The closest double to pi/4 is exactly 0x1.921fb54442d18p-1. The tangent of this double, to more bits than you need, is 0x1.fffffffffffff72cece67p-1. Rounding to the nearest double gives you exactly 0x1.fffffffffffffp-1 because 0x1.fffffffffffff72cece67p-1 is less than 0x1.fffffffffffff8p-1.