Crystal structure of (Z)-1-(ferrocenylethyn-yl)-10-(phenyl-imino)-anthracen-9(10H)-one from synchrotron X-ray powder diffraction

Eiji Nishibori; Shinobu Aoyagi; Makoto Sakata; Ryota Sakamoto; Hiroshi Nishihara

doi:10.1107/S1600536814025252

Crystal structure of (Z)-1-(ferrocenylethyn-yl)-10-(phenyl-imino)-anthracen-9(10H)-one from synchrotron X-ray powder diffraction

Acta Crystallogr Sect E Struct Rep Online. 2014 Nov 26;70(Pt 12):573-6. doi: 10.1107/S1600536814025252. eCollection 2014 Dec 1.

Authors

Eiji Nishibori¹, Shinobu Aoyagi², Makoto Sakata³, Ryota Sakamoto⁴, Hiroshi Nishihara⁴

Affiliations

¹ Division of Physics, Faculty of Pure and Applied Sciences, Center for Integrated Research in Fundamental Science and Engineering, Tsukuba Research Center for Interdisciplinary Materials Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
² Department of Information and Biological Sciences, Nagoya City University, Nagoya 467-8501, Japan.
³ Japan Synchrotron Radiation Research Institute, SPring-8, 1-1-1, Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan.
⁴ Department of Chemistry, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Abstract

In the title compound, [Fe(C5H5)(C27H16NO)], designed and synthesized to explore a new electron-donor (D) and -acceptor (A) conjugated complex, the two cyclo-penta-dienyl rings adopt an eclipsed conformation. The anthracene tricycle is distorted towards a butterfly conformation and the mean planes of the outer benzene rings are inclined each to other at 22.7 (3)°. In the crystal, mol-ecules are paired into inversion dimers via π-π inter-actions. Weak inter-molecular C-H⋯π inter-actions link further these dimers into one-dimensional columns along the b axis, with the ferrocenylethynyl arms arranged between the stacks to fill the voids.

Keywords: C—H⋯π interactions; D–A conjugated complex; ferrocenyl–anthracen-9(10H)-one; powder diffraction; structure determination; synchrotron radiation; π–π interactions.