BRUSSELS — Apple on Tuesday lost its fight against an order by EU competition regulators to pay 13 billion euros in back taxes to Ireland as part of an EU crackdown against sweetheart deals between EU countries and multinationals.

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The European Commission issued the order in 2016, saying that the iPhone maker benefited from two Irish tax rulings for over two decades that artificially reduced its tax burden to as low as 0.005 percent in 2014.