I just finished reading in an older muzzleloading book about George Washington, during the Revolutionary War, commissioning the building of several long-range flintlock rifles for use as sniping weapons. They were 8-gauge, firing a round ball weighing 1/8 of a pound. These guns were required to deliver sufficient accuracy as to place four out of five shots into a " piece of note paper" (10" X 12" ), at " 80 rods" (440 yards). This is 1/4 of a mile, and would certainly kill a deer (or man) at that distance. And, these were flintlocks shooting round balls with the powders available in 1777!! I assume the trajectory would have been very steep, and would require a very good judge of ranges to make hits!!