(Z)-N-Ethyl-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(11)FN(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules form chains through N-H⋯O hydrogen bonds, which are extended by N-H⋯S hydrogen bonds into an infinite three-dimensional network.

(E)-2-[(E)-3-(Hy-droxy-imino)-butan-2-yl-idene]-N-methyl-hydrazinecarbothio-amide.

In the title compound, C(6)H(12)N(4)OS, an intra-molecular N-H⋯N hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [10[Formula: see text]] are formed via pairs of O-H⋯S and N-H⋯S hydrogen bonds. The chains are further stabilized by C-H⋯S interactions.

(Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(10)H(9)N(5)O(3)S, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via N-H⋯S hydrogen bonds into a zigzag chain along the b axis. C-H⋯O inter-actions are observed between the chains.

(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(12)N(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules form a helical chain along the a axis through an N-H⋯O hydrogen bond. These chains are extended by an N-H⋯S hydrogen bond and a C-H⋯π inter-action into a three-dimensional network.

(Z)-2-(2-Oxoindolin-3-yl-idene)-N-phenylhydrazinecarbothio-amide.

In the title compound, C(15)H(12)N(4)OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present, as are weak N-H⋯N inter-actions [graph set S(5)]. In the crystal, mol-ecules form centrosymmetric cyclic dimers through pairs of N-H⋯O hydrogen bonds [graph set R(2) (2)(8)] and these are extended by C-H⋯S inter-actions. The crystal structure also features weak C-H⋯π inter-actions.

Bis[2-(2-oxoindolin-3-yl-idene)-N-phenylhydrazinecarbothio-amidato-κ(3)O,N(2),S]nickel(II) dimethyl-formamide monosolvate.

The asymmetric unit of the title compound, [Ni(C(15)H(11)N(4)OS)(2)]·C(3)H(7)NO, contains one Ni(II) complex mol-ecule and one disordered dimethyl-formamide solvent mol-ecule. The Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by two N, two O and two S atoms. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through inter-molecular N-H⋯S, N-H⋯O, C-H⋯N, C-H⋯O and C-H⋯S hydrogen bonds into infinite two-dimensional network parallel to the ab plane. The structure is further stablized by weak C-H⋯π inter-actions. The dimethylformamide solvent molecule is disordered over two sets of sites in a 0.514 (15):0.486 (15) ratio.

(Z)-2-(5-Chloro-2-oxoindolin-3-yl-idene)-N-methyl-hydrazinecarbothio-amide.

In the title compound, C(10)H(9)ClN(4)OS, an intra-molecular N-H⋯O hydrogen-bonding inter-action and an N-H⋯N inter-action generate ring motifs [graph sets S(6) and S(5), respectively]. In the crystal, mol-ecules form a chain through N-H⋯O hydrogen bonds, and these are extended by N-H⋯S hydrogen-bonding inter-actions into an infinite three-dimensional network. The crystal structure also exhibits weak C-H⋯π inter-actions.

(E)-N-Ethyl-2-[(E)-3-(hy-droxy-imino)-butan-2-yl-idene]hydrazinecarbothio-amide.

In the crystal structure of the title compound, C(7)H(14)N(4)OS, mol-ecules are linked through N-H⋯S and O-H⋯N hydrogen bonds and C-H⋯S interactions, forming chains propagating along [21-1].

Bis{2-[3-(hy-droxy-imino-κN)butan-2-yl-idene]-N-methyl-hydrazinecarbothio-amide-κN,S}nickel(II) dichloride.

The asymmetric unit of the title compound, [Ni(C(6)H(12)N(4)OS)(2)]Cl(2), contains two independent Ni(II) complex cations and four chloride anions. Each Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by four N atoms from the two imine and two oxime groups and two S atoms from the thione group. In the crystal, the cations and anions are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds into infinite chains propagating along [10[Formula: see text]]. Weak inter-molecular C-H⋯O and C-H⋯Cl hydrogen bonds are also observed.

Bis{N-ethyl-2-[3-(hy-droxy-imino-κN)butan-2-yl-idene]hydrazinecarbothio-amide-κN,S}nickel(II) dichloride.

In the title complex, [Ni(C(7)H(14)N(4)OS)(2)]Cl(2), the Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by four N atoms from the two imine and two oxime groups, and two S atoms from the thione groups. Two chloride ions complete the asymmetric unit. In the crystal, mol-ecules are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds into an infinite chain propagating along [101].

(Z)-2-(5-Fluoro-2-oxoindolin-3-yl-idene)-N-phenyl-hydrazinecarbothio-amide.

The title compound, C(15)H(11)FN(4)OS, crystallizes with three independent mol-ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro-indolin-2-one ring system and the benzene ring are 22.14 (11), 12.56 (11) and 3.70 (11)° in mol-ecules A, B and C, respectively. In all three mol-ecules, intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present in the N-N-C-N chain between the ring systems. In the crystal, the A mol-ecules form centrosymmetric cyclic dimers through inter-molecular N-H⋯O hydrogen bonds, which are linked into a supramolecular chain along [100] via C-H⋯F interactions; each type of hydrogen bond has graph set graph set R(2) (2)(8). A similar chain stabilised by similar interactions and also along [100] but, comprising alternating molecules of B and C is found. The latter chains are connected via C-H⋯S interactions, forming a layer with a zigzag topology parallel to (001).

2-Amino-3-nitro-benzoic acid.

The title compound, C(7)H(6)N(2)O(4), is approximately planar (r.m.s. deviation = 0.026 Šfor the 13 non-H atoms). The mol-ecular structure is stabilized by intra-molecular N-H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into a three-dimensional network.

Synthesis, crystal structure and luminescent properties of some Zn(II) Schiff base complexes: experimental and computational study.

A series of Zn(II)-Schiff bases I, II and III complexes were synthesized by reaction of o-phenylenediamine with 3-methylsalicylaldehyde, 4-methylsalicylaldehyde and 5-methylsalicylaldehyde. These complexes were characterized using FT-IR, UV-Vis, Diffuse reflectance UV-Vis, elemental analysis and conductivity. Complex III was characterized by XRD single crystal, which crystallizes in the triclinic system, space group P-1, with lattice parameters a=9.5444(2) Å, b=11.9407(2) Å, c=21.1732(3) Å, V=2390.24(7) Å(3), D ( c )=1.408 Mg m(-3), Z=4, F(000)=1050, GOF=0.981, R1=0.0502, wR2=0.1205. Luminescence property of these complexes was investigated in DMF solution and in the solid state. Computational study of the electronic properties of complex III showed good agreement with the experimental data.

2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-5-methyl-phenol.

In the title compound, C(21)H(17)N(3)O, the imidazole ring is essentially planar, with a maximum deviation of 0.009 (1) Å. The mol-ecule is disordered over two sites corresponding to a rotation of approximately 180° with a refined occupancy ratio of 0.9180 (14):0.0820 (14). The central pyrim-idine ring makes dihedral angles of 5.02 (5), 3.97 (5) and 6.28 (5)°, respectively, with the planes of the imidazole and the terminal phenyl rings for the major component; the values for the minor component are 5.8 (7), 5.0 (6) and 8.5 (6)°, respectively. Part of the observed planarity is accounted for in terms of an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules of the major component are connected by O-H⋯N hydrogen bonds, forming supra-molecular chains along the c axis.

2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-5-meth-oxy-phenol.

In the title quinazoline derivative, C(21)H(17)N(3)O(2), the benzimidazole unit makes dihedral angles of 8.29 (5) and 81.79 (5)° with the benzene rings of the quinazoline and meth-oxy-phenol units, respectively. The nitro-gen-containing six-membered ring adopts a half-chair conformation. In the crystal, the mol-ecules are linked through O-H⋯N hydrogen bonds into screw chains along the b axis; adjacent chains are further connected by N-H⋯O hydrogen bonds, thereby forming a two-dimensional network lying parallel to the bc plane. Weak C-H⋯π and π⋯π inter-actions with centroid-centroid distances of 3.5258 (8) and 3.7184 (7) Šare present and N⋯O [2.6816 (15) and 3.0519 (15) Å] short contacts also occur.

2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-6-eth-oxy-phenol.

In the title compound, C(22)H(19)N(3)O(2), the phenol ring forms dihedral angles of 88.93 (10) and 87.95 (12)° with the benzimidazole system and the quinazoline benzene ring, respectively. In the crystal, mol-ecules are linked via O-H⋯N hydrogen bonds into infinite chains along [100]. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring.

[2-(1H-Benzimidazol-2-yl-κN)aniline-κN]dichloridozinc.

In the title benzimidazole mononuclear complex, [ZnCl(2)(C(13)H(11)N(3))], the Zn(II) ion is four-coordinated in a distorted tetra-hedral geometry by an imidazole N, an amino N and two Cl atoms. The dihedral angle between the benzimidazole and benzene rings is 9.57 (1)°. In the crystal, mol-ecules are linked by weak N-H⋯Cl hydrogen bonds into layers parallel to the bc plane. π-π inter-actions with centroid-centroid distances in the range 3.4452 (8)-3.8074 (8) Šare also observed.

(2-{[2-(1H-Benzimidazol-2-yl-κN)phen-yl]imino-methyl-κN}-5-methyl-phenolato-κO)chloridozinc(II).

In the title mononuclear complex, [Zn(C(21)H(16)N(3)O)Cl], the Zn(II) ion is coordinated in a distorted tetra-hedral geometry by two benzimidazole N atoms and one phenolate O atom from the tridentate Schiff base ligand and a chloride ligand. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the adjacent benzene ring and the methyl-phenolate group benzene ring, respectively. In the crystal, mol-ecules are linked by N-H⋯Cl hydrogen bonds into chains along [100]. Furthermore, weak C-H⋯O and C-H⋯π inter-actions, in addition to π-π inter-actions with centroid-centroid distances in the range 3.5826 (13)-3.9681 (13) Å, are also observed.

4-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)benzene-1,3-diol dimethyl sulfoxide monosolvate.

In the title solvated benzimidazole compound, C(20)H(15)N(3)O(2)·C(2)H(6)OS, both the benzimidazole fused-ring system and the complete dimethyl sulfoxide solvent mol-ecule are disordered over two sets of sites, in 0.750 (5):0.250 (5) and 0.882 (4):0.118 (4) ratios, respectively. The conformation of the pyrimidine ring is close to a half-chair for the major disorder component, whereas for the minor component it is close to a boat. The dihy-droxy-phenyl ring is almost perpendicular to the mean plane of the benzimidazole ring [dihedral angle = 87.3 (2)° for the major disorder component and 88.3 (5)° for the minor disorder component]. In the crystal, mol-ecules are linked into layers parallel to (110) by O-H⋯N and C-H⋯O hydrogen bonds. A bifurcated O-H⋯(O,S) bond links the benzimidazole and solvent mol-ecules.

(2,2'-Bipyridyl-κN,N')chlorido(dl-threoninato-κN,O)copper(II) monohydrate.

In the title compound, [Cu(C(4)H(8)NO(3))Cl(C(10)H(8)N(2))]·H(2)O, the Cu(II) atom is in a slightly distorted square-pyramidal coordination geometry with the basal plane defined by the two N atoms of the bipyridine ligand and the N and O atoms from the threoninate ion and the apical site occupied by the Cl atom. In the crystal, inter-molecular O-H⋯O, N-H⋯O, O-H⋯Cl, C-H⋯O and C-H⋯Cl inter-actions link the mol-ecules into a three-dimensional network. A π-π inter-action with a centroid-centroid distance of 3.461 (1) Šis also present.