its possible to spawn boxes exactly like in your picture but, you will need a bit more knowledge and you will need each crate's model.
you will also need to know a crate's size ( mins, max ).
you can also set each crate's type using EV_INT_iuser1 ( just an example ).
and then when you touch it it'll act depending on its type.
you can also look at
DeathRace plugin. ( it needs a created map< deathrace mod > and it replace crates.. )