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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2008
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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. |
format | Text |
id | pubmed-2961030 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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