3-[1-(Ethylamino)ethylidene]-6-methyl-3H-pyran-2,4-dione

Acta Crystallogr C. 1993 May 15:49 ( Pt 5):980-2. doi: 10.1107/s0108270192010928.

Abstract

The structural results clearly indicate that 3-[1-(ethylamino)ethylidene]-6-methyl-3H-pyran-2,4-dione exists as a keto-enamine tautomer in the solid state. The H atom bonded to N(9) refines with a normal temperature factor and the bond distance of the keto group [C(4)--O(13)] of 1.263 (1) A is elongated due to resonance. This resonance is also indicated by an averaging of the single bonds [C(2)--C(3), C(3)--C(4), C(4)--C(5) and C(8)--N(9)] and double bonds [C(3)--C(8) and C(4)--O(13)] in the crystal structure and by the fact that not only is the pyran ring planar [r.m.s. deviation 0.0212 (9) A] but also there is planarity for the whole molecule [r.m.s. deviation 0.074 (1) A]. A strong intramolecular hydrogen bond is found between the 4-oxo group and the amine H atom.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Hydrogen Bonding
  • Molecular Structure
  • Pyrones / chemistry*
  • X-Ray Diffraction

Substances

  • Pyrones
  • 3-(1-(ethylamino)ethylidene)-6-methyl-3H-pyran-2,4-dione