Crystal structure, hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} indoline-2,3-dione - Université de Lille Accéder directement au contenu
Article Dans Une Revue Acta crystallographica Section E : Crystallographic communications [2015-...] Année : 2019

Crystal structure, hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} indoline-2,3-dione

Omar Abdellaoui
  • Fonction : Auteur
Tuncer Hokelek
  • Fonction : Auteur
Amal Haoudi
  • Fonction : Auteur
Mohamed Khalid Skalli
  • Fonction : Auteur
Youssef Kandri Rodi
  • Fonction : Auteur

Résumé

The title compound, C14H15BrClNO4, consists of a 5-bromo-indoline-2,3-dione unit linked to a 1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl} moiety. In the crystal, a series of C-H⋯O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R 2 2(8), R 2 2(12), R 2 2(18) and R 2 2(22) ring motifs. π-π contacts between the five-membered dione rings may further stabilize the structure, with a centroid-centroid distance of 3.899 (2) Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (28.1%), H⋯O/O⋯H (23.5%), H⋯Br/Br⋯H (13.8%), H⋯Cl/Cl⋯H (13.0%) and H⋯C/C⋯H (10.2%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(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. The chloro-eth-oxy-ethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).

Domaines

Matériaux
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Dates et versions

hal-04441804 , version 1 (06-02-2024)

Identifiants

Citer

Omar Abdellaoui, Tuncer Hokelek, Frederic Capet, Catherine Renard, Amal Haoudi, et al.. Crystal structure, hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} indoline-2,3-dione. Acta crystallographica Section E : Crystallographic communications [2015-..], 2019, Acta crystallographica Section E : Crystallographic communications [2015-..], 75, pp.1372-+. ⟨10.1107/S2056989019011617⟩. ⟨hal-04441804⟩
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