Title of article :
Syntheses and crystal structures of the anhydride 4-oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione and the related imide 4-(4-bromophenyl)-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione
Author/Authors :
Hulsman, Andrew Department of Chemistry - Grand Valley State University, USA , Lorenzana, Isabel Department of Chemistry - Grand Valley State University, USA , Schultz, Theodore Department of Chemistry - Grand Valley State University, USA , Squires, Breezy Department of Chemistry - Grand Valley State University, USA , Stenfors, Brock A. Department of Chemistry - Grand Valley State University, USA , Staplesb, Richard J. Center for Crystallographic Research - Department of Chemistry - Michigan State University,USA , Tolonen. Mason Department of Chemistry - Grand Valley State University, USA , Biros, Shannon M. Department of Chemistry - Grand Valley State University, USA , Winchester, William R. Department of Chemistry - Grand Valley State University, USA
Abstract :
The syntheses and crystal structures of the two title compounds, C11H10O3 (I) and C17H14BrNO2 (II), both containing the bicyclo[2.2.2]octene ring system, are reported here [the structure of I has been reported previously: White & Goh (2014[White, J. M. & Goh, R. Y. W. (2014). Private Communication (refcode HOKRIK). CCDC, Cambridge, England.]). Private Communication (refcode HOKRIK). CCDC, Cambridge, England]. The bond lengths and angles of the bicyclo[2.2.2]octene ring system are similar for both structures. The imide functional group of II features carbonyl C=O bond lengths of 1.209 (2) and 1.210 (2) Å, with C—N bond lengths of 1.393 (2) and 1.397 (2) Å. The five-membered imide ring is nearly planar, and it is positioned exo relative to the alkene bridgehead carbon atoms of the bicyclo[2.2.2]octene ring system. Non-covalent interactions present in the crystal structure of II include a number of C—H⋯O interactions. The extended structure of II also features C—H⋯O hydrogen bonds as well as C—H⋯π and lone pair–π interactions, which combine together to create supramolecular sheets.
Keywords :
crystal structure , C-H⋯O hydrogen bond , C-H⋯π interaction , bicyclo[2.2.2]octene , lone pair–π interaction
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
