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(S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine
The title chiral imine, C(17)H(15)NS, has been obtained via a direct synthesis route. The imine group displays the common E configuration, and is almost coplanar with the thiophene heterocycle; the dihedral angle between the C=N—C group and the thiophene ring is 5.1 (8)°. In contrast, the naphthyl...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969493/ https://www.ncbi.nlm.nih.gov/pubmed/21582915 http://dx.doi.org/10.1107/S1600536809022375 |
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author | Espinosa Leija, Armando Hernández, Guadalupe Portillo, Roberto Gutiérrez, René Bernès, Sylvain |
author_facet | Espinosa Leija, Armando Hernández, Guadalupe Portillo, Roberto Gutiérrez, René Bernès, Sylvain |
author_sort | Espinosa Leija, Armando |
collection | PubMed |
description | The title chiral imine, C(17)H(15)NS, has been obtained via a direct synthesis route. The imine group displays the common E configuration, and is almost coplanar with the thiophene heterocycle; the dihedral angle between the C=N—C group and the thiophene ring is 5.1 (8)°. In contrast, the naphthyl group makes an angle of 83.79 (13)° with the thiophene ring. The observed solid-state molecular conformation is suitable for the use of this molecule as an N,S-bidentate Schiff base ligand. The molecular packing features double C—H⋯π interactions between naphthyl groups of neighboring molecules, which form chains in the [100] direction. The crystal structure is further stabilized by a short C—H⋯π contact involving the methyl group and one ring of a naphthyl group. The resulting two-dimensional network is completed by a weak intermolecular C—H(imine)⋯π(thiophene) interaction. |
format | Text |
id | pubmed-2969493 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29694932010-12-30 (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine Espinosa Leija, Armando Hernández, Guadalupe Portillo, Roberto Gutiérrez, René Bernès, Sylvain Acta Crystallogr Sect E Struct Rep Online Organic Papers The title chiral imine, C(17)H(15)NS, has been obtained via a direct synthesis route. The imine group displays the common E configuration, and is almost coplanar with the thiophene heterocycle; the dihedral angle between the C=N—C group and the thiophene ring is 5.1 (8)°. In contrast, the naphthyl group makes an angle of 83.79 (13)° with the thiophene ring. The observed solid-state molecular conformation is suitable for the use of this molecule as an N,S-bidentate Schiff base ligand. The molecular packing features double C—H⋯π interactions between naphthyl groups of neighboring molecules, which form chains in the [100] direction. The crystal structure is further stabilized by a short C—H⋯π contact involving the methyl group and one ring of a naphthyl group. The resulting two-dimensional network is completed by a weak intermolecular C—H(imine)⋯π(thiophene) interaction. International Union of Crystallography 2009-06-20 /pmc/articles/PMC2969493/ /pubmed/21582915 http://dx.doi.org/10.1107/S1600536809022375 Text en © Espinosa Leija et al. 2009 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 Espinosa Leija, Armando Hernández, Guadalupe Portillo, Roberto Gutiérrez, René Bernès, Sylvain (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title | (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title_full | (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title_fullStr | (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title_full_unstemmed | (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title_short | (S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine |
title_sort | (s)-(+)-1-(1-naphthyl)-1-(2-thienylmethylene)ethylamine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969493/ https://www.ncbi.nlm.nih.gov/pubmed/21582915 http://dx.doi.org/10.1107/S1600536809022375 |
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