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N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine

The title compound, C(22)H(16)N(2), is the first example of an ynamine with H atoms bonded to the terminal C atoms. The environment around each N atom is almost planar. The distances of the N atoms from a least squares plane fitted through each N atom and the surrounding three C atoms, are 0.087 (3)...

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Detalles Bibliográficos
Autores principales: Tabata, Hideyuki, Okuno, Tsunehisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238840/
https://www.ncbi.nlm.nih.gov/pubmed/22199693
http://dx.doi.org/10.1107/S1600536811045351
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author Tabata, Hideyuki
Okuno, Tsunehisa
author_facet Tabata, Hideyuki
Okuno, Tsunehisa
author_sort Tabata, Hideyuki
collection PubMed
description The title compound, C(22)H(16)N(2), is the first example of an ynamine with H atoms bonded to the terminal C atoms. The environment around each N atom is almost planar. The distances of the N atoms from a least squares plane fitted through each N atom and the surrounding three C atoms, are 0.087 (3) and 0.041 (4) Å. The dihedral angles between these two planes and the central phenyl­ene ring are 23.34 (14) and 34.57 (14)°. The two acetyl­ene groups have an anti conformation, keeping a conjugation through the central benzene ring. The freely refined lengths of C(sp)—H are 1.00 (5) and 0.93 (4) Å, consistent with those of reported acetyl­enes. The H atoms bound to terminal C atoms have short contacts with the neighboring acetyl­enic C and N atoms. The closest contacts are an H⋯N distance of 2.67 (5) Å and an H⋯C distance of 2.74 (5) Å.
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spelling pubmed-32388402011-12-23 N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine Tabata, Hideyuki Okuno, Tsunehisa Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(22)H(16)N(2), is the first example of an ynamine with H atoms bonded to the terminal C atoms. The environment around each N atom is almost planar. The distances of the N atoms from a least squares plane fitted through each N atom and the surrounding three C atoms, are 0.087 (3) and 0.041 (4) Å. The dihedral angles between these two planes and the central phenyl­ene ring are 23.34 (14) and 34.57 (14)°. The two acetyl­ene groups have an anti conformation, keeping a conjugation through the central benzene ring. The freely refined lengths of C(sp)—H are 1.00 (5) and 0.93 (4) Å, consistent with those of reported acetyl­enes. The H atoms bound to terminal C atoms have short contacts with the neighboring acetyl­enic C and N atoms. The closest contacts are an H⋯N distance of 2.67 (5) Å and an H⋯C distance of 2.74 (5) Å. International Union of Crystallography 2011-11-05 /pmc/articles/PMC3238840/ /pubmed/22199693 http://dx.doi.org/10.1107/S1600536811045351 Text en © Tabata and Okuno 2011 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
Tabata, Hideyuki
Okuno, Tsunehisa
N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title_full N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title_fullStr N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title_full_unstemmed N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title_short N (1),N (4)-Diethynyl-N (1),N (4)-diphenyl­benzene-1,4-diamine
title_sort n (1),n (4)-diethynyl-n (1),n (4)-diphenyl­benzene-1,4-diamine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238840/
https://www.ncbi.nlm.nih.gov/pubmed/22199693
http://dx.doi.org/10.1107/S1600536811045351
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