, Volume 26, Issue 6, pp 381-388

Distortions in nitramine substituted cubanes: The structures of N,N′-dinitro-1,4-diaminocubane, N,N′-dinitro-N,N′-(2-pyridyl)-1,4-diaminocubane, and 1,2,4,7-tetrakis(N-methoxycarbonylnitramino)cubane

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The structures of three nitramine substituted cubane molecules, N,N′-dinitro-1,4-diaminocubane (1), N,N′-dinitro-N,N′-(2-pyridyl)-1,4-diaminocubane (2), and 1,2,4,7-Tetrakis(N-methoxycarbonylnitramino)-cubane (3), have been determined.1 crystallized in the space group P21/a with cell dimensionsa=6.545(1),b=9.331(1),c=7.459(1) Å, β=105.80(1),2 crystallized in the monoclinic space group P21/a with cell dimensionsa=7.545(2),b=8.697(3),c=12.406(4 Å, β=96.28(3)°, while3 crystallized in the monoclinic space group P21/c with cell dimensionsa=10.866(3),b=6.866(2),c=16.167(6) Å, β=108.79(3)°. The metrical parameters of the cubane skeleton showed no significant deviations from those found in other similarly substituted cubane molecules. For2 and3 there were considerable distortions of the nitramine moiety from planarity in contrast to1 where the nitramine moiety was almost exactly planar. The bond distances and angles for the nitramine group in1 indicates a substantial introduction of double bond character into the N−N bond in1, achieved by delocalization of the amine π lone pair, compared with2 and3.