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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...

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Autores principales: Gopinath, S., Sethusankar, K., Stoeckli-Evans, Helen, Rafiq, Muhamad, Mohanakrishnan, Arasambattu K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
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].
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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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