iTunes crashes on certain songs on iPhone 3GS

It's an old phone of mine that I now use as an iPod for music in my car as the it's the old style connection port (Not the new iphone5 port) certain songs I have already purchased on my iPhone 5 download on my old 3GS and some crash the iTunes app and closes it before it starts downloading...

On the 3GS on iTunes I have to find the song, I've already purchased on my iPhone 5 (which I use for headphone music) click 'buy now' put in my password as if I'm purchasing it again and it shortly comes up with 'you've already purchased this do you wish to download' option. The songs it crashes on crash a couple of seconds after I click the 'buy now' button. Just wondering why it does this and is there any way to sort it out?

Katy Perry - Dark Horse

Justin Timberlake - Take Back The Night

Just 2 of the songs that crash. Haven't looked if it needs updating in years as its been out of action till recently is that the problem? Or is it just the old device can't take the newer songs?