Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methyl-phen-yl)-2-(5-methyl-1 H-pyrazol-3-yl)acetamide

Gamal Al Ati; Karim Chkirate; Joel T Mague; Nadeem Abad; Redouane Achour; El Mokhtar Essassi

doi:10.1107/S205698902100503X

Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methyl-phen-yl)-2-(5-methyl-1 H-pyrazol-3-yl)acetamide

Acta Crystallogr E Crystallogr Commun. 2021 May 14;77(Pt 6):638-642. doi: 10.1107/S205698902100503X. eCollection 2021 Jun 1.

Authors

Gamal Al Ati¹, Karim Chkirate¹, Joel T Mague², Nadeem Abad³, Redouane Achour¹, El Mokhtar Essassi¹

Affiliations

¹ Laboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, Morocco.
² Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
³ Department of Biochemistry, Faculty of Education & Science, Al-Baydha University, Yemen.

Abstract

The title mol-ecule, C₁₃H₁₆N₄O, adopts an angular conformation. In the crystal a layer structure is generated by N-H⋯O and N-H⋯N hydrogen bonds together with C-H⋯π(ring) inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (53.8%), H⋯C/C⋯H (21.7%), H⋯N/N⋯H (13.6%), and H⋯O/O⋯H (10.8%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 5.0452 eV.

Keywords: crystal structure; hydrogen bond; pyrazolylacetamide.