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5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catalysed azide–alkyne cycloaddition (CuAAC) from the corresponding n-octyne and 4-azidobenzoxadiazole. The benzoxadiazole and triazole rings show a roughly planar orien...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515233/ https://www.ncbi.nlm.nih.gov/pubmed/23284453 http://dx.doi.org/10.1107/S1600536812041815 |
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author | Key, Jessie A. Cairo, Christopher W. Ferguson, Michael J. |
author_facet | Key, Jessie A. Cairo, Christopher W. Ferguson, Michael J. |
author_sort | Key, Jessie A. |
collection | PubMed |
description | The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catalysed azide–alkyne cycloaddition (CuAAC) from the corresponding n-octyne and 4-azidobenzoxadiazole. The benzoxadiazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C—H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking interactions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid–centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å. |
format | Online Article Text |
id | pubmed-3515233 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35152332013-01-02 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole Key, Jessie A. Cairo, Christopher W. Ferguson, Michael J. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catalysed azide–alkyne cycloaddition (CuAAC) from the corresponding n-octyne and 4-azidobenzoxadiazole. The benzoxadiazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C—H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking interactions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid–centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å. International Union of Crystallography 2012-10-13 /pmc/articles/PMC3515233/ /pubmed/23284453 http://dx.doi.org/10.1107/S1600536812041815 Text en © Key et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Key, Jessie A. Cairo, Christopher W. Ferguson, Michael J. 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title | 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title_full | 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title_fullStr | 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title_full_unstemmed | 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title_short | 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
title_sort | 5-(4-hexyl-1h-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515233/ https://www.ncbi.nlm.nih.gov/pubmed/23284453 http://dx.doi.org/10.1107/S1600536812041815 |
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