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You need the crank tool, and then you can leave the jail. You also want the club key, which you'll find shortly after you've used up the crank tool. (It's funny how I already know you're doing Leon because that part is Leon specific)
You get the diamond key in the jail but afaik its non-essential, only Claire needs it to progress. However it's still worth using.
From here make your way to 2F East Corridor and use the Crank to unlock the shutter just past the Art Room door. Thru this shutter, head upstairs. Take the flashbang here for when you meet Mr. X. Thru the right door is a storage room with a Large gear that you'll need for the clocktower. Then head thru the left door, climb down the ladder and down the staircase. Flip the switch to activate the water pump, then enter the saveroom next to it. In here is the Club Key which you'll need.
Return upstairs, activate the water pump and head inside. Pass Mr. X and head to 1F West Corridor, to use the Club Key to enter the Records Room. Here take the Mechanical Jack and use that in the Library to access the Clock Tower. Done.
Kilroy was here.