Packing effects in 4,4′-bis(4-hydroxybutyl)-2,2′-bipyridine and 4,4′-bis(4-bromobutyl)-2,2′-bipyridine

Abstract

Structure analyses of 4,4'-bis(4-hydroxybutyl)-2,2'-bipyridine, C18H24N2O2, (I), and 4,4'-bis(4-bromobutyl)-2,2'-bipyridine, C18H22Br2N2, (II), reveal intermolecular hydrogen bonding in both compounds. For (I), O-H...N intermolecular hydrogen bonding leads to the formation of an infinite two-dimensional polymer, and pi stacking interactions are also observed. For (II), C-H...N intermolecular hydrogen bonding leads to the formation of a zigzag polymer. The two compounds crystallize in different crystal systems, but both molecules possess Ci symmetry, with one half molecule in the asymmetric unit.

4,4′-Bis(2,2,2-trifluoroethoxymethyl)-2,2′-bipyridine

“…Compound (I) exhibits a crystallographic inversion centre at the mid-point of the pyridine C ipso -C ipso bond and crystallizes in the space group P2 1 /n. Many free bpy ligands described in the literature [Cambridge Structural Database (CSD; Allen, 2002) refcodes EDOXAW and EDOXEA (Maury et al, 2001), FOBRUK and FOBSAR (Iyer et al, 2005), KIDNAP (Vogtle et al, 1990), MILZUC (Heirtzler et al, 2002), NAMKAN02 (Zhang et al, 2003), NOFZUD (Sengü l et al, 1998), UHIBAO (Viau et al, 2003), VEXQAQ (Spek et al, 2000), VEXQAQ01 (Rice et al, 2002) and VOLLAJ (Butler & Soucy-Breau, 1991)] also possess a crystallographic centre of inversion, two distinctive consequences of which are the planarity of the connected pyridyl units and their anti arrangement (Alboré s et al, 2004;Iyer et al, 2005). The planar bpy C 10 N 2 group in (I) has a weak N1Á Á ÁH3 i -C3 i interaction [symmetry code: (i) Àx + 1, Ày + 1, Àz + 1], suggested by the NÁ Á ÁH distance of 2.49 Å , although the angle organic compounds Acta Cryst.…”

5,5′-Bis[(2,2,2-trifluoroethoxy)methyl]-2,2′-bipyridine

“…For related structures and background to the anti-planar geometry of bpy, see: Lu, Tu, Wu et al (2010); Iyer et al (2005); Heirtzler et al (2002); Maury et al (2001); Vogtle et al (1990). For background to the bipyridine (bpy) ligand, see: Bain et al (1989); Chambron & Sauvage (1986, 1987; Grä tzel (2001); Haga et al (2000); Lu, Tu, Hou et al (2010); ; Lu et al (2007).…”