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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.
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