Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)


organic compounds



cu3036 scheme

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


Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster