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The title compound, [Sn(C4H9)2(C9H10NS2)2], features a tetra­hedrally coordinated SnIV atom; the dithio­carbamate ligands coordinate in a monodentate fashion, accompanied by two n-butyl chains. The non-coordinating thione S atoms are each proximate to the SnIV atom [3.0136 (7) and 2.9865 (8) Å], giving rise to distortions from the ideal geometry as evident in the wide C—Sn—C bond angle of 139.06 (12) °. In the crystal, C—H⋯S inter­actions lead to the formation of a linear supra­molecular chain along the b axis. The chains are aligned into layers by C—H⋯π inter­actions, and the layers stack along [001]. One of the ethyl groups is statistically disordered over two sets of sites.

The title compound, [Sn(C6H5)3(C11H14NS2)], features a tetra­hedrally coordinated Sn atom, as the dithio­carbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetra­hedral geometry about the metal atom are evident with the widest C—Sn—S angle being 117.26 (5)°. In the crystal, mol­ecules are linked by C—H⋯S inter­actions, which generate helical supra­molecular chains along the b axis.

The title compound, [Sn(C6H5)3(C9H10NS2)], has two independent mol­ecules in the asymmetric unit and each features a tetra­hedrally coordinated SnIV atom as the dithio­carbamate ligand coordinates in a monodentate fashion. As the non-coordinating thione S atom is proximate to the Sn atom [Sn⋯S(thione) = 3.1477 (6) and 2.9970 (5) Å for the independent mol­ecules], distortions from the ideal geometry are evident [the widest angle being 120.48 (5)°]. The most notable feature of the crystal packing is the formation of C—H⋯π inter­actions that lead to the formation of supra­molecular layers parallel to (2).

In the title compound, [Cd(C9H10NS2)2(C10H8N2)]·CHCl3, the CdII atom exists in an all-cis distorted octa­hedral geometry. Chelation is isobidentate for one dithio­carbamate ligand and anisobidentate for the other. The chloroform solvent mol­ecule is disordered over two positions of equal occupancy.

In the title compound, [Zn2(C22H36NS2)4], two bidentate dithio­carbamate groups chelate directly to the ZnII atoms, whereas the two remaining dithio­carbamate ligands bridge the Zn atoms via a crystallographic inversion centre. The Zn atoms show a strongly distorted tetra­hedral geometry. Adding the long S⋯S distance with the inversion centre being in the middle, the resulting five-coordinate geometry around the Zn atoms can be considered to be between distorted recta­ngular pyramidal and trigonal bipyramidal, with a calculated τ value of 0.31. In this dimer complex, two inversion-related tetra­decyl carbon chains exhibit all-trans conformations, and the other two chains show a cis conformation at the end of the chains.

The ZnII atom in the title compound, [Zn(C6H12NOS2)Cl(C10H8N2)], is coordinated by a chelating N-2-hy­droxy­ethyl-N-isopropyl­dithio­carbamate ligand, a 2,2′-bipyridine ligand and a Cl atom. The resulting ClN2S2 donor set defines a distorted square-pyramidal coordination geometry. Helical supra­molecular chains sustained by O—H⋯S hydrogen bonds and propagating along the b axis feature in the crystal packing. A three-dimensional architecture is stabilized by C—H⋯O, C—H⋯S and C—H⋯Cl inter­actions.

The Sn atom in the title compound, [Sn(C6H5)3(C8H16NS2)], is penta­coordinated by two S atoms, derived from an asymmetrically coordinating dithio­carbamate ligand, and three ipso-C atoms. The coordination geometry is inter­mediate between square-pyramidal and trigonal-bipyramidal, with a leaning towards the latter. The presence of close intra­molecular C—H⋯S contacts preclude the S atoms from forming significant inter­molecular inter­actions. Rather, mol­ecules are consolid­ated in the crystal structure by C—H⋯π inter­actions.

The molecule of the dinuclear title compound, [Tl2(C9H10NS2)6], possesses a crystallographically imposed centre of symmetry. Each TlIII atom is seven-coordinated by S atoms of four different dithio­carbamate anions in a distorted penta­gonal-bipyramidal coordination geometry. The crystal structure is stabilized by a C—H⋯S hydrogen-bond inter­action linking complex mol­ecules into chains running parallel to the b axis. Intramolecular C—H⋯S hydrogen bonds are also present.

In the title compound, [Cu(C5H10NO2S2)2], the CuII cation is chelated by two bis­(2-hydroxy­ethyl)dithio­carbamate anions with a distorted square-planar coordination geometry. Inter­molecular O—H⋯O hydrogen bonding is observed between the terminal hydr­oxy groups in the crystal structure.

The CdII atom in the title compound, [Cd(C5H10NS2)2(C10H8N2)], exists in an N2S4 donor set defined by two chelating dithio­carbamate anions as well as a 2,2′-bipyridine ligand. The coordination geometry approximates a trigonal prism. The crystal packing features weak C—H⋯S inter­actions, leading to linear supra­molecular chains along the a axis. The primary connections between these are by π–π stacking inter­actions [ring centroid distance between centrosymmetrically related pyridyl rings = 3.7455 (10) Å]. Overall, the crystal structure may be described as comprising double layers of mol­ecules that stack along the b axis.

The SnIV atom in the title organotin dithio­carbamate, [Sn(C6H5)2(C11H14NS2)Cl], is penta-coordinated by an asymmetrically coordinating dithio­carbamate ligand, a Cl and two ispo-C atoms of the Sn-bound phenyl groups. The resulting C2ClS2 donor set defines a coordination geometry inter­mediate between square-pyramidal and trigonal-bipyramidal with a slight tendency towards the latter. The formation of close intra­molecular C–H⋯Cl and C–H⋯S contacts precludes the Cl and S atoms from forming significant inter­molecular contacts. The presence of C–H⋯π contacts leads to the formation of supra­molecular arrays that stack along the b axis.

The dinuclear title compound, [Zn2(C7H14NS2)4(C12H10N2)], is centrosymmetric about the central C=C bond. The five-coordinate Zn atom is bonded to two asymmetrically chelating dithio­carbamate ligands and a pyridine N atom to define an NS4 coordination geometry tending towards a square pyramid, with the N atom in the apical site. In the crystal structure, C—H⋯S contacts lead to supra­molecular chains.

The CdII atom in the title compound, [Cd(C6H12NS2)2(C10H8N2)], is hexa­coordinated by two dithio­carbamate ligands and the N atoms from a bidentate 2,2′-bipyridyl mol­ecule. The coordination geometry is based on a distorted trigonal–prismatic arrangement of the N2S4 donor set. Supra­molecular chains, aligned along the a-axis direction, are mediated by C—H⋯S inter­actions and these are connected into layers that stack along the c axis via π–π inter­actions [Cg(pyrid­yl)⋯Cg(pyrid­yl) = 3.6587 (13) Å].

The title compound, [Cd(C5H10NO2S2)2(C10H8N2)], features a trigonal-prismatic coordination geometry for the CdII ion, based on an N2S4 donor set defined by two chelating dithio­carbamate ligands and a 2,2′-bipyridyl ligand. In the crystal, extensive O—H⋯O hydrogen bonding results in the formation of 12-membered {⋯HO}6 synthons and one-dimensional supra­molecular chains with further O—H⋯S inter­actions providing additional stability to the linear chain with base vector [01].

The ZnII atom in the title compound, [Zn(C5H10NS2)2(C12H8N2)], exists in a distorted cis-octa­hedral N2S4 donor set defined by two chelating dithio­carbamate anions as well as a 1,10-phenanthroline ligand. Each of the ligands coordinates in a symmetric mode. The crystal packing is stabilized by weak C—H⋯S, C—H⋯π(ZnS2C) and π–π [ring centroid distance between centrosymmetrically related pyridyl rings = 3.5955 (13) Å] inter­actions.

Two independent but very similar mol­ecules comprise the asymmetric unit of the title compound, [Zn(C8H16NS2)2(C12H8N2)]. The N2S4 donor set about Zn is defined by two symmetrically chelating dithio­carbamate ligands and a 1,10-phenanthroline ligand. Distortions from the ideal octa­hedral coordination geometry arise from the restricted bite angles of the ligands. The main feature of the crystal packing is the formation of tetra­meric supra­molecular aggregates mediated by C—H⋯S inter­actions. Disorder was found in each of the sec-butyl groups. This was resolved over two positions in each case with the major components of the disorder having site occupancies in the range 0.551 (6)–0.725 (5).

The SnIV atom in the title diorganotin dithio­carbamate, [Sn(C4H9)2Cl(C10H12NS2)], is penta­coordinated by an asymmetrically coordinating dithio­carbamate ligand, a Cl and two C atoms of the Sn-bound tert-butyl groups. The resulting C2ClS2 donor set defines a coordination geometry inter­mediate between square pyramidal and trigonal bipyramidal with a slight tendency towards the former. In the crystal structure, C—H⋯π contacts link centrosymmetrically related mol­ecules into dimeric aggregates.

In the centrosymmetric dimeric title compound, [Cu2(C3H6NS2)4], the CuII atom is five-coordinate in a square-pyramidal environment. The basal coordination positions are occupied by four S atoms from two dimethyl­dithio­carbamate ligands and the apical coordination position is occupied by an S atom also bonded to the other Cu atom.

The mol­ecule of the title compound, [Pb(C16H16NS2)2], is located on a twofold rotation axis, which runs through the PbII atom. The two dithio­carbamate ligands coordinate the metal in a pyramidal configuration through the S atoms. The two phenyl rings of each dithocarbamate ligand are aligned at a dihedral angle of 78.4 (1)°. The mol­ecular conformation is stabilized by intra­molecular C—H⋯S inter­actions.

The crystal structure of the title compound, [Sn(C5H10NS2)4], was originally determined by Harreld & Schlemper [Acta Cryst. (1971), B27, 1964–1969] using intensity data estimated from Weissenberg films. In comparison with the previous refinement, the current redetermination reveals anisotropic displacement parameters for all non-H atoms, localization of the H atoms, and higher precision of lattice parameters and inter­atomic distances. The complex features a distorted S6 octa­hedral coordination geometry for tin and a cis disposition of the monodentate dithio­carbamate ligands.

In the title compound, [Eu(C9H10NS2)3(C12H8N2)], the EuIII atom exists in a distorted square-anti­prismatic coordination geometry. Both dithio­carbamate and the N-heterocyclic ligands function in a chelating mode.

The copper(II) atom in the title compound, [Cu(C5H10NS2)I(C12H8N2)], is chelated by the N-heterocycle and the dithio­carbamate anion in a slightly distorted tetragonal coordination. The tetragonal-pyramidal coorination is completed by the iodine atom in the apical position. One ethyl group is disordered over two positions with site occupancies of 0.31 (2) and 0.69 (2).

The SnIV atom in the title diorganotin dithio­carbamate, [Sn(C4H9)2(C15H14NS2)Cl], is penta­coordinated by an asymmetrically coordinating dithio­carbamate ligand, a Cl atom and two C atoms of the Sn-bound tert-butyl groups. The resulting C2ClS2 donor set defines a coordination geometry inter­mediate between square pyramidal and trigonal bipyramidal with a slight tendency towards the former.

In the centrosymmetric title compound, [Cd2(C13H12NOS2)4], pairs of dithio­carbamate ligands exhibit different structural functions. Each of the terminal ligands is bidentately coordinated to one CdII atom and forms a planar four-membered CS2Cd chelate ring, whereas pairs of the tridentate bridging ligands link two neighbouring CdII atoms, forming extended eight-membered C2S4Cd2 tricyclic units whose geometry can be approximated by a chair conformation. The coordination polyhedron of the CdII atoms is a distorted square-pyramid. The five-membered furan ring and the benzene ring are disordered over two sets of sites with an occupancy ratio of 0.62 (8):0.38 (8).

The Sn atom in the title compound, [Sn(C4H9)2(C7H14NS2)2], exists in a tetra­hedral C2S2Sn coordination geometry. The geometry is distorted towards skew-trapezoidal-bipyramidal owing to the proximity of the double-bond S atoms [Sn—S = 2.521 (2) and Sn⋯S = 2.933 (2) Å]. The Sn atom lies on a special position of mm2 site symmetry and the tin-bound n-butyl chain is disordered about a mirror plane. The ethyl and n-butyl groups of the dithio­carbamate unit are disordered about another mirror plane.