Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 12 (December 2008)

organic compounds

dn3101 scheme

Acta Cryst. (2008). C64, o653-o656 [ doi:10.1107/S0108270108037621 ]

Halide salts of antimigraine agents eletriptan and naratriptan

K. Ravikumar, B. Sridhar, H. Krishnan and A. N. Singh

Abstract: Molecules of eletriptan hydrobromide monohydrate (systematic name: (1S,2R)-1-methyl-2-{5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-ylmethyl}pyrrolidinium bromide monohydrate), C₂₂H₂₇N₂O₂S⁺·Br^-·H₂O, (I), and naratriptan hydrochloride (systematic name: 1-methyl-4-{5-[2-(methylsulfamoyl)ethyl]-1H-indol-3-yl}piperidinium chloride), C₁₇H₂₆N₃O₂S⁺·Cl^-, (II), adopt conformations similar to other triptans. The C-2 and C-5 substituents of the indole ring, both of which are in a region of conformational flexibility, are found to be oriented on either side of the indole ring plane in (I), whilst they are on the same side in (II). The N atom in the C-2 side chain is protonated in both structures and is involved in the hydrogen-bonding networks. In (I), the water molecules create helical hydrogen-bonded chains along the c axis. In (II), the hydrogen bonding of the chloride ions results in macrocyclic R₄²(20) and R₄²(24) ring motifs that form sheets in the bc plane. This structural analysis provides an insight into the molecular structure-activity relationships within this class of compound, which is of use for drug development.

Formula: C₂₂H₂₇N₂O₂S⁺·Br^-·H₂O and C₁₇H₂₆N₃O₂S⁺·Cl^-


	Structure factor file (CIF format) (195.3 kbytes) [ doi:10.1107/S0108270108037621/dn3101Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (161.9 kbytes) [ doi:10.1107/S0108270108037621/dn3101IIsup3.hkl ] Contains datablock II

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