Crystal structure of N-[(methylsulfonyl)oxy]-N-((E)-2-(methylsulfonyl) oxy]imino-1,2-diphenylethylidene)amine, C16H16N2O6S2

Abstract

C16H16N2O6S2, triclinic, P1 (no. 2), a = 5.392(2) A, b = 9.300(4) A, c = 9.420(4) A, * = 93.933(9)°, ) = 90.20(1)°, & = 106.375(9)°, V = 452.0 A, Z = 1, Rgt(F) = 0.047, wRref(F) = 0.157, T = 293 K. Source of material All reagents and solvents use in this work were commercially available and used as purchased. Methanesulfonyl chloride (0.4 g, 3.5×10mole)was dissolved in 20ml of dryTHFand 4ml of redistilled pyridine. The solution was cooled to –5 °C, then treated drop by drop with diphenylglyoxime solution (0.42 g, 1.75×10mole) dissolved in 20 ml of dry THF, during the addition the reaction temperature was kept constant for around one hour, the reaction then lefted to stir at room temperature for 12 h. 40 ml of distilled water and dichloromethane each was added to the reaction mixture, which was transferred to 200 ml separator funnel. The organic layer was separated and after evaporation by dichloromethane. White powder of 1.12 g (80 % yield) was collected. The crystals were grown by slow evaporation of solution of the compound in methanol. Discussion Oximes/dioxime and theirmetal complexes are of current interest for their rich physicochemical properties, reactivity patterns and potential applications in many important chemical processes in the areas of medicine [1], bioorganic systems [2], catalysis, electrochemical and electrooptical sensors [3,4]. The high stability of the complexes with vic-dioxime ligands has been extensively used for various purposes including model compounds for vitamin B12 or trace metal analysis [5]. The E isomer of the title compound as a kinetically favored was detected over the Z isomer due to the steric factor. The single bondC7—C7 is clearly characterized by the distance of 1.439A. The double bond of C7=N1 and C7=N1 is characterized by the distance of 1.281 A. The conjugation of the , bonding electrons in ON1=C7—C7=N1O system reduced the length of the C7—C7 bond. The molecules packing in the crystal structure (figure, bottom) is stabilized by three weak intermolecular interactions, of which oxygen O3 of the sulphonyl functions in both methylsulphonylmoietyworks as acceptor. There are two type of donors which interact with O3. The distance H8A···O3 of the methyl group is 2.611 A and the angle C8–H8A···O3 is 153.85°. The distance of the interactionC1–H1···O3 is 2.702A and the relevant angle is 137.73°. There is no intramolecular H-bond in the molecule. Z. Kristallogr. NCS 225 (2010) 611-612 / DOI 10.1524/ncrs.2010.0267 611 © by Oldenbourg Wissenschaftsverlag, Munchen