Wow.... sorry to hear of your self-inflicted injury! I hate doing that myself! #-o
Now, about that bolt..... A 3/8" extension shouldn't be used here. That's a large nut ( 3/4"-16 thread - 15/16" head ) and you need to get a good grip. A regular old plumbers stillsin wrench (monkey wrench) works good here. Or a proper sized wrench or 1/2" drive socket & rachet. But a world of caution: Thats a hollow bolt. You can possibly twist it off or damage the housing if you over tighten it. My suggestion is to do what's been mentioned already. A THIN coating of silicone on the gasket after checking the housing to see if it's straight. Lay a piece of fine sandpaper on a large piece of plate glass and drag the housing across the glass while holding enough pressure so that you can slide it. If there's a section thats not scratched, do it again. Continue until there's scratches around the entire edge. The oil filter housing is made of aluminum and can be warped, or repaired, very easily. It's just a messy job. :sad1:
And by the way, that's lefty-loosy righty-tighty on the bolt thread....:thumleft: