Crystal structure of (E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one

Abstract

In the title Schiff base, C14H13NO4, which adopts the phenol–imine tautomeric form, the dihedral angle between the planes of the benzene and heterocyclic (r.m.s. deviation = 0.037 Å) rings is 53.31 (11)°. An intramolecular O—H...N hydrogen bond closes an S(6) ring. In the crystal, molecules are linked by O—H...O hydrogen bonds to generate C(11) chains propagating in the [010] direction. A weak C—H...O link is also observed, leading to the formation of R55(32) rings extending parallel to the (101) plane.

Keywords

• crystal structure
• hydroxy Schiff base
• pyran-2-one
• phenol–imine tautomer
• hydrogen bonding
• proton-transfer processes