Ipod not syncing video files?

When I try to sync a video file Itunes crashes and Windows says it's stopped working.
It is a relatively large video file, but theres plenty of space?
Whats wrong?
Update:
I tried to sync a small video file and it got right to the end of the progress bar and crashed.
Message was edited by: Toms2056

Oh, don't worry
My cousin helped out, seemed to be a problem with things relying on other programs, for example contacts.. After these were removed from the sync it all worked fine.

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