Crystal structure of zerumbone [(E,E,E)-2,6,9,9-Tetramethylcycloundeca-2,6,10-trien-1-one]

Abstract

The crystal structure of zerumbone, C₁₅H₂₂O, extracted from the rhizomes of Zingiber zerumbet Smith, has been determined by single-crystal X-ray diffraction at 295(1) K and refined by least squares to a residual of 0.051 for 925 'observed' reflections. Crystals are monoclinic, space group P2₁/c, a 9.036(3), b 9.712(5), c 15.643(6) Å, β 97.19(3)º, Z = 4. Although the molecule has no chiral centre, the presence of the three trans double bonds confers considerable distortion and rigidity on the eleven-membered ring and renders the whole molecule chiral and potentially resolvable.