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) Å,V=3415.8(8) ų. 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) Å,V=3423.3(9) Å₃. 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.