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

The title compound, C 13 H 14 N 4 O, 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-1 H -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 .