Windows Server 2008: Freeing up space on C drive

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C drive
Windows Server 2008
We currently have a Windows Server 2008 with both C and D drives. We have already freed up about 30 GB's of memory on the D drive using the shrink volume option but this also needs to be done to the C drive. But it says the extend volume is disabled on it. How should we free up the space on our C drive? Is there a way to do it through the D? Thanks.
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