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, C 20 H 20 N 4 O·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)° in molecules 1 and 2, respectively. In each molecule there is intramolecular C - H⋯O hydrogen bond forming an S(6) ring motif. In molecule 1 there is an intramolecular N - H⋯π(pyrazole) interaction and an intramolecular C - H⋯π(pyrazole) interaction present. Molecule 1 is linked to molecule 2 by a C - H⋯π(benzene ring) interaction. An intramolecular N - H⋯N hydrogen bond and an intramolecular C - H⋯N hydrogen bond are also present in molecule 2. In the crystal, the three components are linked by O water - H⋯N, N - H⋯O water and N - H⋯N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C - H⋯O and C - H⋯N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C - H⋯π interactions, forming a three-dimensional structure. © Chkirate et al. 2019.