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(–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide

The title mol­ecule, C(26)H(24)N(2)O(2), displays C (2) symmetry, with the mol­ecule located on a twofold axis perpendicular to the plane of the oxalamide unit –NH—CO—CO—NH–. The oxalamide core deviates from planarity, as reflected by the O=C—C=O and N—C—C—N torsion angles of 164.3 (5) and 163.2 (5)...

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Autores principales: Bernès, Sylvain, Hernández, Guadalupe, Vázquez, Jaime, Tovar, Alejandra, Gutiérrez, René
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009003/
https://www.ncbi.nlm.nih.gov/pubmed/21589153
http://dx.doi.org/10.1107/S1600536810043424
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author Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
author_facet Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
author_sort Bernès, Sylvain
collection PubMed
description The title mol­ecule, C(26)H(24)N(2)O(2), displays C (2) symmetry, with the mol­ecule located on a twofold axis perpendicular to the plane of the oxalamide unit –NH—CO—CO—NH–. The oxalamide core deviates from planarity, as reflected by the O=C—C=O and N—C—C—N torsion angles of 164.3 (5) and 163.2 (5)°, respectively. The naphthyl groups are oriented toward the same face of the oxalamide mean plane and make a dihedral angle of 43.76 (8)°. This conformation is suitable for the formation of inter­molecular N—H⋯O hydrogen bonds, giving noncentrosymmetric dimers incorporating R (2) (2)(10) ring motifs. These nonbonding inter­actions propagate along the 6(1) screw axis normal to the mol­ecular twofold axis, resulting in a single-stranded right-handed helix parallel to [001]. In the crystal, Δ helices are arranged side-by-side and inter­act through π–π contacts between naphthyl groups. The shortest centroid–centroid separation between inter­acting benzene rings is 3.623 (4) Å.
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spelling pubmed-30090032010-12-30 (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide Bernès, Sylvain Hernández, Guadalupe Vázquez, Jaime Tovar, Alejandra Gutiérrez, René Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(26)H(24)N(2)O(2), displays C (2) symmetry, with the mol­ecule located on a twofold axis perpendicular to the plane of the oxalamide unit –NH—CO—CO—NH–. The oxalamide core deviates from planarity, as reflected by the O=C—C=O and N—C—C—N torsion angles of 164.3 (5) and 163.2 (5)°, respectively. The naphthyl groups are oriented toward the same face of the oxalamide mean plane and make a dihedral angle of 43.76 (8)°. This conformation is suitable for the formation of inter­molecular N—H⋯O hydrogen bonds, giving noncentrosymmetric dimers incorporating R (2) (2)(10) ring motifs. These nonbonding inter­actions propagate along the 6(1) screw axis normal to the mol­ecular twofold axis, resulting in a single-stranded right-handed helix parallel to [001]. In the crystal, Δ helices are arranged side-by-side and inter­act through π–π contacts between naphthyl groups. The shortest centroid–centroid separation between inter­acting benzene rings is 3.623 (4) Å. International Union of Crystallography 2010-10-31 /pmc/articles/PMC3009003/ /pubmed/21589153 http://dx.doi.org/10.1107/S1600536810043424 Text en © Bernès et al. 2010 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
Bernès, Sylvain
Hernández, Guadalupe
Vázquez, Jaime
Tovar, Alejandra
Gutiérrez, René
(–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title_full (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title_fullStr (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title_full_unstemmed (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title_short (–)-(S)-N,N′-Bis[1-(1-naphth­yl)eth­yl]­oxalamide
title_sort (–)-(s)-n,n′-bis[1-(1-naphth­yl)eth­yl]­oxalamide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009003/
https://www.ncbi.nlm.nih.gov/pubmed/21589153
http://dx.doi.org/10.1107/S1600536810043424
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