Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclo butyl-1H-1,2,4-triazol-5-yl)imino] meth yl}phenol

Abstract

The title compound, C13H14N4O, was developed using the reaction of salicyl aldehyde and 3-amino-5-cyclo butyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclo butyl-1H-1,2,4-triazol-5-yl)imino] meth yl}phenol in good yields and purity. The title compound is a Schiff base that exists in the phenol-imine tautomeric form and adopts an E configuration. The three independent mol ecules in the asymmetric unit (A, B and C) are not planar, the cyclo butyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in mol ecule A, 69.1 (2)° in mol ecule B and 89.1 (2)° in mol ecule C. In each mol ecule an intra molecular O - H⋯N hydrogen bond is present, forming an S(6) ring motif. A Hirshfeld surface analysis was performed to investigate the contributions of the different inter molecular contacts within the supra molecular structure. The major inter actions are H⋯H (53%), C⋯H (19%) and N⋯H (17%) for mol ecule A, H⋯H (50%), N⋯H (20%) and C⋯H (20%) for mol ecule B and H⋯H (57%), C⋯H (14%) and N⋯H (13%) for mol ecule C.