Received 18 June 2013
The title compound, C16H20O3 [systematic name: 1-hydroxy-7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2(1H)-one], is a sesquiterpene isolated from foliar tissues of the cotton plant and is of interest with respect to its antibacterial properties. Its phenyl ring is ideally planar, and the maximum of deviation in the second ring is 0.386 (3) Å. The hydroxy group and the methyl group are oriented in an equatorial fashion and axial, respectively, to the second ring. In the crystal, inversion dimers are formed through pairs of O-HO hydrogen bonds. Weak C-HO hydrogen bonds link the dimers into columns along the c axis. These columns form a crystal structure with a crystal packing factor of 0.66.
For the original isolation from Ulmus laciniata Mayr and proposed structure, see: Suzuki et al. (1972). For isolation from cotton bracts (Gossypium), identification and structure definition, see: Stipanovic et al. (1975, 1981). For information on the biological activity, see: Essenberg et al. (1982). For biosynthetic studies, see: Stipanovic et al. (1981); Essenberg et al. (1985).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2406 ).
The authors thank the Academy of Sciences of the Republic of Uzbekistan for supporting this work (project Nos. F7-T048 and I5-FA-18897)
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