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

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)degrees in molecule A, 69.1 (2)degrees in molecule B and 89.1 (2)degrees in molecule C. In each molecule an intramolecular O-H center dot center dot center dot 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 center dot center dot center dot H (53%), C center dot center dot center dot H (19%) and N center dot center dot center dot H (17%) for molecule A, H center dot center dot center dot H (50%), N center dot center dot center dot H (20%) and C center dot center dot center dot H (20%) for molecule B and H center dot center dot center dot H (57%), C center dot center dot center dot H (14%) and N center dot center dot center dot H (13%) for molecule C.