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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).

In present study, several isatin-derived quaternary ammonium surfactants with different carbon chain lengths were designed and synthesized. They were synthesized by alkylation of indoline-2,3-dione with various dibromo-alkanes, then quaternization with trimethylamine. Nuclear magnetic resonance (1H NMR, 13C NMR) and mass spectroscopy were employed to examine their chemical structures. Further, the critical micelle concentrations (CMC) value of surfactants synthesized was determined in an aqueous solution using electrical conductivity. The synthesized surfactants had CMC ranging from 0.01 to 0.012 mol/L. The antibacterial activity of the titer compounds (3a-3c) was evaluated against Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), as well as Gram-positive bacteria (Staphylococcus aureus). The surfactant with a long hydrocarbon chain (12 carbons) showed activity against all bacteria tested (minimum inhibitory concentration = 1.25-2.5 mg/mL), whereas those with a short hydrocarbon chain proved to be inactive.