Security footage released Wednesday shows a lone gunman approach a group of men in a North York courtyard over the weekend, shoot one of them, and flee.

The video was taken from Toronto Community Housing security cameras at 415 Driftwood Avenue, where Toronto police say the city’s 53rd homicide took place early Sunday morning.

Karim Hirani was with two friends in a courtyard near the building at around 3:20 a.m. when an armed man approached the group and opened fire.

Det.-Sgt. Mike Carbone said the suspect walked “directly toward” Hirani and shot him once in the head.

The 25-year-old died at the scene.

“I could say the shooter would’ve likely seen his face,” Carbone said. “It was definitely targeted.”

Carbone said security footage recovered from the vicinity depicts the movements of the suspect immediately before and after the attack.

A dark-coloured Nissan Maxima can be seen pulling into the building’s eastern lot and reversing into a parking spot. The suspect turns the vehicle off, walks from the driver’s side and through the lot before he disappears from camera view. He is wearing a hooded sweater, dark pants and a light-coloured baseball hat with what appears to be a set of large headphones overtop.

It is at this point, police believe, the man in the video ambushed Hirani and his friends, who were drinking in the nearby courtyard on a hot summer night.

The video shows the suspect running back to the car and speeding out of the lot.

“It seemed to me that he was very, very confident that the vehicle would not be attached to him,” Carbone said

The vehicle, though not yet recovered, is of particular interest to investigators.

Carbone said the car has been registered to a numbered company based in Toronto that operates like a rental company.

“It’s not a traditional one,” he said. “I say rental because I can’t think of another word for describing it. What we’ve come to learn is that folks can go up to this company and make some type of business transaction and they can have a car.”

Investigators have learned that the business is legally registered with the Ministry of Transportation with more than a dozen vehicles.

Despite this, Carbone said he’s had trouble contacting its operators. The vehicle in question has also not been located.

“It’s a mostly cash business. You can see why individuals may want to use this type of service to maintain their anonymity,” he said, adding that police are exploring whether the company is linked to other crimes.

“It’s very possible het met with these people and gave an anonymous name. It’s not one of these companies where you could need a credit card to book your rental period. I’m not even sure if anyone would even care if this vehicle was smashed up and left on the street.”

Since the shooting, Carbone said investigators have spoken with numerous witnesses.

One of the two friends with Hirani when he was shot apparently fled the courtyard when the gunfire erupted but has since contacted investigators.

Toronto Community Housing is working with officers to obtain more security camera footage, Carbone added. He said the “entire neighbourhood” is covered with cameras and that it’s possible more footage could be released in the coming days.

“I’m asking that anyone who has any information about this person, this vehicle or anything about the homicide to give us a call,” he said.

Little is known about Hirani and Carbone refused to provide any further details. He said the 25-year-old worked in construction and lived in the Toronto area, though did not reside at or frequent the Driftwood Avenue neighbourhood where he was killed.

“In the grand scheme of things, the investigation is still very early,” he said. “I don’t know what the killer knew. This is why we’re trying to reach out to as many witnesses as possible.

Anyone with information about the investigation is being asked to call Toronto police or Crime Stoppers anonymously.