Crystal structure, Hirshfeld surface ...
Type de document :
Article dans une revue scientifique: Article original
PMID :
URL permanente :
Titre :
Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione
Auteur(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]
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]
Titre de la revue :
Acta crystallographica Section E : Crystallographic communications [2015-...]
Nom court de la revue :
Acta Crystallogr E Crystallogr Commun
Numéro :
76
Pagination :
467-472
Date de publication :
2020-04-01
ISSN :
2056-9890
Mot(s)-clé(s) en anglais :
benzodiazepine
pyrrole
crystal structure
Hirshfeld surface
pyrrole
crystal structure
Hirshfeld surface
Discipline(s) HAL :
Chimie/Matériaux
Résumé en anglais : [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 ...
Lire la suite >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.Lire moins >
Lire la suite >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.Lire moins >
Langue :
Anglais
Audience :
Internationale
Vulgarisation :
Non
Établissement(s) :
CNRS
Centrale Lille
ENSCL
Univ. Artois
Université de Lille
Centrale Lille
ENSCL
Univ. Artois
Université de Lille
Collections :
Équipe(s) de recherche :
Chimie, matériaux et procédés pour un nucléaire durable (CIMEND)
Date de dépôt :
2022-03-02T07:14:31Z
2024-02-05T10:59:37Z
2024-02-05T11:02:14Z
2024-02-05T10:59:37Z
2024-02-05T11:02:14Z
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