Crystal structure of 1-(4-fluorophenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole

In the title compound, C15H12FN3O, the triazole ring forms dihedral angles of 30.57 (8) and 21.81 (9)° with the fluoro-substituted and methoxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 51.53 (7)°. In the crystal, π–π interactions between the triazole rings [centroid–centroid seperations = 3.774 (2) and 3.841 (2) Å] form chains along [010].


Related literature
anticancer (Soltis et al., 1996) activities. Furthermore 1,4-disubstituted 1,2,3-triazoles have also been used as a ligation tool for the synthesis of neoglyco-conjugates (Perez-Balderas et al., 2003), multivalent dendrimeric peptides (Wu et al., 2004), ionic receptors (Kumar et al., 2008), triazolophanes (Haridas et al., 2008), cyclic peptides (Turner et al., 2007) and peptidomimetics (Angell et al., 2007). 1,2,3-Triazoles are traditionally obtained using the thermal 1,3-dipolar cycloaddition of organic azides with alkynes (Huisgen et al., 1965) that has been known for nearly five decades. Recently, copper based catalysis was found to dramatically accelerate the reaction under mild conditions while achieving a high regioselectivity towards the 1,4-regioisomer of the triazole product (Wang et al., 2010). This powerful, highly reliable, and selective reaction is the paradigm of a click reaction, which placed it in a class of its own and has enabled many novel applications.
The molecular structure of the title compound is shown in Fig. 1. The triazole ring forms dihedral angles of 30.57 (8)° and 21.81 (9)° with the fluoro-substituted and methoxy-substituted benzen rings, respectively. The dihedral angle between the benzene rings is 51.53 (7)°. All bond lengths and angles are normal and correspond to those observed in the related structures (Zhang et al., 2004;Abdel-Wahab et al., 2012). The C15-F1 bond length [1.357 (4) Å] agrees well with the accepted value of 1.340 Å for the F-C aromatic length and is in good agreement with a structure of this type (Abdel-Wahab et al., 2012). In the crystal, π-π interactions observed between the triazole rings [centroid-centroid seperations = 3.774 (2) and 3.841 (2) Å] form chains along [010] (Fig. 2).

S3. Refinement
All H atoms were geometrically fixed and allowed to ride on their parent C atoms, with C-H distances of 0.93-0.96 Å; and with U iso (H) = 1.2U eq (C), except for the methyl group where U iso (H) = 1.5U eq (C).

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

Figure 2
The packing arrangement of molecules viewed along the a axis.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.