I haven't, but I recall messing with it once with my shoulder holster and it seemed to fit fine. Holster I got for a S&W Model 10 4" barrel. My Ruger also has a 4" barrel I believe, adjusted the straps and seemed fine. I set up under my left arm, for a right handed cross draw, so - whatever barrel is pointed directly down, maybe a bit backward. I think anything longer would bug me.
I'm just saying if I had to, carry a .22 I'd go out of my way to carry one with a longer barrel. Although, now that I think of it, I do carry an NAA Mini in the summer sometimes with .22 MAG, and I went with the MAG because the barrel is very short, so - some of it becomes a toss up, can't get everything and something has to bend somewhere, convenience vs. capabilty, just be able to shoot OK, be safe, and make sure the equipment works is my take.