Synthesis, spectral analysis, structural elucidation and quantum chemical studies of (E)-methyl-4-[(2-phenylhydrazono)methyl]benzoate.

The title compound, (E)-methyl-4-[(2-phenylhydrazono)methyl]benzoate, (I), (C15H14N2O2), has been synthesized by condensation reaction of methyl-4-formylbenzoate and phenylhydrazine. The compound has been characterized by elemental analysis, IR, (1)H NMR, (13)C NMR, UV-Vis spectroscopies and single crystal X-ray diffraction techniques. Optimized molecular structure, harmonic vibrational frequencies, (1)H and (13)C NMR chemical shifts have been investigated by B3LYP/6-31G(d,p) method using density functional theory (DFT). Global chemical reactivity descriptors, natural population analysis (NPA), thermodynamic and non-linear optical (NLO) properties have also been studied. The energetic behavior of the compound has been examined in solvent media using the integral equation formalism polarizable continuum model (IEF-PCM).

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].

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.

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.

2-[(4-Ethoxy-phen-yl)imino-meth-yl]-5-methoxy-phenol.

The title compound, C(16)H(17)NO(3), a Schiff base, is stabilized in the solid state in the phenol-imine tautomeric form, with the H atom 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 4.43 (13)°. C-H⋯π inter-actions are also present.

(E)-2-[3-(Trifluoro-meth-yl)phenyl-imino-meth-yl]benzene-1,4-diol.

In the title compound, C(14)H(10)F(3)NO(2), the two benzene rings are oriented at a dihedral angle of 31.94 (14)°. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular structure. In the crystal, inter-molecular O-H⋯O hydrogen bonding links the mol-ecules, forming chains running along the crystallographic a axis. The F atoms of the trifluoro-methyl group are disordered over two positions with refined site occupancies of 0.488 (5) and 0.512 (5).

(E)-2-[(2,4-Dichloro-phen-yl)imino-meth-yl]benzene-1,4-diol monohydrate.

The title compound, C(13)H(9)Cl(2)NO(2)·H(2)O, represents a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The mol-ecule is approximately planar (r.m.s. deviation 0.0818 Å), and the dihedral angle between the two aromatic rings is 7.46 (12)°. An O-H⋯N inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds involving the solvent water mol-ecule, forming chains.

2-[(4-Ethyl-phen-yl)imino-meth-yl]-3,5-dimethoxy-phenol.

The title compound, C(17)H(19)NO(3), adopts the phenol-imine tautomeric form, with a resonance-assisted O-H⋯N intra-molecular hydrogen bond [O⋯N = 2.551 (3) Å]. The dihedral angle between the two benzene rings is 45.42 (7)°. The two meth-oxy groups are coplanar with the attached benzene ring [C-O-C-C torsion angles = -1.1 (5) and 3.2 (4)°].

3,5-Dibenzoyl-2,6-dimethyl-1-pentyl-4-pyridone.

In the crystal structure of the title compound, C(26)H(27)NO(3), a one-dimensional network of C-H⋯O hydrogen bonds and π-ring inter-actions is responsible for crystal stabilization. Inter-molecular hydrogen bonds and C-H⋯ π inter-actions produce R(2) (2)(10), R(4) (4)(27) and R(4) (4)(29) rings.

3,5-Dimeth-oxy-2-[(4-propyl-phen-yl)imino-meth-yl]phenol.

The title compound, C(18)H(21)NO(3), crystallizes in the phenol-imine tautomeric form, with the H atom attached to oxygen rather than on nitro-gen. This H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond. A C-H⋯π inter-action is also present. The dihedral angle between the aromatic rings is 12.23 (7)°.

(E)-2-[(2,4-Dichloro-phen-yl)imino-methyl]-6-methyl-phenol.

The title compound, C(14)H(11)Cl(2)NO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. There are two mol-ecules in the asymmetric unit. Head-to-tail π-π inter-actions [centroid-to-centroid distances of 3.682 (2), 3.708 (2), 3.904 (2) and 3.910 (2) Å] between adjacent mol-ecules produce two symmetry-independent infinite chains running along the b axis.