Abstract
The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetra-hydro-1H-benzo[b][1,4]diazepin-2-yl-idene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant di-hydro-pyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetra-hydro-diazepine ring adopts a boat conformation. The rotational orientation of the pendant di-hydro-pyran ring is partially determined by an intra-molecular N-HDiazp⋯ODhydp (Diazp = diazepine and Dhydp = di-hydro-pyran) hydrogen bond. In the crystal, layers of mol-ecules parallel to the bc plane are formed by N-HDiazp⋯ODhydp hydrogen bonds and slipped π-π stacking inter-actions. The layers are connected by additional slipped π-π stacking inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (46.8%), H⋯O/O⋯H (23.5%) and H⋯C/C⋯H (15.8%) inter-actions, indicating that van der Waals inter-actions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N-H⋯O hydrogen-bond energy is 57.5 kJ mol-1.
Highlights
Mohamed El Hafi,a Sanae Lahmidi,a Lhoussaine El Ghayati,a Tuncer Hokelek,b Joel T
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)
A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from HÁ Á ÁH (46.8%), HÁ Á ÁO/ OÁ Á ÁH (23.5%) and HÁ Á ÁC/CÁ Á ÁH (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing
Summary
1,5-Benzodiazepine derivatives are an important class of nitrogen-containing heterocyclic compounds because of their potent biological activities, acting as antidepressant (Sharma et al, 2017), antitubercular (Singh et al, 2017), antimicrobial (An et al, 2016) and anticonvulsant agents (Jyoti & Mithlesh, 2013). The present study continues the investigation of 1,5benzodiazepine derivatives recently published by our team (El Ghayati et al, 2019, 2021; Essaghouani et al, 2016, 2017). In this context, we report the synthesis, the molecular and crystal structures along with the Hirshfeld surface analysis and the intermolecular interaction energies of the title compound, (I). Symmetry code: (vi) Àx þ 1; y À 12; Àz þ 12
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