Crystal structure and Hirshfeld surface analysis of 3-(hy-droxy-meth-yl)-3-methyl-2,6-di-phenyl-piperidin-4-one

Mustafa Kemal Gümüş; Sevgi Kansiz; Gulzhamal Bagitovna Tulemisova; Necmi Dege; Eiad Saif

doi:10.1107/S2056989021012640

Crystal structure and Hirshfeld surface analysis of 3-(hy-droxy-meth-yl)-3-methyl-2,6-di-phenyl-piperidin-4-one

Acta Crystallogr E Crystallogr Commun. 2022 Jan 1;78(Pt 1):29-32. doi: 10.1107/S2056989021012640.

Authors

Mustafa Kemal Gümüş^{1

2}, Sevgi Kansiz³, Gulzhamal Bagitovna Tulemisova², Necmi Dege⁴, Eiad Saif^{5

6}

Affiliations

¹ Science-Technology Research and Application Center, Artvin Coruh University, Artvin, Turkey.
² Department of Chemistry and Chemical Technologies, Faculty of Natural and Agricultural Sciences, Atyrau State University named after Kh. Dosmukhamedov, 060011, Atyrau, Kazakhstan.
³ Samsun University, Faculty of Engineering, Department of Fundamental Sciences, 55420, Samsun, Turkey.
⁴ Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey.
⁵ Department of Computer and Electronic Engineering Technology, Sanaa Community College, Sanaa, Yemen.
⁶ Department of Electrical and Electronic Engineering, Faculty of Engineering, Ondokuz Mayıs University, 55139, Samsun, Turkey.

Abstract

A new synthesis of the title compound, C₁₉H₂₁NO₂, was developed with good yield and purity using the reaction of 4-hy-droxy-3-methyl-2-butanone, benzaldehyde and ammonium acetate in glacial acetic acid as a solvent. The central piperidine ring adopts a chair conformation, and its least-squares basal plane forms dihedral angles of 85.71 (11) and 77.27 (11)° with the terminal aromatic rings. In the crystal, the mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into double ribbons. The Hirshfeld surface analysis shows that the most important contributions are from H⋯H (68%), C⋯H/H⋯C (19%) and O⋯H/H⋯O (12%) inter-actions.

Keywords: 4-hydroxy-3-methyl-2-butanone; Hirshfeld surface; ammonium acetate; benzaldehyde; crystal structure; hydrogen bonding; piperidone.