Reactions of imidazol(in)-2-ylidenes with electron deficient fluoroolefins

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• The original crystals of 8 that were submitted for X-ray diffraction studies were opaque and diffracted only weakly. After sitting in a vial for several days, smaller crystals grew in between the originals and the glass. The sample and adventitious water probably reacted with silicon in the glass causing it to lose a fluorine atom at C12, forming the double bond C12 = C11 and a SiF5− counterion (9). Crystal data for 9 at −115°C with Mo Kα radiation: a = 1128.5 (2), b = 1857.3 (3), c = 875.1 (1) pm, β = 112.24 (1)°; triclinic, P1; Z = 4; μ(Mo) = 2.60 cm−1; 2483 unique reflections with I ≥ 2.0 σ(I). The structure was solved by direct methods (SHELXS) and refined by full-matrix least-squares on |F|. C, F and N atoms were refined with anisotropic thermal parameters. All H atoms were idealized using a riding model. The Fourier map was 0.70 e/Å3. The data/parameter ratio was 5.10. The final R factors were R = 0.057 and Rw = 0.046. The crystals first submitted looked opaque.
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• Crystal data for 13 at −100°C with Mo Kα radiation: a = 1492.5 (3), b = 1264.1 (2), c = 1726.0 (3) pm, β = 125.30 (1)°; monoclinic, P21/n; Z = 4; μ(Mo) = 1.32 cm−1; 3328 unique reflections with I ≥ 3.0 σ(I). The structure was solved by direct methods (MULTAN) and refined by full-matrix least-squares on |F|. C, F and N atoms were refined with anisotropic thermal parameters. All H atoms were idealized using a riding model. The Fourier map was 0.37 e/Å3. The data/parameter ratio was 7.53. The final R factors were R = 0.050 and Rw = 0.053. The asymmetric unit consists of one carbene derivative co-crystallized with one THF in general positions.
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• Crystal data for 14 at −70°C with Mo Kα radiation: a = 3654.0 (8), b = 1322.4 (2), c = 2582.6 (8) pm; β = 101.96 (1)°;monoclinic, C2/c; Z = 8; μ(Mo) = 1.12 cm−1; 2718 unique reflections with I ≥ 3.0 σ(I). The structure was solved by direct methods (MULTAN) and refined by full-matrix least-squares on |F|. C, F and N atoms were refined with anisotropic thermal parameters. All H atoms were idealized with C-H = 0.95Å. The Fourier map was 0.22 e/Å3. The data/parameter ratio was 4.01. The final R factors were R = 0.047 and Rw = 0.035. The asymmetric unit consists of two carbene molecules co-crystallized with one half a THF molecule lying on the two-fold.
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