3-(9H-Fluoren-9-yl)-3-(4-methyl­phen­yl)-1-phenyl­propan-1-one

Wei-Bing Hu; Zhi-Cai Cui; Xin-Ping Liu; Fu Feng

doi:10.1107/S1600536812036847

. 2012 Aug 31;68(Pt 9):o2820. doi: 10.1107/S1600536812036847

3-(9H-Fluoren-9-yl)-3-(4-methylphenyl)-1-phenylpropan-1-one

Wei-Bing Hu ^a,^*, Zhi-Cai Cui ^a, Xin-Ping Liu ^a, Fu Feng ^a

PMCID: PMC3435844 PMID: 22969690

Abstract

In the title compound, C₂₉H₂₄O, the phenyl and methylphenyl rings are approximately perpendicular to each other, making a dihedral angle of 87.67 (10)°, and are oriented at dihedral angles of 62.49 (9) and 84.77 (7)°, respectively, to the nearly planar fluorene ring system [maximum deviation = 0.077 (2) Å] In the crystal, weak C—H⋯π interactions are observed.

Related literature

For the background to fluorene and its derivatives, see: Kreyenschmidt et al. (1998 ▶).

Experimental

Crystal data

C₂₉H₂₄O
M _r = 388.48
Triclinic,
a = 9.7188 (16) Å
b = 10.8189 (18) Å
c = 11.5132 (19) Å
α = 75.500 (3)°
β = 68.681 (3)°
γ = 84.315 (3)°
V = 1091.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.26 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
11991 measured reflections
4508 independent reflections
3125 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.138
S = 1.07
4508 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036847/xu5614sup1.cif

e-68-o2820-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036847/xu5614Isup2.hkl

e-68-o2820-Isup2.hkl^{(220.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036847/xu5614Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯Cg ⁱ	0.93	2.76	3.617 (2)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the Project of Hubei Provincial Department of Education, China (No. D20122903).

supplementary crystallographic information

Comment

Since the publication of its solid-state structure of fluorene and its derivatives are very useful compounds due to their good optical property and high luminescent efficiencies, and have received a lot of attentiont (Kreyenschmidt et al., 1998). To our knowledge, a great number of studies have appeared on fluorene and its derivatives. The title compound (I) is an example of this class.

In the title compound, the phenyl ring and methylphenyl ring are approximately perpendicular to each other with a dihedral angle of 87.67 (10)°, and they are oriented with respect to the nearly planar fluorene ring systems [the maximum deviation being 0.077 (2) Å] at 62.49 (9) and 84.77 (7)°, respectively. In the crystal, weak intermolecular C—H···π interaction is observed (Table 1).

Experimental

Fluorene (2 mmo1), chalcone (2 mmo1) and NaOH (4 mmo1) were mixed in mortar, and the mixture was ground at room temperature for 30 min. Then, the mixture was washed in sequence with 15 ml aqueous solution of HCl (3%) and alcohol (95%), and the crude product was isolated by filtration. The filtrate was purified by recrystallization from anhydrous ethanol to give compound I as colourless crystals in 73% yield. Suitable crystals for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature (m.p. 445–447 K); IR (KBr, ν cm^-1): 3055, 3010, 2915, 1680, 1596, 1445, 1316, 1238, 813, 685; ¹H NMR (DMSO-d₆, δ): 6.83–8.07 (m, 17H); 3.97 (d, 1H, J = 4.2 Hz), 3.57 (m, 1H), 3.41 (d, 2H, J = 7.0 Hz), 2.19 (s, 3H); Elemental analysis calculated for C₂₉H₂₄O: C 86.69, H6.19%; found: C 86.81, H 6.12%.