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·0.5H2O, 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 Owater—H...N, N—H...Owater 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.

Keywords

• crystal structure
• pyrazole
• hydrogen bonding
• N—H...π interactions
• C—H...π(ring) interactions
• Hirshfeld surface analysis