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DOI: 10.1039/A700494J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 2099-2104

Edge-to-edge aryl C–H · · · N dimer: a new supramolecular synthon

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Christopher E. Marjo, Marcia L. Scudder, Donald C. Craig and Roger Bishop

Abstract

Study of the lattice packing in the crystal structures of the diquinoline compounds 1 [C23H18N2, P[1 with combining macron], a = 6.1953(8), b = 11.427(2), c = 12.686(2) Å, α = 108.428(7), β = 92.189(8), γ = 103.437(7)°, Z = 2, R = 0.038] and 2·CHCl3 [C23H16Br2N2·CHCl3, P21/c, a = 9.865(3), b = 15.307(3), c = 17.946(5) Å, β = 122.12(1)°, Z = 4, R = 0.031] reveals a previously unrecognised mode of intermolecular attraction which we term the edge-to-edge aryl C–H · · · N dimer. Examination of the Cambridge Structural Database shows that this type of contact is present in a wide range of nitrogen-containing aromatic solids. In all 54 identified cases the two weak intermolecular hydrogen bonds are identical producing a symmetrical dimer and, in all cases but one, the arrangement created is centrosymmetric. Hence this new packing mode represents a predictable new synthon for supramolecular assembly.

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