Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of (S)-10-propargyl­pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione - Université de Lille Accéder directement au contenu
Article Dans Une Revue Acta crystallographica Section E : Crystallographic communications [2015-...] Année : 2020

Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of (S)-10-propargyl­pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione

Résumé

The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair and boat conformations, respectively. The absolute configuration was assigned on the the basis of l-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C-HBnz⋯ODiazp and C-HProprg⋯ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = proparg-yl) hydrogen bonds link the mol-ecules into two-dimensional networks parallel to the bc plane, enclosing R 4 4(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (49.8%), H⋯C/C⋯H (25.7%) and H⋯O/O⋯H (20.1%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-H⋯O hydrogen-bond energies are 38.8 (for C-HBnz⋯ODiazp) and 27.1 (for C-HProprg⋯ODiazp) kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Domaines

Matériaux
Fichier principal
Vignette du fichier
lh5947.pdf (1.06 Mo) Télécharger le fichier
Origine Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-04438460 , version 1 (05-02-2024)

Identifiants

Citer

Dounia Jeroundi, Ahmed Mazzah, Tuncer Hokelek, El Mestafa El Hadrami, Catherine Renard, et al.. Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of (S)-10-propargyl­pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione. Acta crystallographica Section E : Crystallographic communications [2015-..], 2020, 76, pp.467-472. ⟨10.1107/S2056989020002698⟩. ⟨hal-04438460⟩
18 Consultations
7 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More