Received 1 October 2013
In the asymmetric unit of the title salt, C14H18N2O2+·2CF3O3S-, the components are linked by two N-HO and one C-HO hydrogen bonds. The dipyridinium salt demonstrates a skew conformation based upon C-O-C-C torsion angles of 61.5 (3) and 15.1 (4)°. A C-O-C angle of 119.3 (2)° and C-O bond distances of 1.364 (3) and 1.389 (3) Å are consistent with other dipyridyl ethers. The planes of the pyridyl rings exhibit a twist angle of 67.89 (8)°. One of the trifluoromethanesulfonate ions shows disorder of the F atoms [in a 0.52 (7):0.48 (7) occupancy ratio] and an O atom [0.64 (8):0.36 (8) occupancy ratio]. In the crystal, the components are linked by C-HO interactions, which form chains along .
For the structure of the unsubstituted 4,4'-oxybisdipyridine, see: Dunne et al. (1996). For the structure of bis[4'-(2,2':6',2''-terpyridinyl)]ether, see: Constable et al. (1995). For the stuctures of the neutral ether 9,9'-oxybisacridine and its dication, see: Maas (1985). For a description of conformations in bridged diphenyls, see: van der Heijden et al. (1975).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: FF2121 ).
AWS thanks the Jean Dreyfus Boissevain Lectureship for Undergraduate Institutions, the UMass Dartmouth Office of Undergraduate Research Award, the Urban Massachusetts Louis Stokes Alliance for Minority Participation (UMLSAMP), the UMass Dartmouth Honors Program and the Northeast Section of the American Chemical Society Norris/Richards Summer Research Scholarship for funding. DRM gratefully acknowledges support from the UMass Dartmouth Chancellor's Research Fund, the Joseph P. Healey Endowment and the National Science Foundation (CHE-1229339).
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