Title :

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

Author(s) :

Jeroundi, Dounia [Auteur]
Université Sidi Mohamed Ben Abdellah [USMBA]
Mazzah, Ahmed [Auteur]
Miniaturisation pour la Synthèse, l’Analyse et la Protéomique - UAR 3290 [MSAP]
Hokelek, Tuncer [Auteur]
Hacettepe University = Hacettepe Üniversitesi
El Hadrami, El Mestafa [Auteur]
Université Sidi Mohamed Ben Abdellah [USMBA]
Renard, Catherine [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Haoudi, Amal [Auteur]
Université Sidi Mohamed Ben Abdellah [USMBA]
Essassi, El Mokhtar [Auteur]
Université Mohammed V de Rabat [Agdal] [UM5]

Journal title :

Acta crystallographica Section E : Crystallographic communications [2015-...]

Pages :

467-472

Publisher :

International Union of Crystallography

Publication date :

2020-04-01

ISSN :

2056-9890

English keyword(s) :

crystal structure
Hirshfeld surface
benzodiazepine
pyrrole

HAL domain(s) :

Chimie/Matériaux

English abstract : [en]

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 ...
Show more >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.Show less >

Language :

Anglais

Peer reviewed article :

Oui

Audience :

Internationale

Popular science :

Non

Collections :

• Miniaturisation pour la Synthèse, l'Analyse et la Protéomique (MSAP) - USR 3290

Source :

Harvested from HAL