The crank pulley bolt is a common point of annoyance. The reason is because it's torqued to about 150 lb/ft, but requires a LOT more than that to loosen. The best way to loosen it is normally to put the car in 5th gear with the wheels on the ground, chocked and the emergency brake on, and get the right socket with a long breaker bar or rachet with a cheater bar and put as much weight on it as you can.