Bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxamide, C9H10N2O2
Abstract
Intramolecular hydrogen bonding between the amido groups [O(81)...H(111)=1.89 (4) A and N(11)-H(111)...O(81)=151 (3) o ] maintains the molecule in a conformation that favours partial delocalization between the amido groups and the adjacent C(2)=C(7) double bond. This can be inferred from a shortening of the C(1)-C(2) and C(7)-C(8) single bonds [1.479 (3) and 1.481 (3) A, respectively] and a small lengthening of the C(2)=C(7) double bond [1.341 (3) A]. Partial relief of the strain in the cycle then allows a shortening of the C(4)=C(5) double bond [1.285 (4) A] [1.330 (3) A in unsubstituted norbornadiene; Morino, Kuchitsu & Yokoseki (1967). Bull. Chem. Soc. Jpn, 40, 1552]
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