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ISSN: 2056-9890

1-Bromo-3,5-di­phenyl­benzene

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[Niu, Y. H., Chen, B. Q., Kim, T. D., Liu, M. S. & Jen, A. K. Y. (2004). Appl. Phys. Lett. 85, 5433-5435.]). For the synthesis of the title compound, see: Kim et al. (2001[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.]). For the importance of C—H⋯π contacts and their geometries, see, for example: Suezawa et al. (2004[Suezawa, H., Ishihara, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2004). Eur. J. Org. Chem. pp. 4816-4822.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13Br

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.375, Tmax = 0.776

  • 7808 measured reflections

  • 4775 independent reflections

  • 4138 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.31 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2006 Friedel pairs

  • Flack parameter: 0.007 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

All of the H atoms were positioned geometrically with C—H of 0.93 Å and were constrained in a riding motion on their parent carbon atoms with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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
C18H13BrF(000) = 624
Mr = 309.19Dx = 1.494 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.0782 (12) ÅCell parameters from 3281 reflections
b = 7.7495 (8) Åθ = 2.7–24.8°
c = 16.7782 (17) ŵ = 2.97 mm1
β = 107.441 (1)°T = 294 K
V = 1374.2 (2) Å3Block, colourless
Z = 40.41 × 0.13 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4775 independent reflections
Radiation source: fine-focus sealed tube4138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ϕ and ω scansθmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.375, Tmax = 0.776k = 98
7808 measured reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0488P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4775 reflectionsΔρmax = 0.23 e Å3
343 parametersΔρmin = 0.31 e Å3
1 restraintAbsolute structure: Flack (1983), 2006 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.007 (7)
Crystal data top
C18H13BrV = 1374.2 (2) Å3
Mr = 309.19Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.0782 (12) ŵ = 2.97 mm1
b = 7.7495 (8) ÅT = 294 K
c = 16.7782 (17) Å0.41 × 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)
Tmin = 0.375, Tmax = 0.776Rint = 0.014
7808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.076Δρmax = 0.23 e Å3
S = 1.00Δρmin = 0.31 e Å3
4775 reflectionsAbsolute structure: Flack (1983), 2006 Friedel pairs
343 parametersAbsolute 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
xyzUiso*/Ueq
Br10.21282 (3)0.79871 (5)0.29748 (2)0.05470 (12)
Br20.04494 (4)0.42942 (6)0.31148 (2)0.06496 (14)
C10.4329 (3)0.2381 (4)0.3577 (2)0.0400 (8)
C20.4454 (3)0.1460 (5)0.4312 (2)0.0484 (9)
H20.37320.10840.44340.058*
C30.5632 (4)0.1100 (5)0.4859 (2)0.0594 (11)
H30.56970.04840.53460.071*
C40.6707 (4)0.1645 (6)0.4690 (3)0.0624 (11)
H40.74980.13920.50600.075*
C50.6613 (4)0.2561 (5)0.3976 (2)0.0587 (11)
H50.73420.29280.38600.070*
C60.5430 (3)0.2944 (6)0.3424 (2)0.0498 (8)
H60.53750.35870.29470.060*
C70.3069 (3)0.2758 (5)0.29839 (19)0.0396 (7)
C80.2064 (3)0.3218 (5)0.3282 (2)0.0430 (8)
H80.21730.32940.38520.052*
C90.0902 (3)0.3555 (4)0.2707 (2)0.0427 (9)
C100.0688 (3)0.3457 (4)0.1861 (2)0.0407 (8)
H100.01100.36930.14960.049*
C110.1686 (3)0.2998 (5)0.15494 (18)0.0350 (6)
C120.2857 (3)0.2664 (4)0.21181 (19)0.0387 (8)
H120.35270.23660.19190.046*
C130.1478 (3)0.2884 (5)0.06339 (18)0.0354 (7)
C140.2206 (3)0.1799 (4)0.0303 (2)0.0389 (7)
H140.28430.11420.06610.047*
C150.1998 (3)0.1679 (5)0.0555 (2)0.0443 (8)
H150.25010.09580.07650.053*
C160.1048 (3)0.2626 (5)0.1094 (2)0.0443 (9)
H160.08960.25260.16680.053*
C170.0325 (3)0.3720 (5)0.0781 (2)0.0451 (9)
H170.03090.43750.11430.054*
C180.0537 (3)0.3850 (4)0.0076 (2)0.0420 (8)
H180.00410.45950.02810.050*
C190.3980 (3)0.7771 (4)0.03861 (19)0.0349 (7)
C200.4802 (3)0.8546 (4)0.0009 (2)0.0390 (8)
H200.55220.91040.03380.047*
C210.4564 (3)0.8499 (4)0.0852 (2)0.0442 (9)
H210.51250.90190.10940.053*
C220.3502 (3)0.7685 (5)0.1344 (2)0.0452 (8)
H220.33440.76540.19200.054*
C230.2669 (3)0.6914 (4)0.0988 (2)0.0431 (8)
H230.19480.63690.13240.052*
C240.2907 (3)0.6950 (4)0.0130 (2)0.0399 (8)
H240.23440.64200.01070.048*
C250.4238 (3)0.7824 (4)0.13106 (18)0.0364 (7)
C260.3245 (3)0.7809 (5)0.16629 (19)0.0390 (7)
H260.24120.77430.13210.047*
C270.3501 (3)0.7894 (5)0.25135 (19)0.0408 (7)
C280.4727 (3)0.7964 (5)0.30482 (18)0.0427 (7)
H280.48750.80160.36230.051*
C290.5735 (3)0.7955 (5)0.27097 (18)0.0383 (7)
C300.5467 (3)0.7882 (5)0.18430 (18)0.0383 (7)
H300.61350.78710.16140.046*
C310.7054 (3)0.8081 (5)0.32689 (19)0.0407 (7)
C320.7968 (3)0.9055 (5)0.3053 (2)0.0488 (9)
H320.77550.96090.25380.059*
C330.9172 (3)0.9211 (6)0.3584 (3)0.0634 (11)
H330.97610.98880.34330.076*
C340.9512 (4)0.8367 (6)0.4342 (3)0.0693 (13)
H341.03320.84670.47010.083*
C350.8638 (4)0.7381 (6)0.4565 (3)0.0625 (11)
H350.88650.68090.50750.075*
C360.7424 (4)0.7236 (5)0.4036 (2)0.0515 (9)
H360.68410.65610.41940.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0503 (2)0.0711 (3)0.0487 (2)0.0041 (2)0.02380 (16)0.0006 (2)
Br20.0576 (2)0.0860 (3)0.0622 (3)0.0117 (2)0.0346 (2)0.0023 (2)
C10.0496 (19)0.0374 (18)0.0336 (18)0.0041 (14)0.0131 (16)0.0058 (13)
C20.057 (2)0.050 (2)0.039 (2)0.0019 (18)0.0156 (18)0.0019 (16)
C30.076 (3)0.056 (3)0.039 (2)0.011 (2)0.007 (2)0.0004 (18)
C40.054 (2)0.071 (3)0.052 (2)0.007 (2)0.001 (2)0.010 (2)
C50.046 (2)0.071 (3)0.055 (2)0.0002 (19)0.0093 (19)0.008 (2)
C60.053 (2)0.053 (2)0.0430 (19)0.001 (2)0.0147 (16)0.003 (2)
C70.0467 (18)0.035 (2)0.0392 (17)0.0043 (16)0.0157 (15)0.0042 (15)
C80.0509 (19)0.044 (2)0.0390 (17)0.0037 (17)0.0204 (16)0.0053 (16)
C90.046 (2)0.043 (2)0.048 (2)0.0015 (14)0.0255 (17)0.0040 (15)
C100.0348 (16)0.042 (2)0.046 (2)0.0021 (13)0.0127 (15)0.0006 (14)
C110.0390 (16)0.0285 (15)0.0383 (16)0.0006 (16)0.0130 (13)0.0014 (15)
C120.0390 (17)0.040 (2)0.0390 (18)0.0007 (14)0.0152 (15)0.0003 (15)
C130.0344 (15)0.0317 (16)0.0408 (17)0.0086 (15)0.0120 (13)0.0023 (16)
C140.0376 (17)0.0400 (19)0.0378 (18)0.0032 (14)0.0093 (15)0.0008 (15)
C150.0437 (19)0.047 (2)0.045 (2)0.0006 (17)0.0181 (17)0.0066 (17)
C160.0475 (19)0.051 (2)0.0343 (18)0.0076 (16)0.0120 (15)0.0008 (16)
C170.0415 (19)0.050 (2)0.039 (2)0.0005 (15)0.0043 (16)0.0077 (15)
C180.0348 (17)0.046 (2)0.044 (2)0.0011 (15)0.0105 (16)0.0012 (16)
C190.0345 (15)0.0327 (18)0.0365 (16)0.0045 (14)0.0090 (13)0.0003 (15)
C200.0361 (17)0.0402 (19)0.0397 (19)0.0039 (13)0.0101 (15)0.0033 (14)
C210.049 (2)0.045 (2)0.042 (2)0.0008 (15)0.0178 (17)0.0013 (15)
C220.0492 (19)0.051 (2)0.0331 (17)0.0039 (17)0.0098 (15)0.0032 (16)
C230.0400 (18)0.047 (2)0.0370 (19)0.0033 (16)0.0034 (15)0.0100 (16)
C240.0369 (17)0.041 (2)0.0422 (19)0.0048 (14)0.0129 (15)0.0010 (15)
C250.0424 (16)0.0324 (18)0.0341 (16)0.0006 (15)0.0108 (13)0.0039 (15)
C260.0380 (16)0.0408 (19)0.0377 (17)0.0023 (15)0.0109 (13)0.0021 (16)
C270.0452 (18)0.0381 (18)0.0427 (18)0.0019 (17)0.0185 (15)0.0014 (17)
C280.0517 (19)0.0433 (18)0.0331 (17)0.0034 (19)0.0129 (15)0.0026 (18)
C290.0411 (16)0.0335 (16)0.0376 (16)0.0008 (16)0.0079 (13)0.0056 (16)
C300.0373 (17)0.0397 (18)0.0393 (17)0.0037 (16)0.0138 (14)0.0002 (18)
C310.0447 (18)0.0406 (19)0.0341 (17)0.0114 (19)0.0078 (14)0.0039 (18)
C320.0439 (19)0.051 (2)0.048 (2)0.0030 (18)0.0086 (17)0.0031 (18)
C330.044 (2)0.066 (3)0.074 (3)0.002 (2)0.008 (2)0.012 (3)
C340.049 (2)0.075 (3)0.065 (3)0.016 (2)0.012 (2)0.022 (2)
C350.068 (3)0.067 (3)0.044 (2)0.017 (2)0.003 (2)0.0024 (19)
C360.055 (2)0.054 (2)0.039 (2)0.0107 (18)0.0048 (18)0.0012 (17)
Geometric parameters (Å, º) top
Br1—C271.903 (3)C18—H180.9300
Br2—C91.911 (3)C19—C201.391 (4)
C1—C61.389 (5)C19—C241.397 (5)
C1—C21.395 (5)C19—C251.491 (4)
C1—C71.480 (5)C20—C211.388 (5)
C2—C31.381 (5)C20—H200.9300
C2—H20.9300C21—C221.372 (5)
C3—C41.371 (6)C21—H210.9300
C3—H30.9300C22—C231.377 (5)
C4—C51.370 (6)C22—H220.9300
C4—H40.9300C23—C241.385 (5)
C5—C61.391 (5)C23—H230.9300
C5—H50.9300C24—H240.9300
C6—H60.9300C25—C301.387 (4)
C7—C121.402 (4)C25—C261.396 (4)
C7—C81.396 (4)C26—C271.371 (4)
C8—C91.382 (5)C26—H260.9300
C8—H80.9300C27—C281.386 (4)
C9—C101.370 (5)C28—C291.397 (4)
C10—C111.403 (4)C28—H280.9300
C10—H100.9300C29—C301.395 (4)
C11—C121.385 (4)C29—C311.484 (4)
C11—C131.486 (4)C30—H300.9300
C12—H120.9300C31—C321.394 (5)
C13—C141.391 (4)C31—C361.392 (5)
C13—C181.392 (5)C32—C331.370 (5)
C14—C151.391 (5)C32—H320.9300
C14—H140.9300C33—C341.378 (6)
C15—C161.376 (5)C33—H330.9300
C15—H150.9300C34—C351.371 (6)
C16—C171.375 (5)C34—H340.9300
C16—H160.9300C35—C361.375 (5)
C17—C181.389 (5)C35—H350.9300
C17—H170.9300C36—H360.9300
C6—C1—C2117.6 (3)C20—C19—C24117.8 (3)
C6—C1—C7121.2 (3)C20—C19—C25120.9 (3)
C2—C1—C7121.2 (3)C24—C19—C25121.3 (3)
C3—C2—C1121.0 (4)C21—C20—C19121.1 (3)
C3—C2—H2119.5C21—C20—H20119.5
C1—C2—H2119.5C19—C20—H20119.5
C4—C3—C2120.4 (4)C22—C21—C20119.9 (3)
C4—C3—H3119.8C22—C21—H21120.0
C2—C3—H3119.8C20—C21—H21120.0
C5—C4—C3119.8 (4)C21—C22—C23120.3 (3)
C5—C4—H4120.1C21—C22—H22119.9
C3—C4—H4120.1C23—C22—H22119.9
C4—C5—C6120.1 (4)C22—C23—C24119.9 (3)
C4—C5—H5119.9C22—C23—H23120.0
C6—C5—H5119.9C24—C23—H23120.0
C1—C6—C5121.0 (4)C23—C24—C19121.0 (3)
C1—C6—H6119.5C23—C24—H24119.5
C5—C6—H6119.5C19—C24—H24119.5
C12—C7—C8118.7 (3)C30—C25—C26118.3 (3)
C12—C7—C1121.1 (3)C30—C25—C19121.0 (3)
C8—C7—C1120.2 (3)C26—C25—C19120.7 (3)
C9—C8—C7118.3 (3)C27—C26—C25119.8 (3)
C9—C8—H8120.8C27—C26—H26120.1
C7—C8—H8120.8C25—C26—H26120.1
C10—C9—C8123.2 (3)C26—C27—C28122.2 (3)
C10—C9—Br2118.5 (3)C26—C27—Br1118.9 (2)
C8—C9—Br2118.2 (2)C28—C27—Br1118.8 (2)
C9—C10—C11119.3 (3)C27—C28—C29119.0 (3)
C9—C10—H10120.3C27—C28—H28120.5
C11—C10—H10120.3C29—C28—H28120.5
C12—C11—C10118.1 (3)C30—C29—C28118.5 (3)
C12—C11—C13121.6 (3)C30—C29—C31121.5 (3)
C10—C11—C13120.3 (3)C28—C29—C31119.9 (3)
C11—C12—C7122.4 (3)C25—C30—C29122.2 (3)
C11—C12—H12118.8C25—C30—H30118.9
C7—C12—H12118.8C29—C30—H30118.9
C14—C13—C18117.6 (3)C32—C31—C36117.3 (3)
C14—C13—C11121.3 (3)C32—C31—C29121.7 (3)
C18—C13—C11121.1 (3)C36—C31—C29121.0 (3)
C13—C14—C15121.1 (3)C33—C32—C31121.4 (4)
C13—C14—H14119.4C33—C32—H32119.3
C15—C14—H14119.4C31—C32—H32119.3
C16—C15—C14120.1 (3)C32—C33—C34120.1 (4)
C16—C15—H15119.9C32—C33—H33119.9
C14—C15—H15119.9C34—C33—H33119.9
C17—C16—C15119.7 (3)C35—C34—C33119.7 (4)
C17—C16—H16120.1C35—C34—H34120.2
C15—C16—H16120.1C33—C34—H34120.2
C16—C17—C18120.2 (3)C34—C35—C36120.3 (4)
C16—C17—H17119.9C34—C35—H35119.9
C18—C17—H17119.9C36—C35—H35119.9
C17—C18—C13121.1 (3)C35—C36—C31121.2 (4)
C17—C18—H18119.4C35—C36—H36119.4
C13—C18—H18119.4C31—C36—H36119.4
C6—C1—C2—C31.1 (5)C24—C19—C20—C210.2 (5)
C7—C1—C2—C3179.5 (3)C25—C19—C20—C21180.0 (3)
C1—C2—C3—C40.0 (6)C19—C20—C21—C220.3 (5)
C2—C3—C4—C50.4 (6)C20—C21—C22—C230.0 (5)
C3—C4—C5—C60.2 (6)C21—C22—C23—C240.4 (5)
C2—C1—C6—C51.7 (5)C22—C23—C24—C190.4 (5)
C7—C1—C6—C5178.9 (4)C20—C19—C24—C230.2 (5)
C4—C5—C6—C11.3 (6)C25—C19—C24—C23179.6 (3)
C6—C1—C7—C1240.4 (5)C20—C19—C25—C3030.1 (5)
C2—C1—C7—C12140.2 (3)C24—C19—C25—C30150.1 (3)
C6—C1—C7—C8139.7 (4)C20—C19—C25—C26150.2 (3)
C2—C1—C7—C839.8 (5)C24—C19—C25—C2629.6 (5)
C12—C7—C8—C90.1 (5)C30—C25—C26—C271.6 (5)
C1—C7—C8—C9179.8 (3)C19—C25—C26—C27178.7 (3)
C7—C8—C9—C100.2 (5)C25—C26—C27—C281.2 (6)
C7—C8—C9—Br2176.9 (3)C25—C26—C27—Br1176.9 (3)
C8—C9—C10—C110.2 (5)C26—C27—C28—C290.3 (6)
Br2—C9—C10—C11176.9 (2)Br1—C27—C28—C29177.8 (3)
C9—C10—C11—C120.1 (5)C27—C28—C29—C300.2 (5)
C9—C10—C11—C13179.9 (3)C27—C28—C29—C31178.2 (4)
C10—C11—C12—C70.5 (5)C26—C25—C30—C291.1 (5)
C13—C11—C12—C7179.7 (3)C19—C25—C30—C29179.1 (3)
C8—C7—C12—C110.4 (5)C28—C29—C30—C250.3 (6)
C1—C7—C12—C11179.5 (3)C31—C29—C30—C25177.7 (3)
C12—C11—C13—C1427.4 (5)C30—C29—C31—C3237.1 (5)
C10—C11—C13—C14152.8 (3)C28—C29—C31—C32140.9 (4)
C12—C11—C13—C18153.2 (3)C30—C29—C31—C36143.4 (4)
C10—C11—C13—C1826.6 (5)C28—C29—C31—C3638.6 (5)
C18—C13—C14—C150.2 (5)C36—C31—C32—C331.7 (6)
C11—C13—C14—C15179.2 (3)C29—C31—C32—C33177.8 (4)
C13—C14—C15—C160.8 (5)C31—C32—C33—C341.4 (6)
C14—C15—C16—C171.5 (5)C32—C33—C34—C350.5 (6)
C15—C16—C17—C181.0 (5)C33—C34—C35—C360.2 (6)
C16—C17—C18—C130.0 (5)C34—C35—C36—C310.2 (6)
C14—C13—C18—C170.6 (5)C32—C31—C36—C351.1 (5)
C11—C13—C18—C17178.7 (3)C29—C31—C36—C35178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg1i0.932.823.601 (4)142
C18—H18···Cg6ii0.932.843.682 (4)152
C20—H20···Cg1iii0.932.923.603 (4)132
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z; (iii) x+1, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC18H13Br
Mr309.19
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)11.0782 (12), 7.7495 (8), 16.7782 (17)
β (°) 107.441 (1)
V3)1374.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)2.97
Crystal size (mm)0.41 × 0.13 × 0.09
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.375, 0.776
No. of measured, independent and
observed [I > 2σ(I)] reflections
7808, 4775, 4138
Rint0.014
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.076, 1.00
No. of reflections4775
No. of parameters343
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.31
Absolute structureFlack (1983), 2006 Friedel pairs
Absolute structure parameter0.007 (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···AD—HH···AD···AD—H···A
C15—H15···Cg1i0.932.823.601 (4)142
C18—H18···Cg6ii0.932.843.682 (4)152
C20—H20···Cg1iii0.932.923.603 (4)132
Symmetry codes: (i) x, y1, 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

First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKim, 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
First citationNiu, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSuezawa, H., Ishihara, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2004). Eur. J. Org. Chem. pp. 4816–4822.  CrossRef Google Scholar

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