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

Authors

• Jonathan P. Bajko
• Richard J. Staples
• Shannon Biros, Grand Valley State UniversityFollow

Keywords

crystal structure, imide, tricylic compound, C—H⋯O hydrogen bond, C—H⋯π inter­action

Disciplines

Chemistry

Abstract

The syntheses and characterization (NMR and XRD) of two substituted [2.2.2]bi­cyclo­octene ring systems are described here. The cyclo­hexene 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 endo relative to a bridgehead cyclo­propyl ring. 4-(2-Phenyl­eth­yl)-4-aza­tetra­cyclo­[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 inter­actions in the crystal. 4-[2-(4-Hy­droxy­phen­yl)eth­yl]-4-aza­tetra­cyclo­[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione, C₁₉H₁₉NO₃, bears a 4-hy­droxy­phenylethyl group on the imide ring and contains O—H⋯O and C—H⋯O hydrogen bonds.

Original Citation

Bajko, J. P., Staples, R. J., & Biros, S. M. (2024). 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. Acta Crystallographica Section E: Crystallographic Communications, 80(Pt 12), 1318–1321. https://doi.org/10.1107/S2056989024011253

ScholarWorks Citation

Bajko, Jonathan P.; Staples, Richard J.; and Biros, Shannon, "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" (2024). Open Access Publishing Support Funded Articles. 191.
https://scholarworks.gvsu.edu/oapsf_articles/191