2-[(1H-Imidazol-1-yl)meth­yl]-1-[4-(trifluoro­meth­yl)phen­yl]-1H-indole

Rui Wang; Hong-fan Shi; Lin Du; Jing-feng Zhao; Jian-ping Liu

doi:10.1107/S1600536812010471

. 2012 Mar 17;68(Pt 4):o1081. doi: 10.1107/S1600536812010471

2-[(1H-Imidazol-1-yl)methyl]-1-[4-(trifluoromethyl)phenyl]-1H-indole

Rui Wang ^a, Hong-fan Shi ^a, Lin Du ^a, Jing-feng Zhao ^a, Jian-ping Liu ^a,^*

PMCID: PMC3344036 PMID: 22589945

Abstract

In the title compound, C₁₉H₁₄F₃N₃, the dihedral angles between the mean planes of the indole ring and the 4-CF₃-phenyl and imidazole rings are 54.95 (4) and 61.36 (7)°, respectively.

Related literature

For background to indole derivatives and their biological activity, see: Muftuoglua & Mustatab (2010 ▶); Jiao et al. (2010 ▶). For related structures, see: Borgne et al. (1999 ▶); Lézé et al. (2006 ▶); Marchand et al. (2003 ▶).

Experimental

Crystal data

C₁₉H₁₄F₃N₃
M _r = 341.33
Orthorhombic,
a = 10.3732 (17) Å
b = 7.9960 (13) Å
c = 37.665 (6) Å
V = 3124.0 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.53 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.943, T _max = 0.994
30000 measured reflections
4505 independent reflections
3217 reflections with I > 2σ(I)
R _int = 0.093

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.214
S = 0.99
4505 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010471/jj2125sup1.cif

e-68-o1081-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010471/jj2125Isup2.hkl

e-68-o1081-Isup2.hkl^{(220.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010471/jj2125Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation of P. R. China (20562012).

supplementary crystallographic information

Comment

Iodole derivatives are an important class of heterocycles in medicinal chemistry (Borgne et al., 1999; Marchand et al., 2003; Lézé et al., 2006; Jiao et al., 2010; Muftuoglua & Mustatab, 2010). In continuation of our studies on N-aromatization in the indole ring, we present here the the crystal structure of the title compound, C₁₉H₁₄F₃N₃, (I). With one molecule in the asymmetric unit, the dihedral angles between the mean planes of the indole ring and the 4-CF₃-phenyl and imidazole rings are 54.95 (4)° and 61.36 (7)°, respectively (Fig. 1). Bond lengths and angles are in normal ranges.

Experimental

The title compound, C₁₉H₁₄F₃N₃, was prepared in one step. (1-(4-(trifluoromethyl)phenyl)-1H-indol-2-yl)methanol (50 mg, 0.17 mmol) and N,N'-carbonyldiimidazole (83 mg, 3 equiv) in dry CH₃CN was stirred for 48 h at room temperature. The solvent was evaporated and the residue purified on silica gel to give the title compound,(I). Yield: 53% (33 mg). Recrystallization from absolute ethyl acetate gave colorless and clear single crystals for X-ray diffraction measurement.