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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)...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-3009003 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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