Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromododecyl)indoline-2,3-dione

In the title compound, C20H28BrNO2, the indoline portion is almost planar and the 12-bromododecyl chain adopts an all-trans conformation apart from the gauche terminal C — C — C — Br fragment. A micellar-like structure is generated in the crystal by C — H...O hydrogen bonds and π -stacking interactions between indolinedione head groups and intercalation of the 12-bromododecyl tails. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (58.9%), H...O/O...H (17.9%) and H...Br/Br...H (9.5%) contacts. A density functional theory (DFT) optimized structure at the B3LYP/ 6 – 311   G(d,p) level shows good agreement with the experimentally determined molecular structure in the solid state.

Source: Acta Crystallographica Section E - October 19, 2023 Category: Chemistry Authors: Rharmili, N. Abdellaoui, O. Haoudi, A. Mague, J.T. H ö kelek, T. Ouazzani Chahdi, F. Kandri Rodi, Y. Mazzah, A. Sebbar, N.K. Tags: crystal structure indoline-2,3-dione hydrogen bond dodecyl π stacking intercalation research communications Source Type: research