Can not empty Trash

Hi there, I have recently had a corrupt iphoto library. I have extracted the pictures and created a new library. After doing this I deleted the old library, which is in my MAC trash (not iphoto trash).
I can not empty my trash and have searched everywhere online for a resolution, these are things I have tried ....help I need to dump this large library.
Thanks
1- Right Click - empty trash
     I get The operation can’t be completed because the item “iPhoto Library .photolibrary” is in use.
          I have searched this error message and tried using terminal to see what has this in use using the following - couldn't find anything
                    xxx-iMac:~ ryanromero$ lsof | grep iPhoto Library .photolibrary
                    grep: Library: Is a directory
                    grep: .photolibrary: No such file or directory
2 - I've tried doing Secure Empty Trash in which i get the below message
        The operation can’t be completed because you don’t have permission to access some of the items.
3- I have tried using terminal to empty the trash using the following command - It acts like it will delete it but the trash is still there.
     Ryan-Romeros-iMac:~ ryanromero$ sudo rm -rf ~/.Trash/*
     Password:
4- I have also tried this which said it would delete the file but doesn't in terminal
     Ryan-Romeros-iMac:~ ryanromero$ sudo rm -rf /Volumes/Iomega_HDD/.Trashes/501/iPhoto\ Library\ .photolibrary
Password:
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._iPhotoAux.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._iPhotoLock.data: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._iPhotoMain.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._Library6.iPhoto: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._ProjectDBVersion.plist: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/._Projects.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/._DataModelVersion.plist: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/._tmSync.plist: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._BigBlobs.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._Faces.db-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._History.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._ImageProxies.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._Library.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._lockfile.pid: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/._Properties.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/BigBlobs.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/Faces.db-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/History.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/ImageProxies.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/Library.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb/Properties.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/apdb: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/DataModelVersion.plist/._ImageProxies.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database/DataModelVersion.plist: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Database: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/iLifeShared/apdb/._ImageProxies.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/iLifeShared/apdb: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/iLifeShared: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/iPhotoAux.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/iPhotoMain.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Masters: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Previews/Database/apdb/._ImageProxies.apdb-journal: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Previews/Database/apdb: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Previews/Database: Directory not empty
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Projects.db: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary/Thumbnails: Input/output error
rm: /Volumes/Iomega_HDD/.Trashes/501/iPhoto Library .photolibrary: Directory not empty

First, never try to empty the Trash in the shell. It's dangerous and unnecessary, and as you've discovered, it doesn't always work.
It's possible that the external drive is malfunctioning, but before you draw that conclusion, quit iPhoto and try again to empty the Trash.

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