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

• Main Authors: Bastian Tewes, Bastian Frehland, Roland Fröhlich, Bernhard Wünsch
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-05-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; NMDA receptor antagonists; GluN2B antagonists; ifenprodil analogs; tetrahydro-3-benzazepines; relative configuration; conformational restriction; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989016005855

In the title compound, C25H27NO4S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH3 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.