Crystal structure of 4-methyl-N-{(E)-methyl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-3-yl]-λ⁴-sulfanylidene}benzenesulfonamide

Abstract

The formulation that the title compound, C18H18N2O4S2, adopts is a zwitterionic core with the charge separated to the sulfilimine S and N atoms and is supported by the two different S—N bond distances about the sulfinimine N atom [1.594 (2) and 1.631 (2) Å, respectively] that are typical for such bonds. The notably unusual bond is S—N(oxazolidinone) [1.692 (2) Å] that is longer than a typical S—N bond [1.603 (18) Å, Mogul analysis; Macrae et al. (2008 ▸). J. Appl. Cryst. 41, 466–470]. The bond-angle sum about sulfilimine sulfur (308.35°) reflects the trigonal–pyramidal geometry of this atom. Two of the angles are less than 100°. Despite the pyramidalization of this sulfur, there are no significant inter­molecular inter­actions, beyond usual van der Waals contacts, in the crystal packing.

Crystal structure and absolute configuration of (3aR,3′aR,7aS,7′aS)-2,2,2′,2′-tetramethyl-3a,6,7,7a,3′a,6′,7′,7′a-octahydro-4,4′-bi[1,3-benzodioxolyl], obtained from a Pd-catalyzed homocoupling reaction

“…Over the last few years, we have focused our efforts on the synthesis of vinylsulfimines as precursors in -lactamization reactions to generate asymmetric pyrrolidone derivatives which are of interest in medicinal chemistry (Silveira et al, 2012(Silveira et al, , 2014Silveira & Marino, 2013;Pereira et al, 2015). Encouraged by our previous experience in functionalizing halo-cyclohexadiendiols (Heguaburu et al, 2008;Labora et al, 2010;Heguaburu et al, 2010;Labora et al, 2008), we synthesized a vinylic sulfide (molecule 3 in Fig.…”