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4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile

In the solid state, the title compound, C(22)H(10)N(2)S, forms centrosymmetric dimers by pairs of non-classical C—H⋯S hydrogen bonds linking approximately coplanar mol­ecules. The benzene ring involved in this inter­action makes a dihedral angle of only 7.21 (16)° with the thio­phene ring, while the...

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Autores principales: Figueira, João, Vertlib, Viatslav, Rodrigues, João, Nättinen, Kalle, Rissanen, Kari
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961030/
https://www.ncbi.nlm.nih.gov/pubmed/21202153
http://dx.doi.org/10.1107/S1600536808008106
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author Figueira, João
Vertlib, Viatslav
Rodrigues, João
Nättinen, Kalle
Rissanen, Kari
author_facet Figueira, João
Vertlib, Viatslav
Rodrigues, João
Nättinen, Kalle
Rissanen, Kari
author_sort Figueira, João
collection PubMed
description In the solid state, the title compound, C(22)H(10)N(2)S, forms centrosymmetric dimers by pairs of non-classical C—H⋯S hydrogen bonds linking approximately coplanar mol­ecules. The benzene ring involved in this inter­action makes a dihedral angle of only 7.21 (16)° with the thio­phene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an inter­planar spacing of 3.44 Å. C—H⋯N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each mol­ecule thus inter­acts with 12 adjacent mol­ecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the mol­ecule.
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spelling pubmed-29610302010-12-30 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile Figueira, João Vertlib, Viatslav Rodrigues, João Nättinen, Kalle Rissanen, Kari Acta Crystallogr Sect E Struct Rep Online Organic Papers In the solid state, the title compound, C(22)H(10)N(2)S, forms centrosymmetric dimers by pairs of non-classical C—H⋯S hydrogen bonds linking approximately coplanar mol­ecules. The benzene ring involved in this inter­action makes a dihedral angle of only 7.21 (16)° with the thio­phene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an inter­planar spacing of 3.44 Å. C—H⋯N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each mol­ecule thus inter­acts with 12 adjacent mol­ecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the mol­ecule. International Union of Crystallography 2008-03-29 /pmc/articles/PMC2961030/ /pubmed/21202153 http://dx.doi.org/10.1107/S1600536808008106 Text en © Figueira et al. 2008 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
Figueira, João
Vertlib, Viatslav
Rodrigues, João
Nättinen, Kalle
Rissanen, Kari
4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title_full 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title_fullStr 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title_full_unstemmed 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title_short 4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
title_sort 4,4′-[thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961030/
https://www.ncbi.nlm.nih.gov/pubmed/21202153
http://dx.doi.org/10.1107/S1600536808008106
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