Hello I really hope I didn’t Messed up my Co2 regulator. Here what I did I thought it would help my o-ring seal the one that goes from regulator to Co2 tank if I put a little keg lube on it here a picture of what I am talking about https://i.imgur.com/iWn6BqA.jpg.
My regulators use a hard plastic ring. It looks like you might have crushed the o ring. Try attaching it and turning it on, then spray with some star san or soapy water and see if it leaks
Our local hardware store has a bin with various rubber/nylon/neoprene washers… I found the hard 1/2" works well, and at .65 cents each, I bought 5… You’ll always need a backup…
Also, I wouldn’t use any type lube for that type of connection… You may think it works for just about everything… well, grease on an O2 connection is very dangerous… There, my public safety announcement for a year! 
Sneezles61
