Crystal structure and DFT study of (E)-2-chloro-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}phenol acetonitrile hemisolvate

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DEGE N., Faizi M. S. H., Doğan O. E., Ağar E., Golenya I. A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.75, ss.770-778, 2019 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 75
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1107/s205698901900642x
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.770-778
  • Anahtar Kelimeler: crystal structure, hydrazine, 2,4-dinitrophenyl, Schiff base, hydrogen bonding, supramolecular framework, DFT
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The title Schiff base compound, C13H9ClN4O5 center dot 0.5CH(3)CN, crystallizes as an acetonitrile hemisolvate; the solvent molecule being located on a twofold rotation axis. The molecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)degrees. The configuration about the C=N bond is E, and there is an intramolecular N-H center dot center dot center dot O-nitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by O-H center dot center dot center dot O and N-H center dot center dot center dot O hydrogen bonds, forming layers lying parallel to (10 (1) over bar). The layers are linked by C-H center dot center dot center dot Cl hydrogen bonds, forming a supramolecular framework. Within the framework there are offset pi-pi stacking interactions [intercentroid distance = 3.833 (2) angstrom] present involving inversion-related molecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-dinitrobenzene ring, and the HOMO-LUMO gap is found to be 0.13061 a.u.