1-Bromo-3,5-diphenyl­benzene

Zhi-Qiang Wang; Hong-Mei Li; Xiao-Juan Sun; Fei-Fei Cen; Bao-Ming Ji

doi:10.1107/S1600536809045061

. 2009 Nov 14;65(Pt 12):o3082. doi: 10.1107/S1600536809045061

1-Bromo-3,5-diphenylbenzene

Zhi-Qiang Wang ^a, Hong-Mei Li ^b, Xiao-Juan Sun ^c, Fei-Fei Cen ^a, Bao-Ming Ji ^a,^*

PMCID: PMC2972017 PMID: 21578812

Abstract

The title compound, C₁₈H₁₃Br, crystallizes with two crystallographically independent molecules in the asymmetric unit. The C—Br bond lengths and the C—C bond lengths between the benzene rings are slightly different in the two molecules. The dihedral angles between adjacent benzene rings are 26.85 (2) and 39.99 (2)° in one molecule, and 29.90 (2) and 38.01 (2)° in the other. There are three types of intermolecular C—H⋯π interactions in the crystal structure.

Related literature

For blue light-emitting diodes based on 3,5-diaryl-phenyl derivatives, see: Niu et al. (2004 ▶). For the synthesis of the title compound, see: Kim et al. (2001 ▶). For the importance of C—H⋯π contacts and their geometries, see, for example: Suezawa et al. (2004 ▶). graphic file with name e-65-o3082-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₃Br
M _r = 309.19
Monoclinic,
a = 11.0782 (12) Å
b = 7.7495 (8) Å
c = 16.7782 (17) Å
β = 107.441 (1)°
V = 1374.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.97 mm⁻¹
T = 294 K
0.41 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.375, T _max = 0.776
7808 measured reflections
4775 independent reflections
4138 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.076
S = 1.00
4775 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ▶), 2006 Friedel pairs
Flack parameter: 0.007 (7)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045061/si2218sup1.cif

e-65-o3082-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045061/si2218Isup2.hkl

e-65-o3082-Isup2.hkl^{(233.9KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg1ⁱ	0.93	2.82	3.601 (4)	142
C18—H18⋯Cg6ⁱⁱ	0.93	2.84	3.682 (4)	152
C20—H20⋯Cg1ⁱⁱⁱ	0.93	2.92	3.603 (4)	132

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg6 are the centroids of the C19–C24 and C13–C18 benzene rings, respectively.

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20872057).

supplementary crystallographic information

Comment

3,5-Diphenylbenzene is a good substituent for organic light-emitting materials. The thermal properties, photophysical properties and film formation properties of organic light-emitting materials can be improved efficiently by introducing 3,5-diphenylbenzene group (Niu, et al., 2004). The title compound, 3, 5-Diphenyl-1-bromobenzene, is generally used as the precursor to produce the 3, 5-diphenylbenzene group by Suzuki coupling reaction. The crystal structure of the title compound has not been reported to the best of our knowledge.

A view of the two independent molecules of the title compound shows distinct rotations of phenyl rings (Fig.1). The dihedral angles between adjacent benzene rings are 26.85 (2)° and 39.99 (2)° in one molecule, 29.90 (2)° and 38.01 (2)° in the other molecule. The C—Br bond lengths in the two crystallographically independent molecules are 1.903 (3) Å and 1.911 (3) Å, and the C—C bond lengths between benzene rings are 1.480 (5) Å (C1—C7), 1.486 (4) Å (C11—C13), 1.491 (4) Å (C19—C25), and 1.484 (4) Å (C29—C31), respectively. Three types of weak intermolecular C—H···π interactions exist in the crystal structure (Table 1, Cg1 and Cg6 are the centroids of the benzene rings C19 - C24 and C13 - C18). A detailed discussion for C—H···π interactions and geometries was presented by Suezawa et al. (2004).

Experimental

The title compound was synthesized according to the reported procedure (Kim, et al., 2001). A mixture of phenylboronic acid (0.49 g, 4 mmol), 1,3, 5-tribromobenzene (0.63 g, 2 mmol) and Pd(PPh₃)₄ (20 mg) was added 20 ml tetrahydrofuran and 8 ml aqueous potassium carbonate (2 M). The mixture was vigorously refluxed under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and then extracted by ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After removing the solvent in vacuum, the crude product was purified by column chromatography using petroleum ether as eluent. The title compound was obtained in 54% yield. The single crystals suitable for the X-ray crystallographic analysis were obtained by slow evaporation of a dichloromethane solution as colorless blocks.