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

In the title compound, C(20)H(28)BrNO(2), 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...

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Detalles Bibliográficos
Autores principales: Rharmili, Nohaila, Abdellaoui, Omar, Haoudi, Amal, Mague, Joel T., Hökelek, Tuncer, Ouazzani Chahdi, Fouad, Kandri Rodi, Youssef, Mazzah, Ahmed, Sebbar, Nada Kheira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10626969/
https://www.ncbi.nlm.nih.gov/pubmed/37936861
http://dx.doi.org/10.1107/S2056989023009052
Descripción
Sumario:In the title compound, C(20)H(28)BrNO(2), 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.