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The title compound, C21H21NO, is a vinyl­ogous amide (enaminone) produced by reaction of 1-(2-phenyl­prop-2-en-1-yl)pyrrolidine-2-thione with phenacyl bromide. In the mol­ecule, the phenyl rings are twisted from the mean plane of the pyrrolidine ring by 11.2 (1) and 67.3 (1)°. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules related by translation along the b axis into chains.

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The asymmetric unit of the title compound, C12H10N2, which may serve as a model for mitosenes, contains two independent mol­ecules. The conformation of the five-membered rings in both molecules is envelope, with the central CH2—CH2—CH2 C atom at the flap in each case. In the crystal, they inter­act by a combination of weak C—H...N and π–π inter­actions [centroid–centroid distances = 3.616 (1) and 3.499 (1) Å] and C—H...π contacts.

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In the title hydrated mol­ecular salt, C5H7N2+·C7H3ClNO4·H2O, the ions and water mol­ecules assemble into ribbons of R65(22) rings along the c axis via O(water)—H...O, N+—H...O(water) and N—H...O hydrogen bonds. N—H...O hydrogen bonds connect adjacent ribbons along the c-axis direction via R44(12) rings, forming hydrogen-bonded layers. The CO2 and NO2 groups make dihedral angles of 81.8 (2) and 1.4 (2)°, respectively, with the ring in the anion.
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