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