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Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene
The title compounds, C(23)H(16)S, (I), and C(26)H(16)S, (II), are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzothiophene ring system makes a dihedral...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5120714/ https://www.ncbi.nlm.nih.gov/pubmed/27920924 http://dx.doi.org/10.1107/S2056989016012937 |
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author | Gopinath, S. Sethusankar, K. Stoeckli-Evans, Helen Rafiq, Muhamad Mohanakrishnan, Arasambattu K. |
author_facet | Gopinath, S. Sethusankar, K. Stoeckli-Evans, Helen Rafiq, Muhamad Mohanakrishnan, Arasambattu K. |
author_sort | Gopinath, S. |
collection | PubMed |
description | The title compounds, C(23)H(16)S, (I), and C(26)H(16)S, (II), are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzothiophene ring system makes a dihedral angle of 2.28 (6)° with the naphthalene ring system, and a dihedral angle of 1.28 (6)° with the anthracene ring system in (II), showing that the fused units are essentially planar. In (I), the 4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9)° with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08 (12)° with the anthracene ring system. In the crystals of both compounds, molecules are linked by C—H⋯π interactions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π–π interactions present within the slabs in (I). In the crystal of (II), they link the chains, forming sheets parallel to (010). The triclinic polymorph of compound (II) has been reported [Sivasakthikumaran et al., (2012 ▸). J. Org. Chem. 77, 9053–9071]. |
format | Online Article Text |
id | pubmed-5120714 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-51207142016-12-05 Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene Gopinath, S. Sethusankar, K. Stoeckli-Evans, Helen Rafiq, Muhamad Mohanakrishnan, Arasambattu K. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, C(23)H(16)S, (I), and C(26)H(16)S, (II), are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzothiophene ring system makes a dihedral angle of 2.28 (6)° with the naphthalene ring system, and a dihedral angle of 1.28 (6)° with the anthracene ring system in (II), showing that the fused units are essentially planar. In (I), the 4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9)° with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08 (12)° with the anthracene ring system. In the crystals of both compounds, molecules are linked by C—H⋯π interactions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π–π interactions present within the slabs in (I). In the crystal of (II), they link the chains, forming sheets parallel to (010). The triclinic polymorph of compound (II) has been reported [Sivasakthikumaran et al., (2012 ▸). J. Org. Chem. 77, 9053–9071]. International Union of Crystallography 2016-08-16 /pmc/articles/PMC5120714/ /pubmed/27920924 http://dx.doi.org/10.1107/S2056989016012937 Text en © Gopinath et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Gopinath, S. Sethusankar, K. Stoeckli-Evans, Helen Rafiq, Muhamad Mohanakrishnan, Arasambattu K. Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title | Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title_full | Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title_fullStr | Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title_full_unstemmed | Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title_short | Crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
title_sort | crystal structure of 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5120714/ https://www.ncbi.nlm.nih.gov/pubmed/27920924 http://dx.doi.org/10.1107/S2056989016012937 |
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