Not intended to be snarky. Sorry if taken that way.
But, every single deer and elk I have shot in the head died, immediately. And the hide kept everything mostly together. The last one was a mule deer finished off with my .300 win mag and a 180 sierra game king between the eyes. Broke the skull, but no mess.
It is against the law in Wyoming to kill a big game animal with a rim-fire. Expense of a single cartridge is insignificant in the total price spent on hunting, and really insignificant when compared to the price of a wildlife violation ticket.
If you are worried about shooting a deer in the head with your hunting rifle, then shoot it in the neck, right behind the head. Should be easy if you are getting close enough to finish it with a .22 LR!