organic compounds
Gossypol and cyclododecanone crystallize at room temperature as an inclusion complex in a 1:2 molar ratio. This complex, viz. 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarboxaldehyde-cyclododecanone (1/2), C30H30O8·2C12H22O, is unusual in that there is limited intermolecular hydrogen bonding within the structure. Each cyclododecanone molecule accepts a hydrogen bond from a gossypol molecule, but there are no gossypol-to-gossypol hydrogen-bond interactions. The gossypol molecules form a framework structure enclosing channels, and the cyclododecanone molecules lie in these channels. In terms of the number of non-H guest atoms, this is the largest gossypol inclusion complex reported to date.