In the title compound, C13H15ClN2S, the dihydropyrimidine ring is essentially planar, with a maximum deviation from the least-squares plane of 0.122 (3) Å for the unsubstitued olefinic C atom. The dihedral angle between the dihydropyrimidine and benzene rings is 86.62 (13)°. The crystal structure is stabilized by intermolecular N—H⋯S hydrogen bonds, which form centrosymmetric dimers arranged along the c axis.
Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.005 Å; R factor = 0.059; wR factor = 0.153; data-to-parameter ratio = 15.9.In the title compound, C 13 H 15 FN 2 S, the dihydropyrimidine ring is essentially planar, with a maximum deviation of 0.086 (3) Å from the mean plane of the rest of the ring for the dimethylated C atom. The benzene ring is almost perpendicular to the dihydropyrimidine ring, with a dihedral angle of 83.97 (14) . The crystal packing is characterized by centrosymmetric dimers resulting from pairs of intermolecular N-HÁ Á ÁS hydrogen bonds. There are also C-HÁ Á Á interactions.
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ExperimentalCrystal data
Refluxing a mixture of 1,10-phenanthroline, (4-fluorophenyl)thiourea and cadmium(II) chloride did not produce the expected mixed-ligand complex but formed a co-crystal of the two ligands, C12H8N2·C7H7FN2S. The asymmetric unit consists of two pairs of the co-crystal molecules. In each (4-fluorophenyl)thiourea molecule, the planes of the N2CS thiourea units are almost perpendicular to the corresponding fluorobenzene rings, subtending angles of 76.53 (7) and 85.25 (7)°. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds form inversion dimers from the co-crystal pairs. A weak π–π interaction between the phenanthroline rings [centroid–centroid distance = 3.7430 (15)Å] is also observed.
The title compound, C6H15N2
+·NCS−, was obtained unexpectedly from the reaction mixture of benzoyl chloride, ammonium thiocyanate and cyclohexane-1,2-diamine. The cyclohexane ring adopts a chair conformation. In the crystal, N—H⋯S and N—H⋯N interactions involving the thiocyanate anion and both the amine and the aminium N atoms link the molecules, forming two-dimensional networks parallel to (001).
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