1,4-Dibromo-2,5-bis-(hex-yloxy)benzene.

In the centrosymmetric title compound, C(18)H(28)Br(2)O(2), the alkyl chains adopt a fully extended all-trans conformation and each of them is almost planar. In addition, the alkyl chains are coplanar with the benzene ring. Inter-molecular Br⋯Br inter-actions [3.410 (3) Å] are present, resulting in a one-dimensional supra-molecular architecture.

Related literature

For related literature, see: Ali et al. (2008 ▶); Brammer (2004 ▶); Desiraju & Parthasarathy (1989 ▶); Kuriger et al. (2008 ▶); Maruyama & Kawanishi (2002 ▶).

Experimental

Crystal data

C18H28Br2O2

M = 436.22

Triclinic,

a = 6.9638 (12) Å

b = 8.2581 (14) Å

c = 9.7321 (17) Å

α = 107.012 (2)°

β = 106.981 (2)°

γ = 99.193 (2)°

V = 493.11 (15) Å3

Z = 1

Mo Kα radiation

μ = 4.12 mm−1

T = 295 (2) K

0.28 × 0.27 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.391, T max = 0.764

3675 measured reflections

1818 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.063

S = 1.06

1818 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028730/si2104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028730/si2104Isup2.hkl

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

C18H28Br2O2	Z = 1
Mr = 436.22	F(000) = 222
Triclinic, P1	Dx = 1.469 Mg m−3
a = 6.9638 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2581 (14) Å	Cell parameters from 1772 reflections
c = 9.7321 (17) Å	θ = 2.3–26.0°
α = 107.012 (2)°	µ = 4.12 mm−1
β = 106.981 (2)°	T = 295 K
γ = 99.193 (2)°	Block, colourless
V = 493.11 (15) Å3	0.28 × 0.27 × 0.07 mm

Bruker SMART CCD diffractometer	1818 independent reflections
Radiation source: fine-focus sealed tube	1567 reflections with I > 2σ(I)
graphite	Rint = 0.018
phi and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.391, Tmax = 0.764	k = −9→9
3675 measured reflections	l = −11→11

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0346P)2 + 0.0096P] where P = (Fo2 + 2Fc2)/3
1818 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.07253 (4)	0.51292 (4)	−0.31314 (3)	0.05768 (13)
O1	0.3731 (2)	0.6878 (2)	0.00755 (19)	0.0577 (5)
C1	−0.1596 (3)	0.4127 (3)	−0.1410 (3)	0.0455 (6)
H1	−0.2656	0.3549	−0.2366	0.055*
C2	0.0292 (3)	0.5069 (3)	−0.1316 (3)	0.0418 (5)
C3	0.1932 (3)	0.5970 (3)	0.0107 (3)	0.0426 (5)
C4	0.5450 (3)	0.7726 (4)	0.1511 (3)	0.0513 (6)
H4A	0.5871	0.6864	0.1944	0.062*
H4B	0.5056	0.8560	0.2240	0.062*
C5	0.7229 (3)	0.8672 (3)	0.1183 (3)	0.0528 (6)
H5A	0.6775	0.9504	0.0722	0.063*
H5B	0.7610	0.7824	0.0455	0.063*
C6	0.9133 (3)	0.9647 (3)	0.2665 (3)	0.0539 (6)
H6A	0.8755	1.0516	0.3377	0.065*
H6B	0.9547	0.8817	0.3143	0.065*
C7	1.0979 (3)	1.0563 (3)	0.2370 (3)	0.0518 (6)
H7A	1.1351	0.9693	0.1653	0.062*
H7B	1.0564	1.1394	0.1894	0.062*
C8	1.2870 (4)	1.1524 (4)	0.3828 (3)	0.0662 (8)
H8A	1.3355	1.0679	0.4259	0.079*
H8B	1.2471	1.2326	0.4576	0.079*
C9	1.4646 (4)	1.2556 (5)	0.3548 (4)	0.0850 (10)
H9A	1.5032	1.1771	0.2795	0.127*
H9B	1.5824	1.3105	0.4494	0.127*
H9C	1.4200	1.3442	0.3179	0.127*

	U11	U22	U33	U12	U13	U23
Br1	0.05214 (17)	0.0815 (2)	0.03895 (16)	0.00640 (13)	0.01726 (12)	0.02627 (13)
O1	0.0382 (9)	0.0797 (12)	0.0427 (9)	−0.0082 (8)	0.0094 (7)	0.0224 (9)
C1	0.0369 (12)	0.0546 (14)	0.0350 (12)	0.0026 (10)	0.0057 (9)	0.0142 (11)
C2	0.0414 (12)	0.0529 (14)	0.0330 (11)	0.0089 (10)	0.0135 (10)	0.0199 (10)
C3	0.0354 (11)	0.0501 (13)	0.0392 (12)	0.0049 (10)	0.0115 (10)	0.0168 (11)
C4	0.0368 (12)	0.0633 (16)	0.0417 (13)	−0.0004 (11)	0.0082 (10)	0.0151 (12)
C5	0.0383 (12)	0.0654 (16)	0.0481 (14)	0.0015 (11)	0.0139 (11)	0.0193 (12)
C6	0.0399 (13)	0.0629 (17)	0.0504 (14)	0.0023 (12)	0.0136 (11)	0.0172 (13)
C7	0.0404 (13)	0.0562 (15)	0.0535 (15)	0.0043 (11)	0.0175 (11)	0.0160 (12)
C8	0.0437 (14)	0.0786 (19)	0.0592 (17)	−0.0001 (13)	0.0128 (13)	0.0150 (15)
C9	0.0468 (16)	0.095 (2)	0.086 (2)	−0.0123 (15)	0.0179 (16)	0.0156 (19)

Br1—C2	1.891 (2)	C5—H5B	0.9700
O1—C3	1.367 (2)	C6—C7	1.529 (3)
O1—C4	1.435 (3)	C6—H6A	0.9700
C1—C3i	1.377 (3)	C6—H6B	0.9700
C1—C2	1.379 (3)	C7—C8	1.514 (3)
C1—H1	0.9300	C7—H7A	0.9700
C2—C3	1.406 (3)	C7—H7B	0.9700
C3—C1i	1.377 (3)	C8—C9	1.525 (4)
C4—C5	1.522 (3)	C8—H8A	0.9700
C4—H4A	0.9700	C8—H8B	0.9700
C4—H4B	0.9700	C9—H9A	0.9600
C5—C6	1.533 (3)	C9—H9B	0.9600
C5—H5A	0.9700	C9—H9C	0.9600
C3—O1—C4	117.26 (18)	C7—C6—H6A	109.1
C3i—C1—C2	120.9 (2)	C5—C6—H6A	109.1
C3i—C1—H1	119.6	C7—C6—H6B	109.1
C2—C1—H1	119.6	C5—C6—H6B	109.1
C1—C2—C3	121.5 (2)	H6A—C6—H6B	107.9
C1—C2—Br1	119.81 (16)	C8—C7—C6	112.7 (2)
C3—C2—Br1	118.73 (16)	C8—C7—H7A	109.1
O1—C3—C1i	125.49 (19)	C6—C7—H7A	109.1
O1—C3—C2	116.8 (2)	C8—C7—H7B	109.1
C1i—C3—C2	117.70 (19)	C6—C7—H7B	109.1
O1—C4—C5	107.30 (19)	H7A—C7—H7B	107.8
O1—C4—H4A	110.3	C7—C8—C9	112.5 (3)
C5—C4—H4A	110.3	C7—C8—H8A	109.1
O1—C4—H4B	110.3	C9—C8—H8A	109.1
C5—C4—H4B	110.3	C7—C8—H8B	109.1
H4A—C4—H4B	108.5	C9—C8—H8B	109.1
C4—C5—C6	111.0 (2)	H8A—C8—H8B	107.8
C4—C5—H5A	109.4	C8—C9—H9A	109.5
C6—C5—H5A	109.4	C8—C9—H9B	109.5
C4—C5—H5B	109.4	H9A—C9—H9B	109.5
C6—C5—H5B	109.4	C8—C9—H9C	109.5
H5A—C5—H5B	108.0	H9A—C9—H9C	109.5
C7—C6—C5	112.4 (2)	H9B—C9—H9C	109.5
C3i—C1—C2—C3	−0.4 (4)	Br1—C2—C3—C1i	−178.52 (18)
C3i—C1—C2—Br1	178.49 (18)	C3—O1—C4—C5	−178.7 (2)
C4—O1—C3—C1i	3.4 (4)	O1—C4—C5—C6	179.1 (2)
C4—O1—C3—C2	−176.9 (2)	C4—C5—C6—C7	178.1 (2)
C1—C2—C3—O1	−179.4 (2)	C5—C6—C7—C8	−179.8 (2)
Br1—C2—C3—O1	1.7 (3)	C6—C7—C8—C9	−175.4 (2)
C1—C2—C3—C1i	0.4 (4)