Get the datetime between multiple records and sort it in python

I need a code that will make me get the datetime between multiple records but in a range of time and sort them in python
for example I my range is from start= 2022-4-27 08:00:00 to end= 2022-4-27 12:00:00
and my data is
check_in = 2022-4-27 08:30:23, check_out = 2022-4-27 08:50:33.
check_in = 2022-4-27 10:20:15, check_out = 2022-4-27 10:50:50.
check_in = 2022-4-27 11:30:00, check_out = 2022-4-27 11:59:10.

The outcome should be like:
late_in: in = 2022-4-27 08:00:00, out =2022-4-27 08:30:23
mid_out: in = 2022-4-27 08:50:33, out =2022-4-27 010:20:15
mid_out: 2022-4-27 010:50:50, out =2022-4-27 011:30:00
early_out: in = 2022-4-27 11:59:10, out =2022-4-27 12:00:00