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In the title pymiridine-2,4-dione derivative, C14H16N2O2S, the dihedral angle between the six-membered rings is 66.69 (10)°. The mol­ecule is twisted about the Cp—S (p = pyrimidine) bond, with a C—S—C—N torsion angle of −19.57 (16)°. In the crystal, adjacent mol­ecules form inversion dimers through pairs of strong N—H...O hydrogen bonds, generating an R22(8) ring motif. The dimers are connected into chains extending along the c-axis direction through additional N—H...O hydrogen bonds.

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In the cation of the title salt, C11H17N2O+·C7H8ClN2O2, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character. Its mean plane makes a dihedral angle of 42.36 (8)° with the phenyl ring of its 2-meth­oxy­phenyl substituent. The 2,4-dioxopyrimidin-1-ide anion is generated by deprotonation of the N atom at the 1-position of the pyrimidine­dione ring. Intra­molecular C—H...O hydrogen bonds generate S(6) ring motifs in both the cation and the anion. In the crystal, N—H...O, N—H...N and C—H...O hydrogen bonds are also observed, resulting in a two-dimensional network parallel to the ab plane. The crystal stability is further consolidated by weak C—H...π inter­actions.

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The title compound, C19H23N3S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007 Å) with a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by pairs of N—H...S hydrogen bonds, forming inversion dimers that enclose R22(8) loops. The crystal packing is further stabilized by weak C—H...π inter­actions that link adjacent dimeric units into supra­molecular chains extending along the a-axis direction.
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