2-[(4-Chloro­phen­yl)(hy­droxy)meth­yl]-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

Wang, C.; Peng, H.; He, H.

doi:10.1107/S1600536811008944

Volume 67
Part 4
Page o926
April 2011

Received 4 March 2011
Accepted 9 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.062
wR = 0.154
Data-to-parameter ratio = 20.9
Details

2-[(4-Chlorophenyl)(hydroxy)methyl]-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

Chubei Wang,^a Hao Peng ^a and Hongwu He ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Correspondence e-mail: he1208@mail.ccnu.edu.cn

In the title compound, C₁₂H₁₆ClO₄P, the phosphonate ring adopts a chair conformation. In the crystal, intermolecular O-HO hydrogen bonds link the molecules into chains propagating along the b axis.

Related literature

For the synthesis of hydroxyphosphonates, see: Zhou et al. (2008). For the synthesis and biological activity of hydroxyphosphonate derivatives, see: Peng et al. (2007); Liu et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₂H₁₆ClO₄P
M_r = 290.67
Monoclinic, P 2₁ /c
a = 12.8965 (11) Å
b = 9.4449 (8) Å
c = 11.6425 (10) Å
= 98.630 (1)°
V = 1402.1 (2) Å³
Z = 4
Mo K radiation
= 0.39 mm^-1
T = 298 K
0.23 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
10123 measured reflections
3463 independent reflections
3141 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.154
S = 1.15
3463 reflections
166 parameters
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4O3ⁱ	0.82	1.89	2.705 (3)	172
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2424 ).

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2010CB126100) and the National Natural Science Foundation of China (Nos. 20772042, 21002037). This work was supported in part by the PCSIRT (No. IRT0953).

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.
Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Liu, H., Zhou, Y. G., Yu, Z. K., Xiao, W. J., Liu, S. H. & He, H. W. (2006). Tetrahedron Lett. 62, 11207-11217.
Peng, H., Wang, T., Xie, P., Chen, T., He, H. W. & Wan, J. (2007). J. Agric. Food Chem. 55, 1871-1880.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhou, X., Liu, X. H., Yang, X., Shang, D. J., Xin, J. G. & Feng, X. M. (2008). Angew. Chem. Int. Ed. 47, 392-394.

organic compounds