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


El Ghayati L., Ramli Y., HÖKELEK T. , Taha M. L. , Mague J. T. , Essassi E. M.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.75, ss.94-105, 2019 (ESCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 75
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1107/s2056989018017565
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Sayfa Sayıları: ss.94-105

Özet

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)degrees. 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-H-Diazp center dot center dot center dot O-Dhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bonds. In the crystal, molecules are linked via pairs of weak intermolecular N-H-Diazp center dot center dot center dot O-Dhydp hydrogen bonds, forming inversion-related dimers with R-2(2)(26) ring motifs. The dimers are further connected along the b-axis direction by pi-pi stacking interactions between the pendant dihydropyran and pyridyl rings with centroid-centroid distances of 3.833 (3) A and a dihedral angle of 14.51 (2)degrees. 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 (50.1%), H center dot center dot center dot C/C center dot center dot center dot H (17.7%), H center dot center dot center dot O/O center dot center dot center dot H (16.8%), C center dot center dot center dot C (7.7%) and H center dot center dot center dot N/N center dot center dot center dot H (5.3%) interactions. Hydrogenbonding and van der Waals interactions are the dominant interactions in the crystal packing.