Just looks like your chain is too long. That series der has no trouble handling an 11-28 with a 53/39 so it will have no trouble with an 11-28 53/42; I have a bike equipped just like that in the basement and I'm no great hill climber so I've always run a 28 with it. Put the gearing in the small/small combination and take out enough links that the chain will connect without touching the spot you keep referencing, then shift up through to make sure everything is fine but it all should be. Alternative is to go big/big and pull the chain tight as it will safely go but I find it harder to do that.