4,4,5,5-Tetra­methyl-1,3,2λ5-dioxa­phospho­lan-2-one

Skarżyńska, A.; Trzeciak, A.M.; Gniewek, A.

doi:10.1107/S160053681102959X

Volume 67
Part 8
Page o2159
August 2011

Received 20 July 2011
Accepted 21 July 2011
Online 30 July 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 13.1
Details

4,4,5,5-Tetramethyl-1,3,2⁵-dioxaphospholan-2-one

Anna Skarzynska,^a Anna M. Trzeciak ^a and Andrzej Gniewek ^a ^*

^aFaculty of Chemistry, University of Wroclaw, 14 F. Joliot-Curie, 50-383 Wroclaw, Poland
Correspondence e-mail: andrzej@netesa.com

The five-membered ring in the title compound, C₆H₁₃O₃P, exists in an envelope conformation with one of the ring C atoms at the flap position. The coordination geometry around the P atom is a distorted tetrahedron. The crystal structure is stabilized by several weak C-HO and P-HO hydrogen bonds, forming a three-dimensional network.

Related literature

For a discussion of 1,3,2-dioxaphospholane chemistry, see: Maffei & Buono (2003); Zwierzak (1967) and for the Heck reaction, see: Beletskaya & Cheprakov (2000); Skarzynska et al. (2011). For hydrogen-bond interactions, see: Desiraju & Steiner (1999). For bond lengths in organic compounds, see: Allen et al. (1987). For details of the temperature control applied during data collection, see: Cosier & Glazer (1986) and for specifications of the analytical numeric absorption correction, see: Clark & Reid (1995).

Experimental

Crystal data

C₆H₁₃O₃P
M_r = 164.13
Monoclinic, P 2₁ /c
a = 7.144 (2) Å
b = 7.570 (2) Å
c = 15.064 (4) Å
= 90.98 (2)°
V = 814.5 (4) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 100 K
0.33 × 0.27 × 0.26 mm

Data collection

Kuma KM-4 diffractometer with CCD detector
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ) T_min = 0.910, T_max = 0.952
7254 measured reflections
1869 independent reflections
1673 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.096
S = 1.10
1869 reflections
143 parameters
All H-atom parameters refined
_max = 0.49 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H113Oⁱ	0.98 (2)	2.70 (2)	3.583 (2)	150 (2)
C12-H123Oⁱ	1.00 (2)	2.60 (2)	3.499 (2)	150 (2)
C21-H213Oⁱ	0.96 (2)	2.68 (2)	3.544 (2)	148 (2)
C22-H222O1ⁱⁱ	0.98 (2)	2.64 (2)	3.515 (2)	148 (2)
P-HO1ⁱⁱⁱ	1.28 (2)	2.58 (2)	3.4713 (12)	124 (1)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5583 ).

Acknowledgements

This work was partially supported by the Polish Ministry of Science and Higher Education through grant No. N204 028538. The financial support is gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Beletskaya, I. P. & Cheprakov, A. V. (2000). Chem. Rev. 100, 3009-3066.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Maffei, M. & Buono, G. (2003). Tetrahedron, 59, 8821-8825.
Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Skarzynska, A., Trzeciak, A. M. & Siczek, M. (2011). Inorg. Chim. Acta, 365, 204-210.
Zwierzak, A. (1967). Can. J. Chem. 45, 2501-2512.

organic compounds

4,4,5,5-Tetramethyl-1,3,25-dioxaphospholan-2-one