On the optical resolution of bicyclic enones through host-guest complex formation: The crystallographic result

Abstract

The structures of two molecular inclusion complexes have been elucidated by X-ray crystallography from single crystal diffraction data. Compound (1): (−)-(R,R)-trans-4,5-bis(hydroxy-diphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane·(−)-R-6-methylbicyclo[4.4.0] dec-1-ene-3-one, C31H30O4·C11H16O, is orthorhombicP212121,a=9.606(2),b=9.708(1),c=36.628(3) A,V=3415.8(8) A3. Compound (2): (−)-(R,R)-trans-4,5-bis(hydroxy-diphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane. (−)-R-6-methylbicyclo[4.4.0]dec-1-ene-3,7-dione, C31H30O4·C11H14O2, is orthorhombicP212121,a=9.671(1),b=9.691(2),c=36.526(4) A,V=3423.3(9) A3. Each structure was solved by direct methods and refined to final R values of 0.051. In each structure there is host-host and host-guest hydrogen bonding: despite the existence of a second H-bond acceptor in the guest of (2), the structures of (1) and (2) are isomorphous; the thermal properties of (1) and (2) have been characterized by DTA and TGA thermograms.