Very strange.

Have you looked at sum of bytes in freespace or looked at individual freespace chunks ?

There should have been 1 individual chunk of freespace after coalesce.
if there were many different sized freespace chunks this may have caused the problem.

If I was you I would investigate dba_segments, dba_freespace when you get the ORA error message and try to work out what happened.

Either that or your maths may be wrong. I have done a similar thing to what you are doing many times and the only time I encountered this problem was when I forgot to coalesce my tablespace after I dropped all the objects in it and then ran an import.