I found an answer, $\displaystyle\int_{\arctan a}^{\frac{\pi}{2}}\int_{0}^{a\csc\theta}\frac{r}{(1+r^2)^2}\,dr\,d\theta=\frac{a}{2\sqrt{a^2+1}}\arctan\left(\frac{1}{\sqrt{a^2+1}}\right)$ for $a>0$.
But I am not sure how to get the result.
First of all, $\displaystyle\int_{0}^{a\csc\theta}\frac{r}{(1+r^2)^2}\,dr=-\frac{1}{2}\left(\frac{1}{1+a^2\csc^2\theta}-1\right)$ and using an integral calculator, $\displaystyle\int-\frac{1}{2}\left(\frac{1}{1+a^2\csc^2\theta}-1\right)\,d\theta=\frac{a}{2\sqrt{a^2+1}}\arctan\left(\frac{\sqrt{a^2+1}\tan \theta}{a}\right)+C$. But I can't evaluate $\tan \theta$ at $\theta=\frac{\pi}{2}$. How can I get to the answer above?
HINTS:
Note that we have
$$\lim_{x\to \pi/2^-}\tan(x)=\infty$$
and
$$\lim_{x\to \infty}\arctan(x)=\pi/2$$
Finally, use $\pi/2 -\arctan(x)=\arctan(1/x)$ for $x>0$.