Abstract
With the present study, we revise earlier results about the title compound 2-mercaptopyridone in which the deformation density was determined from an X–N study in 1982 (X-ray, neutron diffraction). In the current X–X study (X-ray, X-ray), anharmonic motion parameters for the atoms were included and it resulted in a very clean deformation density map without the unexplainable features of the literature results. The presence of anharmonic effects is supported by a study of the thermal expansion in the temperature range 100–260 K. A topological study of the electron density confirms a bond length alternation in the six-membered ring. The calculation of the electrostatic potential indicates that the N–H⋯S hydrogen bond is an electrostatic interaction, and that other attractive intermolecular contacts are probably dispersive.
Highlights
Introduction2-Mercaptopyridone (I) occurs in two tautomeric forms (Scheme 1) which are in equilibrium with each other
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The X–N map gives an impression of the deformation density but it shows unexplainable features in the proximity of the sulfur atom
Summary
2-Mercaptopyridone (I) occurs in two tautomeric forms (Scheme 1) which are in equilibrium with each other. This was elucidated by Penfold in 1953 based on photographic methods and two-dimensional electron density projections [3]. The X–N map gives an impression of the deformation density but it shows unexplainable features in the proximity of the sulfur atom. The authors ascribe this to a difference in the anisotropic displacement parameters between the X-ray and the neutron results. It appeared to be necessary to include a model with anharmonic motion parameters This often concerns heavy-atom compounds but examples of purely organic compounds are well known (e.g., [6,7])
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