Crystal Structure Of An Aryl Cyclohexyl Nonanoid, An Antiproliferative Molecule Isolated From The Spice Myristica Malabarica

The title compound, C21H26O5, an aryl cyclohexyl nonanoid {systematic name: 3,5-dihydroxy-2-[9-(4-hydroxyphenyl) nonanoyl] cyclohexa-2,4-dien-1-one}, extracted from the spice plant Myristica malabarica comprises two ring components, a 4-hydroxyphenyl moiety and a 3,5-dihydroxycyclohexa-2,4-dienone moiety linked by a nonanoyl chain. The molecule has an extended essentially planar conformation stabilized by an intramolecular hydroxy OH center dot center dot center dot O-carbonyl hydrogen bond, giving a dihedral angle between the two ring systems of 6.37 (15)degrees. The C, O and H atoms associated with one of the hydroxy groups of the cyclohexadienone component are disordered over two sets of sites with site occupancies of 0.6972 and 0.3028. In the crystal, hydroxy O-H center dot center dot center dot O hydrogen bonds to carbonyl O-atom acceptors form large centrosymmetric R-2(2) (36) cyclic dimers, which are further extended into supramolecular onedimensional ribbon structures along [111].