Absolute configuration and crystal packing chirality for three conglomerate-forming ortho-halogen substituted phenyl glycerol ethers

Three conglomerate-forming ortho-Hal (Hal = Cl, Br, I) substituted phenyl glycerol ethers 1–3 were investigated by single-crystal X-ray analysis, and the absolute configuration for all substances was established. The molecular structures and crystal packing details for halogen derivatives were compared with the same characteristics for ortho-OCH3 and ortho-CH3 analogues. Two different types of crystal packing were evaluated for these very much alike compounds. The interplay of the supramolecular crystal organization chirality sense and the single molecule absolute configuration was demonstrated. Some stabilizing and destabilizing interactions involving the ortho-substituents were revealed. The resolution of rac-2 by entrainment procedure was successfully realized.