Crystal structure of 2-(2,3-di-methyl-anilino)-N'-[(1E)-2-hy-droxy-benzyl-idene]benzohydrazide

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Alaa F Mohamed; Mustafa R Albayati

doi:10.1107/S2056989015021532

Crystal structure of 2-(2,3-di-methyl-anilino)-N'-[(1E)-2-hy-droxy-benzyl-idene]benzohydrazide

Acta Crystallogr E Crystallogr Commun. 2015 Nov 21;71(Pt 12):o957-8. doi: 10.1107/S2056989015021532. eCollection 2015 Dec 1.

Authors

Shaaban K Mohamed¹, Joel T Mague², Mehmet Akkurt³, Alaa F Mohamed⁴, Mustafa R Albayati⁵

Affiliations

¹ Faculty of Science & Engineering, School of Healthcare Science, Manchester Metropolitan University, M1 5GD, England; Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt.
² Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
³ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁴ National Organization for Drug Control and Research, Giza, Egypt.
⁵ Kirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq.

Abstract

The asymmetric unit of the title compound, C22H21N3O2, consists of two independent mol-ecules (A and B) having differing conformations. The differences mainly concern the dihedral angles which the hy-droxy-phenyl and di-methyl-phenyl rings subtend to the central phenyl-ene ring, these being 30.16 (6) and 58.60 (6)° in mol-ecule A and 13.42 (7) and 60.31 (7)° in B. With the exception of the dimethyphenyl substituent, the conformations of the rest of each mol-ecule are largely determined by intra-molecular O-H⋯N and N-H⋯O hydrogen bonds. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains extending parallel to the a axis in which the types of mol-ecules alternate in an …A…B…A…B… fashion.

Keywords: crystal structure; hydrazide-hydrazone compounds; hydrogen bonding; non-steroidal anti-inflammatory drugs (NSAIDs) mefenamic acid (MA).