Acta Cryst. (2013). E69, o302
[ doi:10.1107/S1600536813002304 ]

Desoxyhemigossypol 6-methyl ether

V. V. Uzbekov, S. A. Talipov, B. T. Ibragimov, R. D. Stipanovic and J. Liu

Abstract: The title sesquiterpene [systematic name: 6-methoxy-10-methyl-7-(propan-2-yl)-2-oxatricyclo[6.3.1.0^4,12]dodeca-1(11),4,6,8(12),9-pentaen-5-ol], C₁₆H₁₈O₃, was isolated from pathogen-infected stele tissue of Gossypium barbadense. There are two molecules in the asymmetric unit and the dihedral angle between their naphthofuran systems is 86.48 (2)°. In the crystal, O-HO hydrogen bonds between the hydroxy groups and etheric O atoms link the molecules into centrosymmetric tetramers. These tetramers are assembled into (010) layers via stacking interactions between the naphthofuran systems [interplanar distance 3.473 (3) Å] and short C-HO contacts.

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