STRUCTURE OF (+)-(S-(E))-N-(ALPHA-METHYLBENZYLIDENE)-P-TOLUENESULFINAMIDE

C15H15NOS, M(r) = 257.35, monoclinic, P2(1), a = 7.710 (2), b = 5.903 (5), c = 14.700 (3) angstrom, beta = 91.48 (2)-degrees, V = 668.8 (6) angstrom-3, Z = 2, D(x) = 1.278 g cm-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 2.18 cm-1, F(000) = 272, T = 296 K, R = 0.043, 944 unique observed reflections. This is the first structure determination of an N-alkylidenesulfinamide. The C=N bond is distorted and lengthened presumably because of the steric interaction and electron-withdrawing effect of the sulfinyl group. The nonplanar conformation is also a result of repulsive steric interaction. The configuration at C=N is trans. The title compound was obtained from the displacement reaction of (-)-1-menthyl (S)-p-toluenesulfinate with methyllithium.