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


Abdellaoui O., HÖKELEK T. , Capet F., Renard C., Haoudi A., Skalli M. K. , ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.75, ss.1372-1385, 2019 (ESCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 75
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1107/s2056989019011617
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Sayfa Sayıları: ss.1372-1385

Özet

The title compound, C14H15BrClNO4, consists of a 5-bromoindoline-2,3-dione unit linked to a 1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} moiety. In the crystal, a series of C-H center dot center dot center dot 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. pi-pi contacts between the five-membered dione rings may further stabilize the structure, with a centroid-centroid distance of 3.899 (2) angstrom. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (28.1%), H center dot center dot center dot O/O center dot center dot center dot H (23.5%), H center dot center dot center dot Br/Br center dot center dot center dot H (13.8%), H center dot center dot center dot Cl/Cl center dot center dot center dot H (13.0%) and H center dot center dot center dot C/C center dot center dot center dot H (10.2%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The chloroethoxyethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).