The title salt, C12H24N+·NCS−, represents a monoclinic polymorph of the previously reported orthorhombic form [Khawar Rauf et al. (2008 ▶). Acta Cryst. E64, o366]. Two independent formula units comprise the asymmetric unit with the major difference in their molecular structures relating to the relative dispositions of the cyclohexyl rings [dihedral angles = 79.88 (6) and 67.72 (5)°]. Further, the independent anions form distinctive patterns of hydrogen-bonding interactions, i.e. 2 × N—H⋯N versus N—H⋯N and N—H⋯S. The resulting supramolecular architecture is a supramolecular chain along the c axis based on a square-wave topology.
In the title compound, C15H14N2O2S, the central C2N2OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intramolecular N—H⋯O hydrogen bond; additional intramolecular N—H⋯O and C—H⋯S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N—H H atoms; the O atoms lie to the same side of the molecule. Centrosymmetric eight-membered {⋯HNC=S}2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C—H⋯O and C—H⋯π interactions.
In the title compound, C17H25N3O2S, the terminal and central amide groups are, respectively, twisted and coplanar with the attached benzene ring [O—C—C—C torsion angles = 22.7 (3) and 5.4 (3)°]. In the central part of the molecule, the amide and thioamide residues are approximately perpendicular [C—N—C—S torsion angle = −104.98 (18)°]. Supramolecular layers with a zigzag topology are formed in the crystal packing by N—H⋯O, N—H⋯S and C—H⋯O interactions; these stack along c, being separated by hydrophobic interactions.
The title compound, C16H24N2OS, is twisted about the central N(H)—C bond with the C—N—C—S torsion angle being 119.6 (3)°. The carbonyl O and thione S atoms are directed to opposite sides of the molecule, a conformation that allows for the formation of a linear supramolecular chain comprising alternating eight-membered {⋯HNCS}2 and 14-membered {⋯HCNCNCO}2 synthons.
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