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
El Ghayati, Lhoussaine
Labd Taha, Mohamed
Mague, Joel T.
Essassi, El Mokhtar
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In the title compound, 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⋯O hydrogen bonds. In the crystal, inversion-related molecules form dimers through intermolecular N—H⋯O hydrogen bonds with the dimers associated along the b-axis direction by slipped π-stacking interactions between the pyridyl and dihydropyran rings., 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 R 2 2(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.