Gosh, I did my normal searches and that's as good a guess as I can come up with. The bust is definitely not Charles III
I believe that "R" may be an assayer's mark - which if we're correct on our Charles II guess means it's Pedro Ramos or Gaspar de los Reyes from the Bogota mint, 1676 at its newest. Hopefully one of the forum "heavyweights" that really knows this stuff will come in and correct us! Cool coin!
I suppose this could be a coin with the bust of Charles II, issued for the Italian kingdom of Naples and Sicily. The kings of Spain were also king of Naples and Sicily. However, as these coins don't appear in Krause, I am not able to give an exact determination. The crowned shield bears the arms of Naples and Sicily.
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