(Biphenyl-2,2′-di­yl)di-tert-butyl­phos­phonium trifluoro­methane­sulfonate

Muller, A.; Holzapfel, C.W.

doi:10.1107/S1600536812049045

Volume 69
Part 1
Page o20
January 2013

Received 15 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.054
wR = 0.117
Data-to-parameter ratio = 20.5
Details

(Biphenyl-2,2'-diyl)di-tert-butylphosphonium trifluoromethanesulfonate

Alfred Muller ^a ^* and Cedric W. Holzapfel ^a

^aDepartment of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: mullera@uj.ac.za

To aid in the elucidation of catalytic reaction mechanism of palladacycles, we found that reaction of trifluoromethanesulfonic acid with a phosphapalladacycle resulted in elimination of the palladium and formation of the title phospholium salt, C₂₀H₂₆P⁺·CF₃SO₃^-. Selected geometrical parameters include P-biphenyl (av.) = 1.801 (3) Å and P-t-Bu (av.) = 1.858 (3) Å, and significant distortion of the tetrahedral P-atom environment with biphenyl-P-biphenyl = 93.93 (13)° and t-Bu-P-t-Bu = 118.82 (14)°. In the crystal, weak C-HO interactions lead to channels along the c axis that are occupied by CF₃SO₃^- anions.

Related literature

For background to catalytic studies on palladacycles, see: Herrman et al. (2003); Beletskaya & Cheprakov (2004); Omondi et al. (2011); Williams et al. (2008); d'Orlye & Jutland (2005). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₂₀H₂₆P⁺·CF₃O₃S^-
M_r = 446.45
Tetragonal, P 4₁ 2₁ 2
a = 12.1339 (10) Å
c = 30.057 (2) Å
V = 4425.4 (6) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.4 × 0.26 × 0.2 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.902, T_max = 0.949
25275 measured reflections
5502 independent reflections
3241 reflections with I > 2(I)
R_int = 0.101

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.117
S = 0.99
5502 reflections
268 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 2283 Friedel pairs
Flack parameter: 0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.93	2.49	3.381 (4)	161
C19-H19AO2ⁱⁱ	0.96	2.52	3.458 (4)	165
C11-H11O3ⁱⁱⁱ	0.93	2.70	3.601 (4)	162
C15-H15BO3ⁱⁱⁱ	0.96	2.69	3.470 (4)	138
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{7\over 4}}]$ ; (ii) y, x, -z+2; (iii) x+1, y, z.

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2079 ).

Acknowledgements

The University of Witwatersrand is thanked for the use of their diffractometer. The research fund of the University of Johannesburg is gratefully acknowledged.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Beletskaya, I. P. & Cheprakov, A. V. (2004). J. Organomet. Chem. 689, 4055-4082.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1998). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Herrman, W. A., Ofele, K., Preysing, D. & Schneider, S. K. (2003). J. Organomet. Chem. 687, 229-248.
Omondi, B., Shaw, M. L. & Holzapfel, C. W. (2011). J. Organomet. Chem. 696, 3091-3096.
Orlye, E. d' & Jutland, A. (2005). Tetrahedron, 61, 9670-9678.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Williams, D. G. B., Shaw, M. L., Green, M. J. & Holzapfel, C. W. (2008). Angew. Chem. Int. Ed. 47, 560-563.

organic compounds