2-[(E)-(1,10-Phenanthrolin-5-yl)iminomethyl]phenol methanol monosolvate

In the title multi-donor Schiff base compound, C19H13N3O·CH3OH, the dihedral angle between the mean planes of the phenanthroline and phenol rings is 59.3 (1)°. The Schiff base molecule is linked to the solvent molecule by an O—H⋯O hydrogen bond. In the crystal, the components are linked by O—H⋯N hydrogen bonds, weak O—H⋯N interactions and π–π stacking interactions [centroid–centroid distances = 3.701 (1) and 3.656 (1) Å].

In the title multi-donor Schiff base compound, C 19 H 13 N 3 OÁ-CH 3 OH, the dihedral angle between the mean planes of the phenanthroline and phenol rings is 59.3 (1) . The Schiff base molecule is linked to the solvent molecule by an O-HÁ Á ÁO hydrogen bond. In the crystal, the components are linked by O-HÁ Á ÁN hydrogen bonds, weak O-HÁ Á ÁN interactions and stacking interactions [centroid-centroid distances = 3.701 (1) and 3.656 (1) Å ].

2-[(E)-(1,10-Phenanthrolin-5-yl)iminomethyl]phenol methanol monosolvate
Sema Öztürk Yíldírím, Nebahat Demirhan, Fikriye Elmalí and Ray J. Butcher Comment 1,10-Phenanthroline and its derivatives play important roles as molecular scaffolding for supramolecular assemblies (Balzani et al., 1996). These have played a major role in the development of polypyridyl metal complexes. The metal chelating property of the 1,10-phenanthroline ligand and its derivatives have been utilized in a range of analytical reagents as well as for the development of bioinorganic probes (Sammes & Yahioglu, 1994). The photochemical and redox properties of complexes can be varied systematically through appropriate substitution on the phenanthroline rings (Camren et al., 1996: Bolger et al., 1996: Msood & Hodgson, 1993. The coordination chemistry of Schiff bases derived from salicylaldehyde has been the subject of many studies because of their interesting properties; e.g. as oxygen-carriers to mimic some complicated biological systems, as photochromic or thermochromic materials (Hobday & Smith, 1973: Gul et al., 1986: Can & Bekaroglu, 1988: Avciata et al. 1995Avciata et al. 1998;Demirhan et al. 2002).
We report here the synthesis and characterization a new multidonor Schiff base derivative, (I), carrying N 3 O donor atoms and prepared from the condensation reaction of 5-amino-1,10-phenanthroline with salicylaldehyde.

Figure 1
View of the molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-hydrogen atoms. Hydrogen bonds are drawn as dashed lines.  The molecular packing of the title compound. Hydrogen bonds are drawn as dashed lines.  In the electronic spectrum two band appears at 281 and 340 nm which can be assigned to the π -π * and n-π * transition of C=C and C=N group. The FTIR spectra were obtained on a Perkin Elmer Spectrum One Bv 5.0 spectrophotometer. 1 H NMR and 13 C NMR spectra were recorded on a Varian UNITY INOVA 500 MHz s pectrometer. Mass spectra were measured on a FinniganTM LCQTM Advantage MAX spectrometer. Electronic spectra were obtained on a Agilent 8453 UV-Vis. Spectroscopy System. Elemental analyses were obtained on a Thermo Finnigan Flash EA 112. All other chemicals employed were of the highest grade available. Absorption correction: CrysAlis RED, (Oxford Diffraction, 2007) Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995). Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1 0.98484 (