Setting up a calendar type layout in Sierra
The optimal way to set up this layout is to first rotate the PDF pages to have their heads to the left, except for the last page (last page head direction is to the right).
This can be done in the PDF before dropping into Sierra, open/edit the Sierra PDF in the Documents list, or rotating the pages in the run list. See the two examples below:
Rotating the pages in Acrobat Rotating pages in the Sierra Run List
Now you can impose the job as normal. Just think of the calendar just being turned counter-clockwise. Now your bind/spine is as it would be for any normal booklet. Creep can also be applied as normal (if needed).
The other method is to leave (almost) all of your pages with the head direction pointing up (as normal), but you still need to rotate the last page to be upside down. Create your imposition pattern as 1 Horizontal by 2 Vertical pages. Make all of the heads point up, and the front of the first pattern will be 4 on top of 1. You will not be able to add creep in this style of pattern, as Sierra only recognizes bind edges of right or left (not top/bottom).