ALANINE-DERIVED HOSTS COMPRISING A ROOF-SHAPED CARBONIMIDE FRAMEWORK - SYNTHESIS, INCLUSION FORMATION AND X-RAY CRYSTAL-STRUCTURES OF RACEMIC AND OPTICALLY RESOLVED FREE HOSTS, AND THEIR CRYSTALLINE COMPLEXES WITH 3-METHYLCYCLOHEXANONE

A chiral crystalline host molecule derived from the amino acid alanine comprising a characteristic -dihydro-9,10-ethanoanthracene-11,12-dica rboximide framework as an inclusion-promoting group has been synthesiz ed in optically resolved and racemic forms and studied with regard to their inclusion behaviour. Dependent on the optical resolution state, this host forms crystalline inclusion compounds with a great variety o f uncharged organic molecules ranging from protic dipolar to rather ap olar compounds (78 different inclusion species) with the racemic host being more efficient. X-Ray crystal structures of the optically resolv ed and racemic uncomplexed host species and of their 1:1 inclusion com plexes with 3-methylcyclohexanone are reported. The host hydroxy group s are always involved in O-H ... O=C intramolecular hydrogen bonds. Th e crystal packings of both complexes are analogous, showing similar ce ll dimensions and space groups P2(1) and P2(1)/a. Moreover, the two in dependent molecules in the resolved complex are almost related by a ps eudo centre of symmetry.