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

Creative Commons License

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

Acta Crystallographica Section E: Crystallographic Communications, cilt.79, sa.Pt 11, ss.1033-1036, 2023 (ESCI) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 79 Sayı: Pt 11
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1107/s2056989023009052
  • Dergi Adı: Acta Crystallographica Section E: Crystallographic Communications
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.1033-1036
  • Anahtar Kelimeler: crystal structure, dodecyl, hydrogen bond, indoline-2,3-dione, intercalation, π stacking
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.