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

Nohaila Rharmili; Omar Abdellaoui; Amal Haoudi; Joel T Mague; Tuncer Hökelek; Fouad Ouazzani Chahdi; Youssef Kandri Rodi; Ahmed Mazzah; Nada Kheira Sebbar

doi:10.1107/S2056989023009052

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

Acta Crystallogr E Crystallogr Commun. 2023 Oct 19;79(Pt 11):1033-1036. doi: 10.1107/S2056989023009052. eCollection 2023 Nov 1.

Authors

Nohaila Rharmili¹, Omar Abdellaoui¹, Amal Haoudi¹, Joel T Mague², Tuncer Hökelek³, Fouad Ouazzani Chahdi¹, Youssef Kandri Rodi¹, Ahmed Mazzah⁴, Nada Kheira Sebbar^{5

6}

Affiliations

¹ Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah BP 2202, Fez, Morocco.
² Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁴ University of Lille, CNRS, UAR 3290, MSAP, Miniaturization for Synthesis, Analysis and Proteomics, F-59000 Lille, France.
⁵ Laboratory of Organic and physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco.
⁶ Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center, Pharmacochemistry Competence Center, Mohammed V University in Rabat, Faculty of Sciences, Morocco.

Abstract

In the title compound, C₂₀H₂₈BrNO₂, the indoline portion is almost planar and the 12-bromo-dodecyl 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 inter-actions between indolinedione head groups and inter-calation of the 12-bromo-dodecyl 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 mol-ecular structure in the solid state.

Keywords: crystal structure; dodecyl; hydrogen bond; indoline-2,3-dione; intercalation; π stacking.

Grants and funding

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).