Polymorphs of nitrofurantoin. 2. Preparation and X-ray crystal structures of two anhydrous forms of nitrofurantoin |
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| Authors: | E W Pienaar M R Caira A P Lötter |
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| Institution: | (1) Research Institute for Industrial Pharmacy, Potchefstroom University for C.H.E., 2520 Potchefstroom, South Africa;(2) Department of Chemistry, University of Cape Town, Private Bag, 7700 Rondebosch, South Africa |
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| Abstract: | The preparation and X-ray crystal structures of two polymorphs of the antibacterial drug nitrofurantoin are reported. The  -polymorph is triclinic, space groupP¯1 witha=6.774(1),b=7.795(1),c=9.803(2)Å, =106.68(1), =104.09(2),  =92.29(1)°,Z=2. The-polymorph is monoclinic, space groupP21/n witha=7.840(5),b=6.486(1),c=18.911(6)Å,=93.17(3)°,Z=4. The nitrofurantoin molecules adopt the same, planar conformation in both polymorphs. Both crystal structures are built up from layers held together by van der Waals forces. In each polymorph, intralayer cohesion is effected by N-H O and C-HO hydrogen bonds, but their arrangements differ in the two crystals. The significance of the C-HO hydrogen bond, now known to occur in four modifications of nitrofurantoin, is discussed. |
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