2-({[4-(1,3-Benzothiazol-2-yl)phenyl]amino}methyl)phenol

In the title compound, C20H16N2OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å). The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2)°. In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O—H⋯N hydrogen bonds. C—H⋯O contacts and N—H⋯π(arene) interactions also occur.

In the title compound, C 20 H 16 N 2 OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å ). The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2) . In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O-HÁ Á ÁN hydrogen bonds. C-HÁ Á ÁO contacts and N-HÁ Á Á(arene) interactions also occur.

Experimental
Cg is the centroid of the C31-C36 ring.  (Gerber et al., 2011), we attempted the coordination reaction of a potentially multidentate ligand towards a rhenium precursor upon which a crystalline reaction product was obtained.

D-HÁ
The crystal structure analysis showed the presence of the free ligand only whose molecular and crystal structure has not been reported to date. The structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl) aniline monohydrate is noted in the literature (Su et al., 2009).
The benzothiazolyl system and the attached aniline system are nearly co-planar (r.m.s. of all fitted non-hydrogen atoms including the nitrogen bound methylene group = 0.0612 Å). The phenolic substituent, however, adopts a nearly perpendicular orientation with respect to the rest of the molecule, with an interplanar angle of 88.36 (2)° between the two least-squares planes defined by both moieties (Fig. 1).
In the crystal, classical hydrogen bonds of the O-H···N type as well as C-H···O contacts (whose range lies by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating) are observed. The latter are supported by one of the hydrogen atoms of the central phenyl ring. In total, the molecules are connected to centrosymmetric dimers by these two interactions. In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for these contacts is R 2 2 (18)R 2 2 (24) on the unitary level. The nitrogen-bonded hydrogen atom forms a hydrogen bond to the aromatic system of the phenolic moiety, connecting the molecules to chains along the crystallographic b axis. Metrical parameters about these contacts as well as information about their symmetry is listed in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 4.6019 (10) Å and is apparent between the phenyl unit of the benzothiazole moiety and the central C 6 aromatic ring (Fig 2.) The packing of the title compound in the crystal structure is shown in Figure 3.

Experimental
A mixture of 2.00 g of 4-aminobenzoic acid and 1.33 g of 2-aminothiophenol was added to hot polyphosphoric acid.
The stirring solution was heated to 220 °C for four hours. The reaction solution was cooled to room temperature and poured into a 10% K 2 CO 3 solution. The yellow precipitate which formed was filtered and dried under vacuum, yielding 4-(benzo[d]thiazol-2-yl)benzenamine. A solution of 1.0 g of this product dissolved in 25 cm 3 of methanol was added to a 25 cm 3 methanol solution of 2-hydroxybenzaldehyde (0.4 g). The solution was refluxed for three hours after which it was cooled to room temperature and stirred overnight. An excess of NaBH 4 (2.0 g) was added in portions with stirring and the mixture was left to stir at room temperature overnight. The solvent was removed by evaporation and 50 cm 3 of water was added. HCl was added to adjust the pH to 6, resulting in the formation of a light yellow precipitate which was filtered and dried under vacuum. Crystals suitable for the X-ray diffraction study were obtained upon the attempted synthesis of a rhenium coordination compound in ethanol.
supplementary materials sup-2 Refinement Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic carbon atoms, C-H 0.99 Å for the methylene group) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U eq (C). The H atom of the hydroxyl group was allowed to rotate with a fixed angle around the C-O bond to best fit the experimental electron density (HFIX 147 in the SHELX program suite (Sheldrick, 2008)), with U(H) set to 1.5U eq (O). The nitrogen-bound H atom was located on a difference Fourier map and refined freely with isotropic parameters. Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).