Diamino­bithia­zole Research Articles

Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N3,N3′)(pyridine-2,6-dicarboxylato-κ3O2,N,O6)zinc tetrahydrate

The title compound, [Zn(C7H3NO4)(C6H6N4S2)(H2O)]·4H2O, assumes a distorted octa­hedral coordination geometry around the Zn2+ cation, formed by a diamino­bithia­zole (DABT) mol­ecule, a pyridine-2,6-dicarboxyl­ate anion and a water mol­ecule. The pyridine-2,6-dicarboxyl­ate anion chelates to the ZnII atom with a facial configuration. Within the chelating DABT ligand, the two thia­zole rings are twisted by a dihedral angle of 14.52 (8)° with respect to each other. O—H⋯O and N—H⋯O hydrogen bonds occur in the crystal structure.

Aqua-(2,2'-diamino-4,4'-bi-1,3-thia-zole-κN,N)(thio-diacetato-κO,S,O')nickel(II) monohydrate.

In the title compound, [Ni(C4H4O4S)(C6H6N4S2)(H2O)]·H2O, the NiII cation assumes a distorted octa­hedral coordination geometry formed by a diamino­bithia­zole (DABT) ligand, a thio­diacetate (TDA) dianion and a coordinated water mol­ecule. The tridentate TDA chelates to the Ni cation in a facial configuration, and both chelating rings display the envelope conformations. The two thia­zole rings of the DABT ligand are twisted with respect to each other, making a dihedral angle of 9.96 (9)°. Extensive O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.

(E)-But-2-enoato-κO]chlorido(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N3,N3′)zinc(II) monohydrate

In the title compound, [Zn(C4H5O2)Cl(C6H6N4S2)]·H2O, the ZnII cation is coordinated by a bidentate diamino­bithia­zole (DABT) ligand, a but-2-enoate anion and a Cl− anion in a distorted tetra­hedral geometry. Within the DABT ligand, the two thia­zole rings are twisted to each other at a dihedral angle of 4.38 (10)°. An intra­molecular N—H⋯O inter­action occurs. The centroid–centroid distance of 3.6650 (17) Å and partially overlapped arrangement between nearly parallel thia­zole rings of adjacent complexes indicate the existence of π–π stacking in the crystal structure. Extensive O—H⋯Cl, O—H⋯O, N—H⋯Cl and N—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Bis(μ-iminodiacetato)bis[(2,2′-diamino-4,4′-bi-1,3-thiazole)lead(II)] tetrahydrate

In the crystal structure of the title compound, [Pb2(C4H5NO4)2(C6H6N4S2)2]·4H2O, the dinuclear PbII complex mol­ecule is centrosymmetric. The Pb atom is chelated by a tridentate imino­diacetate anion (IDA) and a diamino­bithia­zole (DABT) ligand, while a carboxyl­ate O atom from an adjacent IDA anion further bridges the Pb atom with a longer Pb—O bond [2.892 (3) Å]. The lone-pair electrons of the Pb atom occupy an axial site in the Ψ-penta­gonal-bipyramidal coordination polyhedron. The IDA anion displays a facial configuration: its chelating five-membered rings assume an envelope configuration. Within the DABT ligand, the two thia­zole rings are twisted relative to each other, making a dihedral angle of 9.51 (17)°. Extensive N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Bis(μ-pyridine-2,3-dicarboxylato)bis[aqua(2,2′-diamino-4,4′-bi-1,3-thiazole)cobalt(II)] decahydrate

In the centrosymmetric title dimeric CoII complex, [Co2(C7H3NO4)2(C6H6N4OS2)2(H2O)2].10H2O, each CoII cation has a distorted octa­hedral coordination geometry formed by a diamino­bithia­zole (DABT) ligand, two pyridine-2,3-dicarboxyl­ate anions and a coordinated water mol­ecule. With its two carboxyl­ate groups, the pyridine-2,3-dicarboxyl­ate anion bridges two CoII ions to form the dimeric complex. Within the chelating DABT ligand, the two thia­zole rings are twisted with respect to each other [dihedral angle = 3.29 (19)°]. Extensive N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonding helps to stabilize the crystal structure.

Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N,N′)(malonato-κ2O,O′)zinc(II) monohydrate

In the asymmetric unit of the crystal structure of the title compound, [Zn(C3H2O4)(C6H6N4S2)(H2O)]·H2O, there are two independent ZnII complex mol­ecules. Each ZnII ion assumes a distorted square-pyramidal coordination geometry formed by a diamino­bithia­zole (DABT) ligand, a malonate dianion and a water mol­ecule. Within the chelating DABT ligand, the two thia­zole rings are twisted with respect to each other, with dihedral angles of 3.23 (19) and 2.54 (18)°. O—H⋯O and N—H⋯O hydrogen bonding occurs in the crystal structure.

Catena-Poly[(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N,N′)lead(II)]-di-μ-isonicotintato-κ4O:O′

In the polymeric title compound, [Pb(C6H4NO2)2C6H6N4S2)]n, the PbII ion is located on a twofold axis and coordinated by one N,N′-bidentate diamino­bithia­zole (DABT) ligand and four O-monodentate isonicotinate anions in a very distorted cis-PbN2O4 octa­hedral geometry. The carboxyl­ate group of the isonicotinate anion bridges two PbII ions, forming a polymeric chain. The complete DABT mol­ecule is generated by twofold symmetry; its two thia­zole rings are twisted with a dihedral angle of 9.5 (2)°. There are no π–π stacking inter­actions in the title compound, but N—H⋯O and N—H⋯N hydrogen bonds help to stabilize the structure.

(2,2′-Diamino-4,4′-bi-1,3-thiazole-κ2N,N′)bis(glycinato-κ2N,O)zinc(II) dihydrate

In the title ZnII complex, [Zn(C2H4NO2)2(C6H6N4S2)]·2H2O, the ZnII ion is coordinated by two glycinate anions and a diamino­bithia­zole (DABT) mol­ecule in a distorted octa­hedral geometry. Two thia­zole rings of the same DABT are twisted with respect to each other with a dihedral angle of 10.56 (6)°. The glycinate chelates to the ZnII ion by the amino N and carboxylate O atoms; the chelating five-membered ring displays an envelope configuration. A twofold rotation axis passes through the Zn atom and the mid-point of the C—C bond linking the two thiazole rings.

Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N,N′)(thiodiacetato-κ3O,S,O′)cobalt(II) dihydrate

The title CoII complex, [Co(C6H6N4S2)(C4H4O4S)(H2O)]·2H2O, assumes a distorted octa­hedral coordination geometry formed by a diamino­bithia­zole (DABT) ligand, a thio­diacetate dianion (TDA) and a water mol­ecule. The TDA dianion chelates to the CoII atom with a facial configuration. Within the chelating DABT ligand, the two thia­zole rings are twisted with respect to each other [dihedral angle = 12.04 (9)°].

Synthesis and crystal structure of aqua(diaminobithiazole) (iminodiacetato)nickel(II) hydrate

Crystals of the title compound, [(C6H6N4S2)(C4H5NO4)(H2O)Ni]·H2O, consist of the Ni(II) complex and lattice water. The Ni(II) complex adopts a distorted octahedral coordination geometry formed by an iminodiacetate anion (IDA), a diaminobithiazole (DABT) and a coordinated water molecule. A twisted configuration of DABT is the distinguishing feature in the complex, the dihedral angle between thiazole rings of DABT being 20.04(8)°. An aromatic stacking interaction occurs between thiazole rings from neighboring complex molecules, and is considered as the reason for the twisted configuration. The tridentate IDA dianion chelates to a Ni(II) atom in afacialconfiguration. A hydrogen bond network holds the complex molecules together to form a supramolecular structure.

2,2′-Diamino-4,4′-bi-1,3-thiazolium (2R,3R)-tartrate

Crystals of the title chiral compound, C6H8N4S22+·C4H4O62−, were obtained from a solution containing diamino­bithia­zole (DABT) and racemic tartaric acid. The crystal structure consists of a protonated DABT dications (H2DABT) and (2R,3R)-tartrate dianions linked via hydrogen bonding. An overlapped arrangement and a centroid-to-centroid separation of 3.4620 (11) Å between nearly parallel thia­zole rings of adjacent H2DABT cations indicate the existence of π–π stacking in the crystal structure.

Synthesis and crystal structure of aqua (2,2′-diamino-4,4′-bi-1,3-thiazole) (oxydiacetato)manganese(II) trihydrate

The title compound crystallizes in the triclinic space group with a = 7.194(3), b = 9.790(5), c = 12.492(1) Å, α = 82.407(16), β = 86.664(15), γ = 89.882(15)°. The Mn(II) complex assumes distorted octahedral coordination geometry, formed by diaminobithiazole (DABT), an oxydiacetate dianion (ODA) and a water molecule. The tridentate ODA ion chelates to the Mn(II) atom in a meridional configuration. Each carboxyl group coordinates to the Mn(II) atom as a monodentate. Uncoordinated carboxyl oxygen atoms are involved in a hydrogen-bonding network. DABT chelates to the Mn(II) atom with a coplanar configuration. Coordinated water is hydrogen bonded to carboxyl groups of ODA of a neighboring complex to form supramolecular chains. A π–π stacking interaction involving thiazole rings occurs between adjacent supramolecular chains. A difference of 180 cm−1 between asymmetric and symmetric stretching vibrations of the carboxyl group corresponds to the extensive hydrogen-bonding network involving the carboxyl group.

Aqua(2,2'-diamino-4,4'-bi-1,3-thiazole-kappa2N,N')(iminodiacetato-kappa3O,N,O')chromium(III) chloride monohydrate.

Crystals of the title compound, [Cr(C4H5NO4)(C6H6N4S2)(H2O)]Cl.H2O, consist of Cr(III) complex cations, Cl- counter-ions and lattice water molecules. The complex cation assumes an octahedral coordination geometry, formed by a tridentate iminodiacetate dianion (IDA), a diaminobithiazole (DABT) molecule and a water molecule. The planar DABT group chelates the Cr(III) ion with normal Cr-N distances [2.0574 (17) and 2.0598 (17) A], but the DABT molecule is inclined to the coordination plane by a dihedral angle of 17.23 (7) degrees. In the monodentate carboxylate groups of the IDA ion, the coordinated C-O bonds [1.288 (3) and 1.284 (3) A] are much longer than the uncoordinated C-O bonds [1.222 (3) and 1.225 (3) A].

Bis(2,2′-diamino-4,4′-bi-1,3-thiazole-N,N′)(dichloro)cobalt(II) dihydrate

The crystal structure of the title compound, [Co(C6H6N4S2)2Cl2]·2H2O, comprises an octahedral CoII complex and water of crystallization. Two Cl atoms and two di­amino­bi­thia­zole (DABT) ligands coordinate to the CoII atom in a cis configuration. The overlapped arrangement and the short separation of 3.46 (2) A between parallel DABT rings suggest the existence of π–π stacking interactions. A short S⋯S contact of 3.1822 (17) A is observed between DABT ligands.

Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ2N,N′)(oxydiacetato-κ3O,O′,O′′)zinc(II) dihydrate

The title ZnII complex, [Zn(C4H4O5)(C6H6N4S2)(H2O)]·2H2O, with ligands consisting of an oxydi­acetate dianion (ODA), a di­amino­bi­thia­zole (DABT) mol­ecule and a water mol­ecule, displays a distorted octahedral coordination geometry. The tridentate ODA chelates to the ZnII in a meridional configuration, with the Zn—O(ether) distance of 2.216 (5) Å, much longer than the Zn—O(carboxyl) distances of 2.051 (5) and 2.071 (5) Å. The overlapped arrangement of parallel DABT ligands, with a separation of 3.509 (9) Å between neighboring DABT rings, suggests π–π stacking between neighboring mol­ecules.

2,2′-Diamino-4,4′-bi-1,3-thiazolium fumarate

The title compound, C6H8N4S22+·C4H2O42−, consists of a di­amino­bi­thia­zole (DABT) cation and a fumarate anion. The cation and anion are both located on inversion centers. Both ions display a planar configuration and link to each other through hydrogen bonding between carboxyl and amino groups, as well as through weak C—H⋯O hydrogen bonding between thia­zole and carboxyl groups. The C—N(amino) bond distance of 1.323 (4) Å suggests the existence of electron delocalization between the thia­zole ring and the amino group.

Synthesis and Crystal Structure of a Cadmium(II) Complex with 2,2′-diamino-4,4′-bis-1,3-thiazole

Crystals of the title complex with diaminobithiazole (DABT) were obtained by a solution diffusion method. X-ray diffraction analysis shows the complex to be monoclinic, space group P21/c with cell dimensions a=11.684(2), b=13.625(2), c=14.859(1) Å and β=109.970(7)°; R=0.026. The Cd(II) atom lies in a distorted octahedral environment with two DABT and two Cl ligands in a cis arrangement. The average internal dihedral angle of 9.3° between thiazole rings of DABT shows the twisted structure of the ligand in the complex. The Cd(II) atom deviates by some -0.570 Å from the mean plane of the thiazole ring containing N(4), but the Cd-N(4) bond is the shortest among four Cd-N bonds in the structure. Intramolecular H-bonds between Cl atoms and amino groups stabilize the cis-configuration of the complex.