Solid solution of two diastereomers of [3a(R,S),7a(R,S)]-3-[(1′R)-1-phenylethyl]perhydro-1,3-benzothiazol-2-iminium chloride

Abstract

A mixture of two diastereomers with the configurations (3aS,7aS,1′R) and (3aR,7aR,1′R) forms co-crystals in which there is one unique molecule in the asymmetric unit, but the molecule displays disorder which is a result of the presence of the two diastereomers at the same crystallographic site. Theoretical calculations carried out by the DFT method with the 6-311++G(2df,p) basis set allowed for the estimation of the energy difference between the two diastereomers both in the isolated and the solid state, while the natural bond orbital (NBO), Mulliken, natural population (NPA) and CHelpG analyses helped to establish the electronic structure of the thazolidin-2-imine fragment.