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
2018
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 hydroxy groups are linked by an intramolecular 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, molecules are linked by C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular structure. There are also C—H⋯π interactions and offset π–π interactions, involving the pyran rings [intercentroid distance = 3.4156 (8) A], which consolidate the three-dimensional structure. Quantum chemical calculations of the molecule are in good agreement with the solid state keto–amine (NH) form of the title compound.
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