Crystal structures of two hydrazide derivatives of mefenamic acid, 3-(2,3-dimethylanilino)-N '-[(E)-(furan-2-yl)methylidene]benzohydrazide and N '-[(E)-benzylidene]-2-(2,3-dimethylanilino)benzohydrazide


Mohamed S. K. , Mague J. T. , AKKURT M., Albayati M. R. , Elgarhy S. M. , Al-Taifi E. A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.77, pp.242-256, 2021 (ESCI) identifier identifier identifier

Abstract

The conformation about the central benzene ring in the molecule of (I), C20H19N3O2, is partially determined by an intramolecular N-H center dot center dot center dot O hydrogen bond. In the crystal, chains parallel to the c axis are generated by intermolecular N-H center dot center dot center dot O hydrogen bonds with the chains assembled into a three-dimensional network structure by intermolecular C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi(ring) interactions. The molecule of (II), C22H21N3O, differs from (I) only in the substituent at the hydrazide N atom where a phenylmethylene moiety for (II) is present instead of a furanmethylene moiety for (I). Hence, molecules of (I) and (II) show similarities in their molecular and crystal structures. The conformation of the central portion of the molecule of (II) is also therefore partially determined by an intramolecular N-H center dot center dot center dot O hydrogen bond and intermolecular N-H center dot center dot center dot O hydrogen bonds form chains parallel to the c axis. Likewise, the chains are connected into a three-dimensional network by C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi(ring) interactions.