Crystal structure and DFT study of (E)-2,6-di- tert-butyl-4-{[2-(pyridin-2-yl)hydrazin-1-yl-idene)meth-yl}phenol

Md Serajul Haque Faizi; Ashanul Haque; Mustafa Dege; Necmi Dege; Maria L Malysheva

doi:10.1107/S2056989017011707

Crystal structure and DFT study of (E)-2,6-di- tert-butyl-4-{[2-(pyridin-2-yl)hydrazin-1-yl-idene)meth-yl}phenol

Acta Crystallogr E Crystallogr Commun. 2017 Sep 12;73(Pt 10):1449-1452. doi: 10.1107/S2056989017011707. eCollection 2017 Oct 1.

Authors

Md Serajul Haque Faizi¹, Ashanul Haque¹, Mustafa Dege², Necmi Dege³, Maria L Malysheva⁴

Affiliations

¹ Department of Chemistry, College of Science, Sultan Qaboos University, PO Box 36 Al-Khod 123, Muscat, Sultanate of , Oman.
² Spraying Systems Company Turkey, Esentepe Mah. Kore Şehitleri Cad. Kaya Aldoğan Sok., Serhan apt. No:3 Daire:3 Şişli / İstanbul, Turkey.
³ Ondokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, Atakum 55139 Samsun, Turkey.
⁴ Department of Chemistry, Taras Shevchenko National University of Kyiv, 64, Vladimirska Str., Kiev 01601, Ukraine.

Abstract

The title compound, C₂₀H₂₇N₃O, was synthesized by condensation reaction of 3,5-di-tert-butyl-4-hy-droxy-benzaldehyde and 2-hydrazinyl-pyridine, and crystallizes in the centrosymmetric monoclinic space group C2/c. The conformation about the C=N bond is E. The dihedral angle between the rings is 18.1 (3)°. An inter-molecular N-H⋯N hydrogen bond generates an R₂²(8) ring motif. In the crystal, N-H⋯N hydrogen bonds connect pairs of mol-ecules, forming dimers. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state.

Keywords: 2- hydrazinopyridine; 3,5-di-tert-butyl-4-hydroxybenzaldehyde; Schiff base; crystal structure; hydrazine; hydrogen bonding.