Crystal structure of 4-(anthracen-9-yl)pyridine

Acta Crystallogr E Crystallogr Commun. 2021 May 11;77(Pt 6):605-608. doi: 10.1107/S2056989021004710. eCollection 2021 Jun 1.

Abstract

The title compound, C19H13N, which crystallizes in the monoclinic C2/c space group with one half-mol-ecule in the asymmetric unit, was synthesized by Suzuki-Miyaura cross-coupling reaction of 9-bromo-anthracene with pyridin-4-ylboronic acid and purified by column chromatography on silica gel. Light-yellow crystals of 4-(anthracen-9-yl)-pyridine suitable for X-ray diffraction were collected by the solvent evaporation method. In the crystal, pairs of mol-ecules are connected by inter-molecular C-H⋯π (pyridine) inter-actions [d(H7⋯Cg) = 2.7391 (2) Å], forming cyclic centrosymmetric dimers, further resulting in an infinite one-dimensional linear chain along the c-axis direction. Weak face-to-face π-π stacking inter-actions [d(CgCg) = 3.6061 (2) Å] link neighboring lamellar networks into the supra-molecular structure.

Keywords: C—H⋯π inter­actions; anthracene; crystal structure; π–π stacking inter­actions.

Grants and funding

This work was funded by National Natural Science Foundation of China, Incubation Program of the Second Hospital of Anhui Medical University grant 2020GQFY04. Anhui Medical University Research Fund grant 2020xkj024.