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I don't think we can upload pictures but if you look at an Ordnance Survey map and then put lots of locations on it, they will often spread beyond a grid square (eg TQ) which is 100km, but when rotated will then fit inside it. I have my own map with locations and so far I've printed the map and cut the shape out they make but it's not very accurate and won't work when it's a close fit so need a mathematical formula.
To give an example, if you put a spot in Amersham, St Albans, Eastbourne and Ashford (Kent) they all fall outside TQ but if you then rotate the quadrangle (or pentagon if five locations) it may well fit inside the TQ square. It isn't even related to the diagonal length as if you have a rectangle shorter than it over all if a bit sticks out it can't then be rotated at any angle to fit the 100km (or any other size) square.
It is physically impossible to cut out a pentagon for my map that is accurate enough to see if it can fit or not physically but will know exactly given a formula. It's probably between A level and degree level maths, I didn't get O level so haven't a scooby.