First thought - its best if you can be 'quiet' with yourself when he is experiencing this. Sometimes expressing empathy directly just fuels the pain.
Having experienced feelings 1, 2, 4, and 5 in my own life I can say that it sounds like he is experiencing some serious anxiety and some real depression.
Those negative self-evaluations that tend to be very general, they can easily lead to some depression.
M: 32 W: 29 T: 9 Years M: 4 Years I hit rock bottom: 2/11 PA admitted: 4/11 WAW: 5/11 D filed: 6/11 now: Patience, wisdom, and growth - hopefully.