Crystal structure and Hirshfeld surface analysis of 5-hy-droxy-penta-nehydrazide

Acta Crystallogr E Crystallogr Commun. 2024 Apr 9;80(Pt 5):459-462. doi: 10.1107/S2056989024002871. eCollection 2024 Apr 1.

Abstract

Carb-oxy-hydrazides are widely used in medicinal chemistry because of their medicinal properties and many drugs have been developed containing this functional group. A suitable inter-mediate to obtain potential hydrazide drug candidates is the title compound 5-hy-droxy-penta-nehydrazide, C5H12N2O2 (1). The aliphatic compound can react both via the hydroxyl and hydrazide moieties forming derivatives, which can inhibit Mycobacterium tuberculosis catalase-peroxidase (KatG) and consequently causes death of the pathogen. In this work, the hydrazide was obtained via a reaction of a lactone with hydrazine hydrate. The colourless prismatic single crystals belong to the ortho-rhom-bic space group Pca21. Regarding supra-molecular inter-actions, the compound shows classic medium to strong inter-molecular hydrogen bonds involving the hydroxyl and hydrazide groups. Besides, the three-dimensional packing also shows weak H⋯H and C⋯H contacts, as investigated by Hirshfeld surface analysis (HS) and fingerprint plots (FP).

Keywords: 5-hy­droxypentanehydrazide; crystal structure; hydrazide; lactone; medicinal chemistry.

Grants and funding

Funding for this research was provided by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (grant No. 23038.003745/2021-31); Pró-Reitoria de Planejamento, Orçamentos e Finanças - UFPR - PROIND 2020 (grant No. 3527).