The bool of a large range raises OverflowError:

    >>> bool(range(2**63))
    Traceback (most recent call last):
      File "<stdin>", line 1, in <module>
    OverflowError: Python int too large to convert to C ssize_t

This is a side-effect of len raising OverflowError, which is a general problem that's nontrivial to fix (the sq_length slot is constrained to return a ssize_t). In theory, though, it would be possible to implement nb_bool for range objects to do the right thing.

In practice, this may well not be worth fixing, though I think it's at least worth reporting.