Crystal structure and DFT study of the zwitterionic form of 3-{()-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2-pyran-4-olate.

Fiche publication

Date publication

février 2018

Journal

Acta crystallographica. Section E, Crystallographic communications

Auteurs

Membres identifiés du Cancéropôle Est :
Dr CLEYMAND Franck

Tous les auteurs :
Djedouani A, Anak B, Tabti S, Cleymand F, François M, Fleutot S

Lien Pubmed

https://www.ncbi.nlm.nih.gov/pubmed/29850047

Résumé

The title Schiff base compound, CHNO, crystallizes as a zwitterion, with the phenolic H atom having been transferred to the imino group. The resulting iminium and hy-droxy groups are linked by an intra-molecular N-H⋯O hydrogen bond, enclosing an (6) ring motif. The conformation about the C=N bond is and the dihedral angle between the benzene and pyran rings is 70.49 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. There are also C-H⋯π inter-actions and offset π-π inter-actions, involving the pyran rings [inter-centroid distance = 3.4156 (8) Å], which consolidate the three-dimensional structure. Quantum chemical calculations of the mol-ecule are in good agreement with the solid state keto-amine (NH) form of the title compound.