1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole

In the title compound, C17H19N3O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4)° with the mean plane of the benzene ring. The crystal packing is stabilized by π–π stacking interactions, with a centroid–centroid distance of 3.8077 (12) Å, together with weak C—H⋯π interactions. Molecules are stacked along the a axis.

In the title compound, C 17 H 19 N 3 O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å . The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4) with the mean plane of the benzene ring. The crystal packing is stabilized bystacking interactions, with a centroid-centroid distance of 3.8077 (12) Å , together with weak C-HÁ Á Á interactions. Molecules are stacked along the a axis.

Comment
Benzotriazole derivatives show biological activities such as anti-inflammatory, diuretic, antiviral and antihypertensive agents (Katarzyna et al., 2005;Sarala et al., 2007). It is used as a corrosion inhibitor, antifreeze agent, ultraviolet light stabilizer for plastics and as an antifoggant in photography (Krawczyk & Gdaniec, 2005;Smith et al., 2001). N-aryloxy derivatives of benzotriazoles have antimycobacterial activity (Kopec et al., 2008). Benzotriazole possessing three vicinal N atoms, is used as an antifouling and antiwear reagent (Sha et al., 1996). 1-Hydroxybenzotriazole is widely being used as a reagent for peptide synthesis (Anderson et al., 1963). The crystal structure of benzotriazole 1-oxide has been reported (Bosch et al., 1983). Due to the above mentioned applications of benzotriazole we have synthesized and report here the crystal structure of the title compound (I).
The asymmetric unit of (I) comprises of one molecule of the title compound (Fig 1). The bond lengths and angles are found to have normal values (Allen et al., 1987). The benzotriazole ring is essentially planar with the maximum deviation from planarity being 0.0069 (15) Å for atom N2. The mean plane of the benzotriazole ring (N1-N3/C4-C9) forms a dihedral angle of 13.16 (4)° with the mean plane of the phenyl ring (C12-C17).

Experimental
A mixture of 1-(bromomethyl) 2,3,5,6 tetramethyl benzene (0.227 g, 1 mmol) and sSodium salt of 1-hydroxybenzotriazole (0.1571 mmol) in ethanol (10 ml) was heated at 333 K with stirring for 30 min. The compound formed was filtered off, and dried. The compound was dissolved in ethanol and on slow evaporation crystals suitable for x-ray diffraction are formed.

Refinement
All the H atoms were positioned geometrically (C-H = 0.95 Å (aromatic); C-H = 0.98 (methyl) or C-H = 0.99 Å (methylene) and refined using a riding model with, U iso (H) = 1.2U equ (C aromatic, methylene ) and 1.5U equ (C methyl Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.