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In the title compound, C(17)H(24)NO(2) (+)·Br(-)·H(2)O, the pentyl group chain in the cation extends nearly perpendicular [N-C-C-C = -64.4 (3)°] to the mean plane of the indole ring with the carboxyl end group twisted such that the dihedral angle between the mean planes of the indole and carb-oxy groups measures 43.2 (4)°. Both ions in the salt form inter-molecular hydrogen bonds (O-H⋯Br and O-H⋯O) with the water mol-ecule. As a result of the Br⋯H-O-H⋯Br inter-actions, a zigzag chain is formed in the c-axis direction. The crystal packing is influenced by the collective action of the O-H⋯O and O-H⋯Br inter-molecular inter-actions as well as π-π stacking inter-molecular inter-actions between adjacent benzyl rings of the indole group [centroid-centroid distance = 3.721 (13) Å] and inter-molecular C-H⋯π inter-actions between a methyl hydrogen and the benzyl ring of the indole group. The O-H⋯Br inter-actions form a distorted tetra-hedral array about the central Br atom. A MOPAC AM1 calculation provides support to these observations.

1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide monohydrate