Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetra- hydro-1H-1,5-benzodiazepine

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El Hafi M., Lahmidi S., El Ghayati L., HÖKELEK T., Mague J. T., Amer B., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.77, pp.834-844, 2021 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77
  • Publication Date: 2021
  • Doi Number: 10.1107/s2056989021007441
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.834-844
  • Keywords: crystal structure, pyrandione, furan, tetrahydrobenzodiazepine, hydrogen bond, pi-stacking, INTERMOLECULAR INTERACTIONS, 1,5-BENZODIAZEPINE DERIVATIVES, QUANTITATIVE-ANALYSIS, MODEL ENERGIES, EFFICIENT, SERIES
  • Hacettepe University Affiliated: Yes


The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-2-ylidene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)degrees. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) angstrom degrees from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intramolecular N-H-Diazp center dot center dot center dot O-Dhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the bc plane are formed by N-H-Diazp center dot center dot center dot O-Dhydp hydrogen bonds and slipped pi-pi stacking interactions. The layers are connected by additional slipped pi-pi stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (46.8%), H center dot center dot center dot O/ O center dot center dot center dot H (23.5%) and H center dot center dot center dot C/C center dot center dot center dot H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N-H center dot center dot center dot O hydrogen-bond energy is 57.5 kJ mol(-1).