2-(9,9-Diethyl-9H-fluoren-2-yl)-1-benzofuran

In the title compound, C25H22O, the dihedral angle between the benzofuran and fluorene ring systems is 9.06 (6)°, and that between the two benzene rings of the fluorene system is 1.78 (12)°. Weak intermolecular C—H⋯π interactions help to stabilize the crystal structure.

In the title compound, C 25 H 22 O, the dihedral angle between the benzofuran and fluorene ring systems is 9.06 (6) , and that between the two benzene rings of the fluorene system is 1. 78 (12) . Weak intermolecular C-HÁ Á Á interactions help to stabilize the crystal structure.

Related literature
The title compound is a precursor for the production of holetransporting and/or emitting materials, see: Shen et al. (2005). For a related structure, see: Bak et al. (1961). Mo K radiation = 0.07 mm À1 T = 100 K 0.2 Â 0.14 Â 0.08 mm

Comment
The title compound, (I), has been shown to be an precursor for the production of hole transporting and/or emitting materials (Shen et al., 2005). A one pot synthesis of a benzofuran substituted in the 2-position has been achieved by Pd(0) complex catalyzed Sonogashira coupling reaction of 2-iodophenol with terminal alkynes, followed by cyclization of the internal alkynes formed, in high yield (see scheme 1). The molecular structure is shown in Fig. 1. The dihedral angle between the benzofuran and fluorene rings is 9.06 (6)°, and that between the two benzene rings at fluorene is 1.78 (12)°. Weak intermolecular C-H···π interactions help to stabilize the crystal structure.
After drying over anhydrous MgSO 4 and removing the volatiles, the residue was purified by column chromatography using CH 2 Cl 2 /n-hexane as eluent, followed by recrystallization from CH 2 Cl 2 and hexane to yield 0.9 g (59%) of (I) as a white solid. Crystals suitable for X-ray diffraction were grown from a CH 2 Cl 2 solution layered with hexane at room temperature.

Refinement
H atoms were located geometrically and treated as riding atoms, with C-H = 0.93 Å, and with U iso (H) = 1.2U eq (C). In the absence of significant anomalous scattering effects Friedel pairs have been merged. Fig. 1. A molecular structure of (I) with 30% probability displacement ellipsoids, showing the atom-numbering scheme employed. H atoms are shown as small spheres of the arbitrary radii.