Nitrofurantoin methanol monosolvate

Abstract

The antibiotic nitrofurantoin {systematic name: (E)-1-[(5-nitro-2-furyl) methylideneamino]imidazolidine-2,4-dione} crystallizes as a methanol monosolvate, C8H6N4O5·CH 4O. The nitrofurantoin molecule adopts a nearly planar conformation (r.m.s. deviation = 0.0344 Å). Hydrogen bonds involve the co-operative N - H⋯O - H⋯O heterosynthons between the cyclic imide of nitrofurantoin and methanol O - H groups. There are also C - H⋯O hydrogen bonds involving the nitrofurantoin molecules which support the key hydrogen-bonding synthon. The overall crystal packing is further assisted by weak C - H⋯O interactions, giving a herringbone pattern.