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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2,2′,7,7′-Tetra­bromo-9,9′-spiro­bifluorene toluene hemisolvate

aDepartment of Traditional Chinese Pharmacology, Shanxi University of Traditional Chinese Medicine, Taiyuan 030024, People's Republic of China, and bDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
*Correspondence e-mail: ruitaozhu@126.com

(Received 24 May 2009; accepted 3 June 2009; online 10 June 2009)

There are two independent mol­ecules and one toluene solvent mol­ecule in the asymmetric unit of the title compound, C25H12Br4·0.5C7H8. The dihedral angles between the fluorene ring systems are 85.30 (6) and 84.95 (6)° in the two mol­ecules. The disortions in angles from the ideal sp3-hybridization geometry around the tetra­hedral C atoms are due to the strain imposed by the central five-membered ring and steric effects.

Related literature

For applications of spiro­bifluorene compounds, see: Hagen et al. (1997[Hagen, J., Schaffrach, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H.-W. & Haarer, D. (1997). Synth. Met. 89, 215-220.]); Pudzich et al. (2006[Pudzich, R., Fuhrmann-Lieker, T. & Salbeck, J. (2006). Adv. Polym. Sci. 199, 83-142.]); Salbeck et al. (1997[Salbeck, J., Yu, N., Bauer, J., Weissortel, F. & Bestgen, H. (1997). Synth. Met. 91, 209-215.]); Iour et al. (1990[Iour, J. M., Wu, R. L. & Schumn, J. S. (1990). J. Am. Chem. Soc. 112, 5662-5663.]). For details of the synthesis, see: Marsitzky & Carter (2001[Marsitzky, D. & Carter, K. R. (2001). Polym. Prepr. 42, 450-451.]).

[Scheme 1]

Experimental

Crystal data
  • C25H12Br4·0.5C7H8

  • Mr = 678.06

  • Monoclinic, P 21 /c

  • a = 14.6593 (18) Å

  • b = 29.549 (4) Å

  • c = 11.3753 (14) Å

  • β = 96.878 (2)°

  • V = 4891.9 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 6.60 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART-CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.189, Tmax = 0.438 (expected range = 0.161–0.372)

  • 20291 measured reflections

  • 8616 independent reflections

  • 5479 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.091

  • S = 1.01

  • 8616 reflections

  • 586 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Selected bond angles (°)

C19—C9—C8 112.9 (3)
C19—C9—C21 101.0 (4)
C8—C9—C21 116.8 (4)
C19—C9—C6 113.4 (4)
C8—C9—C6 101.6 (3)
C21—C9—C6 111.6 (3)
C31—C34—C33 100.9 (4)
C31—C34—C46 114.2 (4)
C33—C34—C46 116.9 (4)
C31—C34—C44 113.7 (4)
C33—C34—C44 110.2 (4)
C46—C34—C44 101.5 (4)

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Molecules with a spirobifluorene core have gained wide application in molecular electronics, light-emitting materials production and enantioselective molecular recognition. In addition, macro spiro-organic molecules have attracted interest (Hagen et al., 1997; Salbeck et al., 1997), since they may play a key role in the construction of modern electronic systems and can be used in synthesizing hole transport media which have achieved impressive solar-to-electrical energy conversion efficiencies (James et al., 1990). We are interested in the title compound (TBSBF.0.5(C7H8), due to its versatility and utility in organic synthesis and herein we report its crystal structure.

The asymmetric unit of the title compound is shown in Fig. 1. The disortions in angles from the ideal [109.5°] sp3 hybridization geometry around the tetrahedral C atoms in each molecule [C9 and C34] are due to the strain imposed by the central five-membered ring and from steric effects. The dihedral angles between the fluorene ring systems in each molecule are 85.30 (6) and 84.95 (6)°.

Related literature top

For applications of spirobifluorene compounds, see: Hagen et al. (1997); Pudzich et al. (2006); Salbeck et al. (1997); Iour et al. (1990). For details of the synthesis, see: Marsitzky & Carter (2001).

Experimental top

The title compound was synthesized according to the published procedure (Marsitzky & Carter, 2001). To a solution of 9,9'-spirobifluorene (8g, 25.3mmol) in chloroform (100mL) was added bromine (16.6g, 103.7mmol) in 20mL of chloroform (Marsitzky & Carter, 2001). The resulting mixture was stirred overnight at room temperature. The precipitate formed was seperated by filtration and washed with methanol to give the crude target compound. The product, TBSBF, was recrystallized from toluene, giving a yield of 55%.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93-0.96 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl C atoms.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of the title compound: displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown.
2,2',7,7'-Tetrabromo-9,9'-spirobifluorene toluene hemisolvate top
Crystal data top
C25H12Br4·0.5C7H8F(000) = 2616
Mr = 678.06Dx = 1.841 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3526 reflections
a = 14.6593 (18) Åθ = 2.3–20.5°
b = 29.549 (4) ŵ = 6.60 mm1
c = 11.3753 (14) ÅT = 293 K
β = 96.878 (2)°Block, colorless
V = 4891.9 (10) Å30.30 × 0.20 × 0.15 mm
Z = 8
Data collection top
Bruker SMART-CCD
diffractometer
8616 independent reflections
Radiation source: fine-focus sealed tube5479 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1716
Tmin = 0.189, Tmax = 0.438k = 3235
20291 measured reflectionsl = 713
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0144P)2 + 2.4065P]
where P = (Fo2 + 2Fc2)/3
8616 reflections(Δ/σ)max = 0.001
586 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C25H12Br4·0.5C7H8V = 4891.9 (10) Å3
Mr = 678.06Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.6593 (18) ŵ = 6.60 mm1
b = 29.549 (4) ÅT = 293 K
c = 11.3753 (14) Å0.30 × 0.20 × 0.15 mm
β = 96.878 (2)°
Data collection top
Bruker SMART-CCD
diffractometer
8616 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5479 reflections with I > 2σ(I)
Tmin = 0.189, Tmax = 0.438Rint = 0.045
20291 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.01Δρmax = 0.56 e Å3
8616 reflectionsΔρmin = 0.41 e Å3
586 parameters
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
Br10.17970 (4)0.057801 (18)0.07187 (6)0.06389 (18)
Br20.41951 (4)0.06834 (2)0.54188 (6)0.0780 (2)
Br30.35211 (4)0.03188 (2)0.13143 (6)0.0777 (2)
Br40.03438 (4)0.24517 (2)0.36220 (7)0.0814 (2)
C10.0114 (3)0.07959 (15)0.0645 (4)0.0405 (12)
H1A0.01040.10400.01300.049*
C20.0826 (3)0.04904 (16)0.0512 (4)0.0421 (12)
C30.0845 (3)0.01259 (16)0.1269 (5)0.0498 (14)
H3A0.13290.00800.11590.060*
C40.0156 (3)0.00654 (15)0.2183 (5)0.0492 (13)
H4A0.01720.01790.26950.059*
C50.0568 (3)0.03736 (14)0.2340 (4)0.0375 (11)
C60.0580 (3)0.07345 (13)0.1547 (4)0.0340 (11)
C70.1378 (3)0.04009 (14)0.3220 (4)0.0388 (12)
C80.1896 (3)0.07777 (14)0.2979 (4)0.0347 (11)
C90.1442 (3)0.10224 (14)0.1875 (4)0.0376 (11)
C100.1674 (4)0.01268 (16)0.4177 (5)0.0501 (13)
H10A0.13200.01180.43640.060*
C110.2506 (4)0.02223 (17)0.4859 (5)0.0543 (14)
H11A0.27110.00420.55080.065*
C120.3024 (3)0.05870 (17)0.4562 (5)0.0489 (13)
C130.2726 (3)0.08698 (16)0.3627 (4)0.0432 (12)
H13A0.30780.11160.34430.052*
C140.2467 (3)0.06971 (16)0.0368 (4)0.0424 (12)
H14A0.23880.04000.06040.051*
C150.2998 (3)0.07970 (17)0.0519 (5)0.0478 (13)
C160.3145 (3)0.12396 (19)0.0839 (5)0.0560 (15)
H16A0.35220.13000.14230.067*
C170.2743 (3)0.15924 (18)0.0305 (5)0.0534 (14)
H17A0.28470.18900.05180.064*
C180.2180 (3)0.14956 (15)0.0554 (4)0.0394 (12)
C190.2059 (3)0.10493 (15)0.0895 (4)0.0350 (11)
C200.1634 (3)0.17866 (15)0.1246 (4)0.0425 (12)
C210.1203 (3)0.15220 (14)0.2018 (4)0.0367 (11)
C220.1474 (4)0.22495 (17)0.1180 (5)0.0603 (15)
H22A0.17560.24280.06540.072*
C230.0893 (4)0.24409 (18)0.1905 (5)0.0644 (16)
H23A0.07890.27520.18860.077*
C240.0467 (3)0.21714 (18)0.2652 (5)0.0534 (14)
C250.0619 (3)0.17116 (16)0.2738 (5)0.0467 (13)
H25A0.03360.15360.32670.056*
Br50.57872 (4)0.001178 (17)0.78287 (5)0.05951 (17)
Br60.81223 (5)0.319181 (18)0.53771 (6)0.0754 (2)
Br71.08306 (4)0.12112 (2)0.77786 (6)0.06736 (18)
Br80.47421 (4)0.12801 (2)0.17964 (6)0.0820 (2)
C260.6546 (3)0.07355 (16)0.6731 (4)0.0422 (12)
H26A0.67200.05210.62010.051*
C270.6064 (3)0.06097 (15)0.7653 (4)0.0413 (12)
C280.5793 (3)0.09210 (18)0.8438 (4)0.0479 (13)
H28A0.54650.08280.90470.057*
C290.6008 (3)0.13751 (17)0.8321 (5)0.0500 (13)
H29A0.58280.15880.88500.060*
C300.6496 (3)0.15086 (16)0.7401 (4)0.0388 (12)
C310.6764 (3)0.11875 (15)0.6618 (4)0.0360 (11)
C320.6816 (3)0.19535 (15)0.7053 (4)0.0366 (11)
C330.7255 (3)0.19035 (14)0.6042 (4)0.0373 (11)
C340.7297 (3)0.14035 (15)0.5697 (4)0.0381 (11)
C350.6764 (3)0.23790 (17)0.7552 (5)0.0494 (13)
H35A0.64730.24170.82290.059*
C360.7144 (3)0.27440 (17)0.7042 (5)0.0540 (14)
H36A0.71090.30310.73720.065*
C370.7578 (3)0.26854 (15)0.6040 (5)0.0471 (13)
C380.7643 (3)0.22627 (15)0.5533 (4)0.0426 (12)
H38A0.79420.22240.48640.051*
C390.8987 (3)0.12948 (15)0.6703 (4)0.0440 (12)
H39A0.88710.14230.74170.053*
C400.9858 (3)0.11444 (16)0.6533 (5)0.0487 (13)
C411.0036 (3)0.09547 (17)0.5478 (5)0.0533 (14)
H41A1.06270.08570.53900.064*
C420.9350 (3)0.09092 (15)0.4558 (5)0.0507 (14)
H42A0.94720.07790.38490.061*
C430.8474 (3)0.10582 (14)0.4691 (4)0.0391 (12)
C440.8301 (3)0.12461 (14)0.5775 (4)0.0366 (11)
C450.7629 (3)0.10718 (14)0.3877 (4)0.0413 (12)
C460.6939 (3)0.12798 (14)0.4415 (4)0.0394 (12)
C470.7454 (4)0.09201 (16)0.2721 (5)0.0526 (14)
H47A0.79140.07820.23530.063*
C480.6580 (4)0.09780 (17)0.2118 (5)0.0574 (15)
H48A0.64450.08740.13440.069*
C490.5911 (3)0.11913 (17)0.2678 (5)0.0503 (13)
C500.6072 (3)0.13394 (15)0.3832 (4)0.0435 (12)
H50A0.56100.14750.42030.052*
C510.3339 (5)0.1956 (2)0.5276 (6)0.0749 (19)
C520.4214 (6)0.2088 (3)0.5720 (7)0.106 (3)
H52A0.44460.20120.64920.127*
C530.4744 (6)0.2331 (3)0.5035 (10)0.115 (3)
H53A0.53270.24240.53570.138*
C540.4440 (5)0.2438 (2)0.3900 (8)0.095 (2)
H54A0.48080.26020.34420.114*
C550.3587 (5)0.2302 (2)0.3440 (6)0.0751 (18)
H55A0.33750.23660.26540.090*
C560.3035 (4)0.20723 (18)0.4127 (6)0.0645 (16)
H56A0.24430.19930.38080.077*
C570.2722 (5)0.1698 (2)0.5987 (6)0.115 (3)
H57A0.30340.16430.67650.173*
H57B0.25620.14140.56060.173*
H57C0.21740.18700.60470.173*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0470 (3)0.0561 (3)0.0828 (5)0.0033 (3)0.0158 (3)0.0017 (3)
Br20.0596 (4)0.0973 (5)0.0704 (5)0.0069 (3)0.0195 (3)0.0054 (4)
Br30.0682 (4)0.0893 (5)0.0820 (5)0.0022 (3)0.0355 (4)0.0194 (4)
Br40.0723 (4)0.0711 (4)0.1045 (6)0.0105 (3)0.0264 (4)0.0221 (4)
C10.041 (3)0.036 (3)0.046 (3)0.003 (2)0.012 (3)0.002 (2)
C20.037 (3)0.040 (3)0.048 (3)0.001 (2)0.002 (2)0.006 (3)
C30.034 (3)0.040 (3)0.075 (4)0.008 (2)0.007 (3)0.007 (3)
C40.052 (3)0.038 (3)0.061 (4)0.002 (2)0.017 (3)0.005 (3)
C50.042 (3)0.029 (3)0.044 (3)0.004 (2)0.014 (2)0.007 (2)
C60.028 (2)0.029 (2)0.047 (3)0.000 (2)0.011 (2)0.002 (2)
C70.043 (3)0.032 (3)0.042 (3)0.001 (2)0.007 (2)0.002 (2)
C80.038 (3)0.033 (3)0.034 (3)0.004 (2)0.003 (2)0.002 (2)
C90.033 (3)0.034 (3)0.046 (3)0.001 (2)0.004 (2)0.006 (2)
C100.060 (4)0.042 (3)0.049 (3)0.005 (3)0.009 (3)0.010 (3)
C110.068 (4)0.048 (3)0.046 (3)0.020 (3)0.004 (3)0.012 (3)
C120.047 (3)0.053 (3)0.046 (3)0.010 (3)0.002 (3)0.004 (3)
C130.042 (3)0.045 (3)0.042 (3)0.001 (2)0.006 (3)0.003 (3)
C140.031 (3)0.044 (3)0.052 (3)0.000 (2)0.003 (2)0.003 (3)
C150.033 (3)0.059 (3)0.052 (4)0.000 (2)0.005 (3)0.005 (3)
C160.039 (3)0.078 (4)0.052 (4)0.005 (3)0.013 (3)0.012 (3)
C170.049 (3)0.051 (3)0.061 (4)0.010 (3)0.008 (3)0.018 (3)
C180.037 (3)0.041 (3)0.040 (3)0.007 (2)0.000 (2)0.005 (2)
C190.026 (2)0.046 (3)0.032 (3)0.005 (2)0.002 (2)0.004 (2)
C200.044 (3)0.034 (3)0.050 (3)0.008 (2)0.006 (3)0.003 (2)
C210.029 (3)0.035 (3)0.045 (3)0.002 (2)0.002 (2)0.002 (2)
C220.063 (4)0.044 (3)0.075 (4)0.006 (3)0.012 (3)0.010 (3)
C230.067 (4)0.039 (3)0.086 (5)0.004 (3)0.008 (4)0.001 (3)
C240.043 (3)0.054 (4)0.063 (4)0.001 (3)0.006 (3)0.009 (3)
C250.040 (3)0.042 (3)0.058 (4)0.004 (2)0.004 (3)0.005 (3)
Br50.0541 (3)0.0497 (3)0.0768 (4)0.0034 (3)0.0161 (3)0.0126 (3)
Br60.0995 (5)0.0457 (3)0.0841 (5)0.0111 (3)0.0232 (4)0.0011 (3)
Br70.0457 (3)0.0749 (4)0.0777 (4)0.0033 (3)0.0082 (3)0.0151 (3)
Br80.0624 (4)0.1103 (5)0.0674 (4)0.0060 (4)0.0166 (3)0.0071 (4)
C260.033 (3)0.053 (3)0.041 (3)0.010 (2)0.006 (2)0.000 (3)
C270.029 (3)0.045 (3)0.048 (3)0.003 (2)0.002 (2)0.002 (3)
C280.037 (3)0.067 (4)0.040 (3)0.001 (3)0.006 (2)0.001 (3)
C290.045 (3)0.055 (3)0.051 (3)0.005 (3)0.008 (3)0.011 (3)
C300.030 (3)0.048 (3)0.038 (3)0.004 (2)0.003 (2)0.004 (2)
C310.030 (3)0.042 (3)0.037 (3)0.005 (2)0.008 (2)0.004 (2)
C320.032 (3)0.039 (3)0.038 (3)0.003 (2)0.001 (2)0.008 (2)
C330.031 (3)0.036 (3)0.045 (3)0.009 (2)0.005 (2)0.004 (2)
C340.032 (3)0.044 (3)0.039 (3)0.002 (2)0.007 (2)0.001 (2)
C350.048 (3)0.053 (3)0.049 (3)0.005 (3)0.014 (3)0.014 (3)
C360.056 (3)0.040 (3)0.065 (4)0.002 (3)0.002 (3)0.013 (3)
C370.046 (3)0.039 (3)0.055 (4)0.008 (2)0.006 (3)0.007 (3)
C380.044 (3)0.043 (3)0.042 (3)0.006 (2)0.007 (2)0.006 (3)
C390.046 (3)0.046 (3)0.041 (3)0.001 (2)0.009 (3)0.002 (2)
C400.040 (3)0.044 (3)0.062 (4)0.000 (2)0.004 (3)0.014 (3)
C410.038 (3)0.057 (3)0.069 (4)0.009 (3)0.024 (3)0.006 (3)
C420.053 (3)0.045 (3)0.058 (4)0.005 (3)0.021 (3)0.001 (3)
C430.037 (3)0.030 (3)0.052 (3)0.003 (2)0.012 (3)0.002 (2)
C440.035 (3)0.033 (3)0.042 (3)0.000 (2)0.010 (2)0.002 (2)
C450.046 (3)0.033 (3)0.046 (3)0.001 (2)0.011 (3)0.002 (2)
C460.042 (3)0.033 (3)0.044 (3)0.002 (2)0.008 (3)0.001 (2)
C470.061 (4)0.054 (3)0.045 (4)0.003 (3)0.013 (3)0.011 (3)
C480.075 (4)0.054 (3)0.042 (3)0.010 (3)0.003 (3)0.014 (3)
C490.050 (3)0.056 (3)0.043 (3)0.008 (3)0.005 (3)0.005 (3)
C500.042 (3)0.042 (3)0.048 (3)0.003 (2)0.009 (3)0.003 (2)
C510.103 (6)0.063 (4)0.059 (5)0.028 (4)0.012 (4)0.001 (4)
C520.106 (7)0.133 (7)0.071 (6)0.040 (6)0.022 (5)0.024 (5)
C530.073 (6)0.137 (8)0.129 (9)0.011 (5)0.014 (6)0.030 (7)
C540.062 (5)0.097 (5)0.124 (7)0.003 (4)0.009 (5)0.001 (5)
C550.074 (5)0.072 (4)0.077 (5)0.005 (4)0.002 (4)0.005 (4)
C560.061 (4)0.054 (4)0.076 (5)0.007 (3)0.001 (4)0.002 (3)
C570.186 (9)0.066 (4)0.104 (6)0.023 (5)0.062 (6)0.008 (4)
Geometric parameters (Å, º) top
Br1—C21.891 (5)C28—C291.388 (6)
Br2—C121.891 (5)C28—H28A0.9300
Br3—C151.889 (5)C29—C301.393 (6)
Br4—C241.905 (5)C29—H29A0.9300
C1—C61.368 (6)C30—C311.390 (6)
C1—C21.375 (6)C30—C321.466 (6)
C1—H1A0.9300C31—C341.520 (6)
C2—C31.382 (6)C32—C351.385 (6)
C3—C41.372 (7)C32—C331.392 (6)
C3—H3A0.9300C33—C381.366 (6)
C4—C51.394 (6)C33—C341.531 (6)
C4—H4A0.9300C34—C461.534 (6)
C5—C61.398 (6)C34—C441.536 (6)
C5—C71.462 (6)C35—C361.374 (6)
C6—C91.532 (6)C35—H35A0.9300
C7—C101.385 (6)C36—C371.381 (7)
C7—C81.393 (6)C36—H36A0.9300
C8—C131.373 (6)C37—C381.384 (6)
C8—C91.530 (6)C38—H38A0.9300
C9—C191.519 (6)C39—C441.375 (6)
C9—C211.531 (6)C39—C401.388 (6)
C10—C111.394 (7)C39—H39A0.9300
C10—H10A0.9300C40—C411.378 (7)
C11—C121.383 (6)C41—C421.369 (7)
C11—H11A0.9300C41—H41A0.9300
C12—C131.382 (6)C42—C431.383 (6)
C13—H13A0.9300C42—H42A0.9300
C14—C191.374 (6)C43—C441.402 (6)
C14—C151.378 (6)C43—C451.455 (6)
C14—H14A0.9300C45—C471.384 (7)
C15—C161.381 (6)C45—C461.387 (6)
C16—C171.375 (6)C46—C501.373 (6)
C16—H16A0.9300C47—C481.390 (7)
C17—C181.383 (6)C47—H47A0.9300
C17—H17A0.9300C48—C491.383 (7)
C18—C191.392 (6)C48—H48A0.9300
C18—C201.466 (6)C49—C501.377 (6)
C20—C211.383 (6)C50—H50A0.9300
C20—C221.388 (6)C51—C561.374 (8)
C21—C251.373 (6)C51—C521.378 (9)
C22—C231.376 (7)C51—C571.493 (8)
C22—H22A0.9300C52—C531.368 (10)
C23—C241.369 (7)C52—H52A0.9300
C23—H23A0.9300C53—C541.353 (10)
C24—C251.378 (6)C53—H53A0.9300
C25—H25A0.9300C54—C551.357 (8)
Br5—C271.896 (4)C54—H54A0.9300
Br6—C371.894 (4)C55—C561.370 (8)
Br7—C401.896 (5)C55—H55A0.9300
Br8—C491.898 (5)C56—H56A0.9300
C26—C311.383 (6)C57—H57A0.9600
C26—C271.384 (6)C57—H57B0.9600
C26—H26A0.9300C57—H57C0.9600
C27—C281.374 (6)
C6—C1—C2118.8 (4)C31—C30—C29119.9 (4)
C6—C1—H1A120.6C31—C30—C32108.3 (4)
C2—C1—H1A120.6C29—C30—C32131.8 (4)
C1—C2—C3121.0 (5)C26—C31—C30120.9 (4)
C1—C2—Br1119.1 (4)C26—C31—C34127.8 (4)
C3—C2—Br1119.9 (4)C30—C31—C34111.3 (4)
C4—C3—C2120.4 (4)C35—C32—C33119.2 (4)
C4—C3—H3A119.8C35—C32—C30131.9 (4)
C2—C3—H3A119.8C33—C32—C30108.8 (4)
C3—C4—C5119.5 (5)C38—C33—C32121.7 (4)
C3—C4—H4A120.3C38—C33—C34127.6 (4)
C5—C4—H4A120.3C32—C33—C34110.5 (4)
C4—C5—C6119.0 (5)C31—C34—C33100.9 (4)
C4—C5—C7131.9 (5)C31—C34—C46114.2 (4)
C6—C5—C7109.1 (4)C33—C34—C46116.9 (4)
C1—C6—C5121.3 (4)C31—C34—C44113.7 (4)
C1—C6—C9128.8 (4)C33—C34—C44110.2 (4)
C5—C6—C9109.9 (4)C46—C34—C44101.5 (4)
C10—C7—C8119.8 (5)C36—C35—C32119.6 (5)
C10—C7—C5131.2 (4)C36—C35—H35A120.2
C8—C7—C5109.0 (4)C32—C35—H35A120.2
C13—C8—C7121.4 (4)C35—C36—C37120.0 (4)
C13—C8—C9128.1 (4)C35—C36—H36A120.0
C7—C8—C9110.3 (4)C37—C36—H36A120.0
C19—C9—C8112.9 (3)C36—C37—C38121.2 (4)
C19—C9—C21101.0 (4)C36—C37—Br6119.2 (4)
C8—C9—C21116.8 (4)C38—C37—Br6119.6 (4)
C19—C9—C6113.4 (4)C33—C38—C37118.2 (4)
C8—C9—C6101.6 (3)C33—C38—H38A120.9
C21—C9—C6111.6 (3)C37—C38—H38A120.9
C7—C10—C11119.3 (5)C44—C39—C40117.4 (5)
C7—C10—H10A120.3C44—C39—H39A121.3
C11—C10—H10A120.3C40—C39—H39A121.3
C12—C11—C10119.4 (5)C41—C40—C39121.7 (5)
C12—C11—H11A120.3C41—C40—Br7119.3 (4)
C10—C11—H11A120.3C39—C40—Br7119.0 (4)
C13—C12—C11121.8 (5)C42—C41—C40120.5 (5)
C13—C12—Br2119.3 (4)C42—C41—H41A119.7
C11—C12—Br2118.9 (4)C40—C41—H41A119.7
C8—C13—C12118.2 (4)C41—C42—C43119.5 (5)
C8—C13—H13A120.9C41—C42—H42A120.3
C12—C13—H13A120.9C43—C42—H42A120.3
C19—C14—C15118.1 (4)C42—C43—C44119.3 (5)
C19—C14—H14A120.9C42—C43—C45132.0 (5)
C15—C14—H14A120.9C44—C43—C45108.7 (4)
C14—C15—C16121.0 (5)C39—C44—C43121.6 (4)
C14—C15—Br3119.2 (4)C39—C44—C34128.3 (4)
C16—C15—Br3119.8 (4)C43—C44—C34110.0 (4)
C17—C16—C15120.9 (5)C47—C45—C46120.0 (5)
C17—C16—H16A119.6C47—C45—C43130.0 (5)
C15—C16—H16A119.6C46—C45—C43109.9 (4)
C16—C17—C18118.6 (5)C50—C46—C45121.7 (5)
C16—C17—H17A120.7C50—C46—C34128.3 (4)
C18—C17—H17A120.7C45—C46—C34109.9 (4)
C17—C18—C19120.0 (5)C45—C47—C48119.0 (5)
C17—C18—C20131.9 (4)C45—C47—H47A120.5
C19—C18—C20108.1 (4)C48—C47—H47A120.5
C14—C19—C18121.3 (4)C49—C48—C47119.4 (5)
C14—C19—C9127.5 (4)C49—C48—H48A120.3
C18—C19—C9111.2 (4)C47—C48—H48A120.3
C21—C20—C22120.3 (5)C50—C49—C48122.3 (5)
C21—C20—C18109.2 (4)C50—C49—Br8120.0 (4)
C22—C20—C18130.4 (5)C48—C49—Br8117.7 (4)
C25—C21—C20120.8 (4)C46—C50—C49117.5 (5)
C25—C21—C9128.6 (4)C46—C50—H50A121.2
C20—C21—C9110.5 (4)C49—C50—H50A121.2
C23—C22—C20119.0 (5)C56—C51—C52117.3 (7)
C23—C22—H22A120.5C56—C51—C57119.7 (7)
C20—C22—H22A120.5C52—C51—C57123.0 (7)
C24—C23—C22119.6 (5)C53—C52—C51120.5 (8)
C24—C23—H23A120.2C53—C52—H52A119.7
C22—C23—H23A120.2C51—C52—H52A119.7
C23—C24—C25122.4 (5)C54—C53—C52121.4 (8)
C23—C24—Br4118.0 (4)C54—C53—H53A119.3
C25—C24—Br4119.6 (4)C52—C53—H53A119.3
C21—C25—C24117.8 (5)C53—C54—C55118.8 (8)
C21—C25—H25A121.1C53—C54—H54A120.6
C24—C25—H25A121.1C55—C54—H54A120.6
C31—C26—C27118.3 (4)C54—C55—C56120.4 (7)
C31—C26—H26A120.8C54—C55—H55A119.8
C27—C26—H26A120.8C56—C55—H55A119.8
C28—C27—C26121.8 (4)C55—C56—C51121.4 (6)
C28—C27—Br5119.8 (4)C55—C56—H56A119.3
C26—C27—Br5118.4 (4)C51—C56—H56A119.3
C27—C28—C29119.8 (5)C51—C57—H57A109.5
C27—C28—H28A120.1C51—C57—H57B109.5
C29—C28—H28A120.1H57A—C57—H57B109.5
C28—C29—C30119.3 (5)C51—C57—H57C109.5
C28—C29—H29A120.4H57A—C57—H57C109.5
C30—C29—H29A120.4H57B—C57—H57C109.5

Experimental details

Crystal data
Chemical formulaC25H12Br4·0.5C7H8
Mr678.06
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.6593 (18), 29.549 (4), 11.3753 (14)
β (°) 96.878 (2)
V3)4891.9 (10)
Z8
Radiation typeMo Kα
µ (mm1)6.60
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART-CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.189, 0.438
No. of measured, independent and
observed [I > 2σ(I)] reflections
20291, 8616, 5479
Rint0.045
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.091, 1.01
No. of reflections8616
No. of parameters586
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top
C19—C9—C8112.9 (3)C31—C34—C33100.9 (4)
C19—C9—C21101.0 (4)C31—C34—C46114.2 (4)
C8—C9—C21116.8 (4)C33—C34—C46116.9 (4)
C19—C9—C6113.4 (4)C31—C34—C44113.7 (4)
C8—C9—C6101.6 (3)C33—C34—C44110.2 (4)
C21—C9—C6111.6 (3)C46—C34—C44101.5 (4)
 

Acknowledgements

The authors thank Professors Bo Liu and Jianping Guo for supporting this work.

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationMarsitzky, D. & Carter, K. R. (2001). Polym. Prepr. 42, 450–451.  CAS
First citationHagen, J., Schaffrach, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H.-W. & Haarer, D. (1997). Synth. Met. 89, 215–220.  CrossRef CAS Web of Science
First citationIour, J. M., Wu, R. L. & Schumn, J. S. (1990). J. Am. Chem. Soc. 112, 5662–5663.
First citationPudzich, R., Fuhrmann-Lieker, T. & Salbeck, J. (2006). Adv. Polym. Sci. 199, 83–142.  Web of Science CrossRef CAS
First citationSalbeck, J., Yu, N., Bauer, J., Weissortel, F. & Bestgen, H. (1997). Synth. Met. 91, 209–215.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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