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The syntheses and crystal structures of the two title compounds, C 11 H 10 O 3 ( I ) and C 17 H 14 BrNO 2 ( II ), both containing the bi-cyclo-[2.2.2]octene ring system, are reported here [the structure of I has been reported previously: White &amp; Goh (2014 ▸). Private Communication (refcode HOKRIK). CCDC, Cambridge, England]. The bond lengths and angles of the bi-cyclo-[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 bi-cyclo-[2.2.2]octene ring system. Non-covalent inter-actions present in the crystal structure of II include a number of C-H⋯O inter-actions. The extended structure of II also features C-H⋯O hydrogen bonds as well as C-H⋯π and lone pair-π inter-actions, which combine together to create supra-molecular sheets.

acta crystallographica. section e, crystallographic communications

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