Abstract
The crystal structures of three vasodilators of the nitrate ester type have been determined by X-ray diffraction. Compound I, 1,4- trans-cyclohexanedimethanol dinitrate (CDDN), C 8H 14N 2O 6, is a recently developed nitrate ester with a promising haemodynamic profile in the treatment of ischaemic heart diseases. CDDN crystallizes in space group P2 1/a with a = 5.9443(4), b = 16.7052(9), c = 6.2022(2) Å, β = 116.669(4)°, Z = 2 and T = 295 K. The molecule lies on a centre of inversion and the structure refined to R = 0.042 for 991 reflections with I > 2.5σ( I). The cyclohexane ring approaches an ideal chair conformation and the C-O-NO 2 fragment is strictly planar. Compound II is the widely applied vasodilator in angina pectoris, isosorbide dinitrate or 1,4:3,6-dianhydro- d-glucitol-2,5-dinitrate (ISDN), C 6H 8N 2O 8. ISDN crystallizes in space group P22 12 1 with a = 5.7535(2), b = 10.9393(5), c = 14.6599(5)Å, Z = 4 and T = 295 K. The structure refined to R = 0.033 for 1104 reflections with I > 2.5σ( I). The molecular skeleton consists of two cis-fused five-membered rings, which each adopt an envelope conformation such that the torsion angels about the central CC bond are 0.3(2) and −7.8(2)°. The angle between the rings is 60.8(1)° and the two nitrate groups are planar. Compound III, isosorbide-2-mononitrate or 1,4:3,6-dianhydro- d-glucitol-2-mononitrate (IS-2MN), C 6H 9NO 6, is an active metabolite of II and crystallizes in space group P2 12 12 1 with a = 6.4318(4), b = 7.5273(4), c = 15.866(1)Å Z = 4 and T = 100 K. The structure refined to R = 0.031 for 1488 reflections with I > 2.5σ( I). The skeleton of III is very similar to that of II. The torsion angles about the central CC bond are 2.4(2) and −3.1(2)°, the interplanar angle is 61.5(1)° and the nitrate group is strictly planar.
Published Version
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