N-methylcodeinium iodide-Crystal structure and spectroscopic elucidation

The correlation between the structure and the spectroscopic properties of N-methylcodeinium iodide (1) has been studied, using the methods of single crystal X-ray diffraction, IR-LD spectroscopy of oriented samples as a suspension in nematic liquid crystals, UV-vis spectroscopy and H-1 and C-13 NMR spectroscopy. HPLC tandem mass spectrometry (HPLC ESI MS/MS) and thermal methods were also employed. Quantum chemical calculations have been performed with a view to obtaining the electronic structure and vibrational properties of the title compound. Compound (1) crystallizes in the space group P2(1)2(1)2(1) and its cations and anions are joined by moderate intermolecular OH ... I- interaction of length 3.442 angstrom. The codeine molecule exhibits the classical T-shape for opiates. A dihedral angle value of 86.4(5)degrees between the A/B/C and D/E planes is obtained. Rings A and B are effectively coplanar with an interplanar angle of 3.6(3)degrees. (C) 2009 Elsevier B.V. All rights reserved.