Abstract
The title compound, C14H12N2O4, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming dimers with an R 2 2(18) ring motif. The dimers are linked by pairs of C-H⋯O contacts with an R 2 2(10) ring motif, forming ribbons extended along the [20] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) inter-actions.
Highlights
Compounds containing the RHC NR fragment, obtained by the condensation reaction of primary amines with aldehydes or ketones under proper conditions, are named Schiff bases after Hugo Schiff (Schiff, 1864)
We report here the synthesis and the crystal and molecular structures of the title compound along with the results of a Hirshfeld surface analysis
The O4 C9, C9—C8, C8 C7, C7—N2 and N2—C5 bond lengths are typical of double and single bonds, respectively (Table 1), indicating that the title molecule exists as a keto–enamine tautomer (Kansiz et al, 2018)
Summary
Compounds containing the RHC NR fragment, obtained by the condensation reaction of primary amines with aldehydes or ketones under proper conditions, are named Schiff bases after Hugo Schiff (Schiff, 1864). Schiff bases have a wide variety of applications in many areas such as analytical, biological, and inorganic chemistry (Jain et al, 2008; Lozier et al, 1975; Calligaris & Randaccio, 1987). Many Schiff bases are biologically active and some bases show phototochromism which can be used for radiation intensity measurements, display systems or optical devices (Hadjoudis et al, 1987). A new Schiff base, (Z)-6-[(2-hydroxy-5nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one, was obtained in crystalline form from the reaction of 2-amino4-nitrophenol with 2-hydroxy-5-methylbenzaldehyde. We report here the synthesis and the crystal and molecular structures of the title compound along with the results of a Hirshfeld surface analysis
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