IPhone says it is full when it is not

When I sync my phone, the bar at the bottom of the window says I have 1.42 gb of free space remaining, but whenever I try to add more music (even one song), it says that I don't have enough free space on my phone. On my phone settings>general>about, it says I have 361mb of free space. Any idea why I have three different possible amounts of free space (1.4gb, 361mb, or 0mb), and why it won't let me sync more music without deleting some, even though no matter how you cut it, there should be free space enough for one song?

<Edited by Host>
Restore the device to clean up OTHER. If Other is still over 2 gbs after restoring, restore again as new.

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