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

2021 
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.
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