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Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists

In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosyl­ate moiety are incli...

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Autores principales: Tewes, Bastian, Frehland, Bastian, Fröhlich, Roland, Wünsch, Bernhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908544/
https://www.ncbi.nlm.nih.gov/pubmed/27308018
http://dx.doi.org/10.1107/S2056989016005855
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author Tewes, Bastian
Frehland, Bastian
Fröhlich, Roland
Wünsch, Bernhard
author_facet Tewes, Bastian
Frehland, Bastian
Fröhlich, Roland
Wünsch, Bernhard
author_sort Tewes, Bastian
collection PubMed
description In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosyl­ate moiety are inclined to the planar 3-benzazepine ring by 78.39 (15) and 77.03 (14)°, respectively, and to each another by 13.82 (15)°. In the crystal, mol­ecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming double-stranded chains along the a-axis direction. The chains are linked via C—H⋯π inter­actions, forming a three-dimensional architecture.
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spelling pubmed-49085442016-06-15 Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists Tewes, Bastian Frehland, Bastian Fröhlich, Roland Wünsch, Bernhard Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosyl­ate moiety are inclined to the planar 3-benzazepine ring by 78.39 (15) and 77.03 (14)°, respectively, and to each another by 13.82 (15)°. In the crystal, mol­ecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming double-stranded chains along the a-axis direction. The chains are linked via C—H⋯π inter­actions, forming a three-dimensional architecture. International Union of Crystallography 2016-04-15 /pmc/articles/PMC4908544/ /pubmed/27308018 http://dx.doi.org/10.1107/S2056989016005855 Text en © Tewes 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 Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Tewes, Bastian
Frehland, Bastian
Fröhlich, Roland
Wünsch, Bernhard
Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title_full Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title_fullStr Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title_full_unstemmed Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title_short Crystal structure of (1S*,2R*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1H-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
title_sort crystal structure of (1s*,2r*)-7-benz­yloxy-2-methyl-3-tosyl-2,3,4,5-tetra­hydro-1h-3-benz­azepin-1-ol: elucidation of the relative configuration of potent allosteric glun2b selective nmda receptor antagonists
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908544/
https://www.ncbi.nlm.nih.gov/pubmed/27308018
http://dx.doi.org/10.1107/S2056989016005855
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