You must turn the engine with a wrench to check the valve timing, if you crank it, it will "bouce" back from the compression on #1 and all the slack in the chain gets wound off onto the "tight" side since your chain tensioner is loose (no oil pressure). This can be quite a bit depending on the condition of the chain guides.

On a good engine, it will take some force to crank it around by hand, and you will have to hold it until the compression bleeds off around the rings to check.

I'd not be surprised, though, that you are off -- my 220D was about 13 degrees late when I changed the chain (going to check the IP today, still won't start!), and it ran.

If you have an injector that won't fire at low speed, chances are the pressure valve seal in the IP is leaking, will cause a hard knock or dead cylinder at low speed because there is no residual pressure in the injection pipe. Will usually bleed copious fuel with the cap nut loose but not fire. If you don't get fuel, chances are the IP is bad, that sleeve and plunger set is either leaking badly, out of time, or the cam lobe is shot in the IP. I would guess, personally, that the pressure valve seal is bad.

Peter

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1972 220D ?? miles
1988 300E 200,012
1987 300D Turbo killed 9/25/07, 275,000 miles
1985 Volvo 740 GLE Turobodiesel 218,000
1972 280 SE 4.5 165, 000 - It runs!