Abstract
In the title compound, C19H15N3O3, which crystallizes as the phenol-imine tautomer, the dihedral angle between the aromatic rings bridged by the NH unit is 47.16 (16)°. The dihedral angle between the rings bridged by the imine unit is 6.24 (15)°; this near coplanarity is reinforced by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, N-H⋯O hydrogen bonds generate [201] C(13) chains. The chains are reinforced and cross-linked by C-H⋯O inter-actions to generate (001) sheets.
Highlights
6.24 (15) ; this near coplanarity is reinforced by an intramolecular O—H N hydrogen bond, which generates an S(6) ring
As part of our ongoing studies of Schiff bases and their complexes (Faizi et al, 2016), we report the synthesis and crystal structure of the title compound, (I)
The overall twisted conformation of the molecule is largely determined by the orientation of the terminal aminophenyl ring (C14–C19) with respect to the central benzene ring (C8–C13); the dihedral angle between them is 47.18 (4)
Summary
Schiff bases derived from 2-hydroxy-5-nitrobenzaldehyde are widely used either as materials or as intermediates in explosives, dyestuffs, pesticides and organic synthesis (Yan et al., 2006). Intramolecular hydrogen-atom transfer (tautomerism) from the o-hydroxy group to the imine-N atom is of prime importance with respect to the solvato-, thermo- and photochromic properties exhibited by o-hydroxy Schiff bases (Filarowski, 2005; Hadjoudis et al, 2004). As part of our ongoing studies of Schiff bases and their complexes (Faizi et al, 2016), we report the synthesis (from 2-hydroxy-5nitrobenzaldehyde and N-phenyl-p-phenylenediamine) and crystal structure of the title compound, (I)
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