1. It asks for root password for the machine where you're trying to login.
2. It either takes time in establishing connection, or there's some issue with shell on remote machine. May be a different shell configured for root on remote machine as compare to your local machine. So once invoke:
~$ ssh email@example.com "echo $SHELL"
Also check if /home/guest/Desktop/measure.sh exists on remote machine or not? I doubt it's on your local machine, and you're trying to run it on remote machine.
3. If output file isn't generated then I doubt that your script is running on remote server or may be it doesn't exist on remote machine. So once login on remote machine and invoke it (not with ssh) like:
~$ ssh firstname.lastname@example.org
Let's know the results.