Judging by the absence of downtube shifter mounts, the frame is no older than 2000. The crankset is Ultegra 6600, which would date it between 2006 and 2009.

P.S. That said, I can't find any match for the paint scheme or the feature combo in the catalogs. Paint scheme is extremely plain for a 2006+ frame. Wheels aren't stock, fork probably isn't either. The closest match in terms of overall frame appearance and color seems to be 2001-2002 R400 (which would make it CAAD3).