Abstract
The title compound, C14H12ClNO3, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol-ecule is stabilized by a strong intra-molecular N-H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related mol-ecules are linked by O-H⋯O hydrogen bonds, forming R 2 2(10) rings. Besides this, the mol-ecules form stacks along the [001] direction with C-H⋯π and C-H⋯Cl contacts between the stacks. The inter-molecular inter-actions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%).
Highlights
Schiff bases are widely used as ligands in coordination chemistry (Calligaris & Randaccio, 1987) and they are of interest in various fields because of their diverse biological activity (Lozier et al, 1975; Costamagna et al, 1992)
We report the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surfaces
As shown in Fig. 1., the asymmetric unit of the title compound contains only one molecule, which adopts the keto–enamine tautomeric form: the H atom is located at N1, and the lengths of the N1—C7 and C8—C9 bonds indicate their single-bond character, whereas the O2—C9 and C7—C8 bonds are double (Table 1)
Summary
Schiff bases are widely used as ligands in coordination chemistry (Calligaris & Randaccio, 1987) and they are of interest in various fields because of their diverse biological activity (Lozier et al, 1975; Costamagna et al, 1992). Some Schiff bases derived from salicylaldehyde have attracted the interest of chemists and physicists because they show thermochromism and photochromism in the solid state (Cohen et al, 1964; Hadjoudis et al, 1987). The origin of their photo- and thermochromism is related to the reversible intramolecular proton transfer associated with a change in the electronic structure (Hadjoudis et al, 1987). The o-hydroxy Schiff bases obtained by the condensation of o-hydroxyaldehydes with aniline have been extensively examined in this context Such compounds can exist in two tautomeric forms, viz. We report the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surfaces
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