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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...

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Autores principales: Espinosa Leija, Armando, Hernández, Guadalupe, Portillo, Roberto, Gutiérrez, René, Bernès, Sylvain
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
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.
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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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