Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate
Abstract
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)°, 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···O contact [2.756(2)Å], 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···O interactions are observed, which link the molecules into [100] chains.
Citation
Tyumentsev , M S , Foreman , M R S J , Steenari , B-M & Slawin , A M Z 2017 , ' Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate ' , Acta Crystallographica Section E , vol. 73 , no. 10 , pp. 1576-1579 . https://doi.org/10.1107/S2056989017013962
Publication
Acta Crystallographica Section E
Status
Peer reviewed
ISSN
2056-9890Type
Journal article
Rights
© 2017 The Authors. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
The research leading to these results received funding from the European Community's Seventh Framework Programme ([FP7/2007–2013]) under grant agreement No. 607411 (MC-ITN EREAN: European Rare Earth Magnet Recycling Network).Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.