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In the title compound, C25H20N2O5S, the phenyl ring makes dihedral angles of 89.88 (8) and 13.98 (8)°, respectively, with the indole ring system and the nitro­benzene ring. The dihedral angle between the indole ring system and the nitro­benzene ring is 88.48 (11)°. The mol­ecular structure is stabilized by a weak intra­molecular C—H...O inter­action. In the crystal, π–π inter­actions, with centroid–centroid distances of 3.6741 (18) and 3.8873 (17) Å, link the mol­ecules into layers parallel to the ab plane.

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In the title compound C24H17BrN2O5S, the phenyl ring makes dihedral angles of 85.4 (2) and 8.8 (2)° with the indole ring system and the nitro­benzene ring, respectively, while the indole ring system and nitrobenzene ring make a dihedral angle of 80.1 (2)°. In the crystal, weak C—H...O inter­actions link the mol­ecules, forming a two-dimensional network parallel to the bc plane.

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The title salt crystallized with two anions and two cations in the asymmetric unit, together with three water mol­ecules. In the crystal, the anions are linked via O—H...O hydrogen bonds, involving the water mol­ecules, forming chains along [100] and the cations are linked to these chains by N—H...O hydrogen bonds.
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