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1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one
The title compound, C(17)H(15)NO(2), was prepared as one of two products of the AlCl(3)/POCl(3)-catalysed reaction of 9-carbazol-1-ol with 3,3-dimethyacrylic acid. It crystallizes with two crystallographically independent molecules, A and B, which are virtually superimposable but not related by any...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979736/ https://www.ncbi.nlm.nih.gov/pubmed/21579731 http://dx.doi.org/10.1107/S1600536810000322 |
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author | Zeller, Matthias Sridharan, Makuteswaran Rajendra Prasad, Karnam J. Ngendahimana, Aimable |
author_facet | Zeller, Matthias Sridharan, Makuteswaran Rajendra Prasad, Karnam J. Ngendahimana, Aimable |
author_sort | Zeller, Matthias |
collection | PubMed |
description | The title compound, C(17)H(15)NO(2), was prepared as one of two products of the AlCl(3)/POCl(3)-catalysed reaction of 9-carbazol-1-ol with 3,3-dimethyacrylic acid. It crystallizes with two crystallographically independent molecules, A and B, which are virtually superimposable but not related by any translational or other pseudosymmetry. Both independent molecules are almost planar [r.m.s. deviations from planarity = 0.053 (1) and 0.079 (1) Å in A and B, respectively] and contain an intramolecular O—H⋯O hydrogen bond. Each type of molecules is connected via pairs of N—H⋯O hydrogen bonds, forming centrosymmetric A (2) and B (2) dimers which are, in turn, arranged in offset π-stacks extending along the a-axis direction. The offset of the dimers and the tilt angle of the molecules allows the formation of alternating C—H⋯π interactions between A and B molecules of parallel stacks. |
format | Text |
id | pubmed-2979736 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29797362010-12-30 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one Zeller, Matthias Sridharan, Makuteswaran Rajendra Prasad, Karnam J. Ngendahimana, Aimable Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(15)NO(2), was prepared as one of two products of the AlCl(3)/POCl(3)-catalysed reaction of 9-carbazol-1-ol with 3,3-dimethyacrylic acid. It crystallizes with two crystallographically independent molecules, A and B, which are virtually superimposable but not related by any translational or other pseudosymmetry. Both independent molecules are almost planar [r.m.s. deviations from planarity = 0.053 (1) and 0.079 (1) Å in A and B, respectively] and contain an intramolecular O—H⋯O hydrogen bond. Each type of molecules is connected via pairs of N—H⋯O hydrogen bonds, forming centrosymmetric A (2) and B (2) dimers which are, in turn, arranged in offset π-stacks extending along the a-axis direction. The offset of the dimers and the tilt angle of the molecules allows the formation of alternating C—H⋯π interactions between A and B molecules of parallel stacks. International Union of Crystallography 2010-01-09 /pmc/articles/PMC2979736/ /pubmed/21579731 http://dx.doi.org/10.1107/S1600536810000322 Text en © Zeller et al. 2010 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 | Organic Papers Zeller, Matthias Sridharan, Makuteswaran Rajendra Prasad, Karnam J. Ngendahimana, Aimable 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title | 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title_full | 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title_fullStr | 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title_full_unstemmed | 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title_short | 1-(1-Hydroxy-9H-carbazol-2-yl)-3-methylbut-2-en-1-one |
title_sort | 1-(1-hydroxy-9h-carbazol-2-yl)-3-methylbut-2-en-1-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979736/ https://www.ncbi.nlm.nih.gov/pubmed/21579731 http://dx.doi.org/10.1107/S1600536810000322 |
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