Abstract
The title compound, C33H42O5, known as xerophenone A {systematic name: (1R,3R,4R,6S,8E,10R)-10-hydroxy-8-[hydroxy(phenyl)methylene]-4-methyl-1,6-bis(3-methylbut-2-en-1-yl)-3-(3-methylbut-3-en-1-yl)-11-oxatricyclo[4.3.1.14,10]undecane-7,9-dione} is a naturally occurring rearranged benzophenone compound which was isolated from the twigs of Garcinia propinqua. The absolute configuration was determined by refining the Flack parameter to 0.18 (16). The absolute configurations at positions 1, 3, 4, 6 and 10 of the xerophenone A are R, R, R, S and R. In the molecule, the cyclohexane-1,3-dione, tetrahydro-2H-pyran and tetrahydrofuran rings adopt twisted boat, standard chair and envelope conformations, respectively. The 3-methylbut-3-en-1-yl substituent is disordered over two sets of sites in a 0.771 (11):0.229 (11) ratio. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by O—H⋯O and weak C—H⋯O interactions into a chain along the a axis. A very weak C—H⋯π interaction and C⋯O short contact [2.989 (2) Å] are also present.
Highlights
Acta Crystallographica Section E (2005); Xu et al (2010); Yu et al (2007)
For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986)
{systematic name: (1R,3R,4R,6S,8E,10R)-10-hydroxy-8-[hydroxy(phenyl)methylene]-4-methyl-1,6-bis(3-methylbut-2-en1-yl)-3-(3-methylbut-3-en-1-yl)-11-oxatricyclo[4.3.1.1 4,10 ]undecane-7,9-dione} is a naturally occurring rearranged benzophenone compound which was isolated from the twigs of Garcinia propinqua
Summary
USM, Penang, Malaysia, bNatural Products Research Laboratory, School of Science, Mae Fah Luang University, Tasud, Muang Chiang Rai 57100, Thailand, and cCrystal. Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand. Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.003 Å; disorder in main residue; R factor = 0.037; wR factor = 0.099; data-to-parameter ratio = 12.9. The absolute configuration was determined by refining the Flack parameter to 0.18 (16). The absolute configurations at positions 1, 3, 4, 6 and 10 of the xerophenone A are R, R, R, S and R. The cyclohexane-1,3-dione, tetrahydro-2H-pyran and tetrahydrofuran rings adopt twisted boat, standard chair and envelope conformations, respectively. Molecules are linked by O—H O and weak C—H O interactions into a chain along the a axis. H interaction and C O short contact [2.989 (2) Å] are present
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