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  • Syntheses and crystal structures of the anhydride 4-oxatetracyclo[5.3.2.0 2,6 .0 8,10 ]dodec-11-ene-3,5-dione and the related imide 4-(4-bromophenyl)-4-azatetracyclo[5.3.2.0 2,6 .0 8,10 ]dodec-11-ene-3,5-dione
Title: Syntheses and crystal structures of the anhydride 4-oxatetracyclo[5.3.2.0 2,6 .0 8,10 ]dodec-11-ene-3,5-dione and the related imide 4-(4-bromophenyl)-4-azatetracyclo[5.3.2.0 2,6 .0 8,10 ]dodec-11-ene-3,5-dione
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 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.  more » « less
Award ID(s):
1725699 1919817 1919565
PAR ID:
10205958
Author(s) / Creator(s):
; ; ; ; ; ; ; ;
Date Published:
Journal Name:
Acta Crystallographica Section E Crystallographic Communications
Volume:
76
Issue:
8
ISSN:
2056-9890
Page Range / eLocation ID:
1311 to 1315
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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