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Acta Cryst. (2008). E64, o1665    [ doi:10.1107/S1600536808023970 ]

1,5-Bis(4-bromophenyl)-3-phenylpentane-1,5-dione

K.-Z. Li, Y.-T. Chen, C.-W. Zhao, G.-D. Wei and Q.-P. He

Abstract top

The asymmetric unit of the title compound, C23H18Br2O2, contains two independent molecules with slightly different conformations. In the absence of classical intermolecular interactions, the crystal packing is stabilized by van der Waals forces.

Comment top

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis, we describe in this paper a user-friendly, solvent-free protocol for the synthesis of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a a general method for the synthesis of 1,5-diketones, we obtained the title compound, (I). We present here its crystal structure.

In the molecule (Fig. 1), the bond lengths and angles (Table 1) are normal and correspond to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994), 1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al., 2006)

Related literature top

For the crystal structures of two related 1,5-diketones, see: Das et al. (1994); Huang et al. (2006).

Experimental top

4-Bromoacetophenone (10 mmol), freshly distilled benzaldehyde (5 mmol) and NaOH (10 mmol) were aggregated with glass paddle in an open flask. The resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. C23H18Br2O2: C 56.82, H 3.73%; Found: C 56.85, H 3.62%.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Two independent molecules (I) with the atom numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
1,5-Bis(4-bromophenyl)-3-phenylpentane-1,5-dione top
Crystal data top
C23H18Br2O2F000 = 1936
Mr = 486.19Dx = 1.611 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 26.460 (3) ÅCell parameters from 3565 reflections
b = 6.2080 (17) Åθ = 2.5–24.0º
c = 26.320 (3) ŵ = 4.06 mm−1
β = 112.020 (2)ºT = 298 (2) K
V = 4008.0 (12) Å3Needle, colourless
Z = 80.40 × 0.35 × 0.18 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		6974 independent reflections
Radiation source: fine-focus sealed tube3492 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.114
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −31→31
Tmin = 0.294, Tmax = 0.529k = −7→7
18598 measured reflectionsl = −31→25
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)] = 0.099H-atom parameters constrained
wR(F2) = 0.301  w = 1/[σ2(Fo2) + (0.1338P)2 + 45.7826P]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.003
6974 reflectionsΔρmax = 0.98 e Å−3
487 parametersΔρmin = −1.01 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C23H18Br2O2V = 4008.0 (12) Å3
Mr = 486.19Z = 8
Monoclinic, P21/cMo Kα
a = 26.460 (3) ŵ = 4.06 mm−1
b = 6.2080 (17) ÅT = 298 (2) K
c = 26.320 (3) Å0.40 × 0.35 × 0.18 mm
β = 112.020 (2)º
Data collection top
Siemens SMART CCD area-detector
diffractometer		6974 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3492 reflections with I > 2σ(I)
Tmin = 0.294, Tmax = 0.529Rint = 0.114
18598 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.099H-atom parameters constrained
wR(F2) = 0.301  w = 1/[σ2(Fo2) + (0.1338P)2 + 45.7826P]
where P = (Fo2 + 2Fc2)/3
S = 0.93Δρmax = 0.98 e Å−3
6974 reflectionsΔρmin = −1.01 e Å−3
487 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
Br10.73025 (7)0.3535 (3)0.61892 (7)0.0740 (6)
Br20.37401 (6)0.3627 (3)0.99418 (7)0.0764 (6)
Br31.11853 (7)0.2623 (3)0.50238 (7)0.0784 (6)
Br40.74151 (7)0.2505 (3)0.84625 (8)0.0806 (6)
O10.6129 (4)1.0109 (15)0.7515 (4)0.057 (3)
O20.5077 (4)0.9997 (15)0.8761 (5)0.066 (3)
O31.0173 (4)0.9354 (15)0.6476 (4)0.054 (2)
O40.9006 (4)0.9293 (17)0.7644 (4)0.061 (3)
C10.5691 (4)0.8137 (19)0.8217 (5)0.042 (3)
H10.55090.95010.80680.050*
C20.6216 (5)0.8633 (19)0.8677 (5)0.039 (3)
C30.6304 (5)1.060 (2)0.8947 (6)0.051 (3)
H30.60321.16410.88310.062*
C40.6795 (6)1.106 (2)0.9395 (6)0.062 (4)
H40.68421.23850.95720.074*
C50.7200 (6)0.954 (3)0.9566 (6)0.062 (4)
H50.75240.98270.98590.074*
C60.7125 (6)0.760 (3)0.9303 (7)0.063 (4)
H60.74060.65970.94120.076*
C70.6646 (5)0.709 (2)0.8883 (5)0.046 (3)
H70.66000.57240.87300.056*
C80.5795 (6)0.690 (2)0.7748 (5)0.051 (3)
H8A0.59720.55450.78910.061*
H8B0.54470.65860.74590.061*
C90.6137 (5)0.811 (2)0.7511 (5)0.041 (3)
C100.6433 (5)0.6958 (19)0.7214 (5)0.042 (3)
C110.6838 (5)0.806 (2)0.7098 (5)0.046 (3)
H110.69350.94530.72270.056*
C120.7098 (5)0.703 (2)0.6782 (6)0.055 (4)
H120.73700.77320.67020.065*
C130.6944 (5)0.495 (2)0.6594 (5)0.045 (3)
C140.6569 (5)0.382 (2)0.6730 (5)0.047 (3)
H140.64930.23860.66240.056*
C150.6303 (5)0.4833 (18)0.7029 (5)0.041 (3)
H150.60350.40950.71090.049*
C160.5308 (5)0.6795 (19)0.8409 (5)0.042 (3)
H16A0.50160.62130.80910.051*
H16B0.55090.55940.86280.051*
C170.5065 (4)0.814 (2)0.8747 (5)0.037 (3)
C180.4766 (4)0.6866 (18)0.9039 (5)0.035 (3)
C190.4594 (4)0.4805 (19)0.8945 (5)0.039 (3)
H190.46970.39990.87020.046*
C200.4277 (5)0.383 (2)0.9188 (5)0.047 (3)
H200.41450.24390.90910.056*
C210.4159 (5)0.496 (2)0.9581 (5)0.049 (4)
C220.4335 (5)0.707 (2)0.9716 (6)0.055 (4)
H220.42530.78160.99820.066*
C230.4636 (5)0.802 (2)0.9445 (5)0.044 (3)
H230.47550.94360.95290.053*
C240.9374 (4)0.761 (2)0.6852 (5)0.038 (3)
H240.96240.87060.70800.046*
C250.8896 (4)0.8805 (19)0.6407 (5)0.038 (3)
C260.8384 (5)0.781 (2)0.6185 (6)0.054 (4)
H260.83250.64670.63100.065*
C270.7960 (6)0.888 (3)0.5768 (6)0.066 (4)
H270.76170.82560.56180.079*
C280.8050 (6)1.079 (3)0.5588 (6)0.064 (4)
H280.77701.14360.52980.076*
C290.8540 (7)1.186 (2)0.5814 (7)0.071 (5)
H290.85891.32300.56980.085*
C300.8965 (6)1.0765 (19)0.6230 (6)0.051 (3)
H300.93041.14290.63860.062*
C310.9696 (4)0.6227 (19)0.6584 (5)0.039 (3)
H31A0.99140.51900.68530.047*
H31B0.94360.54210.62840.047*
C321.0069 (5)0.742 (2)0.6365 (5)0.044 (3)
C331.0324 (4)0.624 (2)0.6030 (5)0.040 (3)
C341.0175 (5)0.418 (2)0.5843 (5)0.045 (3)
H340.98970.34890.59150.054*
C351.0436 (5)0.314 (2)0.5549 (6)0.053 (4)
H351.03390.17310.54300.064*
C361.0838 (5)0.415 (2)0.5429 (5)0.047 (3)
C371.1004 (5)0.618 (3)0.5617 (5)0.056 (4)
H371.12830.68540.55440.067*
C381.0745 (5)0.719 (2)0.5920 (5)0.049 (3)
H381.08590.85650.60550.058*
C390.9204 (5)0.617 (2)0.7231 (5)0.043 (3)
H39A0.89650.50480.70140.051*
H39B0.95260.54790.74910.051*
C400.8916 (4)0.738 (2)0.7544 (5)0.043 (3)
C410.8558 (4)0.6114 (19)0.7764 (5)0.039 (3)
C420.8393 (5)0.403 (2)0.7599 (5)0.046 (3)
H420.85150.33190.73560.055*
C430.8043 (5)0.301 (2)0.7804 (5)0.047 (3)
H430.79280.16100.76940.057*
C440.7867 (5)0.405 (2)0.8165 (6)0.049 (3)
C450.8037 (6)0.611 (2)0.8350 (6)0.059 (4)
H450.79320.67770.86110.071*
C460.8373 (5)0.713 (2)0.8129 (5)0.044 (3)
H460.84770.85500.82290.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0720 (11)0.0805 (12)0.0863 (12)−0.0038 (9)0.0490 (10)−0.0211 (9)
Br20.0631 (10)0.1033 (14)0.0771 (12)−0.0008 (9)0.0424 (9)0.0248 (10)
Br30.0795 (11)0.1037 (14)0.0675 (11)0.0286 (10)0.0453 (9)−0.0057 (9)
Br40.0786 (11)0.0765 (12)0.1146 (15)−0.0054 (9)0.0681 (11)0.0137 (10)
O10.076 (7)0.046 (6)0.070 (7)−0.008 (5)0.052 (6)−0.014 (5)
O20.061 (6)0.028 (6)0.115 (9)0.010 (4)0.041 (6)−0.004 (5)
O30.059 (6)0.050 (6)0.070 (6)−0.014 (4)0.043 (5)−0.010 (5)
O40.081 (7)0.047 (6)0.069 (7)−0.013 (5)0.045 (6)−0.005 (5)
C10.031 (6)0.035 (7)0.064 (9)−0.008 (5)0.023 (6)−0.016 (6)
C20.041 (7)0.030 (7)0.056 (8)0.000 (5)0.028 (6)−0.001 (6)
C30.043 (8)0.047 (9)0.067 (10)0.001 (6)0.023 (7)−0.008 (7)
C40.065 (10)0.052 (10)0.070 (11)−0.022 (8)0.028 (9)−0.014 (8)
C50.049 (9)0.077 (12)0.050 (9)−0.013 (8)0.008 (7)−0.004 (8)
C60.057 (9)0.053 (10)0.082 (11)−0.002 (7)0.029 (9)0.013 (9)
C70.048 (8)0.040 (8)0.055 (9)−0.007 (6)0.025 (7)−0.002 (6)
C80.070 (9)0.040 (8)0.042 (8)−0.010 (6)0.020 (7)−0.001 (6)
C90.049 (8)0.037 (9)0.038 (7)−0.003 (6)0.018 (6)0.001 (6)
C100.040 (7)0.040 (8)0.044 (8)−0.011 (5)0.013 (6)−0.009 (6)
C110.044 (7)0.035 (8)0.064 (9)−0.004 (5)0.025 (7)0.008 (6)
C120.056 (8)0.060 (10)0.059 (9)0.003 (7)0.035 (7)0.012 (7)
C130.041 (7)0.044 (8)0.052 (8)−0.005 (6)0.021 (6)−0.003 (6)
C140.057 (8)0.044 (8)0.043 (8)−0.006 (6)0.023 (7)−0.004 (6)
C150.049 (7)0.030 (7)0.045 (8)−0.017 (6)0.019 (6)0.002 (6)
C160.042 (7)0.040 (8)0.051 (8)0.003 (5)0.024 (6)0.006 (6)
C170.027 (6)0.034 (8)0.040 (7)0.001 (5)0.001 (5)−0.003 (5)
C180.030 (6)0.038 (8)0.034 (7)0.004 (5)0.010 (5)−0.001 (5)
C190.036 (7)0.035 (8)0.045 (8)−0.005 (5)0.015 (6)−0.012 (6)
C200.055 (8)0.040 (8)0.043 (8)−0.014 (6)0.016 (7)−0.004 (6)
C210.030 (7)0.072 (10)0.046 (8)0.001 (6)0.016 (6)0.018 (7)
C220.061 (9)0.056 (10)0.058 (9)−0.002 (7)0.035 (8)−0.022 (7)
C230.045 (7)0.048 (8)0.042 (7)−0.012 (6)0.019 (6)−0.014 (6)
C240.025 (6)0.039 (7)0.053 (8)−0.001 (5)0.018 (6)−0.003 (6)
C250.032 (6)0.042 (8)0.049 (8)−0.002 (5)0.026 (6)0.002 (6)
C260.044 (8)0.052 (9)0.062 (9)0.003 (6)0.017 (7)0.005 (7)
C270.045 (8)0.097 (14)0.047 (9)0.010 (8)0.007 (7)−0.017 (9)
C280.059 (10)0.063 (11)0.070 (11)0.042 (8)0.025 (9)0.026 (9)
C290.097 (13)0.040 (9)0.084 (12)0.025 (9)0.044 (11)0.010 (8)
C300.061 (9)0.025 (7)0.069 (10)0.008 (6)0.025 (8)0.010 (6)
C310.031 (6)0.037 (7)0.049 (8)−0.001 (5)0.016 (6)0.007 (6)
C320.050 (8)0.033 (8)0.046 (8)−0.020 (6)0.015 (6)−0.012 (6)
C330.031 (6)0.042 (8)0.048 (8)0.003 (5)0.016 (6)0.013 (6)
C340.048 (7)0.042 (8)0.059 (9)0.010 (6)0.035 (7)0.001 (6)
C350.060 (9)0.047 (9)0.058 (9)0.011 (7)0.029 (7)0.004 (7)
C360.043 (7)0.065 (10)0.040 (8)0.021 (7)0.024 (6)0.003 (7)
C370.045 (8)0.083 (11)0.052 (9)−0.015 (7)0.032 (7)−0.019 (8)
C380.041 (7)0.056 (9)0.055 (8)−0.017 (6)0.024 (7)−0.009 (7)
C390.042 (7)0.047 (8)0.049 (8)0.011 (6)0.030 (6)0.011 (6)
C400.029 (6)0.056 (10)0.047 (8)0.011 (6)0.016 (6)0.018 (7)
C410.035 (6)0.032 (7)0.062 (8)0.005 (5)0.031 (6)0.005 (6)
C420.049 (8)0.043 (8)0.049 (8)0.006 (6)0.024 (7)0.000 (6)
C430.052 (8)0.040 (8)0.057 (9)−0.006 (6)0.029 (7)−0.003 (6)
C440.045 (7)0.046 (9)0.063 (9)0.007 (6)0.028 (7)0.024 (7)
C450.069 (9)0.055 (10)0.067 (10)0.011 (7)0.043 (8)0.013 (8)
C460.056 (8)0.031 (8)0.046 (8)−0.002 (6)0.021 (7)−0.007 (6)
Geometric parameters (Å, °) top
Br1—C131.889 (12)C21—C221.387 (19)
Br2—C211.900 (11)C22—C231.386 (17)
Br3—C361.902 (11)C22—H220.9300
Br4—C441.914 (11)C23—H230.9300
O1—C91.240 (14)C24—C391.526 (15)
O2—C171.156 (13)C24—C311.556 (15)
O3—C321.240 (14)C24—C251.553 (16)
O4—C401.223 (15)C24—H240.9800
C1—C21.494 (17)C25—C301.340 (16)
C1—C161.536 (15)C25—C261.403 (17)
C1—C81.561 (16)C26—C271.41 (2)
C1—H10.9800C26—H260.9300
C2—C31.385 (17)C27—C281.33 (2)
C2—C71.427 (17)C27—H270.9300
C3—C41.420 (19)C28—C291.38 (2)
C3—H30.9300C28—H280.9300
C4—C51.37 (2)C29—C301.42 (2)
C4—H40.9300C29—H290.9300
C5—C61.36 (2)C30—H300.9300
C5—H50.9300C31—C321.511 (15)
C6—C71.37 (2)C31—H31A0.9700
C6—H60.9300C31—H31B0.9700
C7—H70.9300C32—C331.488 (16)
C8—C91.481 (16)C33—C341.375 (17)
C8—H8A0.9700C33—C381.384 (15)
C8—H8B0.9700C34—C351.377 (16)
C9—C101.482 (16)C34—H340.9300
C10—C111.398 (15)C35—C361.370 (17)
C10—C151.403 (16)C35—H350.9300
C11—C121.418 (17)C36—C371.363 (19)
C11—H110.9300C37—C381.382 (16)
C12—C131.384 (18)C37—H370.9300
C12—H120.9300C38—H380.9300
C13—C141.371 (16)C39—C401.516 (16)
C14—C151.389 (16)C39—H39A0.9700
C14—H140.9300C39—H39B0.9700
C15—H150.9300C40—C411.503 (15)
C16—C171.527 (16)C41—C421.384 (17)
C16—H16A0.9700C41—C461.385 (15)
C16—H16B0.9700C42—C431.384 (16)
C17—C181.514 (16)C42—H420.9300
C18—C191.349 (16)C43—C441.369 (17)
C18—C231.434 (15)C43—H430.9300
C19—C201.372 (16)C44—C451.38 (2)
C19—H190.9300C45—C461.383 (17)
C20—C211.381 (17)C45—H450.9300
C20—H200.9300C46—H460.9300
C2—C1—C16111.9 (11)C39—C24—C31108.5 (9)
C2—C1—C8110.8 (9)C39—C24—C25114.6 (8)
C16—C1—C8109.1 (9)C31—C24—C25110.6 (9)
C2—C1—H1108.3C39—C24—H24107.6
C16—C1—H1108.3C31—C24—H24107.6
C8—C1—H1108.3C25—C24—H24107.6
C3—C2—C7116.0 (12)C30—C25—C26119.5 (12)
C3—C2—C1121.5 (11)C30—C25—C24121.1 (11)
C7—C2—C1122.5 (11)C26—C25—C24119.4 (11)
C2—C3—C4121.9 (13)C25—C26—C27118.6 (14)
C2—C3—H3119.0C25—C26—H26120.7
C4—C3—H3119.0C27—C26—H26120.7
C5—C4—C3119.5 (14)C28—C27—C26120.2 (15)
C5—C4—H4120.3C28—C27—H27119.9
C3—C4—H4120.3C26—C27—H27119.9
C4—C5—C6119.6 (14)C27—C28—C29122.7 (14)
C4—C5—H5120.2C27—C28—H28118.7
C6—C5—H5120.2C29—C28—H28118.7
C7—C6—C5121.7 (14)C28—C29—C30116.8 (14)
C7—C6—H6119.1C28—C29—H29121.6
C5—C6—H6119.1C30—C29—H29121.6
C6—C7—C2121.1 (13)C25—C30—C29122.2 (14)
C6—C7—H7119.4C25—C30—H30118.9
C2—C7—H7119.4C29—C30—H30118.9
C9—C8—C1113.7 (10)C32—C31—C24116.7 (10)
C9—C8—H8A108.8C32—C31—H31A108.1
C1—C8—H8A108.8C24—C31—H31A108.1
C9—C8—H8B108.8C32—C31—H31B108.1
C1—C8—H8B108.8C24—C31—H31B108.1
H8A—C8—H8B107.7H31A—C31—H31B107.3
O1—C9—C8119.1 (11)O3—C32—C33120.5 (11)
O1—C9—C10120.2 (10)O3—C32—C31120.2 (11)
C8—C9—C10120.3 (11)C33—C32—C31119.3 (11)
C11—C10—C15119.5 (11)C34—C33—C38117.8 (11)
C11—C10—C9118.6 (11)C34—C33—C32122.6 (10)
C15—C10—C9121.9 (10)C38—C33—C32119.5 (11)
C10—C11—C12119.2 (12)C33—C34—C35120.2 (11)
C10—C11—H11120.4C33—C34—H34119.9
C12—C11—H11120.4C35—C34—H34119.9
C13—C12—C11119.1 (11)C36—C35—C34120.6 (13)
C13—C12—H12120.4C36—C35—H35119.7
C11—C12—H12120.4C34—C35—H35119.7
C14—C13—C12122.1 (12)C37—C36—C35120.9 (11)
C14—C13—Br1118.3 (10)C37—C36—Br3120.4 (9)
C12—C13—Br1119.4 (9)C35—C36—Br3118.7 (11)
C13—C14—C15119.0 (12)C36—C37—C38117.9 (11)
C13—C14—H14120.5C36—C37—H37121.1
C15—C14—H14120.5C38—C37—H37121.1
C14—C15—C10120.8 (11)C37—C38—C33122.6 (13)
C14—C15—H15119.6C37—C38—H38118.7
C10—C15—H15119.6C33—C38—H38118.7
C17—C16—C1111.7 (10)C40—C39—C24113.4 (10)
C17—C16—H16A109.3C40—C39—H39A108.9
C1—C16—H16A109.3C24—C39—H39A108.9
C17—C16—H16B109.3C40—C39—H39B108.9
C1—C16—H16B109.3C24—C39—H39B108.9
H16A—C16—H16B107.9H39A—C39—H39B107.7
O2—C17—C18121.2 (11)O4—C40—C41121.7 (11)
O2—C17—C16123.5 (11)O4—C40—C39120.1 (11)
C18—C17—C16115.2 (10)C41—C40—C39118.1 (12)
C19—C18—C23116.9 (10)C42—C41—C46119.6 (10)
C19—C18—C17127.3 (10)C42—C41—C40122.5 (11)
C23—C18—C17115.8 (10)C46—C41—C40117.8 (11)
C18—C19—C20123.9 (11)C41—C42—C43118.9 (11)
C18—C19—H19118.1C41—C42—H42120.5
C20—C19—H19118.1C43—C42—H42120.5
C21—C20—C19118.2 (12)C44—C43—C42120.4 (12)
C21—C20—H20120.9C44—C43—H43119.8
C19—C20—H20120.9C42—C43—H43119.8
C22—C21—C20121.7 (11)C43—C44—C45122.0 (11)
C22—C21—Br2119.0 (10)C43—C44—Br4118.4 (10)
C20—C21—Br2119.3 (10)C45—C44—Br4119.4 (10)
C21—C22—C23118.2 (11)C46—C45—C44117.0 (12)
C21—C22—H22120.9C46—C45—H45121.5
C23—C22—H22120.9C44—C45—H45121.5
C22—C23—C18121.0 (11)C45—C46—C41122.1 (12)
C22—C23—H23119.5C45—C46—H46119.0
C18—C23—H23119.5C41—C46—H46119.0
Acknowledgements top

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X071013).

references
References top

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Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61.

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