Crystal structure and Hirshfeld surface analysis of N-{2-[(E)-(4-methylbenzylidene)amino]phenyl}-2-(5-methyl-1-H-pyrazol-3-yl)acetamide hemihydrate

Abstract

The asymmetric unit of the title compound, C20H20N4O center dot 0.5H(2)O, contains two independent organic molecules (1 and 2) and a water molecule of crystallization. The two molecules differ primarily in the dihedral angles between the aromatic rings, which are 7.79 (7) and 29.89 (7)degrees in molecules 1 and 2, respectively. In each molecule there is intramolecular C-H center dot center dot center dot O hydrogen bond forming an S(6) ring motif. In molecule 1 there is an intramolecular N-H center dot center dot center dot pi(pyrazole) interaction and an intramolecular C-H center dot center dot center dot pi(pyrazole) interaction present. Molecule 1 is linked to molecule 2 by a C-H center dot center dot center dot pi(benzene ring) interaction. An intra-molecular N -H center dot center dot center dot N hydrogen bond and an intramolecular C-H center dot center dot center dot N hydrogen bond are also present in molecule 2. In the crystal, the three components are linked by O-water - H center dot center dot center dot N, N -H center dot center dot center dot O-water and N-H center dot center dot center dot N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C-H center dot center dot center dot pi interactions, forming a three-dimensional structure.