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

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..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 3.89914;(2)14;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%) 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 0.66514;(8):0.33514;(6).