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Volume 67 
Part 6 
Page o1474  
June 2011  

Received 4 May 2011
Accepted 16 May 2011
Online 20 May 2011

Key indicators
Single-crystal X-ray study
T = 195 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.091
Data-to-parameter ratio = 24.4
Details
Open access

N,P,P-Triisopropylphosphinic amide

aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29A, 18059 Rostock, Germany
Correspondence e-mail: normen.peulecke@catalysis.de

The title compound, C9H22NOP, was obtained by slow diffusion of oxygen into a toluene solution of iPr2PNHiPr. In the crystal, an intermolecular N-H...O hydrogen bond occurs.

Related literature

For the synthesis of the starting compound (iPr)2PNHiPr, see: Kuchen et al. (1990[Kuchen, W., Langsch, D. & Peters, W. (1990). Phosphorus Sulfur Silicon Relat. Elem. 54, 55-61.]). For a similar synthesis of the title compound, see: Brück et al. (1995[Brück, A., Kuchen, W. & Peters, W. (1995). Phosphorus Sulfur Silicon Relat. Elem. 107, 129-133.]). For similar structures of R2P(O)NHR in which the P atom has at least one attached alkyl substituent, see: Burns et al. (1997[Burns, B., Gamble, M. P., Simm, A. R. C., Studley, J. R., Alcock, N. W. & Wills, M. (1997). Tetrahedron Asymmetry, 8, 73-78.]); Denmark & Dorow (2002[Denmark, S. E. & Dorow, R. L. (2002). Chirality, 14, 241-257.]); Kolodiazhnyi et al. (2003[Kolodiazhnyi, O. I., Gryshkun, E. V., Andrushko, N. V., Freytag, M., Jones, P. G. & Schmutzler, R. (2003). Tetrahedron Asymmetry, 14, 181-183.]); Francesco et al. (2010[Francesco, I. N., Wagner, A. & Colobert, F. (2010). Chem. Commun. 46, 2139-2141.]).

[Scheme 1]

Experimental

Crystal data
  • C9H22NOP

  • Mr = 191.25

  • Monoclinic, P 21 /c

  • a = 15.030 (3) Å

  • b = 8.4813 (17) Å

  • c = 10.071 (2) Å

  • [beta] = 107.36 (3)°

  • V = 1225.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 195 K

  • 0.42 × 0.26 × 0.20 mm

Data collection
  • Stoe IPDS II diffractometer

  • 19581 measured reflections

  • 2807 independent reflections

  • 2012 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.091

  • S = 0.89

  • 2807 reflections

  • 115 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.88 1.98 2.8344 (17) 165
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2008 ).


Acknowledgements

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

References

Brück, A., Kuchen, W. & Peters, W. (1995). Phosphorus Sulfur Silicon Relat. Elem. 107, 129-133.
Burns, B., Gamble, M. P., Simm, A. R. C., Studley, J. R., Alcock, N. W. & Wills, M. (1997). Tetrahedron Asymmetry, 8, 73-78.  [ChemPort]
Denmark, S. E. & Dorow, R. L. (2002). Chirality, 14, 241-257.  [ISI] [PubMed] [ChemPort]
Francesco, I. N., Wagner, A. & Colobert, F. (2010). Chem. Commun. 46, 2139-2141.  [ChemPort]
Kolodiazhnyi, O. I., Gryshkun, E. V., Andrushko, N. V., Freytag, M., Jones, P. G. & Schmutzler, R. (2003). Tetrahedron Asymmetry, 14, 181-183.  [ChemPort]
Kuchen, W., Langsch, D. & Peters, W. (1990). Phosphorus Sulfur Silicon Relat. Elem. 54, 55-61.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2011). E67, o1474  [ doi:10.1107/S1600536811018551 ]

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