Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 4 (April 2013)

organic compounds

Acta Cryst. (2013). C69, 428-435    [ doi:10.1107/S0108270113005878 ]

Frovatriptan salts of aliphatic carb­oxy­lic acids

K. Ravikumar, B. Sridhar, J. B. Nanubolu, V. Hariharakrishnan and B. V. Rao

Abstract: The inter­action of the anti­migraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)-6-carbamoyl-N-methyl-2,3,4,9-tetra­hydro-1H-carbazol-3-aminium acetate, C14H18N3O+·C2H3O2-, (I), (R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetra­hydro-1H-carbazol-3-aminium 3-carb­oxy­propano­ate monohydrate, C14H18N3O+·C4H5O4-·H2O, (II), and bis­[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetra­hydro-1H-carbazol-3-aminium] succinate trihydrate, 2C14H18N3O+·C4H4O42-·3H2O, (III). The methyl­aza­niumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three-dimensional hydrogen-bonded structures. In (I), the cations form head-to-head hydrogen-bonded amide-amide catemers through N-H...O inter­actions, while in (II) and (III) the cations form head-to-head amide-amide dimers. The cation catemers in (I) are extended into a three-dimensional network through further inter­actions with acetate anion acceptors. The presence of succinate anions and water mol­ecules in (II) and (III) primarily governs the three-dimensional network through water-bridged cation-anion associations via O-H...O and N-H...O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent inter­actions in the aggregation and inter­action patterns of drug mol­ecule adducts.

Formula: C14H18N3O+·C2H3O2-, C14H18N3O+·C4H5O4-·H2O and 2C14H18N3O+·C4H4O42-·3H2O

hkldisplay filedownload file

Structure factor file (CIF format) (140.2 kbytes)
[ doi:10.1107/S0108270113005878/cu3026Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (241.2 kbytes)
[ doi:10.1107/S0108270113005878/cu3026IIsup3.hkl ]
Contains datablock II

hkldisplay filedownload file

Structure factor file (CIF format) (204.1 kbytes)
[ doi:10.1107/S0108270113005878/cu3026IIIsup4.hkl ]
Contains datablock III


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