Abstract

For the purposes of characterizing a novel class of inorganic–organic hybrid epoxy resin materials, a series of amines were reacted with a monoepoxide (1,2-epoxy-3-phenoxypropane) under base catalyzed conditions to produce racemic mixtures of compounds with the general formula PhOCH₂CH(OH)CH₂N(H)R, where R = ⁿPr (1), ⁱPr (2), or ^tBu (3). The crystal structures of these compounds were determined by X-ray crystallography. Compound 1 forms infinite sheets of centrosymmetric dimers. In contrast, as a result of intermolecular hydrogen-bonding, compounds 2 and 3 arrange as tetrameric units in non-centrosymmetric space groups. Through a review of crystal structures found in the Cambridge Crystallographic Database, compounds of the general type X–CH(OH)CH₂N(H)R were investigated and a rationalization for the packing of racemic mixtures in non-centrosymmetric space groups is discussed.