5,6-Dihy-droxy-7,8-di-meth-oxy-flavone.

Lin-Lin Jing,Zheng-Ping Jia,Lei He,Peng-Cheng Fan,Xiao-Fei Fan

doi:10.1107/s1600536813014451

Lin-Lin Jing, Zheng-Ping Jia + Show 3 more

Open Access

https://doi.org/10.1107/s1600536813014451

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Abstract

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 π–π interactions [3.37 (2)–3.39 (2) Å], which build up a three–dimensional network.

Highlights

The title compound, C17H14O6, is a flavone that was isolated from the petroleum ether-soluble fraction of the rare traditional Chinese medicinal herb Saussurea involucrata
The molecules are linked by O—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds and – interactions [3.37 (2)–3.39 (2) A ], which build up a three–dimensional network
R–factors based on F2 are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger

Summary

Structure Reports Online

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 forms an intramolecular O—HÁ Á ÁO contact. The molecules are linked by O—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds and – interactions [3.37 (2)–3.39 (2) A ], which build up a three–dimensional network. Related literature For biological activity of Saussurea involucrata, see: Zheng et al (1993); Gao et al (2005); Tao et al(2010); Ma et al (2011); Jia et al (2005); Liu et al (1985). See: Xiong et al (2009); Vijayalakshmi et al (1986); Paula et al (2002)

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