It happens, but it's more complicated than just hitting "right" or "wrong" boss. And it's hard to organize a clan where CB damage ranges from 300K to 6M per key, without proper communication channels.
I try to advise my clan to hit the boss, from which they can get the best chest.
For example, you have a player who does damage to Normal CB from one key enough to get the top chest. But entire clan still can't kill the boss. This player will then go and spend the rest of his keys on Hard CB. Because there's no reason to waste keys on normal, as there's no chance to get a double chest.
At the same time, this player can send weaker team to Easy CB to do around 1.6M damage just to help the team. He shall not send the strong team as it will prevent 3-4 more players from getting chests.
As I said, complicated :/