Crystal structure of 3,5-bis(imidazole-1-yl)pyridine, C11H9N5

Abstract

Source of material 3,5-Bis(imidazole-1-yl)pyridine (BIP) has been prepared by a procedure reported in the literature [4]. Single crystals suitable for X-ray diffraction were obtained by crystallization of the title compound from CH 2 Cl 2 . DiscussionOrganic ligands based on the rigid pyridine and imidazole rings are excellent candidates for the construction of supramolecular architectures, metal-organic frameworks and cocrystals and exhibit diverse coordination modes and desired properties [1][2][3]. Among them, the newly developed 3,5-bis(imidazole-1-yl)-pyridine (BIP), has been used as a multidentate coordinated ligand to prepare coordination compounds [4][5][6][7][8]. For example, Luo [4] reported six coordination polymers containing BIP molecules, and discussed the influences of the coordination modes, metal ions and counter anions on the crystal structures of these complexes. A view on the title molecular structure and the atom numbering is given in the figure. The asymmetric unit contains one molecule of the title compound, which is constructed by one pyridine and two imidazole moieties. All three rings of BIP are exactly not planar, and the angles between the pyridine and imidazole ring planes are 38.30°and 14.12°, respectively, which are larger than those for 2,6-bis(imidazole-1-yl)pyridine [9]. Additionally, the two imidazole rings of BIP are not equivalent expressed by the different bond lengths and angles. The crystal structure of the title compound is stabilized by two weak intermolecular C-H×××N hydrogen bonds, forming a one-dimensional chain along the a axis. Also, adjacent molecules are connected by the weak p×××p interactionst. The centroid-centroid separation between two neighboring pyridine rings is 3.783(4) Å.