Let's see - the Simulator is running, at the latest, iOS 6. As such it was probably taken before iOS 7 GM (September 18, 2013). Based on the scroll tracks on Xcode, it also looks like it was running Snow Leopard; Lion was released in Mid-2011, so maybe even earlier.

Between iOS and macOS, and given the acquisition was in 2012, I'd imagine these photos were taken around then.