STRUCTURE OF 2-CYANO-4-PHENYL-GLUTARIMIDE STUDIED BY X-RAY-DIFFRACTION, VIBRATIONAL SPECTROSCOPY AND AB-INITIO METHODS

The structure of 2-cyano-4-phenylglutarimide (3c) has been studied by single-crystal X-ray diffraction, infrared and Raman spectroscopies an d ab initio methods. The crystals are monoclinic, space group P2(1)2(1 )2(1), With a = 5.970(2), b = 8.569(1), c = 19.982(3) Angstrom and z = 4. The X-ray diffraction study showed the presence of only one diaste reomer of 3c, the relative configuration of which could be either SC3R C5 or RC3SC5, With both the cyano and phenyl groups in the equatorial positions. The crystal packing is stabilized by a network of weak inte rmolecular N-H ... O, C-H ... O and C-H ... N hydrogen bonds. The mole cular structure calculated at the HF/D95V* ab initio level is in exce llent agreement with the one observed in the crystal. An assignment of characteristic infrared and Raman bands of 2-cyano-4-phenylglutarimid e is reported. (C) 1998 Elsevier Science B,V. All rights reserved.