
I don't understand - you say your dog has been 'done', by which I assume you mean castrated. If so, why are you keeping them separate?

Edit: Sorry, just re-read your post and see you have two males. I apologise, I have other things on my mind at the moment.
It would be much kinder not to let him meet her at all while she is in season. Is there someone he can go and stay with so he gets that tantalising scent out of his nostrils and can get his brain out of his trousers? Do you seriously mean he is being crated all night in the same room as an in-season bitch? Poor lad, no wonder he's upset. It is also possible for them to mate despite one being in a crate - it has been witnessed in the past.