1. 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
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Theodore Schultz, Mason Tolonen, Breezy Squires, Isabel Lorenzana, Shannon M. Biros, Richard J. Staples, Andrew Hulsman, Brock A. Stenfors, and William R. Winchester
- Subjects
crystal structure ,c-h...π interaction ,Crystal structure ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Medicinal chemistry ,chemistry.chemical_compound ,General Materials Science ,Octene ,Imide ,Lone pair ,lone pair–π interaction ,Ene reaction ,chemistry.chemical_classification ,Crystallography ,010405 organic chemistry ,Hydrogen bond ,Chemistry ,Alkene ,bicyclo[2.2.2]octene ,General Chemistry ,Condensed Matter Physics ,0104 chemical sciences ,QD901-999 ,c-h...o hydrogen bond - 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). 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.
- Published
- 2020
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