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

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Rharmili N., Abdellaoui O., Haoudi A., Mague J. T., HÖKELEK T., Chahdi F. O., ...More

Acta Crystallographica Section E: Crystallographic Communications, vol.79, no.Pt 11, pp.1033-1036, 2023 (ESCI) identifier identifier


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.