Ethyl 4-({1-[2-(4-bromophenyl)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methoxy)-8-(trifluoromethyl)quinoline-3-carboxylate

The title compound, C24H18BrF3N4O4, is a 1,2,3-triazole derivative featuring, among others, a quinoline-derived substituent. In the crystal, C—H⋯O, C—H⋯N and C—H⋯F contacts connect the molecules into a three-dimensional network. The shortest centroid–centroid distance between two aromatic systems is 3.896 (2) Å and is found between the two different six-membered rings of the quinoline scaffold in neighbouring molecules.

its derivatives are well known nitrogen-containing heterocyclic compounds and play an important role in medicinal and pesticide chemistry by exhibiting a wide range of activities such as antibacterial, antifungal, antibiotic, anticancer, anticonvulsant, anti-tuberculosis and anti-inflammatory properties (Chen et al., 2004;Kaur et al., 2010;Bekhit et al. 2004). Keeping in mind the biological importance of quinoline-derived compounds, the title compound was synthesized to study its crystal structure.
The least-squares plane defined by the non-hydrogen atoms of the 1,2,3-triazole core encloses angles of 27.2 (2) ° and 48.4 (2) ° with the least-squares planes defined by the intracyclic atoms of the quinoline scaffold as well as the phenyl group, respectively. The latter two mentioned planes intersect at an angle of 41.5 (1) °. The quinoline scaffold is almost planar (r.m.s. of all fitted non-hydrogen atoms = 0.0176 Å) with C35 deviating most from this common plane by 0.028 (3) Å (Fig. 1).
In the crystal, intermolecular C-H···O, C-H···F and C-H···N contacts can be detected whose range falls by at least 0.1 Å below the sum of van-der-Waals radii of the atoms participating in them. The C-H···N contacts -whose angles fall markedly below a linear arrangement for the donor atom, hydrogen atom as well as the acceptor atom -likely are to be seen as a result of the more pronounced C-H···O contacts described below (see below). They are supported by one of the hydrogen atoms on one of the methylene groups directly bonded to the 1,2,3-triazole core as well as the latter one's intracyclic CH group and have the two two-coordinate nitrogen atoms as acceptors. These contacts form two homodromic chains connecting the molecules to chains along the crystallographic a axis. Along these chains, one set of C-H···O contacts between the second methylene group bonded to the 1,2,3-triazole core as well as the double bonded oxygen atom of the ester group can be found. The second set of C-H···O contacts is apparent between one of the hydrogen atoms on the bromophenyl group in ortho position to the keto group as donor and the keto group in a neighbouring molecule as acceptor. The intermolecular C-H···F contact is supported by the second hydrogen atom of the methylene group that is already part of the C-H···N contact system. In addition, an intramolecular C-H···F contact can be hold responsible for the small F-C-C-C H dihedral angle that was measured at 0.6 (4) ° only. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In total, these contacts connect the molecules to a three-dimensional network. According to a graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for the C-H···N contacts is C 1 1 (4)C 1 1 (4) on the unary level while the C-H···O contacts require a C 1 1 (7)R 2 2 (10) descriptor on the same level. The descriptor for the C-H···F contacts is S(5)C 1 1 (13). The shortest intercentroid distance between two aromatic systems was measured at 3.896 (2) Å and is found between the two different sup-2 Acta Cryst. (2012). E68, o3387-o3388 six-membered rings of the quinoline scaffold in neighbouring molecules.
The packing of the title compound in the crystal structure is shown in Figure 3.

Refinement
Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic carbon atoms and C-H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2U eq (C).
The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C-C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite (Sheldrick, 2008)), with U iso (H) set to 1.5U eq (C).