(Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol.
The title compounds, C22H20N2O3S, (I), and C22H22N2O3S, (II), crystallize in space groups P-1 and P2(1)2(1)2(1), respectively. The indole rings are planar and the benzene ring of the phenylsulfonyl group makes a dihedral angle with the mean plane of the indole ring of 90.2 (2) degrees in (I) and 94.0 (2) degrees in (II). In both molecules, the double bond connecting the aza-bicyclic and indole moieties has a Z geometry. Compound (II) was obtained as an enantiomerically pure crystal and has the 3S configuration.
Sonar
Vijayakumar N
VN
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
Parkin
Sean
S
Crooks
Peter A
PA
D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D000442:Octanols / Q000138:chemical synthesis / Q000737:chemistry; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D007211:Indoles; D000442:Octanols; D013450:Sulfones