In a sturdy resealable plastic bag, combine the vinegar with 1/2 cup of the olive oil and the rosemary. Add the steak, seal the bag and refrigerate overnight, turning the bag several times.

Preheat the oven to 425 degrees and bring the steak to room temperature. Heat a grill pan. Remove the steak from the marinade and season with the salt and pepper. Rub the side with the remaining 2 tablespoons of olive oil. Grill over moderately high heat until nicely charred on the top and bottom, about 5 minutes per side. Transfer the steak to a rimmed baking sheet and roast for about 30 minutes, until an instant-read thermometer inserted into the tenderloin (the smaller section) registers 125 degrees. Alternatively, build a fire on one side of a charcoal grill or light a gas grill. Grill the steak over moderate heat for 5 minutes on each side. Transfer the steak to the cool side of the grill, close the lid and cook for 30 minutes longer. Transfer the steak to a carving board and let rest for 10 minutes. Slice the steak across the grain and serve immediately.