Crystal structures of (E)-1-naphthaldehyde oxime and (E)-phenanthrene-9-carbaldehyde oxime.

The aldoximes C11H9NO (I) and C15H11NO (II), synthesized in ca 90% yield, by treatment of 1-naphthaldehyde or phenanthrene-9-carbaldehyde, respectively, with hydroxyl-amine hydro-chloride and sodium carbonate, have been characterized by IR, 1H, 13C and DEPT-135 NMR spectroscopies, and also by single-crystal X-ray diffraction analysis. The mol-ecules of (I) and (II) are conformationally similar, with the aldoxime substituent groups lying outside the planes of the naphthalene or phenanthrene rings, forming dihedral angles with them of 23.9 (4) and 27.9 (6)°, respectively. The crystal structures of both (I) and (II) are similar with a single inter-molecular O-H⋯N hydrogen-bonding inter-action, giving rise to the formation of one-dimensional polymeric chains extending along the 21 (b) screw axes in each.

Crystal structure of trans-di-chloridobis-[N-(5,5-di-methyl-4,5-di-hydro-3H-pyrrol-2-yl-κN)acetamide]palladium(II) dihydrate.

The title complex, [PdCl2(C8H14N2O)2]·2H2O, was obtained by N-O bond cleavage of the oxa-diazo-line rings of the trans-[di-chlorido-bis-(2,5,5-trimethyl-5,6,7,7a-tetra-hydro-pyrrolo-[1,2-b][1,2,4]oxa-diazole-N1)]palladium(II) complex. The palladium(II) atom exhibits an almost square-planar coordination provided by two trans-arranged chloride anions and a nitro-gen atom from each of the two neutral organic ligands. In the crystal, N-H⋯O, O-H⋯O and O-H⋯Cl hydrogen bonds link complex mol-ecules into double layers parallel to the bc plane.

A new thio-Schiff base fluorophore with copper ion sensing, DNA binding and nuclease activity.

Copper ion recognition and DNA interaction of a newly synthesized fluorescent Schiff base (HPyETSC) were investigated using UV-vis and fluorescent spectroscopy. Examination using these two techniques revealed that the detection of copper by HPyETSC is highly sensitive and selective, with a detection limit of 0.39 µm and the mode of interaction between HPyETSC and DNA is electrostatic, with a binding constant of 8.97×10(4) M(-1). Furthermore, gel electrophoresis studies showed that HPyETSC exhibited nuclease activity through oxidative pathway.

Crystal structure of 4-methyl-N-[(4-methyl-pyridin-2-yl)carbamo-thioyl]-benzamide.

In the title compound, C15H15N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds both generate S(6) rings. The C=O and C=S bonds lie to opposite sides of the mol-ecule. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R 2 (2)(8) loops.

4-Methyl-N-[2-(pyridin-2-yl)ethyl-carbamo-thio-yl]benzamide.

In the title compound, C16H17N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 71.33 (15)°. An intra-molecular N-H⋯O hydrogen bond is present. In the crystal, weak aromatic C-H⋯O hydrogen bonds link the mol-ecules into chains extending along a.

Synthesis of isatin thiosemicarbazones derivatives: in vitro anti-cancer, DNA binding and cleavage activities.

New derivatives of thiosemicarbazone Schiff base with isatin moiety were synthesized L1-L6. The structures of these compounds were characterized based on the spectroscopic techniques. Compound L6 was further characterized by XRD single crystal. The interaction of these compounds with calf thymus (CT-DNA) exhibited high intrinsic binding constant (k(b)=5.03-33.00×10(5) M(-1)) for L1-L3 and L5 and (6.14-9.47×10(4) M(-1)) for L4 and L6 which reflect intercalative activity of these compounds toward CT-DNA. This result was also confirmed by the viscosity data. The electrophoresis studies reveal the higher cleavage activity of L1-L3 than L4-L6. The in vitro anti-proliferative activity of these compounds against human colon cancer cell line (HCT 116) revealed that the synthesized compounds (L3, L6 and L2) exhibited good anticancer potency.

(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)-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].

(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.

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).

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

In the title compound, C(15)H(11)ClN(4)OS, the dihedral angle between the nine-membered 5-chloro-indolin-2-one ring system and the benzene ring is 10.00 (6)°. 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, mol-ecules form centrosymmetric cyclic dimers through inter-molecular N-H⋯O hydrogen bonds [graph-set R(2) (2)(8)] and are extended by C-H⋯Cl inter-actions into infinite chains which propagate along [100].

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

In the title compound, C(16)H(14)N(4)OS, the dihedral angle between the nine-membered 5-methyl-indolin-2-one ring system and the benzene ring is 10.21 (7)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present within the N-N-C-N chain between the ring systems. In the crystal, mol-ecules form centrosymmetric cyclic dimers through pairs of N-H⋯O hydrogen bonds [graph set R(2) (2)(8)].

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

The asymmetric unit of the title compound, C(20)H(15)N(3)O, contains two independent mol-ecules, each of which is disordered over two sets of sites corresponding to a rotation of approximately 180° of the dihydro-benzimidazoquinazoline moiety, with refined site occupancies of 0.7479 (13) and 0.2521 (12) for both mol-ecules. The pyrimidine rings are in sofa conformations. In one mol-ecule, the hy-droxy-substituted benzene ring forms dihedral angles of 83.9 (3) and 82.4 (4)° for the major and minor components, respectively, with the mean plane of the benzimidazole ring system. The corres-ponding dihedral angles in the other mol-ecule are 88.31 (14) and 85.8 (6)°. In the crystal, mol-ecules are linked via inter-molecular O-H⋯N and N-H.·O hydrogen bonds into chains along [100].