I spent a good couple hours trying to get my prop shaft coupler bolt out and could not get it to loosen?

I was cranking on it both directions and al it was doing was torquing the shaft....When I pushed the shaft back up to put a couple bolts in to hold it now the coupler and tranny plate are about 1/4 inch offset....Did I bend my prop shaft trying to get the nut off?

I backed out the set screw but could not get the bolt to loosen....Is it a reverse rotation nut? Think its a bad idea to hit it with an air ratchet?
I'm replacing my dripless packing seal that was a steady stream. Think it could have gotten hot enough to "stick" the nut and coupler/shaft together.......HELP

Thanks guys