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Crystal structure, Hirshfeld surface ...
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Document type :
Article dans une revue scientifique: Article original
DOI :
10.1107/S2056989020002698
PMID :
32280485
Permalink :
http://hdl.handle.net/20.500.12210/60730
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]
Mazzah, Ahmed [Auteur] refId
Hokelek, Tuncer [Auteur]
El Hadrami, El Mestafa [Auteur]
RENARD, Catherine [Auteur]
Haoudi, Amal [Auteur]
Essassi, El Mokhtar [Auteur]
Journal title :
Acta crystallographica. Section E, Crystallographic communications
Abbreviated title :
Acta Crystallogr E Crystallogr Commun
Volume number :
76
Pages :
467-472
Publication date :
2020-04-01
ISSN :
2056-9890
Keyword(s) :
benzodiazepine
pyrrole
crystal structure
Hirshfeld surface
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 ...
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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
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
CNRS
Centrale Lille
ENSCL
Univ. Artois
Université de Lille
Collections :
  • Miniaturisation pour la Synthèse, l'Analyse et la Protéomique (MSAP) - USR 3290
  • Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Research team(s) :
Chimie, matériaux et procédés pour un nucléaire durable (CIMEND)
Submission date :
2022-03-02T07:14:31Z
Université de Lille

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