I will personally go to corner to corner because if you use Hb coin holders you want to know the diameter to store your coins, so the side to side is less practical for this use.
By the way it's remind me my work, for mower blades you dont take the lenght from one side to the other but from the 2 farest corners as in the pic below, the reason is simple, when the blade turn it describe a circle so you want to know the exact dimension of your circle to know the exact capacity of your mower.