Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)

organic compounds

Acta Cryst. (2013). C69, 1186-1191    [ doi:10.1107/S0108270113024323 ]

Zolmitriptan oxalate and zolmitriptan camphorsulfonate: the first structural study of salt complexes of the anti­migraine drug zolmitriptan

B. Sridhar, K. Ravikumar and V. Hariharakrishnan

Abstract: Zolmitriptan hydrogen oxalate [(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)aza­nium hydrogen oxalate], C16H22N3O2+·C2HO4-, (I), and zolmitriptan camphorsulfonate [(S)-dimethyl(2-{5-[(2-oxo-1,3-ox­az­ol­idin-4-yl)methyl]-1H-indol-3-yl}ethyl)aza­nium (S,R)-{2-hy­droxy-7,7-di­methylbi­cyclo­[2.2.1]heptan-1-yl}methane­sulfon­ate], C16H22N3O2+·C10H15O4S-, (II), are the first reported salt complexes of the anti­migraine drug zolmitriptan. Compound (I) crystallizes in the space group P21 with two mol­ecules of protonated zolmitriptan and two oxalate monoanions in the asymmetric unit, while compound (II) crystallizes in the space group P212121 with one protonated zolmitriptan mol­ecule and one camphorsulfonate anion in the asymmetric unit. The orientations of the ethyl­amine side chain and the oxazol­idinone ring with respect to the indole ring of the zolmitriptan cation are different for (I) and (II). In (I), they are oriented in opposite directions and the mol­ecule adopts a step-like appearance, while in (II) the corresponding side chains are folded in the same direction, giving the mol­ecule a cup-like appearance. The zolmitriptan mol­ecules of (I) form an R22(8) dimer, while in (II) they form a helical chain with a C(11) motif. The oxalate monoanions of (I) inter­act with the zolmitriptan cations and extend the dimer into a three-dimensional hydrogen-bonded network. In (II), the camphorsulfonate anion forms an R22(15) ring motif with the zolmi­triptan cation.

Formula: C16H22N3O2+·C2HO4- and C16H22N3O2+·C10H15O4S-

Keywords: crystal structure; zolmitriptan salts; triptans; anti­migraine drugs.

hkldisplay filedownload file

Structure factor file (CIF format) (416.2 kbytes)
[ doi:10.1107/S0108270113024323/cu3036Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (309.1 kbytes)
[ doi:10.1107/S0108270113024323/cu3036IIsup3.hkl ]
Contains datablock II


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