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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 16.9
Details
Open access

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

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-H...O 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[Wang, H. & Murphy, P. A. (1994). J. Agric. Food Chem. 42, 1666-1673.]); Yoshio et al. (1989[Yoshio, I., Kenji, Y., Yukinori, T. & Shoshiro, N. (1989). J. Antibiot. 42, 1523-1525.]). For bond-length data, see: Allen et al. (1987[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.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the preparation, see: Aalten et al. (1989[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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12O4

  • Mr = 196.20

  • Monoclinic, P 21 /n

  • a = 7.733 (4) Å

  • b = 8.059 (4) Å

  • c = 14.851 (7) Å

  • [beta] = 91.416 (10)°

  • V = 925.3 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA]) Tmin = 0.972, Tmax = 0.987

  • 10288 measured reflections

  • 2212 independent reflections

  • 1621 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.04

  • 2212 reflections

  • 131 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O4 0.84 1.83 2.5666 (14) 145

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ChemPort] [ISI]
Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, H. & Murphy, P. A. (1994). J. Agric. Food Chem. 42, 1666-1673.  [CrossRef] [ChemPort] [ISI]
Yoshio, I., Kenji, Y., Yukinori, T. & Shoshiro, N. (1989). J. Antibiot. 42, 1523-1525.  [PubMed]


Acta Cryst (2012). E68, o116  [ doi:10.1107/S1600536811052974 ]

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