There isn't really an issue here. The reason the cosine value is rounded to -1 while the sine value isn't rounded to 0 is because the cosine value is much closer to -1 than the sine value is to 0. The unrounded (or less rounded) values are cos(355/113) = -0.99999999999996441843 and sin(355/113) = -0.00000026676418906242. So while the sine value is about 10^-7 from 0, the cosine value is about 10^-13 from -1, 6 orders of magnitude closer. Your calculator's threshold for rounding is just somewhere between those magnitudes.
As for why the latter two calculations give identical answers, that's just a feature of sine itself: For very small inputs it's an excellent approximation of the identity function, f(x) = x. If you give it any input of similar size to π - 355/113, it'll more likely than not give you the exact same value back out. As x → 0, sin(x) → x. Try it out with other values like 0.0000000123456789.