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
Autor: | Theodore Schultz, Mason Tolonen, Breezy Squires, Isabel Lorenzana, Shannon M. Biros, Richard J. Staples, Andrew Hulsman, Brock A. Stenfors, William R. Winchester |
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Rok vydání: | 2020 |
Předmět: |
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 |
Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 76, Iss 8, Pp 1311-1315 (2020) |
ISSN: | 2056-9890 |
DOI: | 10.1107/s2056989020009512 |
Popis: | 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. |
Databáze: | OpenAIRE |
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