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
| Autor: | K. Sethusankar, Arasambattu K. Mohanakrishnan, S. Gopinath, Helen Stoeckli-Evans, Muhamad Rafiq |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
crystal structure
benzothiophene Stereochemistry Substituent Thio Crystal structure Dihedral angle Triclinic crystal system 010402 general chemistry Ring (chemistry) C—H⋯π interactions 01 natural sciences Research Communications lcsh:Chemistry chemistry.chemical_compound C—H...π interactions offset π–π interactions benzothiophene anthra[2 3-b]benzo[d]thiophene Moiety General Materials Science anthra[2 3-b]benzo[d]thiophene Anthracene 010405 organic chemistry benzo[b]naphtho[2 3-d]thiophene General Chemistry Condensed Matter Physics 0104 chemical sciences offset π–π interactions Crystallography chemistry lcsh:QD1-999 benzo[b]naphtho[2 3-d]thiophene |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications Acta Crystallographica Section E: Crystallographic Communications, Vol 72, Iss 9, Pp 1310-1314 (2016) |
| ISSN: | 2056-9890 |
| Popis: | The title compounds, 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and 7-phenylanthra[2,3-b]benzo[d]thiophene, are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in the former and with an anthracene ring system in the latter. In the former, the 4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9)° with the mean plane of the naphthalene ring system, while the phenyl ring substituent in the latter makes a dihedral angle of 67.08 (12)° with the mean plane of the anthracene ring system. The title compounds, C23H16S, (I), and C26H16S, (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]. |
| Databáze: | OpenAIRE |
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