Nitrofurantoin methanol monosolvate

The antibiotic nitrofurantoin {systematic name: (E)-1-[(5-nitro-2-furyl) methylideneamino] imidazolidine-2,4-dione} crystallizes as a methanol monosolvate, C8H6N4O5 center dot CH4O. The nitrofurantoin molecule adopts a nearly planar conformation (r.m.s. deviation = 0.0344 angstrom). Hydrogen bonds involve the cooperative N-H center dot center dot center dot O-H center dot center dot center dot O heterosynthons between the cyclic imide of nitrofurantoin and methanol O-H groups. There are also C-H center dot center dot center dot 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 center dot center dot center dot O interactions, giving a herringbone pattern.