Abstract
The title compound, C15H15NO2, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra-molecular N-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers with an R 2 2(18) ring motif. The dimers are linked by very weak π-π inter-actions, forming layers parallel to (01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter-actions.
Highlights
Schiff bases contain the azomethine moiety (–RCH N–R0) and are prepared by condensation reactions between amines and active carbonyl compounds (Schiff, 1864)
We report here its synthesis conditions and the molecular and crystal structures, supplemented by Hirshfeld surface analysis
The C1—O1 bond length [1.356 (3) A ] to the hydroxy group is in the normal range, while the C14 O2 bond length is comparatively elongated [1.302 (4) A ] due to the involvement of the carbonyl O atom in an intramolecular N—HÁ Á ÁO hydrogen bond, forming an S(6) ring motif
Summary
Schiff bases contain the azomethine moiety (–RCH N–R0) and are prepared by condensation reactions between amines and active carbonyl compounds (Schiff, 1864). In the majority of cases, the synthesis involves an aromatic amine and an aldehyde (Schiff et al, 1881). Schiff bases are very important for production of chemical specialties such as pharmaceuticals including antibiotics, and of antiallergic, antitumor, antifungal, antibacterial, antimalarial or antiviral drugs. Schiff bases are employed as catalyst carriers (Grigoras et al, 2001), thermo-stable materials (Vanco et al, 2004), metal–cation complexing agents or in biological systems (Taggi et al, 2002). Schiff bases containing phenol indicate two possible tautomeric forms, viz. A new Schiff base, (Z)-6-{[(2-hydroxy4-methylphenyl)amino]methylidene}-4-methylcyclohexa-2,4dien-1-one, was obtained in crystalline form from the reaction of 2-amino-5-methylphenol with 2-hydroxy-5-methylbenzaldehyde.
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