Structure of 1,3-dihydro-4-[(2R)-2,5-dihydro-2-furyl]-3-phenyl-1-(p-tolyl)-2H-imidazole-2-thione, C20H18N2OS

Abstract

M r = 3 3 4 . 4 , orthorhombic, P212~2 ~, a = 9.366(4), b = 2 0 . 6 1 6 ( 5 ) , c = 9 . 1 3 7 ( 4 ) A , V = 1764 (1) A 3, Z = 4, D x = 1.26 Mg m -3, 2(Mo Ka) = 0.7107 A, g = 0.18 mm -~, F(000) = 704, T = 300 K, final R 0 . 0 5 6 (wR =0 .052) for 1979 observed reflections [I > 2a(/)]. The furanose ring is approximately planar because of the double bond, 1.289 (9) A, which affects the conformation of the ring. The dihedral angle between the furanose and imidazole least-squares planes is 69.9 (2) °. A possible C--H. . .O hydrogen bond has been detected involving C and O atoms in the furanose ring, giving infinite helical chains along [001 ]. Introduction. The title compound (I) has been obtained by the reaction of 1,3-dihydro-4-(2,3-di-O-tosyl-fl-Derythrofuranosyl)-3-phenyl1-(p-tolyl)-2H-imidazole-2thione with sodium iodide and zinc powder in dimethylformamide. A study with the ~H NMR technique in solution showed an approximate planar conformation for the furyl ring (Fernfindez-Bolafios Guzm~n, 1984), in agreement with the solid-state results from X-ray data.