1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-phenyl-1H-1,2,3-triazole

In the title compound, C15H9ClF3N3, the phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the molecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.

In the title compound, C 15 H 9 ClF 3 N 3 , the phenyl and chlorotrifluoromethyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11) , respectively. In the crystal, the molecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å .

Comment
The structure of the title compound, (I), was determined as part of an ongoing project developing N-aryl-1,2,3-triazoles as amide mimetics for medicinal applications. The synthesis of 1,2,3-triazoles via copper mediated 1,3-dipolar reactions has become one of the most widely used methodologies to tether molecules together or to a surface (Bock et al., 2006;Irie et al., 2012). Electronically deactivated N-phenyl-1,2,3-triazoles have been employed in several areas such as the combinatorial development of kinase inhibitors (Jia & Zhu, 2010) in the development of monoamine oxidase inhibitors, androgen receptor antagonists (Henderson et al., 2012) and as GABA receptor antagonists (Alam et al., 2006;Alam et al., 2007). This compound provides an aryl chloride moiety in the para-position relative to the triazole ring providing a synthetic handle for further structural elaboration.
In the molecular structure of (I) (Fig. 1) the planar phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the central planar triazole group with dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the triazole ring, the N1-N2 and N2-N3 bond lengths are 1.357 (3) and 1.310 (3) Å, respectively. and are similar to those reported for related compounds (Lin et al., 2008;Lin, 2010). In the crystal lattice, the molecules stack in a head to tail arrangement along the a axis ( Fig. 2) with the centroid-centroid distances between the triazole rings 4.1494 (12) and 3.7372 (12) Å.

Refinement
The carbon-bound H atoms were constrained as riding with C-H = 0.95 Å, and with U iso (H) = 1.2U eq of the parent C atom.

Figure 1
The molecular structure of the title compound with atom labelling and displacement ellipsoids for non-H atoms drawn at the 40% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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.