Acta Crystallographica Section E: Crystallographic Communications (Jan 2019)

Crystal structure and Hirshfeld surface analysis of 3,4-dihydro-2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-pyridin-4-yl)-1,5-benzodiazepine

  • Lhoussaine El Ghayati,
  • Youssef Ramli,
  • Tuncer Hökelek,
  • Mohamed Labd Taha,
  • Joel T. Mague,
  • El Mokhtar Essassi

DOI
https://doi.org/10.1107/s2056989018017565
Journal volume & issue
Vol. 75, no. 1
pp. 94 – 98

Abstract

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The title compound, C20H17N3O3 [systematic name: 2-(6-methyl-2,4-dioxopyran-3-ylidene)-4-(pyridin-4-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine], is built up from a benzodiazepine ring system linked to pyridyl and pendant dihydropyran rings, where the benzene and pyridyl rings are oriented at a dihedral angle of 43.36 (6)°. The pendant dihydropyran ring is rotationally disordered in a 90.899 (3):0.101 (3) ratio with the orientation of each component largely determined by intramolecular N—HDiazp...ODhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bonds. In the crystal, molecules are linked via pairs of weak intermolecular N—HDiazp...ODhydp hydrogen bonds, forming inversion-related dimers with R22(26) ring motifs. The dimers are further connected along the b-axis direction by π–π stacking interactions between the pendant dihydropyran and pyridyl rings with centroid–centroid distances of 3.833 (3) Å and a dihedral angle of 14.51 (2)°. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (50.1%), H...C/C...H (17.7%), H...O/O...H (16.8%), C...C (7.7%) and H...N/N...H (5.3%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing.

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