Crystal structure and computational study of 2,4-dichloro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline

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Köysal Y., Bülbül H., Gumus S., Ağar E., SOYLU M. S.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.72, ss.1187-1193, 2016 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 72
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1107/s2056989016011816
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.1187-1193
  • Anahtar Kelimeler: crystal structure, Schiff base, nitrothiophene, pi-pi interactions, quantum-chemical calculations, EQUILIBRIUM GEOMETRIES, DENSITY, BASES
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

The title compound, C11H6Cl2N2O2S, is a Schiff base that incorporates an N-bound 2,4-dichlorophenyl and a C-bound 5-nitrothiophene ring. The molecule is approximately planar, the maximum deviation from the mean plane being 0.233 (4) angstrom for the C=N N atom. The dihedral angle between the benzene and thiophene rings is 9.7 (2)degrees. The C=N double bond has an E configuration. The crystal structure features C-H center dot center dot center dot O hydrogen bonds, forming sheets parallel to (10 (1) over bar), and pi-pi stacking interactions between symmetry-related thiophene and benzene rings, in which the distance between adjacent ring centroids is 3.707 (4) angstrom, forming a three-dimensional supramolecular structure. Geometric parameters from quantum-chemical calculations are in good agreement with experimental X-ray diffraction results.