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In the title compound, C16H15N3S2, the central C2N2S2 residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the mol­ecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supra­molecular chains along [1-10] are stabilized by N—H...N(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C—H...π(pyridine) inter­actions.

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The title compound, C12H16N2S3, was obtained by the condensation reaction of S-benzyl dithio­carbazate and 3-mercaptobutan-2-one. The phenyl ring and thiol (SH) group are approximately perpendicular [S—C—C—C and N—C—C—S torsion angles = 67.8 (3) and 116.9 (2)°, respectively] to the rest of the mol­ecule. In the crystal, mol­ecules are linked by weak S—H...S and N—H...S hydrogen bonds, π–π inter­actions between the benzene rings [centroid–centroid distance = 3.823 (2) Å] and C—H...π inter­actions.

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In the title salt, C14H17N2+·Cl, the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N—H...Cl hydrogen bonds, which lead to a supra­molecular undulating ribbon along the a axis comprising edge-shared eight-membered {...HNH...Cl}2 synthons. The chains are connected into layers in the ab plane by C—H...π inter­actions.
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