Title of article :
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
Author/Authors :
Tewes, Bastian Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Germany , Frehland, Bastian Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Germany , ¨hlichb, Roland Fro Organisch-chemisches Institut der Westfälischen Wilhelms-Universität Münster, Germany , Wünsch, Bernhard Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Germany
Abstract :
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.
Keywords :
relative configuration , hydrogen bonding , conformational restriction , tetrahydro-3-benzazepines , ifenprodil analogs , GluN2B antagonists , crystal structure , NMDA receptor antagonists
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
