Alpha,beta-unsaturated ketoximes carrying a terminal pyridine or quinoline subunit as building blocks for supramolecular syntheses. 
[Structure: see text].  The crystal structures of a new series of alpha,beta-unsaturated ketoximes, 8-14, carrying the terminal 4-pyridinyl, 3-pyridinyl, or 4-quinolinyl subunit have been investigated by X-ray structural analysis.  The dominating intermolecular interaction in all structures, except 11, is the head-tail OH...N hydrogen bond between the oxime moiety and the nitrogen atom of the heterocyclic unit.  This intermolecular interaction generates infinite chains, which are cross-linked by CH...O/N/Cl or CH...pi interactions.  Compound 10 has been shown to adopt a double-helical structure in the crystalline state.  Compound 11 represents the only case where the unexpected head-head NOH...N(OH) hydrogen bonds determine the crystal packing.  Both hydrogen-bonding and aromatic interactions stabilize the crystal structures of 8-14.