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

ABSTRACT: The title Schiff base compound, C16H17NO4, 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 S(6) ring motif. The conformation about the C=N bond is E 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?? inter-actions and offset ?-? 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.

SUBMITTER: Djedouani A 

PROVIDER: S-EPMC5956330 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Djedouani Amel A   Anak Barkahem B   Tabti Salima S   Cleymand Franck F   François Michel M   Fleutot Solenne S  

Acta crystallographica. Section E, Crystallographic communications 20180116 Pt 2

The title Schiff base compound, C<sub>16</sub>H<sub>17</sub>NO<sub>4</sub>, 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 <i>S</i>(6) ring motif. The conformation about the C=N bond is <i>E</i> 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  ...[more]

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