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

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

doi:10.1107/S1600536808023970

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1665

doi:10.1107/S1600536808023970

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

Kao-Zhen Li,^a ^* Yu-Ting Chen,^b Chuan-Wen Zhao,^c Guo-Dong Wei ^d and Qing-Peng He ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, ^bDepartment of Chemsitry, Dezhou University, Dezhou 100835, People's Republic of China, ^cBureau of Quality and Technical Supervision, Liaocheng 252000, Shandong, People's Republic of China, and ^dShandong Donge Experimental High School, Donge, Shandong Province 252200, People's Republic of China
^*Correspondence e-mail: hxqqxh2008@163.com

(Received 17 July 2008; accepted 29 July 2008; online 6 August 2008)

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.

Related literature

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

Experimental

Crystal data

C₂₃H₁₈Br₂O₂
M_r = 486.19
Monoclinic, P 2₁ /c
a = 26.460 (3) Å
b = 6.2080 (17) Å
c = 26.320 (3) Å
β = 112.020 (2)°
V = 4008.0 (12) Å³
Z = 8
Mo Kα radiation
μ = 4.06 mm⁻¹
T = 298 (2) K
0.40 × 0.35 × 0.18 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.293, T_max = 0.529 (expected range = 0.267–0.482)
18598 measured reflections
6974 independent reflections
3492 reflections with I > 2σ(I)
R_int = 0.114

Refinement

R[F² > 2σ(F²)] = 0.099
wR(F²) = 0.301
S = 0.93
6974 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023970/cv2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023970/cv2434Isup2.hkl

checkCIF report

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%.

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

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

C₂₃H₁₈Br₂O₂	F(000) = 1936
M_r = 486.19	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.460 (3) Å	Cell parameters from 3565 reflections
b = 6.2080 (17) Å	θ = 2.5–24.0°
c = 26.320 (3) Å	µ = 4.06 mm⁻¹
β = 112.020 (2)°	T = 298 K
V = 4008.0 (12) Å³	Needle, colourless
Z = 8	0.40 × 0.35 × 0.18 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	6974 independent reflections
Radiation source: fine-focus sealed tube	3492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.114
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
T_min = 0.294, T_max = 0.529	k = −7→7
18598 measured reflections	l = −31→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.301	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1338P)² + 45.7826P] where P = (F_o² + 2F_c²)/3
6974 reflections	(Δ/σ)_max = 0.003
487 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −1.01 e Å⁻³

Crystal data top

C₂₃H₁₈Br₂O₂	V = 4008.0 (12) Å³
M_r = 486.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 26.460 (3) Å	µ = 4.06 mm⁻¹
b = 6.2080 (17) Å	T = 298 K
c = 26.320 (3) Å	0.40 × 0.35 × 0.18 mm
β = 112.020 (2)°

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)
T_min = 0.294, T_max = 0.529	R_int = 0.114
18598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.099	0 restraints
wR(F²) = 0.301	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.1338P)² + 45.7826P] where P = (F_o² + 2F_c²)/3
6974 reflections	Δρ_max = 0.98 e Å⁻³
487 parameters	Δρ_min = −1.01 e Å⁻³

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	0.73025 (7)	0.3535 (3)	0.61892 (7)	0.0740 (6)
Br2	0.37401 (6)	0.3627 (3)	0.99418 (7)	0.0764 (6)
Br3	1.11853 (7)	0.2623 (3)	0.50238 (7)	0.0784 (6)
Br4	0.74151 (7)	0.2505 (3)	0.84625 (8)	0.0806 (6)
O1	0.6129 (4)	1.0109 (15)	0.7515 (4)	0.057 (3)
O2	0.5077 (4)	0.9997 (15)	0.8761 (5)	0.066 (3)
O3	1.0173 (4)	0.9354 (15)	0.6476 (4)	0.054 (2)
O4	0.9006 (4)	0.9293 (17)	0.7644 (4)	0.061 (3)
C1	0.5691 (4)	0.8137 (19)	0.8217 (5)	0.042 (3)
H1	0.5509	0.9501	0.8068	0.050*
C2	0.6216 (5)	0.8633 (19)	0.8677 (5)	0.039 (3)
C3	0.6304 (5)	1.060 (2)	0.8947 (6)	0.051 (3)
H3	0.6032	1.1641	0.8831	0.062*
C4	0.6795 (6)	1.106 (2)	0.9395 (6)	0.062 (4)
H4	0.6842	1.2385	0.9572	0.074*
C5	0.7200 (6)	0.954 (3)	0.9566 (6)	0.062 (4)
H5	0.7524	0.9827	0.9859	0.074*
C6	0.7125 (6)	0.760 (3)	0.9303 (7)	0.063 (4)
H6	0.7406	0.6597	0.9412	0.076*
C7	0.6646 (5)	0.709 (2)	0.8883 (5)	0.046 (3)
H7	0.6600	0.5724	0.8730	0.056*
C8	0.5795 (6)	0.690 (2)	0.7748 (5)	0.051 (3)
H8A	0.5972	0.5545	0.7891	0.061*
H8B	0.5447	0.6586	0.7459	0.061*
C9	0.6137 (5)	0.811 (2)	0.7511 (5)	0.041 (3)
C10	0.6433 (5)	0.6958 (19)	0.7214 (5)	0.042 (3)
C11	0.6838 (5)	0.806 (2)	0.7098 (5)	0.046 (3)
H11	0.6935	0.9453	0.7227	0.056*
C12	0.7098 (5)	0.703 (2)	0.6782 (6)	0.055 (4)
H12	0.7370	0.7732	0.6702	0.065*
C13	0.6944 (5)	0.495 (2)	0.6594 (5)	0.045 (3)
C14	0.6569 (5)	0.382 (2)	0.6730 (5)	0.047 (3)
H14	0.6493	0.2386	0.6624	0.056*
C15	0.6303 (5)	0.4833 (18)	0.7029 (5)	0.041 (3)
H15	0.6035	0.4095	0.7109	0.049*
C16	0.5308 (5)	0.6795 (19)	0.8409 (5)	0.042 (3)
H16A	0.5016	0.6213	0.8091	0.051*
H16B	0.5509	0.5594	0.8628	0.051*
C17	0.5065 (4)	0.814 (2)	0.8747 (5)	0.037 (3)
C18	0.4766 (4)	0.6866 (18)	0.9039 (5)	0.035 (3)
C19	0.4594 (4)	0.4805 (19)	0.8945 (5)	0.039 (3)
H19	0.4697	0.3999	0.8702	0.046*
C20	0.4277 (5)	0.383 (2)	0.9188 (5)	0.047 (3)
H20	0.4145	0.2439	0.9091	0.056*
C21	0.4159 (5)	0.496 (2)	0.9581 (5)	0.049 (4)
C22	0.4335 (5)	0.707 (2)	0.9716 (6)	0.055 (4)
H22	0.4253	0.7816	0.9982	0.066*
C23	0.4636 (5)	0.802 (2)	0.9445 (5)	0.044 (3)
H23	0.4755	0.9436	0.9529	0.053*
C24	0.9374 (4)	0.761 (2)	0.6852 (5)	0.038 (3)
H24	0.9624	0.8706	0.7080	0.046*
C25	0.8896 (4)	0.8805 (19)	0.6407 (5)	0.038 (3)
C26	0.8384 (5)	0.781 (2)	0.6185 (6)	0.054 (4)
H26	0.8325	0.6467	0.6310	0.065*
C27	0.7960 (6)	0.888 (3)	0.5768 (6)	0.066 (4)
H27	0.7617	0.8256	0.5618	0.079*
C28	0.8050 (6)	1.079 (3)	0.5588 (6)	0.064 (4)
H28	0.7770	1.1436	0.5298	0.076*
C29	0.8540 (7)	1.186 (2)	0.5814 (7)	0.071 (5)
H29	0.8589	1.3230	0.5698	0.085*
C30	0.8965 (6)	1.0765 (19)	0.6230 (6)	0.051 (3)
H30	0.9304	1.1429	0.6386	0.062*
C31	0.9696 (4)	0.6227 (19)	0.6584 (5)	0.039 (3)
H31A	0.9914	0.5190	0.6853	0.047*
H31B	0.9436	0.5421	0.6284	0.047*
C32	1.0069 (5)	0.742 (2)	0.6365 (5)	0.044 (3)
C33	1.0324 (4)	0.624 (2)	0.6030 (5)	0.040 (3)
C34	1.0175 (5)	0.418 (2)	0.5843 (5)	0.045 (3)
H34	0.9897	0.3489	0.5915	0.054*
C35	1.0436 (5)	0.314 (2)	0.5549 (6)	0.053 (4)
H35	1.0339	0.1731	0.5430	0.064*
C36	1.0838 (5)	0.415 (2)	0.5429 (5)	0.047 (3)
C37	1.1004 (5)	0.618 (3)	0.5617 (5)	0.056 (4)
H37	1.1283	0.6854	0.5544	0.067*
C38	1.0745 (5)	0.719 (2)	0.5920 (5)	0.049 (3)
H38	1.0859	0.8565	0.6055	0.058*
C39	0.9204 (5)	0.617 (2)	0.7231 (5)	0.043 (3)
H39A	0.8965	0.5048	0.7014	0.051*
H39B	0.9526	0.5479	0.7491	0.051*
C40	0.8916 (4)	0.738 (2)	0.7544 (5)	0.043 (3)
C41	0.8558 (4)	0.6114 (19)	0.7764 (5)	0.039 (3)
C42	0.8393 (5)	0.403 (2)	0.7599 (5)	0.046 (3)
H42	0.8515	0.3319	0.7356	0.055*
C43	0.8043 (5)	0.301 (2)	0.7804 (5)	0.047 (3)
H43	0.7928	0.1610	0.7694	0.057*
C44	0.7867 (5)	0.405 (2)	0.8165 (6)	0.049 (3)
C45	0.8037 (6)	0.611 (2)	0.8350 (6)	0.059 (4)
H45	0.7932	0.6777	0.8611	0.071*
C46	0.8373 (5)	0.713 (2)	0.8129 (5)	0.044 (3)
H46	0.8477	0.8550	0.8229	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0720 (11)	0.0805 (12)	0.0863 (12)	−0.0038 (9)	0.0490 (10)	−0.0211 (9)
Br2	0.0631 (10)	0.1033 (14)	0.0771 (12)	−0.0008 (9)	0.0424 (9)	0.0248 (10)
Br3	0.0795 (11)	0.1037 (14)	0.0675 (11)	0.0286 (10)	0.0453 (9)	−0.0057 (9)
Br4	0.0786 (11)	0.0765 (12)	0.1146 (15)	−0.0054 (9)	0.0681 (11)	0.0137 (10)
O1	0.076 (7)	0.046 (6)	0.070 (7)	−0.008 (5)	0.052 (6)	−0.014 (5)
O2	0.061 (6)	0.028 (6)	0.115 (9)	0.010 (4)	0.041 (6)	−0.004 (5)
O3	0.059 (6)	0.050 (6)	0.070 (6)	−0.014 (4)	0.043 (5)	−0.010 (5)
O4	0.081 (7)	0.047 (6)	0.069 (7)	−0.013 (5)	0.045 (6)	−0.005 (5)
C1	0.031 (6)	0.035 (7)	0.064 (9)	−0.008 (5)	0.023 (6)	−0.016 (6)
C2	0.041 (7)	0.030 (7)	0.056 (8)	0.000 (5)	0.028 (6)	−0.001 (6)
C3	0.043 (8)	0.047 (9)	0.067 (10)	0.001 (6)	0.023 (7)	−0.008 (7)
C4	0.065 (10)	0.052 (10)	0.070 (11)	−0.022 (8)	0.028 (9)	−0.014 (8)
C5	0.049 (9)	0.077 (12)	0.050 (9)	−0.013 (8)	0.008 (7)	−0.004 (8)
C6	0.057 (9)	0.053 (10)	0.082 (11)	−0.002 (7)	0.029 (9)	0.013 (9)
C7	0.048 (8)	0.040 (8)	0.055 (9)	−0.007 (6)	0.025 (7)	−0.002 (6)
C8	0.070 (9)	0.040 (8)	0.042 (8)	−0.010 (6)	0.020 (7)	−0.001 (6)
C9	0.049 (8)	0.037 (9)	0.038 (7)	−0.003 (6)	0.018 (6)	0.001 (6)
C10	0.040 (7)	0.040 (8)	0.044 (8)	−0.011 (5)	0.013 (6)	−0.009 (6)
C11	0.044 (7)	0.035 (8)	0.064 (9)	−0.004 (5)	0.025 (7)	0.008 (6)
C12	0.056 (8)	0.060 (10)	0.059 (9)	0.003 (7)	0.035 (7)	0.012 (7)
C13	0.041 (7)	0.044 (8)	0.052 (8)	−0.005 (6)	0.021 (6)	−0.003 (6)
C14	0.057 (8)	0.044 (8)	0.043 (8)	−0.006 (6)	0.023 (7)	−0.004 (6)
C15	0.049 (7)	0.030 (7)	0.045 (8)	−0.017 (6)	0.019 (6)	0.002 (6)
C16	0.042 (7)	0.040 (8)	0.051 (8)	0.003 (5)	0.024 (6)	0.006 (6)
C17	0.027 (6)	0.034 (8)	0.040 (7)	0.001 (5)	0.001 (5)	−0.003 (5)
C18	0.030 (6)	0.038 (8)	0.034 (7)	0.004 (5)	0.010 (5)	−0.001 (5)
C19	0.036 (7)	0.035 (8)	0.045 (8)	−0.005 (5)	0.015 (6)	−0.012 (6)
C20	0.055 (8)	0.040 (8)	0.043 (8)	−0.014 (6)	0.016 (7)	−0.004 (6)
C21	0.030 (7)	0.072 (10)	0.046 (8)	0.001 (6)	0.016 (6)	0.018 (7)
C22	0.061 (9)	0.056 (10)	0.058 (9)	−0.002 (7)	0.035 (8)	−0.022 (7)
C23	0.045 (7)	0.048 (8)	0.042 (7)	−0.012 (6)	0.019 (6)	−0.014 (6)
C24	0.025 (6)	0.039 (7)	0.053 (8)	−0.001 (5)	0.018 (6)	−0.003 (6)
C25	0.032 (6)	0.042 (8)	0.049 (8)	−0.002 (5)	0.026 (6)	0.002 (6)
C26	0.044 (8)	0.052 (9)	0.062 (9)	0.003 (6)	0.017 (7)	0.005 (7)
C27	0.045 (8)	0.097 (14)	0.047 (9)	0.010 (8)	0.007 (7)	−0.017 (9)
C28	0.059 (10)	0.063 (11)	0.070 (11)	0.042 (8)	0.025 (9)	0.026 (9)
C29	0.097 (13)	0.040 (9)	0.084 (12)	0.025 (9)	0.044 (11)	0.010 (8)
C30	0.061 (9)	0.025 (7)	0.069 (10)	0.008 (6)	0.025 (8)	0.010 (6)
C31	0.031 (6)	0.037 (7)	0.049 (8)	−0.001 (5)	0.016 (6)	0.007 (6)
C32	0.050 (8)	0.033 (8)	0.046 (8)	−0.020 (6)	0.015 (6)	−0.012 (6)
C33	0.031 (6)	0.042 (8)	0.048 (8)	0.003 (5)	0.016 (6)	0.013 (6)
C34	0.048 (7)	0.042 (8)	0.059 (9)	0.010 (6)	0.035 (7)	0.001 (6)
C35	0.060 (9)	0.047 (9)	0.058 (9)	0.011 (7)	0.029 (7)	0.004 (7)
C36	0.043 (7)	0.065 (10)	0.040 (8)	0.021 (7)	0.024 (6)	0.003 (7)
C37	0.045 (8)	0.083 (11)	0.052 (9)	−0.015 (7)	0.032 (7)	−0.019 (8)
C38	0.041 (7)	0.056 (9)	0.055 (8)	−0.017 (6)	0.024 (7)	−0.009 (7)
C39	0.042 (7)	0.047 (8)	0.049 (8)	0.011 (6)	0.030 (6)	0.011 (6)
C40	0.029 (6)	0.056 (10)	0.047 (8)	0.011 (6)	0.016 (6)	0.018 (7)
C41	0.035 (6)	0.032 (7)	0.062 (8)	0.005 (5)	0.031 (6)	0.005 (6)
C42	0.049 (8)	0.043 (8)	0.049 (8)	0.006 (6)	0.024 (7)	0.000 (6)
C43	0.052 (8)	0.040 (8)	0.057 (9)	−0.006 (6)	0.029 (7)	−0.003 (6)
C44	0.045 (7)	0.046 (9)	0.063 (9)	0.007 (6)	0.028 (7)	0.024 (7)
C45	0.069 (9)	0.055 (10)	0.067 (10)	0.011 (7)	0.043 (8)	0.013 (8)
C46	0.056 (8)	0.031 (8)	0.046 (8)	−0.002 (6)	0.021 (7)	−0.007 (6)

Geometric parameters (Å, º) top

Br1—C13	1.889 (12)	C21—C22	1.387 (19)
Br2—C21	1.900 (11)	C22—C23	1.386 (17)
Br3—C36	1.902 (11)	C22—H22	0.9300
Br4—C44	1.914 (11)	C23—H23	0.9300
O1—C9	1.240 (14)	C24—C39	1.526 (15)
O2—C17	1.156 (13)	C24—C31	1.556 (15)
O3—C32	1.240 (14)	C24—C25	1.553 (16)
O4—C40	1.223 (15)	C24—H24	0.9800
C1—C2	1.494 (17)	C25—C30	1.340 (16)
C1—C16	1.536 (15)	C25—C26	1.403 (17)
C1—C8	1.561 (16)	C26—C27	1.41 (2)
C1—H1	0.9800	C26—H26	0.9300
C2—C3	1.385 (17)	C27—C28	1.33 (2)
C2—C7	1.427 (17)	C27—H27	0.9300
C3—C4	1.420 (19)	C28—C29	1.38 (2)
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.37 (2)	C29—C30	1.42 (2)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.36 (2)	C30—H30	0.9300
C5—H5	0.9300	C31—C32	1.511 (15)
C6—C7	1.37 (2)	C31—H31A	0.9700
C6—H6	0.9300	C31—H31B	0.9700
C7—H7	0.9300	C32—C33	1.488 (16)
C8—C9	1.481 (16)	C33—C34	1.375 (17)
C8—H8A	0.9700	C33—C38	1.384 (15)
C8—H8B	0.9700	C34—C35	1.377 (16)
C9—C10	1.482 (16)	C34—H34	0.9300
C10—C11	1.398 (15)	C35—C36	1.370 (17)
C10—C15	1.403 (16)	C35—H35	0.9300
C11—C12	1.418 (17)	C36—C37	1.363 (19)
C11—H11	0.9300	C37—C38	1.382 (16)
C12—C13	1.384 (18)	C37—H37	0.9300
C12—H12	0.9300	C38—H38	0.9300
C13—C14	1.371 (16)	C39—C40	1.516 (16)
C14—C15	1.389 (16)	C39—H39A	0.9700
C14—H14	0.9300	C39—H39B	0.9700
C15—H15	0.9300	C40—C41	1.503 (15)
C16—C17	1.527 (16)	C41—C42	1.384 (17)
C16—H16A	0.9700	C41—C46	1.385 (15)
C16—H16B	0.9700	C42—C43	1.384 (16)
C17—C18	1.514 (16)	C42—H42	0.9300
C18—C19	1.349 (16)	C43—C44	1.369 (17)
C18—C23	1.434 (15)	C43—H43	0.9300
C19—C20	1.372 (16)	C44—C45	1.38 (2)
C19—H19	0.9300	C45—C46	1.383 (17)
C20—C21	1.381 (17)	C45—H45	0.9300
C20—H20	0.9300	C46—H46	0.9300

C2—C1—C16	111.9 (11)	C39—C24—C31	108.5 (9)
C2—C1—C8	110.8 (9)	C39—C24—C25	114.6 (8)
C16—C1—C8	109.1 (9)	C31—C24—C25	110.6 (9)
C2—C1—H1	108.3	C39—C24—H24	107.6
C16—C1—H1	108.3	C31—C24—H24	107.6
C8—C1—H1	108.3	C25—C24—H24	107.6
C3—C2—C7	116.0 (12)	C30—C25—C26	119.5 (12)
C3—C2—C1	121.5 (11)	C30—C25—C24	121.1 (11)
C7—C2—C1	122.5 (11)	C26—C25—C24	119.4 (11)
C2—C3—C4	121.9 (13)	C25—C26—C27	118.6 (14)
C2—C3—H3	119.0	C25—C26—H26	120.7
C4—C3—H3	119.0	C27—C26—H26	120.7
C5—C4—C3	119.5 (14)	C28—C27—C26	120.2 (15)
C5—C4—H4	120.3	C28—C27—H27	119.9
C3—C4—H4	120.3	C26—C27—H27	119.9
C4—C5—C6	119.6 (14)	C27—C28—C29	122.7 (14)
C4—C5—H5	120.2	C27—C28—H28	118.7
C6—C5—H5	120.2	C29—C28—H28	118.7
C7—C6—C5	121.7 (14)	C28—C29—C30	116.8 (14)
C7—C6—H6	119.1	C28—C29—H29	121.6
C5—C6—H6	119.1	C30—C29—H29	121.6
C6—C7—C2	121.1 (13)	C25—C30—C29	122.2 (14)
C6—C7—H7	119.4	C25—C30—H30	118.9
C2—C7—H7	119.4	C29—C30—H30	118.9
C9—C8—C1	113.7 (10)	C32—C31—C24	116.7 (10)
C9—C8—H8A	108.8	C32—C31—H31A	108.1
C1—C8—H8A	108.8	C24—C31—H31A	108.1
C9—C8—H8B	108.8	C32—C31—H31B	108.1
C1—C8—H8B	108.8	C24—C31—H31B	108.1
H8A—C8—H8B	107.7	H31A—C31—H31B	107.3
O1—C9—C8	119.1 (11)	O3—C32—C33	120.5 (11)
O1—C9—C10	120.2 (10)	O3—C32—C31	120.2 (11)
C8—C9—C10	120.3 (11)	C33—C32—C31	119.3 (11)
C11—C10—C15	119.5 (11)	C34—C33—C38	117.8 (11)
C11—C10—C9	118.6 (11)	C34—C33—C32	122.6 (10)
C15—C10—C9	121.9 (10)	C38—C33—C32	119.5 (11)
C10—C11—C12	119.2 (12)	C33—C34—C35	120.2 (11)
C10—C11—H11	120.4	C33—C34—H34	119.9
C12—C11—H11	120.4	C35—C34—H34	119.9
C13—C12—C11	119.1 (11)	C36—C35—C34	120.6 (13)
C13—C12—H12	120.4	C36—C35—H35	119.7
C11—C12—H12	120.4	C34—C35—H35	119.7
C14—C13—C12	122.1 (12)	C37—C36—C35	120.9 (11)
C14—C13—Br1	118.3 (10)	C37—C36—Br3	120.4 (9)
C12—C13—Br1	119.4 (9)	C35—C36—Br3	118.7 (11)
C13—C14—C15	119.0 (12)	C36—C37—C38	117.9 (11)
C13—C14—H14	120.5	C36—C37—H37	121.1
C15—C14—H14	120.5	C38—C37—H37	121.1
C14—C15—C10	120.8 (11)	C37—C38—C33	122.6 (13)
C14—C15—H15	119.6	C37—C38—H38	118.7
C10—C15—H15	119.6	C33—C38—H38	118.7
C17—C16—C1	111.7 (10)	C40—C39—C24	113.4 (10)
C17—C16—H16A	109.3	C40—C39—H39A	108.9
C1—C16—H16A	109.3	C24—C39—H39A	108.9
C17—C16—H16B	109.3	C40—C39—H39B	108.9
C1—C16—H16B	109.3	C24—C39—H39B	108.9
H16A—C16—H16B	107.9	H39A—C39—H39B	107.7
O2—C17—C18	121.2 (11)	O4—C40—C41	121.7 (11)
O2—C17—C16	123.5 (11)	O4—C40—C39	120.1 (11)
C18—C17—C16	115.2 (10)	C41—C40—C39	118.1 (12)
C19—C18—C23	116.9 (10)	C42—C41—C46	119.6 (10)
C19—C18—C17	127.3 (10)	C42—C41—C40	122.5 (11)
C23—C18—C17	115.8 (10)	C46—C41—C40	117.8 (11)
C18—C19—C20	123.9 (11)	C41—C42—C43	118.9 (11)
C18—C19—H19	118.1	C41—C42—H42	120.5
C20—C19—H19	118.1	C43—C42—H42	120.5
C21—C20—C19	118.2 (12)	C44—C43—C42	120.4 (12)
C21—C20—H20	120.9	C44—C43—H43	119.8
C19—C20—H20	120.9	C42—C43—H43	119.8
C22—C21—C20	121.7 (11)	C43—C44—C45	122.0 (11)
C22—C21—Br2	119.0 (10)	C43—C44—Br4	118.4 (10)
C20—C21—Br2	119.3 (10)	C45—C44—Br4	119.4 (10)
C21—C22—C23	118.2 (11)	C46—C45—C44	117.0 (12)
C21—C22—H22	120.9	C46—C45—H45	121.5
C23—C22—H22	120.9	C44—C45—H45	121.5
C22—C23—C18	121.0 (11)	C45—C46—C41	122.1 (12)
C22—C23—H23	119.5	C45—C46—H46	119.0
C18—C23—H23	119.5	C41—C46—H46	119.0

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈Br₂O₂
M_r	486.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	26.460 (3), 6.2080 (17), 26.320 (3)
β (°)	112.020 (2)
V (Å³)	4008.0 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.06
Crystal size (mm)	0.40 × 0.35 × 0.18

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.294, 0.529
No. of measured, independent and observed [I > 2σ(I)] reflections	18598, 6974, 3492
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.099, 0.301, 0.93
No. of reflections	6974
No. of parameters	487
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1338P)² + 45.7826P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.98, −1.01

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

References

Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Crystallogr. 24, 511–515. CSD CrossRef CAS Web of Science Google Scholar
Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61. Web of Science CSD CrossRef IUCr Journals 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar