Using CrossOver Office 3.0.1, Diamond installs flawless, but crashes during startup. Using the CVS version of WINE it is running (20040615 should work as well).
I encountered only these two issues:
a) Atoms can either be drawn or rendered. Rendered atoms look nicer (3D instead of 2D), but unfortunally the off-screen rendering is not supported by wine; you get such a message: "err:opengl:X11DRV_ChoosePixelFormat Flag not supported".
If you are happy (like me), you can simply close the error message box and disable rendering by clicking the rightmost toolbar button. If you are unlucky, Diamond & WINE crash before you can disable the rendering. See WINE bug 2320.
Note: Since rendering is enabled by default, this may render Diamond unusable for you.
b) While the general information about the molecule works (well, the format is richer under Windows than under WINE and instead of the A with the ring (Angström) one gets only an [Ang]), the list display doesn't. One possible solution is to use the native dll, but I haven't tried it.