1-(2-Hy­droxy-3,5-dimeth­oxy­phen­yl)ethanone

Li, W.; Li, X.; Duan, Y.; Deng, Z.; Wang, R.

doi:10.1107/S1600536811052974

Volume 68
Part 1
Page o116
January 2012

Received 1 December 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 16.9
Details

1-(2-Hydroxy-3,5-dimethoxyphenyl)ethanone

Wenming Li,^a Xiaobo Li,^a Yuqing Duan,^a Zhirong Deng ^a and Runling Wang ^a ^*

^aTianjin Key Laboratory on Technologies Enabling Development of Clinical, Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China
Correspondence e-mail: wangrunling@tijmu.edu.cn

In title compound, C₁₀H₁₂O₄, all of the non-H atoms lie approximately in a plane with the largest deviation being 0.061 (2) Å. An intramolecular O-HO hydrogen bond generates an S(6) ring motif. No classical intermolecular hydrogen bonding occurs, with only van der Waals forces stabilizing the crystal structure.

Related literature

For the biological activity of isoflavones, see: Wang & Murphy (1994); Yoshio et al. (1989). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the preparation, see: Aalten et al. (1989).

Experimental

Crystal data

C₁₀H₁₂O₄
M_r = 196.20
Monoclinic, P 2₁ /n
a = 7.733 (4) Å
b = 8.059 (4) Å
c = 14.851 (7) Å
= 91.416 (10)°
V = 925.3 (7) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 113 K
0.26 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) T_min = 0.972, T_max = 0.987
10288 measured reflections
2212 independent reflections
1621 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.091
S = 1.04
2212 reflections
131 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O4	0.84	1.83	2.5666 (14)	145

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5147 ).

Acknowledgements

This study was supported by the National Natural Science Foundation of China (grant No. 20972112), the Research Fund for the Doctoral Program of Higher Education of China (grant No. 20091202110010), the Key Program of Tianjin Municipal Natural Science Foundation (grant No. 09JCZDJC21600), as well by Beijing Honghui Meditech Co. Ltd.

References

Aalten, H. L., Van Koten, G., Grove, D. M., Kuilman, T., Piekstra, O. G., Hulshof, L. A. & Sheldon, R. A. (1989). Tetrahedron, 45, 5565-5578.
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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, H. & Murphy, P. A. (1994). J. Agric. Food Chem. 42, 1666-1673.
Yoshio, I., Kenji, Y., Yukinori, T. & Shoshiro, N. (1989). J. Antibiot. 42, 1523-1525.

organic compounds