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Journal of Structural Chemistry

2009 year, number 4

CONFORMATIONS AND INTERMOLECULAR CONTACTS OF 4- AND 4,4′-SUBSTITUTED BIPHENYL MOLECULES IN CRYSTALS

O. V. Grineva
Keywords: conformations of nonrigid molecules, Cambridge Structural Databank, intermolecular hydrogen bonds, halogenhalogen contacts
Pages: 753-760

Abstract

Based on the data of the Cambridge Structural Databank, we analyzed the conformations of 139 4-X-C6H4-C6H4-4′-Y molecules (X, Y = H, F, Cl, Br, I, CH3, OH, COOH, NH2, NO2, CN) and intermolecular contacts formed by these molecules in 95 homo- and heteromolecular crystals. As would be expected, the percent of planar and almost planar molecules (the angle between the planes of the phenyl fragments (ϕ) is 0-5) in the group was higher (37%) than in biphenyl containing any substituents in the 3,3′,4,4′,5,5′-positions (26%). The percent of almost planar molecules increased considerably when X = OH (48% among molecules having at least one OH group), while equal substituents (X = Y) did not lead to a substantial increase in the relative content of conformers with ϕ in this range. In the given group of crystal structures, the specific intermolecular contacts (hydrogen bonds, HalHal and HalN≡C contacts, etc.) often led to the formation of infinite molecular chains or their fragments (trimers and dimers). The structures containing molecules with an NH2 group typically formed layered (2D) and framework (3D) H associates.