Erratum: anti-1-(Benzyl-amino)-glyoxime. Corrigendum.

[This corrects the article DOI: 10.1107/S1600536804004799.].

Synthesis, anticonvulsant and antimicrobial activities of some new [1-(2-naphthyl)-2-(pyrazol-1-yl)ethanone]oxime ethers.

In this study, 12 new oxime ether derivatives, which were expected to show anticonvulsant and antimicrobial activities, were synthesized. Oxime ether derivatives were synthesized by the reaction of various alkyl halides with 1-(2- naphthyl)-2-(pyrazol-1-yl)ethanone oxime. Anticonvulsant activity of the compounds was determined by maximal electroshock (MES) and subcutaneous metrazol (ScM) seizure tests, while neurological disorders were evaluated using rotorod toxicity test according to the ASP of NIH. Compound 1, 6 and 7 showed anticonvulsant activity at 300 mg/kg dose at 4 h, but compounds 1 and 7 showed toxicity at 300 mg/kg dose at half an hour. Antimicrobial activities of the compounds were also determined using agar microdilution method. Compound 1 and 5 were found to have the highest antifungal activity among the other compounds.

(E)-(2,5-Difluoro-benz-yl)[(2-eth-oxy-naphthalen-1-yl)methyl-idene]amine.

In the title mol-ecule, C20H17F2NO, which adopts an E conformation with respect to the imine C=N double bond, the mean planes of the naphthalene ring system and the difluoro-phenyl ring form a dihedral angle of 85.82 (7)°. An intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, weak C-H⋯F hydrogen bonds link the mol-ecules into zigzag chains along [010].

Synthesis, structural characterization and comparison of experimental and theoretical results by DFT level of molecular structure of 4-(4-methoxyphenethyl)-3,5-dimethyl-4H-1,2,4-triazole.

4-(4-Methoxyphenethyl)-3,5-dimethyl-4H-1,2,4-triazole (3) was synthesized from the reaction of ethyl N'-acetylacetohydrazonate (1) with 2-(4-methoxyphenyl)ethanamine (2). The structure of the title compound 3 has been inferred through IR, (1)H/(13)C NMR, mass spectrometry, elemental analyses and combination of X-ray crystallography and theoretical methods. In addition to the molecular geometry from X-ray determination, the molecular geometry and vibrational frequencies of the title compound 3 in the ground state, were calculated using the density functional method (B3LYP) with the 6-31G(d) basis set. The calculated results show that the optimized geometry can well reproduce the crystal structure and the theoretical vibrational frequencies show good agreement with experimental values. The nonlinear optical properties are also addressed theoretically. The predicted nonlinear optical properties of 3 are greater than ones of urea. In addition, DFT calculations of molecular electrostatic potentials and frontier molecular orbitals of the title compound were carried out at the B3LYP/6-31G(d) level of theory.

2-Methyl-3-nitro-N-{(E)-[5-(4-nitro-phen-yl)furan-2-yl]methyl-idene}aniline.

In the title Schiff-base type compound, C(18)H(13)N(3)O(5), the central furan ring makes dihedral angles of 12.80 (7) and 51.43 (4)° with the terminal benzene rings. The dihedral angle between the benzene rings is 45.43 (3)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (010). In addition, there are π-π stacking inter-actions within the layer [centroid-centroid distance = 3.584 (1) Å] and between the layers [centroid-centroid distance 3.751 (1) Å].

(Z)-2-[(E)-2-(1-Benzothio-phen-3-yl-methyl-idene)hydrazin-1-yl-idene]-1,2-diphenyl-ethanone.

The title compound, C(23)H(16)N(2)OS, is not planar, the phenyl ring of the benzoyl group making a dihedral of 77.61 (7)° with the benzothio-phene system ring. The benzothio-phene system and the remaining phenyl ring make an angle of 12.71 (13)°. The conformation around the imine functions is E for the C=N bond towards the benzothio-phene system and Z for the C=N bond towards the benzoyl group. The packing of the mol-ecules shows C-H⋯π inter-actions. A weak intramolecular C-H⋯N bond also occurs.

2-{(E)-[(3-Iodo-4-methyl-phen-yl)imino]-meth-yl}-4-(trifluoro-meth-oxy)phenol.

The title compound, C(15)H(11)F(3)INO(2), adopts the enol-imine tautomeric form. The mol-ecule displays an E conformation with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 12.4 (2)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. The trifluoro-meth-oxy-phenyl group is disordered over two sites with an occupancy ratio of 0.621 (6):0.379 (6). The crystal structure features C-H⋯π inter-actions.

2-[(E)-(Naphthalen-2-yl-imino)-meth-yl]-4-(trifluoro-meth-oxy)phenol.

In the title compound, C(18)H(12)F(3)NO(2), the planes of the benzene ring and the naphthalene system form a dihedral angle of 47.21 (3)°. The hy-droxy group is involved in an intra-molecular O-H⋯N hydrogen bond. In the crystal, weak C-H⋯O and C-H⋯F inter-actions link the mol-ecules related by translations along the c and a axes, respectively, into sheets.

2-Chloro-4-{(E)-[(4-chloro-phen-yl)imino]-meth-yl}phenol.

In the title Schiff base compound, C(13)H(9)Cl(2)NO, the dihedral angle between the mean planes of the benzene rings is 10.20 (10)°. The crystal structure is stabilized by O-H⋯N hydrogen bonds and weak π-π stacking inter-actions [centroid-centroid distance = 3.757 (1) Å].

3-Chloro-4-(4-chloro-phen-oxy)-N-[(Z)-(5-nitro-thio-phen-2-yl)methyl-idene]aniline.

In the title compound, C(17)H(10)Cl(2)N(2)O(3)S, the thio-phene ring and the central benzene ring are almost coplanar [dihedral angle = 8.44 (3)°], while the dihedral angle between the two benzene rings rings is 77.49 (9)°. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds.

3-Meth-oxy-2-[(E)-(4-meth-oxy-phen-yl)imino-meth-yl]phenol.

The title compound, C(15)H(15)NO(3), adopts the enol-imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intra-molecular O-H⋯N hydrogen bond. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into sheets parallel to (010). These sheets are inter-connected by weak C-H⋯π inter-actions.

Structural properties of trans-cyclohexane-1,2-diamine complexes of copper(II) and zinc(II) acesulfamates.

The title compounds, trans-bis(trans-cyclohexane-1,2-diamine)bis(6-methyl-2,2,4-trioxo-3,4-dihydro-1,2,3-oxathiazin-3-ido)copper(II), [Cu(C(4)H(4)NO(4)S)(2)(C(6)H(14)N(2))(2)], (I), and trans-diaquabis(cyclohexane-1,2-diamine)zinc(II) 6-methyl-2,2,4-trioxo-3,4-dihydro-1,2,3-oxathiazin-3-ide dihydrate, [Zn(C(6)H(14)N(2))(2)(H(2)O)(2)](C(4)H(4)NO(4)S)(2)·2H(2)O, (II), are two-dimensional hydrogen-bonded supramolecular complexes. In (I), the Cu(II) ion resides on a centre of symmetry in a neutral complex, in a tetragonally distorted octahedral coordination environment comprising four amine N atoms from cyclohexane-1,2-diamine ligands and two N atoms of two acesulfamate ligands. Intermolecular N-H...O and C-H...O hydrogen bonds produce R(2)(2)(12) motif rings which lead to two-dimensional polymeric networks. In contrast, the Zn(II) ion in (II) resides on a centre of symmetry in a complex dication with a less distorted octahedral coordination environment comprising four amine N atoms from cyclohexane-1,2-diamine ligands and two O atoms from aqua ligands. In (II), an extensive two-dimensional network of N-H...O, O-H...O and C-H...O hydrogen bonds includes R(2)(1)(6) and R(4)(4)(16) motif rings.

Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives.

In this study, as a continuation of our research for new (arylalkyl)imidazole anticonvulsant compounds, the design, synthesis and anticonvulsant/antimicrobial activity evaluation of a series of 2-acetylnaphthalene derivatives have been described. Molecular design of the compounds has been based on the modification of nafimidone [1-(2-naphthyl)-2-(imidazol-1-yl)ethanone], which is a representative of the (arylalkyl)imidazole anticonvulsant compounds as well as its active metabolite, nafimidone alcohol (3, 4). In general, these compounds were variously substituted at the alkyl chain between naphthalene and imidazole rings and subjected to some other modifications to evaluate additional structure-activity relationships. The anticonvulsant activity profile of those compounds was determined by maximal electroshock seizure (MES) and subcutaneous metrazol (scM) seizure tests, whereas their neurotoxicity was examined using rotarod test. All the ester derivatives of nafimidone alcohol (5a-h), which were designed as prodrugs, showed anticonvulsant activity against MES-induced seizure model. Four of the most active compounds were chosen for further anticonvulsant evaluations. Quantification of anticonvulsant protection was calculated via the ip route (ED(50) and TD(50)) for the most active candidate (5d). Observed protection in the MES model was 38.46mgkg(-1) and 123.83mgkg(-1) in mice and 20.44mgkg(-1), 56.36mgkg(-1) in rats, respectively. Most of the compounds with imidazole ring also showed antibacterial and/or antifungal activities to a certain extent in addition to their anticonvulsant activity.

Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate.

In the title compound, C(13)H(15)N(3)O(3), the dihedral angle between the two aromatic ring is 51.06 (1)°. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into centrosymmetric dimers.

(E)-2-[(3-Fluoro-phen-yl)imino-meth-yl]-4-(trifluoro-meth-oxy)phenol.

The title compound, C(14)H(9)F(4)NO(2), is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The H atom is located on the hydr-oxy O atom rather than on the N atom. This H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond. The mol-ecule is almost planar, the angle between the benzene rings being 2.14 (13)°.

2,5-Dihexyl-3,6-diphenyl-pyrrolo-[3,4-c]pyrrole-1,4(2H,5H)-dione.

The asymmetric unit of the title compound, C(30)H(36)N(2)O(2), contains one half-mol-ecule, the other half being generated by a crystallographic inversion centre. The crystal structure is devoid of any classical hydrogen bonds however, non-classical C-H⋯O inter-actions link the mol-ecules into chains propagating in [001] and a C-H⋯π inter-action leads to the formation of a two-dimensional network in (011).

(E)-2-[(4-Iodo-phen-yl)imino-meth-yl]-6-methyl-phenol.

The title compound, C(14)H(12)INO, adopts the phenol-imine tautomeric form. The dihedral angle between the aromatic rings is 20.6 (3)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond while in the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a zigzag chain parallel to the b axis.

4-(4-Meth-oxy-pheneth-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-one.

The dihedral angle between the two rings in the title compound, C(12)H(15)N(3)O(2), is 49.03 (1)°. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds and π-π stacking inter-actions between the triazole rings with a centroid-centroid distance of 3.394 Å.

1-[(E)-(2-Methyl-3-nitro-phen-yl)imino-meth-yl]-2-naphthol.

The title Schiff base compound, C(18)H(14)N(2)O(3), has an inter-mediate state between NH and OH tautomers. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 37.44 (5)°.

Di-mu-acesulfamato-kappa3N,O:O;kappa3O:N,O-bis[(acesulfamato-kappa2N,O)bis(3-methylpyridine)cadmium(II)].

In the structure of the title compound, [Cd(2)(C(4)H(4)NO(4)S)(2)(C(6)H(7)N)(2)], the dinuclear Cd(II) complex is located on a twofold axis with two Cd(2+) ions bridged by two oxide O atoms. Each Cd(2+) ion is additionally coordinated in an equatorial plane by two N and three O atoms of the acesulfamate ligands and axially by two N atoms of the 3-methylpyridine ligands, resulting in a distorted pentagonal bipyramidal coordination. We present here an example of a supramolecular assembly based on hydrogen bonds in a mixed-ligand metal complex; intermolecular C-H...O hydrogen bonds give rise to R(4)(4)(40) rings, which lead to one-dimensional chains.