Crystal structure, and infrared and proton magnetic resonance spectra of 3-cyanomethylsulphonyl-2-morpholinocyclohexene : evidence for a C–H ⋯ N intramolecular hydrogen bond

Abstract

The crystal and molecular structure of the title compound (1) has been determined from three-dimensional X-ray data by direct methods, and refined to R 0.038 for 2 263 independent reflections. Crystals are monoclinic a= 11.635(1), b= 9.315(1), c= 12.103(1)Å, β= 93.00(1)°(at 23 °C), space group P2₁c, and Z= 4. A close C–H ⋯ N interaction, with H ⋯ N 2.47 Å, is found between a hydrogen atom of the cyanomethylsulphonyl group and the morpholino-nitrogen atom. I.r. spectroscopic evidence confirms the existence of the interaction in the solid state, thus permitting it to be classified as a weak hydrogen bond. ¹H N.m.r. and i.r. evidence indicates that the interaction may also exist in solution.