OK, so I would call that stretch, rather than squeeze, but I see what you mean. You want to put some squeeze on the seal by the bolt sliding over it.
Is it atmosphere on one side and chamber pressure on the other? If so, then very little squeeze is needed. I have to admit that I would always deal with this kind of problem with a suck it and see approach. I would spec the internal diameter of the bolt first, because this is the critical dimension for your force calculations. Then I would take the seal closest to the bolt ID that is smaller than the ID. I would then guestimate the groove dimension for the gland, based on previous experience, and then add a little bit. I'd have the parts made, test it, and if I wasn't happy with the frictional result (testing by feel and by hand) I would offer up the part in the lathe and skim 0.05-0.10mm at a time out of te groove until I was happy with the fit. Then I'd measure it, amend the drawing, and have a second sample made at the factory.
I know that may not be much help, but I hope it shows that there isn't really a cast-iron method of doing this and it is still, for me, a case of trial and error.
That process is for dynamic seals, of course. Static is far easier and more forgiving.
Regarding the other scenario I asked about, I have never had ANY success in doing that. Putting a larger o-ring into a smaller internal groove to squeeze it down to a shaft has never worked for me.
Jack