Abstract
The title Schiff base compound, C17H13N3O3, crystallizes in a zwitterionic form and exists in a trans configuration about the C=N bond. The molecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80 (9)°. The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88 (12)°]. Bifurcated intramolecular N—H⋯N and N—H⋯O hydrogen bonds formed between iminium groups and amine N atoms and naphthalen-2-olate O atoms generate S(5) and S(6) ring motifs, respectively. In the crystal, neighbouring zwitterions are linked through weak C—H⋯O interactions, giving rise to screw chains along [010]. Molecules in these chains are linked to those of an adjacent chains through N—H⋯O hydrogen bonds and weak C—H⋯O interactions, forming sheets parallel to the ac plane. O⋯C [2.895 (3) Å] short contacts and π–π interactions [centroid–centroid distance = 3.8249 (19) Å] are also observed.
Highlights
The title Schiff base compound, C17H13N3O3, crystallizes in a zwitterionic form and exists in a trans configuration about the
In the crystal, neighbouring zwitterions are linked through weak C—H O interactions, giving rise to screw chains along [010]
For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986)
Summary
The title Schiff base compound, C17H13N3O3, crystallizes in a zwitterionic form and exists in a trans configuration about the. The molecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80 (9). The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88 (12) ]. Bifurcated intramolecular N—H N and N—H O hydrogen bonds formed between iminium groups and amine. In the crystal, neighbouring zwitterions are linked through weak C—H O interactions, giving rise to screw chains along [010]. Molecules in these chains are linked to those of an adjacent chains through N—. H O hydrogen bonds and weak C—H O interactions, forming sheets parallel to the ac plane.
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