The golden rule of timing chains/belts:

Always rotate the engine 2 full turns by HAND, the re-check the marks.

I have seen much damage done due to failing to observe this rule.
Even licensed mechanics in various shops I have worked in don't always do this.

This has saved my @$$ more than once

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I choose to be happy, even when the Mercedes is being awkward, lol

Done lots of belts and chains. And I did spin it over a few times till the marks re-aligned. Nothing is 180* out I'm pretty sure.

What I think happened is the crank got bumped forward throwing the IP timing off.

Bringing back a memory or two here... it's been a month since I did the head gasket and it's been sitting because I was pissed at it. I had my buddy helping me and I vaguely remember him bumping the crank with the ratchet as it was all going back together.

Also rolled the crank over to check the rods with the head off. Error could have been there. Kind of weird for it to run 180* out though and crank over just fine.

I believe there are a number of instances recorded on the forum of the engine running 180 degrees out. (I think).

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1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

Hmmm. Interesting. So even if the engine is 180* out, it can fixed by re installing the pump properly I would think. The crank doesn't care - up is up and down is down, it's the camshaft that determines the stroke. But if the IP is 180* out along with the crank (that doesn't care)... that's what really needs to be fixed?

Did you adjust the valves? If the valves are reworked than all valve clearance goes away so hence no compression and no start.

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600SEL '91
300E 4Matic '88
240D '83
280SE '77
350SE '73
The most complex systems can fail in the simplest way.
Contra verbosus noli contendere verbis, sermo datur cunctis, animi sapientia paucis.

i don't believe in the lord! He's never bought me a Mercedes Benz.

Yep

That is exactly correct. That camshaft cannot be 180* out relative to the crankshaft, just the IP.

Simplest test is to get the tang on the injection pump basically centered and in view.. Then look over and see if the valve lobes on the number one cylinder are generally pointing upward at a 45 degree angle type of thing.

If they are pointing otherwise the stroke relationship is off. Your description is consistant with that possibility. Although it could be something else of course.