Mart, the castings of the 221ci and 239ci 59 engines aren't the same, the 221city has thinner cylinder walls. And the smaller bore. They won't bore as Big as the 239ci. I think I've said before, I think Glen had a 21 stud bored to 3 3/16". Yes you get close to the bottom stud, but it does go. Theirs also a 255ci 21 stud build in the Tex Smith flathead book. And Don Ferrara had a 1937 engine bored to 3 3/16 + 0.60. There more but they are from the top of my head. As far as I know big bore gaskets went/arnt available for the 21 stud. Stock gaskets appear to be ok for use. If you look at the pics above, that's 0.080" over at 0.125" over the bore edge would still be under the fire ring, the piston edge on stock pistons doesn't normally reach the deck surface, so no problems with them hitting.
Martin.