Crystal Structure, Hirshfeld Surface Analysis And Dft Studies Of 5-Bromo-1-{2-[2-(2-Chloro­Eth­Oxy)Eth­Oxy]Eth­Yl}Indoline-2,3-Dione

Abstract

The title compound consists of the 5-bromo­indoline-2,3-dione unit linked by a 1-{2-[2-(2 chloro­eth­oxy)eth­oxy]eth­yl} moiety. In the crystal, inter­molecular C—HBrmind⋯ODio, C—HBrmind⋯OEthy, C—HChlethy⋯ODio and C—HChlethy⋯OChlethy (Brmind = bromo­indoline, Dio = dione, Ethy = eth­oxy and Chlethy = chloro­eth­oxy) hydrogen bonds link the mol­ecules into a three-dimensional structure, enclosing (8), (12), (18) and (22) ring motifs. The π–π contacts between the five-membered dione rings may further stabilize the structure., 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 3.899 (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%) 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).