Received 28 June 2013
The 1,3-diketone group of the title compound, C21H20O6, exists in a keto-enol form stabilized by a strong intramolecular O-HO hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C-O and C-C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, molecules are packed in a layered structure parallel to the b axis through C-HO and - interactions [centroid-centroid distance between stacked benzene rings = 3.868 (2) Å].
For background to this study, see: Ishikawa & Fujii (2011). For related structures, see: Wang et al. (2008); Pillay et al. (2013). For the biological activity of related compounds, see: Tomassini et al. (1994).
Data collection: WinAFC (Rigaku, 1999); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2109 ).
This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for supporting this study.
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