Using itunes to perm delete files from ext hard drive

hello. the ext hard drives that contain my music crashed some time ago, and most of the files were thankfully restored, but in a slightly messy fashion, so now there's a lot of duplicate files and folders.
the easiest way for me to clean this up would be through itunes, using the show duplicate songs feature, but i cant figure out how to clear a file from itunes and make that permanently delete the file from my external hard drive.
ive read some discussion in other forums about shift-delete vs ctrl-delete, but not enough consistent information to be convinced.
can anyone help me out here?
thanks in advance,
bob

Are you "clearing" songs from a playlist or the Library?
To remove (send to Recycle bin) songs from a playlist and the library, select the song(s) and shift-delete them.
I've had the podcast problem once with a few podcasts a while ago. I 'solved' it by removing the duplicates. Some time later iTunes stopped duplicating.
Never discovered the actual cause. Sorry, can't help you with that one.
M

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