# Charcoal, 34 bytes

    ＮςＡ²ξＦMDCLXVI«×ι÷ςφＡ﹪ςφςＡ÷φξφＡ÷χξξ

Originally based on @CarlosAlego's answer. A port of @xnor's Python solution is also 34 bytes:

    ＮθＡ⁵ξＦIVXLCD«←×ι﹪θξＡ÷θξθＡ÷χξξ»←×Mθ