{2-[(9,9-Dihexylfluoren-2-yl)carbonyl]phenyl}(4-methoxyphenyl)methanone

In the title compound, C40H44O3, the fluorene ring system is essentially planar, with a maximum deviation of 0.075 (3) Å, and forms dihedral angles of 70.62 (8) and 70.31 (8)° with the mean planes of the central benzene ring and the methoxyphenyl ring, respectively. Both the hexyl side chains have different conformations, i.e. an anti–gauche–anti–gauche conformation with C—C—C—C torsion angles of −169.3 (2), 74.2 (4), −178.0 (3) and −76.0 (6)° for one hexyl side chain and an anti–anti–anti–gauche conformation with C—C—C—C torsion angles of −177.9 (2), −176.5 (3), 171.7 (4) and 80.4 (9)° for the other. Four C atoms in one and two C atoms in the other hexyl side chains are each disordered over two sets of sites, with occupancy factors of 0.761 (3):0.239 (3) and 0.660 (6):0.340 (6). In the crystal, molecules are via pairs of C—H⋯O hydrogen bonds, forming inversion dimers and resulting in R 2 2(28) graph-set motifs.


Experimental
In the crystal packing, molecules are linked into centrosymmetric dimers via C26-H26···O2 i hydrogen bonds, resulting in R 2 2 (28) graph-set motifs (Bernstein et al., 1995) (Table 1 and Fig. 2). The bond lengths and bond angles in the title compound agree with the corresponding bond lengths and angles reported for closely related compounds (Narayanan et al., 2011);Schollmeyer & Detert, 2011).

Experimental
To a solution of benzo[c]furan (0.50 g, 0.898 mmol) in dichloromethane (15 ml), meta-chloroperoxybenzoic acid (m-CPBA) (0.23 g, 1.347 mmol) was added and the reaction mixture was stirred at room temperature for 5 minutes. It was then poured into saturated sodium bicarbonate solution, extracted with dichloromethane (3x30 ml). The combined organic extract was washed with water (2x30 ml) and dried (Na 2 SO 4 ). Removal of solvent followed by column chromatographic purification (silica gel, 5% ethyl acetate/hexane) afforded the diketone as a pale yellow solid (yield = 0.46 g, 81%). The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected
The H atoms were placed at calculated positions in the riding model approximation with C-H = 0.93, 0.96 and 0.97 Å for aryl, methyl and methylene H-atoms, respectively, with U iso (H) = 1.5U eq (methyl C) and 1.2U eq (non-methyl C). The rotation angles for methyl groups were optimized by least squares.

Figure 1
The molecular structure of the title compound showing only the atoms representing major fractions of the disordered dihexyl side chains, with the atom numbering scheme. The displacement ellipsoids are drawn at 30% probability level.  The crystal packing of the title compound, viewed down the a-axis, showing the centrosymmetric dimer via C-H···O hydrogen bonds. The dihexyl side chains and H atoms not involved in hydrogen bonding have been excluded for clarity.

{2-[(9,9-Dihexylfluoren-2-yl)carbonyl]phenyl}(4-methoxyphenyl)methanone
Crystal data   196.7, 195.4, 163.6, 152.1, 150.8, 146.0, 140.0, 139.8, 135.8, 132.3, 130.3, 129.8, 129.7, 129.2, 128.4, 127.0, 124.0, 123.1, 120.7, 119.2, 113.6, 55.4, 55.2, 40.1, 31.5, 29.7, 23.7, 22.6, 14.0. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.