Chocolate Cookie Cheesecake

• 2 pounds cream cheese, softened
• 1 ½ cups white sugar, divided
• ⅓ cup heavy whipping cream
• 2 tablespoons all-purpose flour
• 2 teaspoons vanilla extract, divided
• 4 large eggs
• 1 ½ cups chocolate sandwich cookie crumbs
• 16 ounces sour cream

Chocolate Topping:

• 1 ½ cups semisweet chocolate chips
• 1 cup heavy whipping cream
• 1 teaspoon vanilla extract