2-[2-(2,6-Dichlorobenzyloxy)-2-phenylethyl]-2H-indazole

In the title compound, C22H18Cl2N2O, the indazole ring system is approximately planar [maximum deviation = 0.031 (2) Å], its mean plane is oriented at 3.17 (4) and 19.34 (4)° with respect to the phenyl and benzene rings. In the crystal, weak C—H⋯π interactions link the molecules into supramolecular chains running along the b-axis direction.

In the title compound, C 22 H 18 Cl 2 N 2 O, the indazole ring system is approximately planar [maximum deviation = 0.031 (2) Å ], its mean plane is oriented at 3.17 (4) and 19.34 (4) with respect to the phenyl and benzene rings. In the crystal, weak C-HÁ Á Á interactions link the molecules into supramolecular chains running along the b-axis direction.

Experimental
Cg2 and Cg3 are the centroids of the C2-C7 and C10-C15 rings, respectively.

Comment
The azole antifungals possesing an imidazole ring such as miconazole and econazole have been developed for clinical uses (Godefroi et al., 1969). Some indazole derivatives have been known as antifungal also (Lebouvier et al., 2007;Park et al., 2007). The crystal structure of indazole group containing ketone has been reported recently (Özel Güven et al., 2013). The crystal structures of imidazole ring containg ethers like miconazole (Peeters et al., 1979) and econazole (Freer et al., 1986) have been reported before. The crystal structures of benzimidazole ring containing ether (Özel Güven et al., 2008) and 1,2,4-triazole ring containg ether have been reported previously (Özel Güven et al., 2010). Now, we report herein the crystal structure of the title indazole derivative, (I).
In the crystal structure, weak C-H···π interactions (Table 1) may be effective in the stabilization of the structure.

Experimental
The title compound, (I), was synthesized by the reaction of 1-phenyl-2-(2H-indazol-2-yl)ethanol with NaH and appropriate benzyl halide. NaH (0.025 g, 0.63 mmol) was added in small fractions to a solution of alcohol (0.150 g, 0.63 mmol) in DMF (3-4 ml). Then, appropriate benzyl halide (0.151 g, 0.63 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, and the excess hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, small amount of water was added and extracted with methylene chloride.
The organic layer was separated, dried over anhydrous sodium sulfate, and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using hexane-ethyl acetate mixture (10:1) as eluent. The ether was recrystallized from 2-propanol to obtain colourless crystals suitable for X-ray analysis (yield; 0.178 g, 71%).

Refinement
Atom H9 (for C9) was located in a difference Fourier map and was refined freely. The remaining H atoms were positioned geometrically with C-H = 0.93, 0.97 and 0.98 Å for aromatic, methylene and methine H, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2 U eq (C).  The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

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 > 2sigma(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