Depends on the application...the general rule is to keep the ratio under 9:1, with the closer to square=the better. Most low tuned boxes (unless they're huge) have to round a corner and usually are thinner to make it practical. If that's the route you need to go, then you look at minimizing turbulence at the points of restriction; the inner mouth, any bends, and the outer mouth. 3/8" radius would be the absolute minimum you should ever use and of coarse more is usually better. If there needs to be a 90 degree angle in the port then you should add a 45 degree corner to the box side and roundover the port corner joint as much as you can. Think of it this way, a continous radius would be ideal since it wouldn't introduce velocity changes to the airflow in the port. I'll show you an example of something I've done to overcome this. Note that the end panel (which is the other port wall) isn't attached yet.
Finished pic