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Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid
The title compound, C(23)H(19)NO(2)S(2), was obtained as an unexpected regioisomer from an attempted synthesis of an intermediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole monothioating at the 2- and 3-positions to give a 3H-indole. In the crystal,...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
International Union of Crystallography
2015
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645081/ https://www.ncbi.nlm.nih.gov/pubmed/26594523 http://dx.doi.org/10.1107/S2056989015020241 |
| _version_ | 1782400757708881920 |
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| author | Noland, Wayland E. Brown, Christopher D. Bisel, Amanda M. Schneerer, Andrew K. Tritch, Kenneth J. |
| author_facet | Noland, Wayland E. Brown, Christopher D. Bisel, Amanda M. Schneerer, Andrew K. Tritch, Kenneth J. |
| author_sort | Noland, Wayland E. |
| collection | PubMed |
| description | The title compound, C(23)H(19)NO(2)S(2), was obtained as an unexpected regioisomer from an attempted synthesis of an intermediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole monothioating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carboxy conformation and forms centrosymmetric O—H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related molecule. Together with a weak C—H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100]. |
| format | Online Article Text |
| id | pubmed-4645081 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2015 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-46450812015-11-20 Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid Noland, Wayland E. Brown, Christopher D. Bisel, Amanda M. Schneerer, Andrew K. Tritch, Kenneth J. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(23)H(19)NO(2)S(2), was obtained as an unexpected regioisomer from an attempted synthesis of an intermediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole monothioating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carboxy conformation and forms centrosymmetric O—H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related molecule. Together with a weak C—H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100]. International Union of Crystallography 2015-10-31 /pmc/articles/PMC4645081/ /pubmed/26594523 http://dx.doi.org/10.1107/S2056989015020241 Text en © Noland 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 | Research Communications Noland, Wayland E. Brown, Christopher D. Bisel, Amanda M. Schneerer, Andrew K. Tritch, Kenneth J. Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title | Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title_full | Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title_fullStr | Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title_full_unstemmed | Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title_short | Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid |
| title_sort | crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3h-indol-3-yl]propanoic acid |
| topic | Research Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645081/ https://www.ncbi.nlm.nih.gov/pubmed/26594523 http://dx.doi.org/10.1107/S2056989015020241 |
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