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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2023
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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. |
format | Online Article Text |
id | pubmed-10626969 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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