Can you please get a journal from shutdown, as described in
/usr/share/doc/systemd/README.Debian ? Once it hangs, switch to the
debug shell, and do

  journalctl -ab > /root/journal.txt
  reboot -f

and then attach /root/journal.txt here. I suppose it's the "umount"
which times out on the network file system. There is not much that we
can do about it in systemd then (as it's umount itself which is
hanging), but let's first confirm what is the actual problem here.
Thanks!

** Changed in: systemd (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/1467943

Title:
  system shutdown hangs if btrfs on file image (mounted via cifs) is
  mounted

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