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The 20-year-old Briton, fresh off of a final appearance at the Metz Open, relinquished a 5-2 second-set lead to hand the Serbian number two an easy path to the quarter-finals where he will face Czech Radek Stepanek.

Murray failed on repeated set points in the second frame and was a woeful 1-for-10 on break opportunities.

It was a frustrating afternoon for Murray, making his first appearance in Moscow, as the world number 18 argued in vain with the umpire about a number of disputed calls in the second set.

"I didn't feel like I played too badly. I played one bad game to lose my serve in the first set, but in the second I had so many chances," he said.

"I was 5-2 at 15-40 on his serve, then I lost my serve, I also had 0-40 on his serve at 5-4, but I had some pretty rough calls go against me. It was tough as I felt like I should have been in the third set."

Murray's match was played on court one which was not equipped with the Hawk-Eye electronic system, allowing the players to challenge a call.

The 20-year-old said he was not feeling tired after reaching the final at last week's Metz Open.

"No, I wasn't that tired, I'm still upset because I feel like I deserved to win that second set."

Russian second seed Mikhail Youzhny also crashed out of the indoor hardcourt event, going down to little-known German Michael Berrer 7-5 6-4 in the second round.

The 72nd-ranked Berrer broke Youzhny in the 11th game to take the opening set before repeating the trick at the start of the second to record only his second win against a top 20 opponent this year.

"I don't think I played that badly," world number 17 Youzhny said.

"But you have to give him credit, he played really well, especially in those three games from 5-5 in the first set."

Berrer, who has reached only his third quarter-final on the ATP Tour this year, will face eighth-seeded compatriot Philipp Kohlschreiber in the last eight.

Another Russian seed, number five Marat Safin, crashed out in the second round losing 6-4 6-4 to compatriot Igor Andreev.

The former world number one was playing in his first tournament since the US Open.

Top seeded Russian and home favourite Nikolay Davydenko, meanwhile, had an easier time of it than his two seeded compatriots, strolling into the quarter-finals after beating Ecuador's Nicolas Lapentti 6-4 6-4.

Reuters / Eurosport