Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromododecyl)indoline-2,3-dione
Acta Crystallographica Section E: Crystallographic Communications, vol.79, no.Pt 11, pp.1033-1036, 2023 (ESCI, Scopus)
- Publication Type: Article / Article
- Volume: 79 Issue: Pt 11
- Publication Date: 2023
- Doi Number: 10.1107/s2056989023009052
- Journal Name: Acta Crystallographica Section E: Crystallographic Communications
- Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
- Page Numbers: pp.1033-1036
- Keywords: crystal structure, dodecyl, hydrogen bond, indoline-2,3-dione, intercalation, π stacking
- Open Archive Collection: AVESIS Open Access Collection
- Hacettepe University Affiliated: Yes
Abstract
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.