Он сидел в саду до тех пор пока не

Он сидел в саду до тех пор пока не стало совсем темно и он не мог больше читать

Results (English) 1:

He sat in the garden until it became quite dark and he could no longer read

Results (English) 2:

He sat in the garden until it became not quite dark and he could no longer read

Results (English) 3:

It seated in garden as long as did not become at all darkly and it could not more read