Why Doesn't iBook open all pdf's on iPad

I have just copied Aircraft Maintenance Manuals onto my computer (PDF Form), copied them to iTunes and then synced my iPad and all but 1 work, the one wich isnt working is the largest (553MB) and the most important. Does anyone have any ideas why this is the case. Any help would be good

It just keeps coming up with
                                                      Book Format Error
                                              This book Cannot be opened
                                                 Because the format is not
                                                   reconised, or is invalid.
The other 3 ar the same format and they work fine.

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