No, that won't work.
DD doesn't care about file systems or files or anything like that. It's not that smart. It's just copying the harddrive block by block. It doesn't care if there is any information there or not.. 0's cost as much to copy as 1's. it's going to produce a faithfull duplicate of that harddrive.
With your file system your going to have files spread all throughout the harddrive. Some will be in the beginning, some will be in the middle, some will be in the end, and others are going to be spread around the entire drive... so with 50 gigs lobbed off the end of the drive image your going to lose a lot of stuff.
What you want to do is shrink the partition of the drive small enough that you can just dd that partition to another drive. That should work 'ok'.
But what would probably work better is to format the second drive and then mount both of them. Then use the 'rsync' command to copy the data from one drive to another. Rsync uses a special algorythm that ensures that the copies of the files are not corrupted. That way your actually only copying the data and not the entire drive.
So say you set them up so that they are mounted /mnt1 and /mnt2. With /mnt1 being the original drive. Then you can go:
rsync -av /mnt1/ /mnt2
Rsync is a bit odd that it uses that trailing backspace....
rsync -av /mnt/ == copy the contents of this directory
rsync -av /mnt == copy this directory
Rsync is also special because it only copies the differences of files. Say you have to shut your computer off half-way through the copying and it's not finished. Then the next day you can start off again and it'll go through and checks the files and fix any differences and finish copying them. So you can use it to keep a mirror of data on multiple machines... it'll use ssh encryption when copying stuff over a network.