Abstract
In the crystal of the title compound, C15H13NO4·CH3OH, the Schiff base mol-ecule exists in the zwitterionic form; an intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular structure. The benzene rings are nearly co-planar, subtending a dihedral angle of 5.34 (2)°. In the crystal, classical O-H⋯O and weak C-H⋯O hydrogen bonds link the Schiff base mol-ecules and methanol solvent mol-ecules into a three-dimensional supra-molecular architecture. The crystal studied was refined as an inversion twin.
Highlights
The asymmetric unit of the title compound contains a Schiff base molecule and a methanol molecule of crystallization
We report the crystal structure of the title compound synthesized by the condensation reaction of 2-hydroxy-3-methoxybenzaldehyde and PABA
All bond lengths are in normal ranges
Summary
Vanillin and o-vanillin are natural compounds that have both a phenolic OH and an aldehyde group. Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and PABA have not been investigated so thoroughly. Schiff bases often exhibit various biological activities and in many cases have been shown to possess antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al, 1975). They are used as anion sensors (Dalapati et al, 2011), as non-linear optical compounds (Sun et al, 2012) and as versatile polynuclear ligands for multinuclear magnetic exchange clusters (Moroz et al, 2012). We report the crystal structure of the title compound synthesized by the condensation reaction of 2-hydroxy-3-methoxybenzaldehyde and PABA. Symmetry codes: (i) Àx þ 2; y À 12; Àz þ 12; (ii) x þ 1; y þ 1; z; (iii) Àx þ 1; y þ 12; Àz þ 12
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