Sum_{k=1..(m-1)/2} tan^(2n) (k*Pi/m) is an integer when m >= 3 is an odd integer (see AMM and Crux Mathematicorum links); twice this sequence is the particular case m = 5. - Bernard Schott, Apr 25 2022
Michel Bataille and Li Zhou, A Combinatorial Sum Goes on Tangent, The American Mathematical Monthly, Vol. 112, No. 7 (Aug. - Sep., 2005), Problem 11044, pp. 657-659.
D. J. Smeenk, Problem 3452, Crux Mathematicorum, Vol. 35, No. 5 (2009), pp. 325 and 327; Solution to Problem 3452 by Roy Barbara, ibid., Vol. 36, No. 5 (2010), pp. 341-342.