Easy synthesis and crystal structure of a novel ortho hydroxyl Schiff base compound CH2—{cyclo-C6H10)—NCH—C6H4—OH-2}2

Abstract

A one-pot and neat reaction procedure is used for the synthesis of CH2—{cyclo-C6H10)—NCH—C6H4—OH-2}2. 1H NMR shows a mixture of ZE and EE isomers in a ratio of 2:0.9. The EE isomer is easily isolated as crystals suitable for the X-ray analysis. 1H,13C NMR and UV-visible spectra of the title compound are studied in different solvents. The crystal structure shows intramolecular H bonds as an EE isomer. The molecule lies about a twofold symmetry axis, passing through the C1 atom. The cyclo-hexyl ring C2—7 shows a chair conformation, with both C2—C1 and C5—N1 bonds in equatorial orientations. The phenolic hydrogen atom H1a forms a good hydrogen bond with the imino nitrogen atom N1 and the N1—C8 bond is short, as expected for a double bond (1.265(4) Å).