The N'-(1-methyl-1H-indol-3-ylmethyl-idene)hydrazine-carbo-dithio-ate portion of the title mol-ecule, C(18)H(17)N(3)S(2), is nearly planar; this unit and the phenyl ring subtend an angle of 112.9 (2)° at the methyl-ene C atom.
The two aromatic parts of the title compound, C(16)H(13)N(3)O(4)·5H(2)O, are connected through a conjugated -CH=N-NH-C(O)- fragment, giving an almost planar mol-ecule. The organic mol-ecules and uncoordinated water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into a three-dimensional network.
In the title compound, [Mn(NCS)(2)(C(13)H(19)N(3)O)(H(2)O)], the Schiff base acts as an N,N',N"-tridentate ligand, forming two five-membered chelating rings with the Mn(II) atom. The distorted octa-hedral geometry around the metal atom is completed by two cis-positioned N-bound thio-cyanate ligands and one water mol-ecule. In the crystal, adjacent mol-ecules are linked through O-H⋯O, O-H⋯S and C-H⋯S hydrogen bonds into a three-dimensional supra-mol-ecular structure. An intra-molecular C-H⋯O hydrogen bond also occurs.
In the crystal structure of the title compound, C(4)H(7)N(4)O(+)·Cl(-)·2H(2)O, adjacent cations are connected to one another through N-H⋯O hydrogen bonds, forming infinite chains along the b axis. These chains are further hydrogen bonded to the chloride anions and water mol-ecules, resulting in a three-dimensional network. The pyrimidine rings of adjacent mol-ecules are arranged in an anti-parallel manner above each other with centroid-centroid distances of 3.435 (1) Å, indicative of π-π inter-actions.
A new thiosemicarbazone (LH2) derived from indole-7-carbaldehyde was synthesized and reacted with Zn(II), Cd(II), Pd(II) and Pt(II) salts. The reactions with zinc and cadmium salts in 2 : 1 (ligand-metal) molar ratio afforded complexes of the type MX2(LH2)2, (X = Cl, Br or OAc), in which the thiosemicarbazone acts as a neutral S-monodentate ligand. In the presence of potassium hydroxide, the reaction of LH2 with ZnBr2 resulted in deprotonation of the thiosemicarbazone at the hydrazine and indole nitrogens to form Zn(L)(CH3OH). The reaction of LH2 with K2PdCl4 in the presence of triethylamine, afforded Pd(L)(LH2) which contains two thiosemicarbazone ligands: one being dianionic N,N,S-tridentate while the other one is neutral S-monodentate. When PdCl2(PPh3)2 was used as the Pd(II) ion source, Pd(L)(PPh3) was obtained. In a similar manner, the analogous platinum complex, Pt(L)(PPh3), was synthesized. The thiosemicarbazone in the latter two complexes behaves in a dianionic N,N,S-tridentate fashion. The platinum complex was found to have significant cytotoxicity toward four cancer cells lines, namely MDA-MB-231, MCF-7, HT-29, and HCT-116 but not toward the normal liver WRL-68 cell line. The apoptosis-inducing properties of the Pt complex was explored through fluorescence microscopy visualization, DNA fragmentation analysis and propidium iodide flow cytometry.
The asymmetric unit of the title compound, [MnCl(2)(C(11)H(17)N(3))], contains two crystallographically independent mol-ecules with slightly different geometries. In each mol-ecule, the Mn(II) ion is five coordinated by the N,N',N''-tridentate Schiff base and two Cl atoms in a distorted square-pyramidal geometry. In the crystal, C-H⋯Cl hydrogen bonds link adjacent mol-ecules into a three-dimensional network.
The asymmetric unit of the title compound, [Zn(NCS)(2)(C(13)H(19)N(3)O)], contains two crystallographically independent mol-ecules. In each mol-ecule, the Zn(II) ion is five-coordinated by the N,N',N"-tridentate Schiff base and the N atoms of two thio-cyanate ligands in a distorted square-pyramidal geometry. The two mol-ecules differ mainly in the deviations from the ideal geometry, with τ values of 0.14 and 0.33. In the crystal, inter-molecular C-H⋯S hydrogen bonds are observed. An intra-molecular C-H⋯N hydrogen bond occurs in one of the independent mol-ecules.
In the title compound, [CdCl(2)(C(13)H(19)N(3)O)], the Cd(II) ion is five-coordinate, with the N,N',N''-tridentate Schiff base ligand 2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine and two Cl atoms in a distorted square-pyramidal geometry. In the crystal structure, C-H⋯Cl hydrogen-bonding inter-actions connect the mol-ecules into a three-dimensional network.
In the title compound, [Cu(NCS)(2)(C(13)H(19)N(3)O)], the Cu(II) ion is five-coordinated by the N,N',N''-tridentate Schiff base and the N atoms of two isothio-cyanate ligands in a square-pyramidal geometry. In the crystal, C-H⋯N, C-H⋯O and C-H⋯S inter-actions link adjacent mol-ecules into layers parallel to the ac plane. A weak inter-molecular π-π inter-action occurs between the aromatic rings with a centroid-centroid distance of 3.9412 (9) Å.
In the title compound, [CuCl(C(14)H(19)N(2)O(2))], the Cu(II) ion is four-coordinated by one deprotonated N,N',O-tridentate Schiff base and one chloride ion in a distorted square-planar geometry. In the crystal, adjacent mol-ecules are linked via C-H⋯Cl and C-H⋯O inter-actions, forming infinite layers parallel to the (100) plane. The structure was determined from a non-merohedrally twined crystal [twin ratio 0.777 (3):0.223 (3)].
In the title compound, [ZnCl(2)(C(13)H(19)N(3)O)], the Schiff base ligand acts as an N,N',N''-tridentate chelating agent, making two five-membered rings with the Zn(II) ion. The metal atom is five-coordinated by the Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry. An intra-molecular C-H⋯Cl inter-action occurs. In the crystal, adjacent mol-ecules are linked together via C-H⋯Cl hydrogen-bonding and long range C-H⋯O and C-H⋯Cl inter-actions into a three-dimensional network.
In the title compound, [MnCl(2)(C(13)H(19)N(3)O)], the Mn(II) ion is penta-coordinated in a distorted square-pyramidal geometry. The coordination environment is defined by the N,N',N''-tridentate Schiff base ligand and one Cl atom in the basal positions and one Cl atom in the apical position. In the crystal, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into a three-dimensional network. An intra-molecular C-H⋯Cl hydrogen bond is also observed.
The metal atom in the title compound, [Cd(C(15)H(13)N(2)O(4))(2)]·2C(2)H(6)OS, is twice O,N,O'-chelated by two symmetry-related Schiff base ligands to define a trans-N(2)O(4) octa-hedral geometry. Each anion occupies meridional sites of the octa-hedron; the metal atom lies on a special position of site symmetry 2. The dimethyl sulfoxide mol-ecule is a hydrogen-bond acceptor to the -NH- unit, and O-H⋯O hydrogen bonds link mol-ecules into a supra-molecular chain.
Each of the two independent mol-ecules of the title comound, C(14)H(20)N(2)O(3), exists in the zwitterionic form as the imino N atoms are protonated. The =N-H unit forms an intra-molecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N-H⋯O bond, the latter resulting in inversion dimers.
The title compound, [Sn(C(6)H(5))(3)(C(17)H(25)O(3)S)](n), comprises two symmetry-independent five-coordinated triphenyl-tin mol-ecules which are linked by carboxyl-ate bridges into a polymeric chain. The Sn(IV) atom is in a distorted trans-C(3)SnO(2) trigonal-bipyramidal geometry. The presence of two bulky tert-butyl groups on the benzene ring prevents any hydrogen-bonding inter-actions involving the hydroxyl substituents.
The asymmetric unit of the crystal structure of the title compound, [Ni(C(14)H(19)N(2)O(3))(2)], contains two independent Ni(II) complex mol-ecules, with the metal atoms each located on a center of inversion. Each metal atom is chelated by two Schiff base anions in a distorted square-planar coordination environment.
The Sn(IV) atom in the title compound, [Sn(CH(3))(2)(C(18)H(11)ClN(2)O(3))], shows a trans-C(2)NO(2)Sn trigonal-bipyramidal coordin-ation; the axial O-Sn-O angle is 155.22 (5)°. The tridentate N'-(5-chloro-2-oxidobenzyl-idene)-3-hydr-oxy-2-naphthohydrazidate dianion is stabilized by an intra-molecular O-H⋯N hydrogen bond.
The Cu(II) atom in the title compound, [Cu(C(13)H(16)ClN(2)O(2))Cl], exists in a distorted square-planar coordination environment as the deprotonated Schiff base chelates to the Cu(II) atom through three atom sites. In the crystal structure, adjacent mol-ecules are linked by a Cu⋯Cl [3.011 (1) Å] bridge, generating a linear chain running along the b axis of the ortho-rhom-bic unit cell.
In the title compound, (C(7)H(11)N(2))(2)[SnBr(4)(C(7)H(7))(2)], the tetra-bromidobis(4-methyl-phen-yl)stannate(IV) anion possesses a centre of inversion located at the Sn(IV) atom. In the crystal structure, two inversion-related cations are linked to the anion via weak N-H⋯Br hydrogen bonds.