Syntheses and crystal structures of the anhydride 4-oxa-tetra-cyclo-[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione and the related imide 4-(4-bromo-phen-yl)-4-aza-tetra-cyclo-[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione.

ABSTRACT: The syntheses and crystal structures of the two title compounds, C11H10O3 (I) and C17H14BrNO2 (II), both containing the bi-cyclo-[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 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?? and lone pair-? inter-actions, which combine together to create supra-molecular sheets.

SUBMITTER: Hulsman A 

PROVIDER: S-EPMC7405554 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature