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

Özden Özel Güven; Gökhan Türk; Philip D F Adler; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536814004887

. 2014 Mar 8;70(Pt 4):o410. doi: 10.1107/S1600536814004887

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

Özden Özel Güven ^a, Gökhan Türk ^a, Philip D F Adler ^b, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC3998539 PMID: 24826125

Abstract

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.

Related literature

For clinical uses of azole antifungals possessing an imidazole ring such as micozanole and econazole, see: Godefroi et al. (1969 ▶). Some indazole derivatives have been known as antifungal also, see: Lebouvier et al. (2007 ▶); Park et al. (2007 ▶). For related structures, see: Freer et al. (1986 ▶); Özel Güven et al. (2008 ▶, 2010 ▶, 2013 ▶); Peeters et al. (1979 ▶).

Experimental

Crystal data

C₂₂H₁₈Cl₂N₂O
M _r = 397.28
Monoclinic,
a = 15.2399 (4) Å
b = 5.3814 (3) Å
c = 23.0461 (6) Å
β = 90.871 (3)°
V = 1889.84 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 294 K
0.35 × 0.20 × 0.15 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T _min = 0.918, T _max = 0.948
18118 measured reflections
4737 independent reflections
3685 reflections with I > 2σ(I)
R _int = 0.038
3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.109
S = 1.08
4737 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004887/xu5774sup1.cif

e-70-0o410-sup1.cif^{(27.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004887/xu5774Isup2.hkl

e-70-0o410-Isup2.hkl^{(227.4KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814004887/xu5774Isup3.cml

CCDC reference: 989513

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg3ⁱ	0.93	2.91	3.591 (2)	131
C11—H11⋯Cg2ⁱ	0.93	2.87	3.616 (2)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2012-10-03-12).

supplementary crystallographic information

1. 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 molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The indazole [B (N1/N2/(C9—C15)] ring system is approximately planar with a maximum deviation of -0.031 (2)Å (for atom C12). Its mean plane is oriented with respect to the phenyl [A (C2—C7)] and benzene [ C (C17—C22)] rings at dihedral angles of A/B = 3.17 (4) and B/C = 19.34 (4) °. The dihedral angle between phenyl and benzene rings is A/C = 17.20 (5)°. Atom C8 is 0.016 (2) Å away from the indazole ring plane, while atoms C1 and O1 are -0.026 (2) and 0.599 (1) Å away from the phenyl ring plane. On the other hand, atoms Cl1, Cl2 and C16 are at distances of -0.0258 (5), -0.0693 (5) and -0.074 (2) Å to the benzene ring plane.

In the crystal structure, weak C—H···π interactions (Table 1) may be effective in the stabilization of the structure.

2. 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%).