiation
b = 12.042 (2) ŵ = 0.21 mm1
c = 15.389 (3) ÅT = 200 K
α = 112.31 (3)°0.30 × 0.23 × 0.15 mm
β = 94.51 (3)°
Data collection top
Stoe IPDS II
diffractometer
4256 reflections with I > 2σ(I)
24084 measured reflectionsRint = 0.031
6557 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.20 e Å3
6557 reflectionsΔρmin = 0.24 e Å3
450 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.23991 (17)0.30327 (14)0.67250 (11)0.0311 (3)
C20.33984 (17)0.36491 (15)0.63024 (11)0.0341 (3)
C30.37910 (19)0.30153 (17)0.54731 (12)0.0391 (4)
C40.3198 (2)0.16833 (17)0.50170 (11)0.0421 (4)
C50.22222 (19)0.10115 (15)0.54084 (12)0.0404 (4)
C60.18568 (18)0.16856 (15)0.62327 (11)0.0348 (4)
C70.00162 (17)0.30725 (14)0.73956 (10)0.0311 (3)
C80.08453 (17)0.32198 (14)0.67075 (11)0.0327 (3)
C90.23652 (18)0.26740 (15)0.64192 (11)0.0366 (4)
C100.31631 (18)0.19121 (16)0.68202 (12)0.0390 (4)
C110.24162 (19)0.17148 (16)0.74982 (12)0.0397 (4)
C120.08921 (18)0.22759 (15)0.77625 (11)0.0362 (4)
C130.25420 (17)0.37488 (14)0.86700 (11)0.0320 (3)
C140.22187 (18)0.44094 (15)0.95346 (11)0.0365 (4)
C150.2796 (2)0.45011 (17)1.04117 (12)0.0443 (4)
C160.37549 (19)0.39040 (18)1.04639 (12)0.0453 (4)
C170.41270 (18)0.32459 (16)0.96440 (13)0.0420 (4)
C180.35269 (18)0.31783 (15)0.87707 (11)0.0361 (4)
C190.8368 (2)0.14093 (16)0.09712 (12)0.0437 (4)
C200.9725 (2)0.1684 (2)0.05404 (14)0.0576 (5)
H20A1.04530.14290.08050.086*
H20B1.01680.26140.07030.086*
H20C0.94240.11850.01630.086*
C210.7709 (3)0.00456 (17)0.07480 (16)0.0636 (6)
H21A0.74640.05700.00480.095*
H21B0.68090.02330.09940.095*
H21C0.84360.02580.10600.095*
C220.7245 (2)0.1750 (2)0.04734 (13)0.0587 (5)
H22A0.76390.26880.06600.088*
H22B0.63080.14990.06720.088*
H22C0.70720.12800.02280.088*
C230.7343 (2)0.20913 (17)0.29229 (14)0.0449 (4)
C240.7288 (3)0.0981 (2)0.32003 (18)0.0687 (6)
H24A0.65000.08290.35460.103*
H24B0.82430.12180.36170.103*
H24C0.70870.01870.26150.103*
C250.5834 (2)0.1725 (2)0.22956 (17)0.0599 (5)
H25A0.55910.09060.17240.090*
H25B0.58720.24130.20940.090*
H25C0.50720.16220.26670.090*
C260.7618 (2)0.33412 (19)0.38274 (14)0.0550 (5)
H26A0.67410.32310.41020.082*
H26B0.78110.40700.36510.082*
H26C0.84760.35190.43050.082*
C271.0711 (2)0.27172 (17)0.29329 (13)0.0446 (4)
C281.0933 (3)0.3432 (2)0.40278 (14)0.0666 (6)
H28A1.19600.36690.43440.100*
H28B1.02570.28630.42580.100*
H28C1.07260.42200.41820.100*
C291.1911 (2)0.3614 (2)0.26475 (16)0.0611 (5)
H29A1.17240.44030.27590.092*
H29B1.18890.31620.19630.092*
H29C1.28870.38500.30380.092*
C301.0909 (2)0.1425 (2)0.26836 (17)0.0614 (5)
H30A1.07890.09780.19850.092*
H30B1.01610.08760.28920.092*
H30C1.19010.15970.30150.092*
F10.40912 (11)0.49630 (8)0.67088 (7)0.0447 (2)
F20.47413 (12)0.36859 (11)0.50949 (8)0.0551 (3)
F30.35817 (14)0.10532 (11)0.42120 (7)0.0622 (3)
F40.16501 (13)0.02981 (9)0.49855 (7)0.0580 (3)
F50.09291 (11)0.09601 (8)0.65966 (7)0.0454 (2)
F60.01457 (10)0.39236 (9)0.62464 (7)0.0459 (2)
F70.30771 (11)0.28541 (11)0.57324 (8)0.0575 (3)
F80.46452 (11)0.13439 (11)0.65281 (8)0.0570 (3)
F90.31768 (12)0.09451 (11)0.78874 (8)0.0612 (3)
F100.02586 (11)0.19765 (10)0.84141 (7)0.0538 (3)
F110.12531 (11)0.49906 (10)0.95367 (7)0.0494 (3)
F120.24301 (13)0.51617 (12)1.12182 (7)0.0662 (3)
F130.43409 (12)0.39742 (12)1.13126 (8)0.0681 (3)
F140.51001 (12)0.26803 (10)0.96855 (8)0.0599 (3)
F150.39801 (12)0.25147 (10)0.80060 (7)0.0517 (3)
B10.1813 (2)0.37833 (16)0.76764 (12)0.0312 (4)
O10.21571 (15)0.51498 (10)0.78731 (8)0.0353 (3)
P10.88590 (5)0.24737 (4)0.22942 (3)0.03315 (10)
H10.304 (3)0.549 (2)0.7996 (15)0.067 (8)*
H20.9035 (16)0.3605 (13)0.2343 (10)0.027 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0295 (8)0.0347 (8)0.0334 (8)0.0150 (7)0.0059 (7)0.0172 (7)
C20.0318 (9)0.0358 (8)0.0390 (8)0.0150 (7)0.0073 (7)0.0189 (7)
C30.0397 (10)0.0534 (10)0.0409 (9)0.0263 (8)0.0163 (8)0.0289 (8)
C40.0503 (11)0.0557 (11)0.0319 (8)0.0342 (9)0.0142 (8)0.0182 (8)
C50.0458 (10)0.0352 (9)0.0377 (9)0.0213 (8)0.0025 (8)0.0097 (7)
C60.0345 (9)0.0348 (8)0.0398 (9)0.0145 (7)0.0082 (7)0.0198 (7)
C70.0332 (9)0.0307 (8)0.0319 (8)0.0134 (7)0.0091 (7)0.0148 (7)
C80.0334 (9)0.0343 (8)0.0352 (8)0.0134 (7)0.0114 (7)0.0187 (7)
C90.0335 (9)0.0427 (9)0.0374 (9)0.0178 (8)0.0062 (7)0.0187 (7)
C100.0257 (9)0.0424 (9)0.0425 (9)0.0095 (7)0.0073 (7)0.0146 (8)
C110.0378 (10)0.0387 (9)0.0397 (9)0.0057 (8)0.0136 (8)0.0203 (7)
C120.0370 (9)0.0382 (8)0.0350 (8)0.0116 (7)0.0050 (7)0.0204 (7)
C130.0283 (8)0.0294 (8)0.0370 (8)0.0079 (7)0.0060 (7)0.0159 (7)
C140.0313 (9)0.0385 (9)0.0396 (9)0.0100 (7)0.0082 (7)0.0194 (7)
C150.0406 (10)0.0492 (10)0.0348 (9)0.0055 (8)0.0103 (8)0.0192 (8)
C160.0354 (10)0.0546 (10)0.0408 (10)0.0007 (8)0.0006 (8)0.0310 (9)
C170.0294 (9)0.0408 (9)0.0577 (11)0.0063 (8)0.0014 (8)0.0312 (9)
C180.0350 (9)0.0321 (8)0.0403 (9)0.0117 (7)0.0049 (7)0.0164 (7)
C190.0522 (11)0.0369 (9)0.0435 (9)0.0211 (8)0.0118 (8)0.0153 (8)
C200.0748 (15)0.0619 (12)0.0485 (11)0.0353 (11)0.0290 (10)0.0258 (10)
C210.0714 (15)0.0362 (10)0.0717 (14)0.0204 (10)0.0136 (11)0.0124 (10)
C220.0717 (14)0.0570 (12)0.0429 (10)0.0320 (11)0.0009 (10)0.0133 (9)
C230.0444 (10)0.0458 (10)0.0623 (11)0.0212 (8)0.0261 (9)0.0354 (9)
C240.0778 (16)0.0680 (13)0.1029 (17)0.0370 (12)0.0521 (14)0.0663 (13)
C250.0424 (12)0.0564 (12)0.0889 (15)0.0177 (10)0.0245 (11)0.0386 (11)
C260.0655 (13)0.0676 (12)0.0562 (11)0.0395 (11)0.0346 (10)0.0355 (10)
C270.0419 (10)0.0530 (10)0.0504 (10)0.0231 (9)0.0111 (8)0.0296 (9)
C280.0649 (14)0.0878 (16)0.0520 (12)0.0383 (13)0.0014 (10)0.0298 (11)
C290.0392 (11)0.0630 (13)0.0807 (14)0.0134 (10)0.0118 (10)0.0362 (12)
C300.0594 (13)0.0714 (13)0.0835 (15)0.0420 (11)0.0229 (11)0.0483 (12)
F10.0430 (6)0.0367 (5)0.0561 (6)0.0122 (4)0.0195 (5)0.0226 (5)
F20.0597 (7)0.0738 (7)0.0633 (6)0.0378 (6)0.0376 (6)0.0465 (6)
F30.0838 (8)0.0728 (7)0.0429 (6)0.0491 (7)0.0274 (6)0.0195 (5)
F40.0728 (8)0.0373 (5)0.0535 (6)0.0250 (5)0.0081 (5)0.0069 (5)
F50.0507 (6)0.0336 (5)0.0567 (6)0.0164 (5)0.0192 (5)0.0227 (5)
F60.0402 (6)0.0579 (6)0.0502 (6)0.0138 (5)0.0100 (4)0.0383 (5)
F70.0407 (6)0.0777 (7)0.0643 (7)0.0211 (6)0.0008 (5)0.0443 (6)
F80.0284 (6)0.0688 (7)0.0674 (7)0.0095 (5)0.0086 (5)0.0309 (6)
F90.0486 (7)0.0672 (7)0.0612 (7)0.0018 (5)0.0127 (5)0.0409 (6)
F100.0472 (6)0.0596 (6)0.0576 (6)0.0051 (5)0.0003 (5)0.0433 (5)
F110.0513 (6)0.0613 (6)0.0453 (5)0.0316 (5)0.0204 (5)0.0227 (5)
F120.0705 (8)0.0830 (8)0.0378 (6)0.0220 (7)0.0194 (5)0.0233 (6)
F130.0519 (7)0.1004 (9)0.0526 (6)0.0096 (6)0.0018 (5)0.0525 (7)
F140.0465 (6)0.0617 (7)0.0822 (8)0.0207 (5)0.0019 (6)0.0451 (6)
F150.0572 (7)0.0556 (6)0.0500 (6)0.0372 (5)0.0086 (5)0.0184 (5)
B10.0332 (10)0.0296 (9)0.0341 (9)0.0124 (8)0.0079 (8)0.0168 (7)
O10.0356 (7)0.0298 (6)0.0430 (6)0.0130 (5)0.0090 (5)0.0179 (5)
P10.0358 (2)0.0319 (2)0.0392 (2)0.01505 (18)0.01272 (18)0.02023 (18)
Geometric parameters (Å, º) top
C1—C21.388 (2)C19—P11.8667 (19)
C1—C61.390 (2)C20—H20A0.9800
C1—B11.660 (2)C20—H20B0.9800
C2—F11.3567 (18)C20—H20C0.9800
C2—C31.374 (2)C21—H21A0.9800
C3—F21.3461 (19)C21—H21B0.9800
C3—C41.371 (2)C21—H21C0.9800
C4—F31.3405 (19)C22—H22A0.9800
C4—C51.375 (2)C22—H22B0.9800
C5—F41.3471 (19)C22—H22C0.9800
C5—C61.369 (2)C23—C251.531 (3)
C6—F51.3562 (18)C23—C261.537 (3)
C7—C81.383 (2)C23—C241.538 (2)
C7—C121.389 (2)C23—P11.8639 (18)
C7—B11.653 (2)C24—H24A0.9800
C8—F61.3593 (17)C24—H24B0.9800
C8—C91.373 (2)C24—H24C0.9800
C9—F71.3442 (18)C25—H25A0.9800
C9—C101.369 (2)C25—H25B0.9800
C10—F81.3410 (19)C25—H25C0.9800
C10—C111.364 (2)C26—H26A0.9800
C11—F91.3478 (18)C26—H26B0.9800
C11—C121.376 (2)C26—H26C0.9800
C12—F101.3574 (17)C27—C281.532 (3)
C13—C181.384 (2)C27—C301.536 (2)
C13—C141.389 (2)C27—C291.536 (3)
C13—B11.657 (2)C27—P11.8710 (19)
C14—F111.3466 (19)C28—H28A0.9800
C14—C151.371 (2)C28—H28B0.9800
C15—F121.345 (2)C28—H28C0.9800
C15—C161.369 (3)C29—H29A0.9800
C16—F131.3451 (18)C29—H29B0.9800
C16—C171.362 (3)C29—H29C0.9800
C17—F141.3497 (19)C30—H30A0.9800
C17—C181.386 (2)C30—H30B0.9800
C18—F151.3489 (19)C30—H30C0.9800
C19—C201.528 (3)B1—O11.469 (2)
C19—C221.538 (2)O1—H10.79 (2)
C19—C211.542 (2)P1—H21.288 (14)
C2—C1—C6112.68 (14)H21A—C21—H21C109.5
C2—C1—B1125.07 (13)H21B—C21—H21C109.5
C6—C1—B1122.16 (14)C19—C22—H22A109.5
F1—C2—C3114.64 (14)C19—C22—H22B109.5
F1—C2—C1120.90 (14)H22A—C22—H22B109.5
C3—C2—C1124.45 (15)C19—C22—H22C109.5
F2—C3—C4119.39 (15)H22A—C22—H22C109.5
F2—C3—C2120.84 (15)H22B—C22—H22C109.5
C4—C3—C2119.77 (15)C25—C23—C26106.75 (16)
F3—C4—C3120.34 (16)C25—C23—C24108.96 (16)
F3—C4—C5120.90 (16)C26—C23—C24110.57 (16)
C3—C4—C5118.75 (15)C25—C23—P1111.06 (13)
F4—C5—C6120.76 (16)C26—C23—P1107.30 (13)
F4—C5—C4119.86 (15)C24—C23—P1112.07 (13)
C6—C5—C4119.38 (15)C23—C24—H24A109.5
F5—C6—C5116.17 (14)C23—C24—H24B109.5
F5—C6—C1118.86 (14)H24A—C24—H24B109.5
C5—C6—C1124.94 (15)C23—C24—H24C109.5
C8—C7—C12112.44 (14)H24A—C24—H24C109.5
C8—C7—B1120.11 (13)H24B—C24—H24C109.5
C12—C7—B1127.43 (13)C23—C25—H25A109.5
F6—C8—C9115.40 (13)C23—C25—H25B109.5
F6—C8—C7119.61 (14)H25A—C25—H25B109.5
C9—C8—C7124.97 (14)C23—C25—H25C109.5
F7—C9—C10119.58 (15)H25A—C25—H25C109.5
F7—C9—C8120.82 (14)H25B—C25—H25C109.5
C10—C9—C8119.58 (14)C23—C26—H26A109.5
F8—C10—C11121.04 (15)C23—C26—H26B109.5
F8—C10—C9120.31 (15)H26A—C26—H26B109.5
C11—C10—C9118.63 (15)C23—C26—H26C109.5
F9—C11—C10119.66 (15)H26A—C26—H26C109.5
F9—C11—C12120.45 (15)H26B—C26—H26C109.5
C10—C11—C12119.86 (14)C28—C27—C30109.52 (16)
F10—C12—C11115.05 (14)C28—C27—C29106.15 (17)
F10—C12—C7120.43 (14)C30—C27—C29110.30 (16)
C11—C12—C7124.51 (14)C28—C27—P1110.65 (14)
C18—C13—C14113.37 (14)C30—C27—P1112.04 (14)
C18—C13—B1127.75 (14)C29—C27—P1108.01 (12)
C14—C13—B1118.80 (13)C27—C28—H28A109.5
F11—C14—C15115.91 (15)C27—C28—H28B109.5
F11—C14—C13119.51 (14)H28A—C28—H28B109.5
C15—C14—C13124.57 (16)C27—C28—H28C109.5
F12—C15—C16119.63 (15)H28A—C28—H28C109.5
F12—C15—C14121.01 (17)H28B—C28—H28C109.5
C16—C15—C14119.36 (17)C27—C29—H29A109.5
F13—C16—C17119.98 (17)C27—C29—H29B109.5
F13—C16—C15120.87 (18)H29A—C29—H29B109.5
C17—C16—C15119.15 (15)C27—C29—H29C109.5
F14—C17—C16119.98 (15)H29A—C29—H29C109.5
F14—C17—C18120.08 (17)H29B—C29—H29C109.5
C16—C17—C18119.93 (15)C27—C30—H30A109.5
F15—C18—C13121.25 (14)C27—C30—H30B109.5
F15—C18—C17115.12 (14)H30A—C30—H30B109.5
C13—C18—C17123.63 (16)C27—C30—H30C109.5
C20—C19—C22106.21 (15)H30A—C30—H30C109.5
C20—C19—C21109.34 (16)H30B—C30—H30C109.5
C22—C19—C21109.95 (16)O1—B1—C7106.05 (13)
C20—C19—P1110.77 (13)O1—B1—C13107.91 (13)
C22—C19—P1108.44 (12)C7—B1—C13111.45 (13)
C21—C19—P1111.96 (13)O1—B1—C1111.68 (13)
C19—C20—H20A109.5C7—B1—C1106.95 (13)
C19—C20—H20B109.5C13—B1—C1112.63 (12)
H20A—C20—H20B109.5B1—O1—H1106.0 (16)
C19—C20—H20C109.5C23—P1—C19114.47 (9)
H20A—C20—H20C109.5C23—P1—C27114.13 (8)
H20B—C20—H20C109.5C19—P1—C27113.94 (9)
C19—C21—H21A109.5C23—P1—H2105.0 (6)
C19—C21—H21B109.5C19—P1—H2103.9 (6)
H21A—C21—H21B109.5C27—P1—H2103.7 (6)
C19—C21—H21C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
P1—H2···O1i1.288 (14)2.276 (14)3.4080 (13)144.6 (9)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC12H28P+·C18HBF15O
Mr732.31
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)9.798 (2), 12.042 (2), 15.389 (3)
α, β, γ (°)112.31 (3), 94.51 (3), 108.93 (3)
V3)1546.2 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.30 × 0.23 × 0.15
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
24084, 6557, 4256
Rint0.031
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.069, 0.84
No. of reflections6557
No. of parameters450
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.24

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED32 (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
P1—H2···O1i1.288 (14)2.276 (14)3.4080 (13)144.6 (9)
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

This work was supported by the Leibniz-Institut für Katalyse e·V. an der Universität Rostock.

References

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First citationStephan, D. W. & Erker, G. (2010). Angew. Chem. Int. Ed. 49, 46–76.  Web of Science CrossRef CAS Google Scholar
First citationStoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWelch, G. C., Cabrera, L., Chase, P. A., Hollink, E., Masuda, J. D., Wei, P. & Stephan, D. W. (2007). Dalton Trans. pp. 3407–3414.  Web of Science CSD CrossRef Google Scholar
First citationWelch, G. C. & Stephan, D. W. (2007). J. Am. Chem. Soc. 129, 1880–1881.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 68| Part 5| May 2012| Page o1549
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