2-(2H-Benzotriazol-2-yl)-6-[(diethylamino)methyl]-4-methylphenol

In the title compound, C18H22N4O, the dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phenoxy group is 6.4 (2)°. There is an intramolecular O—H⋯N hydrogen bond between the phenol and benzotriazol groups.

In the title compound, C 18 H 22 N 4 O, the dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phenoxy group is 6.4 (2) . There is an intramolecular O-HÁ Á ÁN hydrogen bond between the phenol and benzotriazol groups.   Table 1 Hydrogen-bond geometry (Å , ). We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC97-2113-M-033-005-MY2) and in part from the project of specific research fields in Chung Yuan Christian University, Taiwan (No. CYCU-98-CR-CH). yl)-phenolate (BTP) ligand (Li et al., 2009;Tsai et al., 2009). Therefore, our group is interested in the synthesis and preparation of amino-phenolate ligand derived from BTP-H. Herein, we report the synthesis and crystal structure of the title compound, (I), a potential ligand for the preparations of aluminium, palladium and zinc complexes (Scheme 1).

Related literature
The molecular structure of I is composed of the benzotriazol-phenolate moiety and the diethylamino functionalized group (Fig. 1). The dihedral angle between the planes of the benzotriazol unit and the phenyl ring of the phenoxy group is 6.4 (2)°.
There is an intramolecular O-H0···N1 hydrogen bond between the phenol and benzotriazol groups (Tab. 1). The distance of N1···H0 is substantially shorter, than the van der Waals distance of 2.75Å for the N and H distance. It is interesting to note that the six-member ring (O/C1/C2/N2/N1/H0) formed from the O-H···N hydrogen-bond is almost coplanar with the mean deviation of 0.016 (2)Å. Beside H-bonded motif, these bond distances of benzotriazol-phenolate group are similar to those found in the crystal structure of 2-(2H-benzotriazol-2-yl)-4-methylphenyl diphenylphosphinate (Liu et al., 2009).
The resulting mixture was heated under reflux for 2 day and then dried under reduced pressure to yield the oil residue. The residue was extracted with ethyl acetate (3 × 150 ml) and the organic layers were dried over MgSO 4 . The final solution was removed the solvent under vacuum to give white solids. Yield: 7.12 g (77%). Colourless crystals were obtained from the saturated hexane solution.

Refinement
The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C-H = 0.93Å with U iso (H) = 1.2 U eq (C) for phenyl hydrogen; 0.96Å with U iso (H) = 1.5 U eq (C) for CH 3 group; 0.97Å with U iso (H) = 1.2    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.