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

Abstract

The title compound, C13H14N4O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-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-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}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 molecules in the asymmetric unit (A, B and C) are not planar, the cyclobutyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in molecule A, 69.1 (2)° in molecule B and 89.1 (2)° in molecule C. In each molecule an intramolecular 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 intermolecular contacts within the supramolecular structure. The major interactions are H...H (53%), C...H (19%) and N...H (17%) for molecule A, H...H (50%), N...H (20%) and C...H (20%) for molecule B and H...H (57%), C...H (14%) and N...H (13%) for molecule C.