Several esters of chiral mono- and dialcohols and N-(1,8-naph- thaloyl)-2-amino benzoic acid (NAB) have been investigated by X-ray crystallography and quantum-chemical methods. The investigated molecules can be considered as consisting of two parts: the aliphatic core (either linear or cyclic) and the aromatic NAB moiety(ies). Mutual arrangement of the two parts is such that either the aliphatic skeleton is put away from the naphtalimide unit (conformer A, extended) or it is situated above the unit (conformer B, folded) (1). Quantum chemical calculations (ONIOM method (2)) indicate that the A conformer is energet- ically preferred over the B one, in both mono- and diesters, and that the two aromatic rings constituting the NAB chromophore are inclined to each other at exactly right angles. In crystals the situation is more complex, as we observe both the A and B conformers, and deviations from orthogonality of the aromatic fragments. The latter effect combined with severe twisting around the Caryl-Cester bond induces plus (P) or minus (M) helicity into the NAB moiety. The investigated crystals, being chiral, display a tendency to form multiple asymmetric units and non-merohedral twins. These structural peculiarities may be connected with the fact that the face stacking interactions involve molecules of opposite helicity and that both the molecular helicity and the crystal packing are mostly stabi- lized by antiparallel dipolar interactions.