The effect of nitrogen atom on double bond pyramidalization

The title compound 6-phenyl-4,6,8-triazatetracyclo9.2.1.0^2,10.0^4,8]tetradec-2(10)-ene-5,7-dione (6) has been synthesized by the addition of 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) to 2,3-dimethylenebicyclo2.2.1]heptane. The cell parameters are a = 9.991(5), b = 11.754(9), c = 6.549(5) Å, = 101.08(7)°, = 103.31(5)°, = 98.24(5)°. The crystal structure of 6 was determined. The obtained geometrical parameters were highly correlated with the DFT calculations. The experimentally determined folding angle of the double bond was found to be 8.44°. The effect of the electron-withdrawing ability of nitrogen atom on the degree of pyramidalization is discussed.