Syntheses and crystal structures of the imides 4-(2-phenylethyl)- and 4-[2-(4-hydroxyphenyl)ethyl]-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione

The syntheses and characterization (NMR and XRD) of two substituted [2.2.2]bi-cyclo-octene ring systems are described here. The cyclo-hexene rings of these systems adopt a nearly perfect boat conformation according to analysis using Cremer-Pople parameters. Both structures contain a nearly planar imide ring that is oriented <i>endo</i> relative to a bridgehead cyclo-propyl ring. 4-(2-Phenyl-eth-yl)-4-aza-tetra-cyclo-[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione, C₁₉H₁₉NO₂, is substituted with a phenylethyl group that hosts C-H⋯π inter-actions in the crystal. 4-[2-(4-Hy-droxy-phen-yl)eth-yl]-4-aza-tetra-cyclo-[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione, C₁₉H₁₉NO₃, bears a 4-hy-droxy-phenylethyl group on the imide ring and contains O-H⋯O and C-H⋯O hydrogen bonds.