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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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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
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author Rharmili, Nohaila
Abdellaoui, Omar
Haoudi, Amal
Mague, Joel T.
Hökelek, Tuncer
Ouazzani Chahdi, Fouad
Kandri Rodi, Youssef
Mazzah, Ahmed
Sebbar, Nada Kheira
author_facet Rharmili, Nohaila
Abdellaoui, Omar
Haoudi, Amal
Mague, Joel T.
Hökelek, Tuncer
Ouazzani Chahdi, Fouad
Kandri Rodi, Youssef
Mazzah, Ahmed
Sebbar, Nada Kheira
author_sort Rharmili, Nohaila
collection PubMed
description 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.
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spelling pubmed-106269692023-11-07 Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione Rharmili, Nohaila Abdellaoui, Omar Haoudi, Amal Mague, Joel T. Hökelek, Tuncer Ouazzani Chahdi, Fouad Kandri Rodi, Youssef Mazzah, Ahmed Sebbar, Nada Kheira Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2023-10-19 /pmc/articles/PMC10626969/ /pubmed/37936861 http://dx.doi.org/10.1107/S2056989023009052 Text en © Rharmili et al. 2023 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Rharmili, Nohaila
Abdellaoui, Omar
Haoudi, Amal
Mague, Joel T.
Hökelek, Tuncer
Ouazzani Chahdi, Fouad
Kandri Rodi, Youssef
Mazzah, Ahmed
Sebbar, Nada Kheira
Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title_full Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title_fullStr Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title_full_unstemmed Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title_short Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
title_sort synthesis, crystal structure and hirshfeld surface analysis of 1-(12-bromo­dodec­yl)indoline-2,3-dione
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10626969/
https://www.ncbi.nlm.nih.gov/pubmed/37936861
http://dx.doi.org/10.1107/S2056989023009052
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