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Volume 69 
Part 7 
Page o1096  
July 2013  

Received 12 April 2013
Accepted 25 May 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.070
wR = 0.236
Data-to-parameter ratio = 15.9
Details
Open access

5,6-Dihydroxy-7,8-dimethoxyflavone

aDepartment of Pharmacy, Lanzhou General Hospital of PLA, Key laboratory of the prevention and cure, for the plateau environment damage PLA, 730050, Lanzhou Gansu, People's Republic of China
Correspondence e-mail: zhengping_jia@yahoo.cn

The title compound (systematic name: 5,6-dihydroxy-7,8-dimethoxy-2-phenylchromen-4-one), C17H14O6, is a flavone that was isolated from the petroleum ether-soluble fraction of the rare traditional Chinese medicinal herb Saussurea involucrata. The flavone molecule is almost planar, with a dihedral angle between the planes of the benzopyran-4-one group and the attached phenyl group of 1.89 (6)°. The 5-hydroxy group forms a strong intramolecular hydrogen bond with the carbonyl group, resulting in a six-membered hydrogen-bonded ring. The 6-hydroxy group also forms an intramolecular O-H...O contact. In the crystal, the molecules are linked by O-H...O and C-H...O hydrogen bonds and [pi]-[pi] interactions [3.37 (2)-3.39 (2) Å], which build up a three-dimensional network.

Related literature

For biological activity of Saussurea involucrata, see: Zheng et al. (1993[Zheng, R. L., Liu, G. S., Xing, G. X., Jia, Z. J., Du, M. & Tan, L. Q. (1993). Acta Pharmacol. Sin. 14, S47-S49.]); Gao et al. (2005[Gao, X., Zhang, Z. M., Xu, A. X. & Lei, X. Y. (2005). Zhongguo Yao Xue Za Zhi, 40, 1062-1065.]); Tao et al.(2010[Tao, Y., Zhong, Z. Z., Zhi, L. Y. & Chen, H. B. (2010). J. Ethnopharmacol. 128, 405-411.]); Ma et al. (2011[Ma, H. P., Fan, P. C., Jing, L. L., Yao, J., He, X. Y., Yang, Y., Chen, K. M. & Jia, Z. P. (2011). J. Ethnopharmacol. 137, 1510-1515.]); Jia et al. (2005[Jia, J. M., Wu, C. F. & Liu, W. (2005). Biol. Pharm. Bull. 9, 1612-1614.]); Liu et al. (1985[Liu, L. S., Xiao, X. H. & Zhang, L. D. J. (1985). Lanzhou Univ. Nat. Sci., 4, 80-83.]). For related structures, see: Xiong et al. (2009[Xiong, H.-P., Wu, Z.-J., Chen, F.-T. & Chen, W.-S. (2009). Acta Cryst. E65, o3276-o3277.]); Vijayalakshmi et al. (1986[Vijayalakshmi, J., Rajan, S. S., Srinivasan, R. & Ramachandran Nair, A. G. (1986). Acta Cryst. C42, 1752-1754.]); Paula et al. (2002[Paula, V. F., Barbosa, L. C. A., Errington, W., Howarth, O. W. & Cruz, M. P. (2002). J. Braz. Chem. Soc. 13, 276-280.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14O6

  • Mr = 314.28

  • Triclinic, [P \overline 1]

  • a = 7.953 (6) Å

  • b = 8.548 (6) Å

  • c = 10.951 (8) Å

  • [alpha] = 96.602 (8)°

  • [beta] = 92.282 (8)°

  • [gamma] = 100.279 (7)°

  • V = 726.3 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 295 K

  • 0.21 × 0.16 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 5252 measured reflections

  • 3368 independent reflections

  • 1786 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.236

  • S = 1.03

  • 3368 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O3i 0.82 2.05 2.764 (4) 146
C12-H12...O6ii 0.93 2.58 3.234 (4) 128
O3-H3...O2 0.82 1.84 2.564 (3) 146
O4-H4...O3 0.82 2.34 2.767 (3) 113
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2401 ).


Acknowledgements

We thank the Natural Science Foundation of China (grant No. 81202458) and China Postdoctoral Science Foundation (grant No. 2012M521926) for financial support.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gao, X., Zhang, Z. M., Xu, A. X. & Lei, X. Y. (2005). Zhongguo Yao Xue Za Zhi, 40, 1062-1065.  [ChemPort]
Jia, J. M., Wu, C. F. & Liu, W. (2005). Biol. Pharm. Bull. 9, 1612-1614.  [CrossRef]
Liu, L. S., Xiao, X. H. & Zhang, L. D. J. (1985). Lanzhou Univ. Nat. Sci., 4, 80-83.
Ma, H. P., Fan, P. C., Jing, L. L., Yao, J., He, X. Y., Yang, Y., Chen, K. M. & Jia, Z. P. (2011). J. Ethnopharmacol. 137, 1510-1515.  [Web of Science] [CrossRef] [PubMed]
Paula, V. F., Barbosa, L. C. A., Errington, W., Howarth, O. W. & Cruz, M. P. (2002). J. Braz. Chem. Soc. 13, 276-280.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tao, Y., Zhong, Z. Z., Zhi, L. Y. & Chen, H. B. (2010). J. Ethnopharmacol. 128, 405-411.  [Web of Science] [CrossRef] [PubMed]
Vijayalakshmi, J., Rajan, S. S., Srinivasan, R. & Ramachandran Nair, A. G. (1986). Acta Cryst. C42, 1752-1754.  [CrossRef] [IUCr Journals]
Xiong, H.-P., Wu, Z.-J., Chen, F.-T. & Chen, W.-S. (2009). Acta Cryst. E65, o3276-o3277.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Zheng, R. L., Liu, G. S., Xing, G. X., Jia, Z. J., Du, M. & Tan, L. Q. (1993). Acta Pharmacol. Sin. 14, S47-S49.  [ChemPort]


Acta Cryst (2013). E69, o1096  [ doi:10.1107/S1600536813014451 ]

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