Crystal and molecular structure ofN-benzyl-1-phenylsulfinyl-1-propenyl-2-amine monohydrate, C₁₆H₁₇NOS·H₂O

Abstract

The crystal and molecular structure ofN-benzyl-1-phenylsulfinyl-1-propenyl-2-amine monohydrate, named enamineI, has been determined on the basis of X-ray data. The structure found in the solid state was compared with the structure found from NMR spectra in solution. CompoundI exists as enamine in theE configuration in the crystal, whereas the enamine is in theZ configuration and as a mixture of both theZ and theE imines in solution. Three intermolecular H bonds involving each molecule ofI and water of crystallization have been found in the crystal. The NMR spectra in a range of the solvents of different H-bond donor-acceptor properties and polarizability suggest the formation of hydrogen-bonded molecule-solvent aggregates stabilizing the enamine structure ofI in solution. Crystal data:a=9.42(1),b=16.924(4),c=10.557(6) Å,β=111.01(2)°, space groupP2₁/n,Z=4, MoKα radiation,R=0.050 for 1059 independent reflections.