5-(Adamantan-1-yl)-N-methyl-1,3,4-thia­diazol-2-amine

In the title compound, C₁₃H₁₉N₃S, the methyl­amine substituent is coplanar with the thia­diazole ring to which it is attached [C—N—C—S torsion angle = 175.9 (2)°] and the amine H atom is syn to the thia­diazole S atom. Supra­molecular chains along [101], sustained by N—H...N hydrogen bonding, feature in the crystal packing.

3-[(4-Phenyl­piperazin-1-yl)meth­yl]-5-(thio­phen-2-yl)-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₇H₁₈N₄OS₂, the 2-thienyl ring is disordered over two co-planar, opposite orientations in a 0.684 (2): 0.316 ratio. The 1,3,4-oxa­diazole ring is almost co-planar with the attached 2-thienyl ring [dihedral angles of 5.34 (19) and 4.8 (5)° for the major and minor components, respectively]. The relative disposition of the thione- and ring-S atoms is anti for the major orientation of the 2-thienyl residue. Overall, the shape of the mol­ecule approximates the letter V. In the crystal, a three-dimensional architecture is consolidated by a combination of weak C—H...S and C—H...π contacts.

3-(Adamantan-1-yl)-4-[(E)-(2,6-di­fluoro­benzyl­idene)amino]-1-[(4-ethyl­piperazin-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₂₆H₃₄F₂N₆S, the triazole ring is linked to a benzene ring via an imine bond [N=C = 1.255 (2) Å; conformation: E], with a dihedral angle of 25.21 (11)° between the rings. The 4-ethyl­piperazinyl residue is folded away from the thione-S atom. In the crystal, helical supra­molecular chains propagating along [010] and sustained by weak C—S...π(triazole) inter­actions occur [S...centroid distance = 3.2872 (10) Å]. Links between these chains are of the type benzene-C—H...N(imine) and π–π [between centrosymmetrically related benzene rings with an inter-centroid distance of 3.9241 (15) Å] and result in a three-dimensional architecture.

3-(Adamantan-1-yl)-4-methyl-1-({4-[3-(tri­fluoro­meth­yl)phen­yl]piperazin-1-yl}meth­yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₂₅H₃₂F₃N₅S, two independent mol­ecules comprise the asymmetric unit and are related across a pseudo-centre of inversion. The piperazine rings have chair conformations with each N-bound substituent occupying an equatorial position so that the dihedral angles between the planes of the triazole and benzene ring are 78.20 (19) and 79.10 (19)° for the two independent mol­ecules, indicating that the mol­ecules have an L-shape. In the crystal, a three-dimensional architecture is stabilized by C—H...π inter­actions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.27 (9).

4-Benzyl-3-(thio­phen-2-yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₁₃H₁₁N₃S₂, the triazole and thio­phene rings are coplanar [dihedral angle = 6.22 (13)°]. By contrast, the phenyl ring is perpendicular to the triazole ring [dihedral angle = 85.58 (13)°], so that the mol­ecule has an L-shape. The thio­phene S atom is syn with the ring imine N atom. In the crystal, eight-membered {...HNCS}₂ synthons form between centrosymmetrically related mol­ecules, leading to dimeric aggregates that are connected into a supra­molecular layer parallel to (101) by π–π inter­actions between centrosymmetrically related triazole rings [centroid–centroid distance = 3.6091 (15) Å] and C—H...π inter­actions.

5-(Adamantan-1-yl)-3-anilinomethyl-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₉H₂₃N₃OS, the oxa­diazole and benzene rings are inclined at a dihedral angle of 50.30 (11)°, with the major twist between them occurring at the ring–methyl­ene N—C bond [N—N—C—N torsion angle = −101.2 (2)°]. In the crystal, helical supra­molecular chains along [010] are sustained by N—H...S hydrogen bonds. These are linked into layers lying parallel to (-101) by methyl­ene–phenyl C—H...π inter­actions.

5-(Adamantan-1-yl)-3-[(4-fluoro­anilino)meth­yl]-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₉H₂₂FN₃OS, the dihedral angle between the inclined oxa­diazole and benzene rings is 52.7 (3)°. In the crystal, helical supra­molecular chains along [100] are sustained by N—H...S hydrogen bonds supported by methyl­ene–benzene C—H...π inter­actions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.33 (14).

3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C₂₆H₃₇N₅S, the piperazine ring adopts a chair conformation with the exocyclic N-C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47 (9) and 73.07 (9)° with the triazole and benzene rings, respectively, resulting in an approximate U-shape for the mol­ecule. No significant inter­molecular inter­actions are observed in the crystal.

N-(Adamantan-1-yl)-1,2,3,4-tetra­hydro­iso­quinoline-2-carbo­thio­amide

In the title compound, C₂₀H₂₆N₂S, the N-containing six-membered ring adopts a boat conformation and the dihedral angle between the thio­carbamide group and the benzene ring is 49.67 (9)°. An intra­molecular C—H...S hydrogen bond generates an S(6) ring motif. The N—H group is sterically hindered and there are no significant inter­molecular inter­actions beyond van der Waals contacts.