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Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione
The title compound, C(23)H(20)N(2)O(6)S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each molecule. Centrosymmetric pairs of molecules are tandem hydrogen bonded between the hydroperoxy H atom and carbonyl O atom. A different centrosymmetric pairing has st...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
International Union of Crystallography
2014
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257163/ https://www.ncbi.nlm.nih.gov/pubmed/25484649 http://dx.doi.org/10.1107/S1600536814019874 |
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| author | Noland, Wayland E. Gullickson, Glen C. Dickson, Rozalin R. Groess, Leah L. Tritch, Kenneth J. |
| author_facet | Noland, Wayland E. Gullickson, Glen C. Dickson, Rozalin R. Groess, Leah L. Tritch, Kenneth J. |
| author_sort | Noland, Wayland E. |
| collection | PubMed |
| description | The title compound, C(23)H(20)N(2)O(6)S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each molecule. Centrosymmetric pairs of molecules are tandem hydrogen bonded between the hydroperoxy H atom and carbonyl O atom. A different centrosymmetric pairing has stacked S-tolyl rings, and a third pairing is L,J-interlocked by the short leg. Except for stacked tolyl pairs, neighboring π-systems are much closer to orthogonal than coaxial. The title compound is the first example of a hydroperoxide obtained from the autoxidation of a Diels–Alder adduct of a 2-vinylpyrrole. |
| format | Online Article Text |
| id | pubmed-4257163 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2014 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-42571632014-12-05 Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione Noland, Wayland E. Gullickson, Glen C. Dickson, Rozalin R. Groess, Leah L. Tritch, Kenneth J. Acta Crystallogr Sect E Struct Rep Online Research Communications The title compound, C(23)H(20)N(2)O(6)S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each molecule. Centrosymmetric pairs of molecules are tandem hydrogen bonded between the hydroperoxy H atom and carbonyl O atom. A different centrosymmetric pairing has stacked S-tolyl rings, and a third pairing is L,J-interlocked by the short leg. Except for stacked tolyl pairs, neighboring π-systems are much closer to orthogonal than coaxial. The title compound is the first example of a hydroperoxide obtained from the autoxidation of a Diels–Alder adduct of a 2-vinylpyrrole. International Union of Crystallography 2014-09-13 /pmc/articles/PMC4257163/ /pubmed/25484649 http://dx.doi.org/10.1107/S1600536814019874 Text en © Noland et al. 2014 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. Gullickson, Glen C. Dickson, Rozalin R. Groess, Leah L. Tritch, Kenneth J. Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title | Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title_full | Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title_fullStr | Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title_full_unstemmed | Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title_short | Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione |
| title_sort | crystal structure of (±)-(3ar,5r,8br)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2h,3ah)-dione |
| topic | Research Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257163/ https://www.ncbi.nlm.nih.gov/pubmed/25484649 http://dx.doi.org/10.1107/S1600536814019874 |
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