Crystal structure and Hirshfeld surface analysis of (±)- N'-(2-hy-droxy-3-meth-oxy-benzyl-idene)-2-(4-iso-butyl-phen-yl)propionohydrazide

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Laila H Abdel-Rahman; Mohamed Abdel-Hameed; Mustafa R Albayati; Elham A Al-Taif

doi:10.1107/S2056989022007605

Crystal structure and Hirshfeld surface analysis of (±)- N'-(2-hy-droxy-3-meth-oxy-benzyl-idene)-2-(4-iso-butyl-phen-yl)propionohydrazide

Acta Crystallogr E Crystallogr Commun. 2022 Jul 29;78(Pt 8):860-863. doi: 10.1107/S2056989022007605. eCollection 2022 Aug 1.

Authors

Shaaban K Mohamed^{1

2}, Joel T Mague³, Mehmet Akkurt⁴, Laila H Abdel-Rahman⁵, Mohamed Abdel-Hameed⁵, Mustafa R Albayati⁶, Elham A Al-Taif⁷

Affiliations

¹ Chemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England.
² Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt.
³ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁴ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁵ Chemistry Department, Faculty of Science, Sohag University, 82534 Sohag, Egypt.
⁶ Department of Chemistry, College of Science, Kirkuk University, Kirkuk, Iraq.
⁷ Chemistry Department, Faculty of Science, Sana'a University, Sana'a, Yemen.

Abstract

The title mol-ecule, C₂₁H₂₆N₂O₃, adopts a V-shaped conformation and is chiral at the C atom with methyl group attached at the common cut of the edges of the V-conformation and crystallizes as a racemate. It also contains an intra-molecular O-H⋯N hydrogen bond. In the crystal, N-H⋯O hydrogen bonds form chains of mol-ecules extending along the c-axis direction, together with normal van der Waals contacts. The roles of the various inter-molecular inter-actions were clarified by Hirshfeld surface analysis, which reveals that the most important contributions to the crystal packing are from H⋯H (62.6%), C⋯H/H⋯C (15.8%) and O⋯H/H⋯O (15.3%) contacts.

Keywords: Hirshfeld surface analysis; Schiff base; crystal structure; hydrazide; hydrogen bond; ibuprofen.

Grants and funding

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.