When did Amy rose saw shadow the hedgehog cry

First of all, Shadow doesn't actually cry, he just has a tear fall from his eye. Amy sees this when Sonic, Tails, Knuckles, Rouge, and Robotnik try to destroy the Eclipse Cannon. Amy tries to convince Shadow to help out and gives this senseless speech which some how triggers memories of Maria Robotnik dying, and results in Shadow's tear. This all happens in Sonic Adventure 2 , by the way.