Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzo-furan-1-ylidene)malonate
Journal article, 2017

The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45 (3) and 83.30 (3)degrees, respectively]. The C-C and C-O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O center dot center dot center dot O contact [2.756 (2) angstrom], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C-H center dot center dot center dot O interactions are observed, which link the molecules into [100] chains.

acylation

Author

Mikhail S Tyumentsev

Chalmers, Chemistry and Chemical Engineering, Energy and Material

Mark Foreman

Chalmers, Chemistry and Chemical Engineering, Energy and Material

Britt-Marie Steenari

Chalmers, Chemistry and Chemical Engineering, Energy and Material

Alexandra M. Z. Slawin

University of St Andrews

Acta Crystallographica Section E: Crystallographic Communications

2056-9890 (eISSN)

Vol. 73 10 1576-1579

Subject Categories

Chemical Sciences

DOI

10.1107/S2056989017013962

More information

Latest update

10/26/2022