3,4,4a,5,6,7,8,8a-Octahydro-8a-hydroxy-2-quinolone and its 8a-hydroperoxy derivative

The crystal structures of the title compounds, 3,4,4a,5,6,7,8,8a-octahydro-8a-hydroxy-2-quinolone, C9H15NO2, (I), and 3,4,4a,5,6,7,8,8a-octahydro-8a-hydroperoxy-2-quinolone, C9H15NO3, (II), show a trans- and cis-fused-ring configuration, respectively, with the cyclohexane rings in a chair conformation in both compounds. In (I), the molecules are linked about 21 axes via intermolecular N-HO hydrogen bonds, forming an infinite helix; further O-HO interactions result in a two-dimensional hydrogen-bond network. In (II), the molecules form centrosymmetric dimers via pairwise N-HO interactions, and these dimers are connected by O-HO hydrogen bonds, giving infinite parallel chains