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Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene

The title compound, C(20)H(19)IS, features a 1,3-disubstituted azulene involving an ethynylene elongated 4-(tert-butyl­sulfanyl)­phenyl sidearm and an iodine atom as the substituents. The azulene ring system is almost planar (r.m.s. deviation = 0.012 Å) and subtends a dihedral angle of 35.7 (1)° wit...

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Detalles Bibliográficos
Autores principales: Förster, Sebastian, Seichter, Wilhelm, Weber, Edwin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571388/
https://www.ncbi.nlm.nih.gov/pubmed/26396788
http://dx.doi.org/10.1107/S2056989015012542
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author Förster, Sebastian
Seichter, Wilhelm
Weber, Edwin
author_facet Förster, Sebastian
Seichter, Wilhelm
Weber, Edwin
author_sort Förster, Sebastian
collection PubMed
description The title compound, C(20)H(19)IS, features a 1,3-disubstituted azulene involving an ethynylene elongated 4-(tert-butyl­sulfanyl)­phenyl sidearm and an iodine atom as the substituents. The azulene ring system is almost planar (r.m.s. deviation = 0.012 Å) and subtends a dihedral angle of 35.7 (1)° with the benzene ring. As a result of the inherent dipole character of the azulene core, a supra­molecular π–π dimer [separation between the centroids of the five- and seven-membered rings = 3.7632 (10) Å] with anti­parallel orientated mol­ecules can be observed in the crystal. The packing is consolidated by an unusual I⋯π(acetyl­ene) contact [I⋯Cg = 3.34 Å, C—I⋯Cg = 173.3°], and a very weak C—H⋯π inter­action is also found in the structure, with the azulene five-membered ring as the acceptor.
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spelling pubmed-45713882015-09-22 Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene Förster, Sebastian Seichter, Wilhelm Weber, Edwin Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(20)H(19)IS, features a 1,3-disubstituted azulene involving an ethynylene elongated 4-(tert-butyl­sulfanyl)­phenyl sidearm and an iodine atom as the substituents. The azulene ring system is almost planar (r.m.s. deviation = 0.012 Å) and subtends a dihedral angle of 35.7 (1)° with the benzene ring. As a result of the inherent dipole character of the azulene core, a supra­molecular π–π dimer [separation between the centroids of the five- and seven-membered rings = 3.7632 (10) Å] with anti­parallel orientated mol­ecules can be observed in the crystal. The packing is consolidated by an unusual I⋯π(acetyl­ene) contact [I⋯Cg = 3.34 Å, C—I⋯Cg = 173.3°], and a very weak C—H⋯π inter­action is also found in the structure, with the azulene five-membered ring as the acceptor. International Union of Crystallography 2015-07-04 /pmc/articles/PMC4571388/ /pubmed/26396788 http://dx.doi.org/10.1107/S2056989015012542 Text en © Förster et al. 2015 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 Data Reports
Förster, Sebastian
Seichter, Wilhelm
Weber, Edwin
Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title_full Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title_fullStr Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title_full_unstemmed Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title_short Crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
title_sort crystal structure of 1-iodo-3-{[4-(tert-butyl­sulfan­yl)phen­yl]ethyn­yl}azulene
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571388/
https://www.ncbi.nlm.nih.gov/pubmed/26396788
http://dx.doi.org/10.1107/S2056989015012542
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