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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 [sigma](C-C) = 0.005 Å
R = 0.054
wR = 0.117
Data-to-parameter ratio = 20.5
Details
Open access

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

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-H...O 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[Herrman, W. A., Ofele, K., Preysing, D. & Schneider, S. K. (2003). J. Organomet. Chem. 687, 229-248.]); Beletskaya & Cheprakov (2004[Beletskaya, I. P. & Cheprakov, A. V. (2004). J. Organomet. Chem. 689, 4055-4082.]); Omondi et al. (2011[Omondi, B., Shaw, M. L. & Holzapfel, C. W. (2011). J. Organomet. Chem. 696, 3091-3096.]); Williams et al. (2008[Williams, D. G. B., Shaw, M. L., Green, M. J. & Holzapfel, C. W. (2008). Angew. Chem. Int. Ed. 47, 560-563.]); d'Orlye & Jutland (2005[Orlye, E. d' & Jutland, A. (2005). Tetrahedron, 61, 9670-9678.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C20H26P+·CF3O3S-

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.902, Tmax = 0.949

  • 25275 measured reflections

  • 5502 independent reflections

  • 3241 reflections with I > 2[sigma](I)

  • Rint = 0.101

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.117

  • S = 0.99

  • 5502 reflections

  • 268 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2283 Friedel pairs

  • Flack parameter: 0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.93 2.49 3.381 (4) 161
C19-H19A...O2ii 0.96 2.52 3.458 (4) 165
C11-H11...O3iii 0.93 2.70 3.601 (4) 162
C15-H15B...O3iii 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[Bruker (1998). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [ISI] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Beletskaya, I. P. & Cheprakov, A. V. (2004). J. Organomet. Chem. 689, 4055-4082.  [CrossRef] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [CSD] [CrossRef] [ChemPort]
Orlye, E. d' & Jutland, A. (2005). Tetrahedron, 61, 9670-9678.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Williams, D. G. B., Shaw, M. L., Green, M. J. & Holzapfel, C. W. (2008). Angew. Chem. Int. Ed. 47, 560-563.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o20  [ doi:10.1107/S1600536812049045 ]

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