2,3-Dibromo-1-[4-(2,3-dibromo-4,5-di-meth-oxy-benz-yl)-2,5-dimeth-oxy-benz-yl]-4,5-dimeth-oxy-benzene.

The mol-ecule of the title compound, C(26)H(26)Br(4)O(6), is located around a crystallographic inversion center. The dihedral angle between the central benzene ring and the outer benzene ring is 89.26 (1)°.

Related literature

For information related to the synthesis of the title compound, see: Ford & Davidson (1993 ▶); Glombitza et al. (1985 ▶); Akbaba et al. (2010 ▶); Balaydın et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C26H26Br4O6

M = 754.07

Monoclinic,

a = 11.193 (5) Å

b = 9.645 (4) Å

c = 13.212 (5) Å

β = 107.125 (5)°

V = 1363.1 (10) Å3

Z = 2

Mo Kα radiation

μ = 5.94 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.250, T max = 0.552

27932 measured reflections

2793 independent reflections

2564 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.125

S = 1.45

2793 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043758/gk2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043758/gk2308Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H26Br4O6	F(000) = 740
Mr = 754.07	Dx = 1.837 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6447 reflections
a = 11.193 (5) Å	θ = 2.7–26.4°
b = 9.645 (4) Å	µ = 5.94 mm−1
c = 13.212 (5) Å	T = 293 K
β = 107.125 (5)°	Prism, colourless
V = 1363.1 (10) Å3	0.3 × 0.2 × 0.1 mm
Z = 2

Rigaku R-AXIS RAPID-S diffractometer	2564 reflections with I > 2σ(I)
graphite	Rint = 0.080
ω scans	θmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→13
Tmin = 0.250, Tmax = 0.552	k = −12→12
27932 measured reflections	l = −16→16
2793 independent reflections

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.45	w = 1/[σ2(Fo2) + (0.0035P)2 + 2.976P] where P = (Fo2 + 2Fc2)/3
2793 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Br1	0.34470 (6)	0.34698 (9)	0.98736 (6)	0.0672 (3)
Br2	0.53324 (6)	0.33264 (8)	0.83484 (5)	0.0593 (2)
O1	0.6334 (4)	0.0000 (5)	1.2376 (3)	0.0564 (12)
O2	0.4301 (4)	0.1588 (5)	1.1761 (3)	0.0560 (12)
O3	1.0448 (4)	−0.2703 (5)	0.9540 (4)	0.0617 (13)
C1	0.6977 (5)	0.0659 (6)	1.0834 (4)	0.0404 (13)
H1	0.7682	0.0096	1.1038	0.049*
C2	0.6735 (5)	0.1422 (6)	0.9902 (4)	0.0387 (13)
C3	0.5684 (5)	0.2278 (6)	0.9617 (4)	0.0396 (13)
C4	0.4892 (5)	0.2351 (6)	1.0257 (5)	0.0429 (14)
C5	0.5125 (5)	0.1579 (6)	1.1164 (5)	0.0411 (14)
C6	0.6183 (5)	0.0727 (6)	1.1462 (5)	0.0431 (14)
C7	0.7351 (7)	−0.0943 (7)	1.2701 (6)	0.0602 (18)
H7A	0.7309	−0.1595	1.2142	0.09*
H7B	0.7307	−0.1431	1.3322	0.09*
H7C	0.8124	−0.044	1.2858	0.09*
C8	0.4678 (8)	0.2424 (9)	1.2687 (6)	0.076 (2)
H8A	0.5509	0.2169	1.3096	0.114*
H8B	0.4114	0.2284	1.3101	0.114*
H8C	0.4667	0.3382	1.2487	0.114*
C9	0.7554 (5)	0.1280 (7)	0.9173 (5)	0.0458 (15)
H9A	0.7093	0.0755	0.8556	0.055*
H9B	0.7691	0.22	0.8931	0.055*
C10	0.8809 (5)	0.0600 (7)	0.9629 (4)	0.0430 (14)
C11	0.9001 (6)	−0.0763 (6)	0.9392 (5)	0.0450 (14)
H11	0.8332	−0.1287	0.8988	0.054*
C12	1.0184 (5)	−0.1362 (6)	0.9752 (5)	0.0422 (14)
C13	0.9451 (7)	−0.3596 (7)	0.9009 (6)	0.0652 (19)
H13A	0.8909	−0.3738	0.9444	0.098*
H13B	0.9784	−0.4471	0.8874	0.098*
H13C	0.8986	−0.3182	0.835	0.098*

	U11	U22	U33	U12	U13	U23
Br1	0.0497 (4)	0.0838 (6)	0.0731 (5)	0.0230 (4)	0.0257 (4)	−0.0002 (4)
Br2	0.0595 (4)	0.0687 (5)	0.0533 (4)	0.0172 (3)	0.0221 (3)	0.0135 (3)
O1	0.063 (3)	0.062 (3)	0.055 (3)	0.009 (2)	0.035 (2)	0.015 (2)
O2	0.048 (3)	0.071 (3)	0.060 (3)	−0.007 (2)	0.034 (2)	−0.012 (2)
O3	0.056 (3)	0.055 (3)	0.078 (3)	0.005 (2)	0.025 (3)	−0.012 (2)
C1	0.040 (3)	0.043 (3)	0.044 (3)	0.005 (2)	0.020 (3)	0.000 (3)
C2	0.032 (3)	0.044 (3)	0.044 (3)	−0.006 (2)	0.017 (2)	−0.007 (3)
C3	0.039 (3)	0.044 (3)	0.036 (3)	0.000 (3)	0.010 (3)	−0.002 (3)
C4	0.032 (3)	0.050 (4)	0.048 (4)	0.004 (3)	0.012 (3)	−0.006 (3)
C5	0.033 (3)	0.049 (4)	0.047 (3)	−0.008 (3)	0.021 (3)	−0.012 (3)
C6	0.044 (3)	0.045 (3)	0.046 (3)	−0.006 (3)	0.022 (3)	−0.004 (3)
C7	0.070 (5)	0.055 (4)	0.060 (4)	0.004 (4)	0.025 (4)	0.004 (3)
C8	0.093 (6)	0.088 (6)	0.065 (5)	−0.004 (5)	0.053 (4)	−0.021 (4)
C9	0.036 (3)	0.065 (4)	0.042 (3)	0.007 (3)	0.020 (3)	0.007 (3)
C10	0.039 (3)	0.060 (4)	0.038 (3)	0.003 (3)	0.024 (3)	0.006 (3)
C11	0.042 (3)	0.055 (4)	0.043 (3)	0.000 (3)	0.020 (3)	−0.003 (3)
C12	0.045 (3)	0.045 (4)	0.043 (3)	0.007 (3)	0.023 (3)	0.002 (3)
C13	0.075 (5)	0.053 (4)	0.073 (5)	−0.001 (4)	0.031 (4)	−0.002 (4)

Br2—C3	1.897 (6)	C9—H9B	0.97
Br1—C4	1.886 (6)	C11—H11	0.93
O1—C6	1.363 (6)	C8—H8A	0.96
O1—C7	1.422 (5)	C8—H8B	0.96
O2—C5	1.379 (6)	C8—H8C	0.96
O2—C8	1.421 (5)	C1—C6	1.385 (5)
O3—C12	1.374 (5)	C1—C2	1.390 (6)
O3—C13	1.420 (6)	C1—H1	0.93
C12—C10i	1.392 (6)	C6—C5	1.400 (6)
C12—C11	1.393 (6)	C4—C5	1.370 (6)
C3—C4	1.394 (6)	C13—H13A	0.96
C3—C2	1.395 (6)	C13—H13B	0.96
C10—C11	1.383 (6)	C13—H13C	0.96
C10—C12i	1.392 (6)	C7—H7A	0.96
C10—C9	1.507 (6)	C7—H7B	0.96
C9—C2	1.518 (5)	C7—H7C	0.96
C9—H9A	0.97
C6—O1—C7	118.4 (5)	C6—C1—C2	120.9 (5)
C5—O2—C8	114.6 (5)	C6—C1—H1	119.6
C12—O3—C13	119.1 (5)	C2—C1—H1	119.6
O3—C12—C10i	115.5 (5)	C1—C2—C3	118.8 (5)
O3—C12—C11	124.1 (6)	C1—C2—C9	121.1 (5)
C10i—C12—C11	120.4 (5)	C3—C2—C9	120.0 (5)
C4—C3—C2	120.1 (5)	O1—C6—C1	125.0 (5)
C4—C3—Br2	120.3 (4)	O1—C6—C5	115.1 (5)
C2—C3—Br2	119.6 (4)	C1—C6—C5	119.9 (5)
C11—C10—C12i	118.8 (5)	C5—C4—C3	120.8 (5)
C11—C10—C9	120.8 (6)	C5—C4—Br1	118.2 (4)
C12i—C10—C9	120.2 (6)	C3—C4—Br1	120.9 (4)
C10—C9—C2	116.9 (5)	C4—C5—O2	120.7 (5)
C10—C9—H9A	108.1	C4—C5—C6	119.5 (5)
C2—C9—H9A	108.1	O2—C5—C6	119.7 (5)
C10—C9—H9B	108.1	O3—C13—H13A	109.5
C2—C9—H9B	108.1	O3—C13—H13B	109.5
H9A—C9—H9B	107.3	H13A—C13—H13B	109.5
C10—C11—C12	120.8 (6)	O3—C13—H13C	109.5
C10—C11—H11	119.6	H13A—C13—H13C	109.5
C12—C11—H11	119.6	H13B—C13—H13C	109.5
O2—C8—H8A	109.5	O1—C7—H7A	109.5
O2—C8—H8B	109.5	O1—C7—H7B	109.5
H8A—C8—H8B	109.5	H7A—C7—H7B	109.5
O2—C8—H8C	109.5	O1—C7—H7C	109.5
H8A—C8—H8C	109.5	H7A—C7—H7C	109.5
H8B—C8—H8C	109.5	H7B—C7—H7C	109.5
C13—O3—C12—C10i	173.5 (5)	C7—O1—C6—C5	176.8 (5)
C13—O3—C12—C11	−6.3 (9)	C2—C1—C6—O1	178.8 (5)
C11—C10—C9—C2	102.1 (7)	C2—C1—C6—C5	−0.5 (9)
C12i—C10—C9—C2	−81.7 (7)	C2—C3—C4—C5	−0.7 (9)
C12i—C10—C11—C12	−0.9 (9)	Br2—C3—C4—C5	178.8 (4)
C9—C10—C11—C12	175.4 (5)	C2—C3—C4—Br1	−178.7 (4)
O3—C12—C11—C10	−179.3 (5)	Br2—C3—C4—Br1	0.8 (7)
C10i—C12—C11—C10	0.9 (9)	C3—C4—C5—O2	−176.0 (5)
C6—C1—C2—C3	1.0 (8)	Br1—C4—C5—O2	2.0 (8)
C6—C1—C2—C9	−175.9 (5)	C3—C4—C5—C6	1.2 (9)
C4—C3—C2—C1	−0.4 (8)	Br1—C4—C5—C6	179.3 (4)
Br2—C3—C2—C1	−179.9 (4)	C8—O2—C5—C4	−102.1 (7)
C4—C3—C2—C9	176.5 (5)	C8—O2—C5—C6	80.7 (7)
Br2—C3—C2—C9	−3.0 (7)	O1—C6—C5—C4	180.0 (5)
C10—C9—C2—C1	−16.1 (8)	C1—C6—C5—C4	−0.7 (9)
C10—C9—C2—C3	167.1 (5)	O1—C6—C5—O2	−2.8 (8)
C7—O1—C6—C1	−2.6 (9)	C1—C6—C5—O2	176.6 (5)