[2-(Biphenyl-4-yl)-1,3-thiazol-4-yl]methanol

In the title compound, C16H13NOS, the central benzene ring makes dihedral angles of 3.25 (7) and 41.32 (8)°, respectively, with the thiazole and phenyl rings. In the crystal, O—H⋯N hydrogen bonds link the molecules into a chain along the c axis. A weak C—H⋯O interaction further connects the chains into a layer parallel to the ac plane.

In the title compound, C 16 H 13 NOS, the central benzene ring makes dihedral angles of 3.25 (7) and 41.32 (8) , respectively, with the thiazole and phenyl rings. In the crystal, O-HÁ Á ÁN hydrogen bonds link the molecules into a chain along the c axis. A weak C-HÁ Á ÁO interaction further connects the chains into a layer parallel to the ac plane.

Experimental
MK thanks UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

Experimental
The title compound was prepared by the following procedure (Miyaura et al., 1979;Finholt et al., 1947). A mixture of 2bromo-thiazole-4-carboxylic acid ethyl ester (1 g, 4.24 mmol), biphenyl boronic acid (1 g, 5.08 mmol), Xantphos (122.54 mg,0.212 mmol), tripotassium phosphate (2.6 g, 12.71 mmol) and palladium acetate (47.55 mg, 0.212 mmol) in THF as solvent was degassed for 15 mins and sealed. The sealed tube was heated at 383 K for 16 h under N 2 atmosphere. After completion, the reaction mixture was diluted with ethyl acetate and filtered through a celite bed. It was then quenched with water and extracted with ethyl acetate. Organic layers were collected, dried over sodium sulphate and concentrated.
Crude mass was purified through silica gel column chromatography (60:120 mesh) using 30% ethyl acetate in petroleum ether to afford 2-biphenyl-4-yl-thiazole-4-carboxylic acid ethyl ester (80% yield). Lithium aluminium hydride (122 mg, 3.23 mmol) was dissolved in minimum amount of THF in a RB flask and cooled to 0 °C under N 2 atmosphere (Fig. 3). To this was added drop-wise a solution of 2-biphenyl-4-yl-thiazole-4-carboxylic acid ethyl ester (1 g, 3.23 mmol) in THF and stirred the reaction mixture for an hour. After completion of reaction, the reaction mixture was quenched with 10% sodium carbonate solution at 273 K and extracted with ethyl acetate. Organic layers were collected, dried over sodium sulphate and concentrated. Crude mass was purified through silica gel column chromatography (60:120 mesh) using 40% ethyl acetate in petroleum ether to afford the title compound (93% yield). X-ray quality crystals were obtained by slow

Refinement
All of the H atoms were placed in their calculated positions and then refined using the riding model with O-H = 0.82 Å and C-H = 0.93 Å (CH) or 0.97 Å (CH 2 ). The U iso (H) values were set to 1.5U eq (O) and 1.2U eq (C).

Figure 1
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.   Experimental preparation summary of the title compound, C 16 H 13 NOS. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.30 e Å −3 Δρ min = −0.27 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0044 (7) Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.