Application works with Wine, but not with Bottles

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I use a couple of Windows or macOS-only pieces of software for chemical research. I've gotten all of them running with Bottles except one, ChemDraw 23. I have it running in Wine using the instructions posted on WineHQ. I would prefer to use it in Bottles because the installation procedure is, to me, more straight forward. I think Bottles would be better to use on computers in my department. I was able to use the native installer to get it installed (which you can't do with Wine), but the app itself seems to silently crash when it's run. On the first run, I would expect it to ask for the product activation code, but it doesn't. Running it with the terminal open doesn't reveal any relevant error messages. It just seems to quietly die.

Is there any way I could diagnose this? It seems strange that it would work with Wine and not Bottles?