Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide

Abstract

The title compound, C15H14N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit that differ in the orientation of the 3-methoxyphenyl group with respect to the methylidenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02 (10) and 29.30 (9)° in molecules A and B, respectively. In molecule A, the methoxy group is twisted slightly relative to its bound benzene ring, with a Cmethyl—O—C—C torsion angle of 14.2 (3)°, whereas it is almost co-planar in molecule B, where the corresponding angle is −2.4 (3)°. In the crystal, the molecules are linked by N—H...O, O—H...N and O—H...O hydrogen bonds, as well as by weak C—H...O interactions, forming sheets parallel to the bc plane. The N—H...O hydrogen bond and weak C—H...O interaction link different molecules (A...B) whereas both O—H...N and O—H...O hydrogen bonds link like molecules (A...A) and (B...B). Pairs of inversion-related B molecules are stacked approximately along the a axis by π–π interactions in which the distance between the centroids of the 3-methoxyphenyl rings is 3.5388 (12) Å. The B molecules also participate in weak C—H...π interactions between the 4-hydroxyphenyl and the 3-methoxyphenyl rings.

Keywords

• Benzohydrazides
• α-glucosidase inhibitory
• X-ray
• crystal structure