TOLEDO, Ohio (AP) — A Michigan man led authorities on a 30-mile chase into Ohio where officers shot and killed him after he pointed a gun at them during a standoff early Monday, police said.

The man crashed his car in a Toledo neighborhood, came out holding a handgun to his head and began walking a few blocks where he stopped outside a convenience store, police said.

Negotiators talked with the 50-year-old man from Monroe, Michigan, and tried to de-escalate the situation for nearly 20 minutes while he kept the gun pointed at his head, Toledo police said in a statement. At one point, a trooper with Michigan state police tried to take him down with a stun gun.

Minutes later, the man began indicating he was going to point the gun at the officers and repeatedly said “tick tock” before he lowered the gun into a shooting stance and raised it toward the officers, police said.

Toledo police officers and troopers with the Michigan state police shot the man. He was pronounced dead at the scene.

The chase began after authorities were called about a man who had fired at least one shot outside a mall in Monroe, police said.