%0 Journal Article
%T The zwitterion (23′E)-(23R,25S)-23-[1-(oxidoiminio)ethyl]-5β-spirostan-3β-yl acetate
%A Mar&#237
%A a-Guadalupe Hern&#225
%A ndez Linares
%A Jes&#250
%A s Sandoval Ram&#237
%A rez
%A Socorro Meza Reyes
%A Sara Montiel Smith
%J Acta Crystallographica Section E
%D 2009
%I International Union of Crystallography
%R 10.1107/s1600536809044651
%X The title steroidal compound, C31H49NO5, resulted from the selective oximation of (23R)-23-acetylsarsasapogenin acetate. One- and two-dimensional 1H and 13C NMR spectra, as well as IR data, are in agreement with the presence of a ketoxime group at C-23. However, recrystallization in slightly acidic media affords the title compound in the rare zwitterionic oxime form, as a consequence of migration of the hydroxy H atom to the N atom in the oxime group. This H atom is clearly detected and its position was refined from X-ray data. The geometry for the C=N+(H)¡ªO  group features long C=N and short N¡ªO bond lengths compared to non-zwitterionic oximes. The ketoxime is stabilized with the E configuration, avoiding steric hindrance between the oxime O atom and H atom at C-23. The sum of the angles around the oxime N atom is 359.6¡ã, giving a planar configuration for that atom, as expected for sp2 hybridization.
%U http://scripts.iucr.org/cgi-bin/paper?S1600536809044651