1-Bromo-3,5-diphenyl­benzene

Wang, Z.-Q.; Li, H.-M.; Sun, X.-J.; Cen, F.-F.; Ji, B.-M.

doi:10.1107/S1600536809045061

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3082

doi:10.1107/S1600536809045061

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1-Bromo-3,5-diphenylbenzene

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

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, ^bLibrary of Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^cLiming Research Institute of Chemical Industry, Luoyang 471001, People's Republic of China
^*Correspondence e-mail: lyhxxjbm@126.com.cn

(Received 20 October 2009; accepted 28 October 2009; online 14 November 2009)

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 ).

Experimental

Crystal data

C₁₈H₁₃Br
M_r = 309.19
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.030
wR(F²) = 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)

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
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ . Cg1 and Cg6 are the centroids of the C19–C24 and C13–C18 benzene rings, respectively.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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). Cg1 and Cg6 are the centroids of the C19–C24 and C13– C18 benzene rings, respectively.

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The two independent molecules of the title compound with labelled non-hydrogen atoms using 30% probability ellipsoids.

1-Bromo-3,5-diphenylbenzene top

Crystal data top

C₁₈H₁₃Br	F(000) = 624
M_r = 309.19	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.0782 (12) Å	Cell parameters from 3281 reflections
b = 7.7495 (8) Å	θ = 2.7–24.8°
c = 16.7782 (17) Å	µ = 2.97 mm⁻¹
β = 107.441 (1)°	T = 294 K
V = 1374.2 (2) Å³	Block, colourless
Z = 4	0.41 × 0.13 × 0.09 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4775 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.375, T_max = 0.776	k = −9→8
7808 measured reflections	l = −20→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0488P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4775 reflections	Δρ_max = 0.23 e Å⁻³
343 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2006 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.007 (7)

Crystal data top

C₁₈H₁₃Br	V = 1374.2 (2) Å³
M_r = 309.19	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.0782 (12) Å	µ = 2.97 mm⁻¹
b = 7.7495 (8) Å	T = 294 K
c = 16.7782 (17) Å	0.41 × 0.13 × 0.09 mm
β = 107.441 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4775 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4138 reflections with I > 2σ(I)
T_min = 0.375, T_max = 0.776	R_int = 0.014
7808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.23 e Å⁻³
S = 1.00	Δρ_min = −0.31 e Å⁻³
4775 reflections	Absolute structure: Flack (1983), 2006 Friedel pairs
343 parameters	Absolute structure parameter: 0.007 (7)
1 restraint

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.21282 (3)	0.79871 (5)	0.29748 (2)	0.05470 (12)
Br2	−0.04494 (4)	0.42942 (6)	0.31148 (2)	0.06496 (14)
C1	0.4329 (3)	0.2381 (4)	0.3577 (2)	0.0400 (8)
C2	0.4454 (3)	0.1460 (5)	0.4312 (2)	0.0484 (9)
H2	0.3732	0.1084	0.4434	0.058*
C3	0.5632 (4)	0.1100 (5)	0.4859 (2)	0.0594 (11)
H3	0.5697	0.0484	0.5346	0.071*
C4	0.6707 (4)	0.1645 (6)	0.4690 (3)	0.0624 (11)
H4	0.7498	0.1392	0.5060	0.075*
C5	0.6613 (4)	0.2561 (5)	0.3976 (2)	0.0587 (11)
H5	0.7342	0.2928	0.3860	0.070*
C6	0.5430 (3)	0.2944 (6)	0.3424 (2)	0.0498 (8)
H6	0.5375	0.3587	0.2947	0.060*
C7	0.3069 (3)	0.2758 (5)	0.29839 (19)	0.0396 (7)
C8	0.2064 (3)	0.3218 (5)	0.3282 (2)	0.0430 (8)
H8	0.2173	0.3294	0.3852	0.052*
C9	0.0902 (3)	0.3555 (4)	0.2707 (2)	0.0427 (9)
C10	0.0688 (3)	0.3457 (4)	0.1861 (2)	0.0407 (8)
H10	−0.0110	0.3693	0.1496	0.049*
C11	0.1686 (3)	0.2998 (5)	0.15494 (18)	0.0350 (6)
C12	0.2857 (3)	0.2664 (4)	0.21181 (19)	0.0387 (8)
H12	0.3527	0.2366	0.1919	0.046*
C13	0.1478 (3)	0.2884 (5)	0.06339 (18)	0.0354 (7)
C14	0.2206 (3)	0.1799 (4)	0.0303 (2)	0.0389 (7)
H14	0.2843	0.1142	0.0661	0.047*
C15	0.1998 (3)	0.1679 (5)	−0.0555 (2)	0.0443 (8)
H15	0.2501	0.0958	−0.0765	0.053*
C16	0.1048 (3)	0.2626 (5)	−0.1094 (2)	0.0443 (9)
H16	0.0896	0.2526	−0.1668	0.053*
C17	0.0325 (3)	0.3720 (5)	−0.0781 (2)	0.0451 (9)
H17	−0.0309	0.4375	−0.1143	0.054*
C18	0.0537 (3)	0.3850 (4)	0.0076 (2)	0.0420 (8)
H18	0.0041	0.4595	0.0281	0.050*
C19	0.3980 (3)	0.7771 (4)	0.03861 (19)	0.0349 (7)
C20	0.4802 (3)	0.8546 (4)	0.0009 (2)	0.0390 (8)
H20	0.5522	0.9104	0.0338	0.047*
C21	0.4564 (3)	0.8499 (4)	−0.0852 (2)	0.0442 (9)
H21	0.5125	0.9019	−0.1094	0.053*
C22	0.3502 (3)	0.7685 (5)	−0.1344 (2)	0.0452 (8)
H22	0.3344	0.7654	−0.1920	0.054*
C23	0.2669 (3)	0.6914 (4)	−0.0988 (2)	0.0431 (8)
H23	0.1948	0.6369	−0.1324	0.052*
C24	0.2907 (3)	0.6950 (4)	−0.0130 (2)	0.0399 (8)
H24	0.2344	0.6420	0.0107	0.048*
C25	0.4238 (3)	0.7824 (4)	0.13106 (18)	0.0364 (7)
C26	0.3245 (3)	0.7809 (5)	0.16629 (19)	0.0390 (7)
H26	0.2412	0.7743	0.1321	0.047*
C27	0.3501 (3)	0.7894 (5)	0.25135 (19)	0.0408 (7)
C28	0.4727 (3)	0.7964 (5)	0.30482 (18)	0.0427 (7)
H28	0.4875	0.8016	0.3623	0.051*
C29	0.5735 (3)	0.7955 (5)	0.27097 (18)	0.0383 (7)
C30	0.5467 (3)	0.7882 (5)	0.18430 (18)	0.0383 (7)
H30	0.6135	0.7871	0.1614	0.046*
C31	0.7054 (3)	0.8081 (5)	0.32689 (19)	0.0407 (7)
C32	0.7968 (3)	0.9055 (5)	0.3053 (2)	0.0488 (9)
H32	0.7755	0.9609	0.2538	0.059*
C33	0.9172 (3)	0.9211 (6)	0.3584 (3)	0.0634 (11)
H33	0.9761	0.9888	0.3433	0.076*
C34	0.9512 (4)	0.8367 (6)	0.4342 (3)	0.0693 (13)
H34	1.0332	0.8467	0.4701	0.083*
C35	0.8638 (4)	0.7381 (6)	0.4565 (3)	0.0625 (11)
H35	0.8865	0.6809	0.5075	0.075*
C36	0.7424 (4)	0.7236 (5)	0.4036 (2)	0.0515 (9)
H36	0.6841	0.6561	0.4194	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0503 (2)	0.0711 (3)	0.0487 (2)	−0.0041 (2)	0.02380 (16)	−0.0006 (2)
Br2	0.0576 (2)	0.0860 (3)	0.0622 (3)	0.0117 (2)	0.0346 (2)	−0.0023 (2)
C1	0.0496 (19)	0.0374 (18)	0.0336 (18)	0.0041 (14)	0.0131 (16)	−0.0058 (13)
C2	0.057 (2)	0.050 (2)	0.039 (2)	0.0019 (18)	0.0156 (18)	−0.0019 (16)
C3	0.076 (3)	0.056 (3)	0.039 (2)	0.011 (2)	0.007 (2)	−0.0004 (18)
C4	0.054 (2)	0.071 (3)	0.052 (2)	0.007 (2)	0.001 (2)	−0.010 (2)
C5	0.046 (2)	0.071 (3)	0.055 (2)	0.0002 (19)	0.0093 (19)	−0.008 (2)
C6	0.053 (2)	0.053 (2)	0.0430 (19)	0.001 (2)	0.0147 (16)	−0.003 (2)
C7	0.0467 (18)	0.035 (2)	0.0392 (17)	−0.0043 (16)	0.0157 (15)	−0.0042 (15)
C8	0.0509 (19)	0.044 (2)	0.0390 (17)	−0.0037 (17)	0.0204 (16)	−0.0053 (16)
C9	0.046 (2)	0.043 (2)	0.048 (2)	0.0015 (14)	0.0255 (17)	−0.0040 (15)
C10	0.0348 (16)	0.042 (2)	0.046 (2)	−0.0021 (13)	0.0127 (15)	−0.0006 (14)
C11	0.0390 (16)	0.0285 (15)	0.0383 (16)	0.0006 (16)	0.0130 (13)	−0.0014 (15)
C12	0.0390 (17)	0.040 (2)	0.0390 (18)	0.0007 (14)	0.0152 (15)	−0.0003 (15)
C13	0.0344 (15)	0.0317 (16)	0.0408 (17)	−0.0086 (15)	0.0120 (13)	−0.0023 (16)
C14	0.0376 (17)	0.0400 (19)	0.0378 (18)	0.0032 (14)	0.0093 (15)	−0.0008 (15)
C15	0.0437 (19)	0.047 (2)	0.045 (2)	−0.0006 (17)	0.0181 (17)	−0.0066 (17)
C16	0.0475 (19)	0.051 (2)	0.0343 (18)	−0.0076 (16)	0.0120 (15)	0.0008 (16)
C17	0.0415 (19)	0.050 (2)	0.039 (2)	−0.0005 (15)	0.0043 (16)	0.0077 (15)
C18	0.0348 (17)	0.046 (2)	0.044 (2)	0.0011 (15)	0.0105 (16)	−0.0012 (16)
C19	0.0345 (15)	0.0327 (18)	0.0365 (16)	0.0045 (14)	0.0090 (13)	−0.0003 (15)
C20	0.0361 (17)	0.0402 (19)	0.0397 (19)	−0.0039 (13)	0.0101 (15)	−0.0033 (14)
C21	0.049 (2)	0.045 (2)	0.042 (2)	0.0008 (15)	0.0178 (17)	−0.0013 (15)
C22	0.0492 (19)	0.051 (2)	0.0331 (17)	0.0039 (17)	0.0098 (15)	−0.0032 (16)
C23	0.0400 (18)	0.047 (2)	0.0370 (19)	−0.0033 (16)	0.0034 (15)	−0.0100 (16)
C24	0.0369 (17)	0.041 (2)	0.0422 (19)	−0.0048 (14)	0.0129 (15)	−0.0010 (15)
C25	0.0424 (16)	0.0324 (18)	0.0341 (16)	0.0006 (15)	0.0108 (13)	−0.0039 (15)
C26	0.0380 (16)	0.0408 (19)	0.0377 (17)	−0.0023 (15)	0.0109 (13)	−0.0021 (16)
C27	0.0452 (18)	0.0381 (18)	0.0427 (18)	−0.0019 (17)	0.0185 (15)	0.0014 (17)
C28	0.0517 (19)	0.0433 (18)	0.0331 (17)	0.0034 (19)	0.0129 (15)	0.0026 (18)
C29	0.0411 (16)	0.0335 (16)	0.0376 (16)	0.0008 (16)	0.0079 (13)	−0.0056 (16)
C30	0.0373 (17)	0.0397 (18)	0.0393 (17)	0.0037 (16)	0.0138 (14)	0.0002 (18)
C31	0.0447 (18)	0.0406 (19)	0.0341 (17)	0.0114 (19)	0.0078 (14)	−0.0039 (18)
C32	0.0439 (19)	0.051 (2)	0.048 (2)	0.0030 (18)	0.0086 (17)	0.0031 (18)
C33	0.044 (2)	0.066 (3)	0.074 (3)	−0.002 (2)	0.008 (2)	−0.012 (3)
C34	0.049 (2)	0.075 (3)	0.065 (3)	0.016 (2)	−0.012 (2)	−0.022 (2)
C35	0.068 (3)	0.067 (3)	0.044 (2)	0.017 (2)	0.003 (2)	−0.0024 (19)
C36	0.055 (2)	0.054 (2)	0.039 (2)	0.0107 (18)	0.0048 (18)	−0.0012 (17)

Geometric parameters (Å, º) top

Br1—C27	1.903 (3)	C18—H18	0.9300
Br2—C9	1.911 (3)	C19—C20	1.391 (4)
C1—C6	1.389 (5)	C19—C24	1.397 (5)
C1—C2	1.395 (5)	C19—C25	1.491 (4)
C1—C7	1.480 (5)	C20—C21	1.388 (5)
C2—C3	1.381 (5)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.372 (5)
C3—C4	1.371 (6)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.377 (5)
C4—C5	1.370 (6)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.385 (5)
C5—C6	1.391 (5)	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—C30	1.387 (4)
C7—C12	1.402 (4)	C25—C26	1.396 (4)
C7—C8	1.396 (4)	C26—C27	1.371 (4)
C8—C9	1.382 (5)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.386 (4)
C9—C10	1.370 (5)	C28—C29	1.397 (4)
C10—C11	1.403 (4)	C28—H28	0.9300
C10—H10	0.9300	C29—C30	1.395 (4)
C11—C12	1.385 (4)	C29—C31	1.484 (4)
C11—C13	1.486 (4)	C30—H30	0.9300
C12—H12	0.9300	C31—C32	1.394 (5)
C13—C14	1.391 (4)	C31—C36	1.392 (5)
C13—C18	1.392 (5)	C32—C33	1.370 (5)
C14—C15	1.391 (5)	C32—H32	0.9300
C14—H14	0.9300	C33—C34	1.378 (6)
C15—C16	1.376 (5)	C33—H33	0.9300
C15—H15	0.9300	C34—C35	1.371 (6)
C16—C17	1.375 (5)	C34—H34	0.9300
C16—H16	0.9300	C35—C36	1.375 (5)
C17—C18	1.389 (5)	C35—H35	0.9300
C17—H17	0.9300	C36—H36	0.9300

C6—C1—C2	117.6 (3)	C20—C19—C24	117.8 (3)
C6—C1—C7	121.2 (3)	C20—C19—C25	120.9 (3)
C2—C1—C7	121.2 (3)	C24—C19—C25	121.3 (3)
C3—C2—C1	121.0 (4)	C21—C20—C19	121.1 (3)
C3—C2—H2	119.5	C21—C20—H20	119.5
C1—C2—H2	119.5	C19—C20—H20	119.5
C4—C3—C2	120.4 (4)	C22—C21—C20	119.9 (3)
C4—C3—H3	119.8	C22—C21—H21	120.0
C2—C3—H3	119.8	C20—C21—H21	120.0
C5—C4—C3	119.8 (4)	C21—C22—C23	120.3 (3)
C5—C4—H4	120.1	C21—C22—H22	119.9
C3—C4—H4	120.1	C23—C22—H22	119.9
C4—C5—C6	120.1 (4)	C22—C23—C24	119.9 (3)
C4—C5—H5	119.9	C22—C23—H23	120.0
C6—C5—H5	119.9	C24—C23—H23	120.0
C1—C6—C5	121.0 (4)	C23—C24—C19	121.0 (3)
C1—C6—H6	119.5	C23—C24—H24	119.5
C5—C6—H6	119.5	C19—C24—H24	119.5
C12—C7—C8	118.7 (3)	C30—C25—C26	118.3 (3)
C12—C7—C1	121.1 (3)	C30—C25—C19	121.0 (3)
C8—C7—C1	120.2 (3)	C26—C25—C19	120.7 (3)
C9—C8—C7	118.3 (3)	C27—C26—C25	119.8 (3)
C9—C8—H8	120.8	C27—C26—H26	120.1
C7—C8—H8	120.8	C25—C26—H26	120.1
C10—C9—C8	123.2 (3)	C26—C27—C28	122.2 (3)
C10—C9—Br2	118.5 (3)	C26—C27—Br1	118.9 (2)
C8—C9—Br2	118.2 (2)	C28—C27—Br1	118.8 (2)
C9—C10—C11	119.3 (3)	C27—C28—C29	119.0 (3)
C9—C10—H10	120.3	C27—C28—H28	120.5
C11—C10—H10	120.3	C29—C28—H28	120.5
C12—C11—C10	118.1 (3)	C30—C29—C28	118.5 (3)
C12—C11—C13	121.6 (3)	C30—C29—C31	121.5 (3)
C10—C11—C13	120.3 (3)	C28—C29—C31	119.9 (3)
C11—C12—C7	122.4 (3)	C25—C30—C29	122.2 (3)
C11—C12—H12	118.8	C25—C30—H30	118.9
C7—C12—H12	118.8	C29—C30—H30	118.9
C14—C13—C18	117.6 (3)	C32—C31—C36	117.3 (3)
C14—C13—C11	121.3 (3)	C32—C31—C29	121.7 (3)
C18—C13—C11	121.1 (3)	C36—C31—C29	121.0 (3)
C13—C14—C15	121.1 (3)	C33—C32—C31	121.4 (4)
C13—C14—H14	119.4	C33—C32—H32	119.3
C15—C14—H14	119.4	C31—C32—H32	119.3
C16—C15—C14	120.1 (3)	C32—C33—C34	120.1 (4)
C16—C15—H15	119.9	C32—C33—H33	119.9
C14—C15—H15	119.9	C34—C33—H33	119.9
C17—C16—C15	119.7 (3)	C35—C34—C33	119.7 (4)
C17—C16—H16	120.1	C35—C34—H34	120.2
C15—C16—H16	120.1	C33—C34—H34	120.2
C16—C17—C18	120.2 (3)	C34—C35—C36	120.3 (4)
C16—C17—H17	119.9	C34—C35—H35	119.9
C18—C17—H17	119.9	C36—C35—H35	119.9
C17—C18—C13	121.1 (3)	C35—C36—C31	121.2 (4)
C17—C18—H18	119.4	C35—C36—H36	119.4
C13—C18—H18	119.4	C31—C36—H36	119.4

C6—C1—C2—C3	−1.1 (5)	C24—C19—C20—C21	−0.2 (5)
C7—C1—C2—C3	179.5 (3)	C25—C19—C20—C21	180.0 (3)
C1—C2—C3—C4	0.0 (6)	C19—C20—C21—C22	0.3 (5)
C2—C3—C4—C5	0.4 (6)	C20—C21—C22—C23	0.0 (5)
C3—C4—C5—C6	0.2 (6)	C21—C22—C23—C24	−0.4 (5)
C2—C1—C6—C5	1.7 (5)	C22—C23—C24—C19	0.4 (5)
C7—C1—C6—C5	−178.9 (4)	C20—C19—C24—C23	−0.2 (5)
C4—C5—C6—C1	−1.3 (6)	C25—C19—C24—C23	179.6 (3)
C6—C1—C7—C12	40.4 (5)	C20—C19—C25—C30	−30.1 (5)
C2—C1—C7—C12	−140.2 (3)	C24—C19—C25—C30	150.1 (3)
C6—C1—C7—C8	−139.7 (4)	C20—C19—C25—C26	150.2 (3)
C2—C1—C7—C8	39.8 (5)	C24—C19—C25—C26	−29.6 (5)
C12—C7—C8—C9	0.1 (5)	C30—C25—C26—C27	1.6 (5)
C1—C7—C8—C9	−179.8 (3)	C19—C25—C26—C27	−178.7 (3)
C7—C8—C9—C10	0.2 (5)	C25—C26—C27—C28	−1.2 (6)
C7—C8—C9—Br2	−176.9 (3)	C25—C26—C27—Br1	176.9 (3)
C8—C9—C10—C11	−0.2 (5)	C26—C27—C28—C29	0.3 (6)
Br2—C9—C10—C11	176.9 (2)	Br1—C27—C28—C29	−177.8 (3)
C9—C10—C11—C12	−0.1 (5)	C27—C28—C29—C30	0.2 (5)
C9—C10—C11—C13	−179.9 (3)	C27—C28—C29—C31	178.2 (4)
C10—C11—C12—C7	0.5 (5)	C26—C25—C30—C29	−1.1 (5)
C13—C11—C12—C7	−179.7 (3)	C19—C25—C30—C29	179.1 (3)
C8—C7—C12—C11	−0.4 (5)	C28—C29—C30—C25	0.3 (6)
C1—C7—C12—C11	179.5 (3)	C31—C29—C30—C25	−177.7 (3)
C12—C11—C13—C14	27.4 (5)	C30—C29—C31—C32	37.1 (5)
C10—C11—C13—C14	−152.8 (3)	C28—C29—C31—C32	−140.9 (4)
C12—C11—C13—C18	−153.2 (3)	C30—C29—C31—C36	−143.4 (4)
C10—C11—C13—C18	26.6 (5)	C28—C29—C31—C36	38.6 (5)
C18—C13—C14—C15	−0.2 (5)	C36—C31—C32—C33	−1.7 (6)
C11—C13—C14—C15	179.2 (3)	C29—C31—C32—C33	177.8 (4)
C13—C14—C15—C16	−0.8 (5)	C31—C32—C33—C34	1.4 (6)
C14—C15—C16—C17	1.5 (5)	C32—C33—C34—C35	−0.5 (6)
C15—C16—C17—C18	−1.0 (5)	C33—C34—C35—C36	−0.2 (6)
C16—C17—C18—C13	0.0 (5)	C34—C35—C36—C31	−0.2 (6)
C14—C13—C18—C17	0.6 (5)	C32—C31—C36—C35	1.1 (5)
C11—C13—C18—C17	−178.7 (3)	C29—C31—C36—C35	−178.5 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z; (iii) −x+1, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Br
M_r	309.19
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	11.0782 (12), 7.7495 (8), 16.7782 (17)
β (°)	107.441 (1)
V (Å³)	1374.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.97
Crystal size (mm)	0.41 × 0.13 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.375, 0.776
No. of measured, independent and observed [I > 2σ(I)] reflections	7808, 4775, 4138
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.00
No. of reflections	4775
No. of parameters	343
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.31
Absolute structure	Flack (1983), 2006 Friedel pairs
Absolute structure parameter	0.007 (7)

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z; (iii) −x+1, y+1/2, −z.

Acknowledgements

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

References

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kim, Y. H., Shin, D. C., Kim, S. H., Ko, C. H., Yu, H. S., Chae, Y. S. & Kwon, S. K. (2001). Adv. Mater. 13, 1690–1693. Web of Science CrossRef CAS Google Scholar
Niu, Y. H., Chen, B. Q., Kim, T. D., Liu, M. S. & Jen, A. K. Y. (2004). Appl. Phys. Lett. 85, 5433–5435. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suezawa, H., Ishihara, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2004). Eur. J. Org. Chem. pp. 4816–4822. CrossRef Google Scholar