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

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Chkirate K., Kansiz S., Karrouchi K., Mague J. T., DEGE N., Essassi E. M.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.154-167, 2019 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989018017747
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.154-167
  • Keywords: crystal structure, pyrazole, hydrogen bonding, N-H center dot center dot center dot pi interactions, C-H center dot center dot center dot pi(ring) interactions, Hirshfeld surface analysis, SCHIFF-BASES, PYRAZOLE, DERIVATIVES, COMPLEXES, ANTIOXIDANT, VALIDATION, ANALOGS
  • Ondokuz Mayıs University Affiliated: Yes

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.