Molecular structures and supramolecular architectures of two chromogenic 13-membered azobenzocrown ethers with a peripheral hydroxyl group in the benzene ring

Structures of two derivatives of 13-membered azobenzocrown ether with a peripheral hydroxyl group in the benzene ring were determined by single crystal X-ray crystallography. In the solid state the 13-membered azobenzocrown ether with OH side substituent in the aromatic residue in para position to azo group exist in a quinone–hydrazone form. This form is stabilized by a strong intramolecular hydrogen bond. The second compound bears peripheral OH group in ortho position and bulky tert-butyl group in para position to the ether bonding. The effect of peripheral groups on supramolecular architecture is discussed. q 2004 Elsevier B.V. All rights reserved.