I am having the same error or just crashes back to Steam. With Crossover games 7.2 I managed to install the orange box from discs (The only issues were needing to change the Keyboard layout to U.S. in order to create an account on steam, and having to eject disc 1 with a terminal command in order to finish) - I loaded Half Life 2 - set it to 1680 x 1050 and changed to anisotropic filtering and 4x AA (I have a Apple OEM 4870). The game ran fine for 5-10 minutes walking about the station areas until there was a cut seen - after playing this the game quit to steam. Will 7.2.1 I can't get past the black loading screen - it gets part way then crashes. I tried turning off FSAA and choosing trilinear filtering but no change.
I also tried Portal for the first time with 7.2.1 and this locked up at the main menu with the sound looping. I force quit and even after quiting Crossover games the sound was still playing - I managed to find a wine related process in activity monitor to kill it.
In other bottles I have Max Payne 2 and Tomb Raider: Legend running just fine.