What a friends is trying to do is to film ISS while it's crossing the Earthlight bathed side of the Moon (thus the moon shadow), while the station is still bathed by sunlight and the sun has set for us. It's possible.
I saw Mir cross the Moon on january 6th 2001 at 17:23 and it took less than 2 seconds. To have a slower transit, the station must be coming towards us or leaving us, fairly low above the horizon. But then, the station can be very distant. It's impossible to take a picture of the station while it's crossing the sun bathed side of the Moon (too much light from the Moon). I've seen a film, taken during the day of a sun crossing ISS! It happens quite often. We don't see it, but the movie can. It's a dark spot crossing the Sun.

Raoul