8-(2,2,2-Trifluoroethoxy)quinolinium perchlorate-8-(2,2,2-trifluoroethoxy)quinoline (1/1)

The title compound, C(11)H(9)F(3)NO(+)center dot ClO(4)(-)center dot C(11)H(8)F(3)NO or [(C(11)H(8)F(3)NO)H(C(11)H(8)F(3)NO)]ClO(4), contains two 8-(2,2,2-trifluoroethoxy)quinoline molecules, one of which combines a proton from perchloric acid to form the corresponding quinolinium cation. The quinolinium and quinoline rings form a cationic unit via an intermolecular N-H center dot center dot center dot N hydrogen bond. The heterocyclic units are almost perpendicular to each other [interplanar angle 86.97 (6)degrees]. In the crystal, each perchlorate anion bridges two adjacent cationic units and creates a chain by a combination of C-H center dot center dot center dot O hydrogen bonds. Two inversion-related chains associate into a molecular column by pi-pi stacking interactions between the quinolinium rings. The perpendicular and centroid-centroid distances between adjacent quinolinium rings are 3.501 (3) and 3.634 (9) angstrom, respectively. The molecular column is linked to its neighbors, creating a two-dimensional network via the weak pi-pi stacking between the quinoline rings [perpendicular and centroid-centroid separations 3.340 (4) and 4.408 (4) angstrom, respectively]. Finally, a three-dimensional framework is formed by a combination of intermolecular C-F center dot center dot center dot pi contacts. One -CF(3) group is disordered over two positions of equal occupancy.