Liverpool were sent tumbling into the Europa League after Fiorentina claimed a victory over Lyon which secured the Italians' progress to the knockout stage at the expense of the 2005 champions.

David Ngog scored the only goal as Liverpool battled to a 1-0 win over Group E minnows Debrecen, but the result was academic as a Juan Vargas penalty in Florence secured the three points the Viola needed to reach the last 16 for the first time.

Liverpool, who conclude their Champions League campaign against Fiorentina at Anfield next month, must now content themselves with a place in the Europa League.

Arsenal secured a place in the last 16 with a 2-0 win over Standard Liege while in the other Group H game, AZ Alkmaar slipped meekly out of the competition with a goalless draw at home to Olympiacos.

Ronald Koeman's side needed a win to keep alive any hope of progressing after taking just two points from their opening four games.

But they were unable to find a way past visiting goalkeeper Antonis Nikopolidis as Olympiacos moved three points clear of third-placed Standard with one game remaining.

Holders Barcelona moved two points clear at the top of Group F after producing a classy display to defeat Inter Milan at the Nou Camp.

Barca could have found themselves out of the competition if results had gone against them but Pep Guardiola's side are now within touching distance of a place in the last 16 after brushing aside Inter thanks to early goals from Gerard Pique and Pedro Rodriguez.

The result leaves Barca on eight points after five games, two clear of Inter and Rubin Kazan and three above Dynamo Kiev - who played out a goalless draw with Rubin in Tuesday night's other Group F contest.

Rangers crashed out of Europe with a dispiriting 2-0 home defeat to Stuttgart in their penultimate Group G match.

Meanwhile, a calamitous Ivica Dragutinovic headed own goal inflicted Sevilla's first defeat in the tournament this season as Unirea Urziceni remained on course for a place in the next round with a 1-0 win.

Despite a host of further chances, the second-placed Romanians had to be content with the solitary goal and meet Stuttgart in their final Group G game next month as they bid to join Sevilla in the knockout stages.