Abstract
The title compound, C19H12ClN, was synthesizedviareaction of 9-fluorenone and 4-chloroaniline usingp-toluenesulfonic acid in toluene. The dihedral angle between the fluorene moiety (r.m.s. deviation = 0.027 Å) and the chlorophenyl ring is 64.59 (6)° and a possible weak intramolecular C—H...π interaction occurs.
Highlights
Acid-catalyzed imine formation reactions between 9-fluorenone and anilines are easy, high-yield projects for undergraduate research
Fluoren-9-imines are of interest because of their interesting fluorescence (Dufresne et al, 2011) and use as potential organics in materials with tunable HLG (HOMO–LUMO gap) systems (Eakins et al, 2013)
As part of our studies in this area, we describe the synthesis and structure of the title compound
Summary
Acid-catalyzed imine formation reactions between 9-fluorenone and anilines are easy, high-yield projects for undergraduate research. Fluoren-9-imines are of interest because of their interesting fluorescence (Dufresne et al, 2011) and use as potential organics in materials with tunable HLG (HOMO–LUMO gap) systems (Eakins et al, 2013). The crystal structure of N-phenyl-9H-fluoren-9-imine, the stripped-down combination between 9-fluorenone and aniline, has been published three times. Unsolvated monoclinic and orthorhombic forms were published by Eakins et al (2013) and Dufresne et al (2011), respectively. The crystal structure of N-mesityl-9H-fluoren-9-imine was communicated privately to the CSD in 2016 (Evans et al 2016). In the title molecule (Fig. 1), all bond lengths and angles are within expected values: the dihedral angle between the fluorene ring system and the chlorophenyl ring is 64.59 (6).
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