N,P,P-Triisopropyl­phosphinic amide

Peulecke, N.; Aluri, B.R.; Müller, B.H.; Spannenberg, A.; Rosenthal, U.

doi:10.1107/S1600536811018551

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 (C-C) = 0.003 Å
R = 0.039
wR = 0.091
Data-to-parameter ratio = 24.4
Details

N,P,P-Triisopropylphosphinic amide

Normen Peulecke,^a ^* Bhaskar R. Aluri,^a Bernd H. Müller,^a Anke Spannenberg ^a and Uwe Rosenthal ^a

^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-HO hydrogen bond occurs.

Related literature

For the synthesis of the starting compound (ⁱPr)₂PNHⁱPr, see: Kuchen et al. (1990). For a similar synthesis of the title compound, see: Brück et al. (1995). For similar structures of R₂P(O)NHR in which the P atom has at least one attached alkyl substituent, see: Burns et al. (1997); Denmark & Dorow (2002); Kolodiazhnyi et al. (2003); Francesco et al. (2010).

Experimental

Crystal data

C₉H₂₂NOP
M_r = 191.25
Monoclinic, P 2₁ /c
a = 15.030 (3) Å
b = 8.4813 (17) Å
c = 10.071 (2) Å
= 107.36 (3)°
V = 1225.3 (4) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.091
S = 0.89
2807 reflections
115 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	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); cell refinement: X-AREA; data reduction: X-AREA; 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: 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.
Denmark, S. E. & Dorow, R. L. (2002). Chirality, 14, 241-257.
Francesco, I. N., Wagner, A. & Colobert, F. (2010). Chem. Commun. 46, 2139-2141.
Kolodiazhnyi, O. I., Gryshkun, E. V., Andrushko, N. V., Freytag, M., Jones, P. G. & Schmutzler, R. (2003). Tetrahedron Asymmetry, 14, 181-183.
Kuchen, W., Langsch, D. & Peters, W. (1990). Phosphorus Sulfur Silicon Relat. Elem. 54, 55-61.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.

organic compounds