Murray bows out

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Murray received treatment on an apparent groin problem in the first set and struggled with his mobility throughout, but will nevertheless rue the chance to get more practice on clay before Roland Garros.

It was a good opportunity for the British number one to make the latter stages of the tournament after Rafael Nadal, his likely third round opponent, suffered a rare defeat at the hands of Carlos Ferrero earlier in the day.

With Murray serving to restore parity at 2-2, Wawrinka broke the Scot on the first break point of the match to move to 3-1 up.

Murray then slumped to 4-1 down before seeking treatment on his injury. The Dunblane native battled hard in pursuit of a break of his own before the Swiss served out to take his third consecutive game.

After Murray had won the sixth game Wawrinka wrapped up the next two in quick succession, breaking the Scot's vulnerable serve once more after a first double fault of the day to take the opening set 6-2.

That seemed to spur Murray into action as he won for the first time against serve, before taking a two-game lead early in the second set.

Wawrinka made no mistakes in his next service and Murray survived a brief scare to retain his lead in the following game. It was soon 4-3, with no major worries for either player but the 20-year-old Briton conceded two break points in the eighth game, eventually handing his opponent the game on a second serve

Murray could not launch a counter-attack in the next game and at 5-4 behind, the sudden shift in momentum left him serving to stay in the tournament.

Wawrinka quickly amassed four match points as the Murray serve crumbled but he launched a gutsy fightback to take the game with a belated, but concerted, effort. Both men then won their final games to go into a tie-break, which Wawrinka won after collecting another two match points.