When you say 5 points of the pentagon must vary in a circumscribed circle, do you mean that the pentagon has to be circumscribed but not regular?
Is the leave radius constant for all pentagons being generated or different for each of the 100 and is it the same for each vertex or possibly different for each vertex?
If the pentagon must be inscribed, does that mean the diameter of the circle vary?

No idea if this is what you are looking for as the randomise is a bit random, if you want to retain the pentagon shape, maybe split the circle that circumscribed into 5 and then evaluate on each part to get a more pentagon shape. pentagon.gh (11.7 KB)

you will have to add more rules to the grasshopper script to generate something that fills more of the space.

Thank you for your answers.
Christopher Ho, i will look at your file next week !
Markz, your link seems very intersting. I take time to look deeply next week !