Crystal structure of 2,2′′-bis(2,7-dichloro-9-hydroxy-9H-fluoren-9-yl)-1,1′:4′,1′′-terphenyl triethylamine trisolvate

Abstract

In the title solvate, C44H26Cl4O2·3C6H15N, the asymmetric part of the unit cell comprises two halves of the diol molecules, 2,2′′-bis(2,7-dichloro-9-hydroxy-9H-fluoren-9-yl)-1,1′:4′,1′′-terphenyl, and three molecules of triethylamine,i. e. the diol molecules are located on crystallographic symmetry centres. Two of the solvent molecules are disordered over two positions [occupancy ratios of 0.567 (3):0.433 (3) and 0.503 (3):0.497 (3)]. In the diol molecules, the outer rings of the 1,1′:4′,1′′-terphenyl elements are twisted with reference to their central arene ring and the mean planes of the fluorenyl moieties are inclined with respect to the terphenyl ring to which they are connected, the latter making dihedral angles of 82.05 (8) and 82.28 (8)°. The presence of two 9-fluoren-9-ol units attached at positions 2 and 2′′ of the terphenyl moiety induces a `folded' geometry which is stabilized by intramolecular C—H...O hydrogen bonds and π–π stacking interactions, the latter formed between the fluorenyl units and the central ring of the terphenyl unit [centroid–centroid distances = 3.559 (1) and 3.562 (1) Å]. The crystal is composed of 1:2 complex units, in which the solvent molecules are associated with the diol moleculesviaO—H...N hydrogen bonds, while the remaining solvent molecule is linked to the host by a C—H...N hydrogen bond. The given pattern of intermolecular interactions results in formation of chain structures extending along [010].