1,4-Dibromo-2,5-dibut-oxy-benzene.

The asymmetric unit of the title compound, C(14)H(20)Br(2)O(2), contains one half-mol-ecule located on an inversion centre. The mol-ecule is essentially planar, with a maximum deviation from the best plane of the non-H atoms of 0.054 (2) Å for the O atoms. The but-oxy group adopts a fully extended all-trans conformation. In the crystal, mol-ecules are connected via C-Br⋯O halogen bonds [Br⋯O = 3.2393 (19) Å] into a two-dimensional corrugated network in the bc plane.

Related literature

For related structures, see: Choi et al. (2010 ▶); Fun et al. (2010 ▶); Li et al. (2008 ▶). For applications of dialk­oxy­benzenes, see: Brandon et al. (1997 ▶); Huang et al. (2007 ▶); Lightowler & Hird (2005 ▶); Promarak & Ruchirawat (2007 ▶). For the synthetic procedure, see: Lopez-Alvarado et al. (2002 ▶).

Experimental

Crystal data

C14H20Br2O2

M = 380.10

Monoclinic,

a = 8.3685 (4) Å

b = 12.6395 (5) Å

c = 7.1083 (3) Å

β = 96.461 (5)°

V = 747.10 (6) Å3

Z = 2

Cu Kα radiation

μ = 6.82 mm−1

T = 150 K

0.07 × 0.06 × 0.01 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.647, T max = 0.935

5426 measured reflections

1442 independent reflections

1303 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.07

1442 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033338/gk2508sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033338/gk2508Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033338/gk2508Isup3.cml

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

C14H20Br2O2	F(000) = 380
Mr = 380.10	Dx = 1.690 Mg m−3
Monoclinic, P21/c	Melting point = 343–345 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 8.3685 (4) Å	Cell parameters from 2679 reflections
b = 12.6395 (5) Å	θ = 3–71°
c = 7.1083 (3) Å	µ = 6.82 mm−1
β = 96.461 (5)°	T = 150 K
V = 747.10 (6) Å3	Plate, colourless
Z = 2	0.07 × 0.06 × 0.01 mm

Oxford Diffraction Gemini diffractometer	1442 independent reflections
Radiation source: fine-focus sealed tube	1303 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 71.6°, θmin = 5.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→10
Tmin = 0.647, Tmax = 0.935	k = −15→15
5426 measured reflections	l = −8→6

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.4756P] where P = (Fo2 + 2Fc2)/3
1442 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer 1986) with a nominal stability of 0.1 K.Cosier, J. & Glazer, A.M., (1986)., J. Appl. Cryst.105 107.

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	−0.15758 (3)	1.17923 (2)	0.20385 (4)	0.01819 (14)
O1	0.2931 (2)	0.90585 (15)	0.4561 (3)	0.0186 (4)
C1	−0.0674 (3)	1.0747 (2)	0.3762 (4)	0.0165 (6)
C2	0.0787 (3)	1.0299 (2)	0.3466 (4)	0.0170 (6)
H2	0.1301	1.0506	0.2431	0.020*
C3	0.1490 (3)	0.9538 (2)	0.4722 (4)	0.0160 (5)
C4	0.3733 (4)	0.9319 (2)	0.2931 (4)	0.0188 (6)
H4A	0.4017	1.0064	0.2949	0.023*
H4B	0.3034	0.9175	0.1776	0.023*
C5	0.5229 (3)	0.8644 (2)	0.3018 (4)	0.0199 (6)
H5A	0.4923	0.7904	0.2966	0.024*
H5B	0.5883	0.8766	0.4213	0.024*
C6	0.6222 (3)	0.8887 (2)	0.1394 (4)	0.0202 (6)
H6A	0.5590	0.8727	0.0198	0.024*
H6B	0.6483	0.9635	0.1403	0.024*
C7	0.7771 (4)	0.8243 (2)	0.1556 (5)	0.0249 (7)
H7A	0.8411	0.8413	0.2724	0.037*
H7B	0.8363	0.8409	0.0513	0.037*
H7C	0.7516	0.7503	0.1535	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.0183 (2)	0.01468 (19)	0.0219 (2)	0.00149 (10)	0.00335 (13)	0.00358 (10)
O1	0.0161 (10)	0.0183 (9)	0.0223 (10)	0.0030 (8)	0.0061 (8)	0.0029 (8)
C1	0.0200 (15)	0.0114 (12)	0.0174 (13)	0.0022 (10)	−0.0003 (10)	0.0031 (10)
C2	0.0185 (14)	0.0134 (12)	0.0200 (14)	−0.0002 (10)	0.0063 (11)	0.0002 (10)
C3	0.0149 (13)	0.0127 (12)	0.0202 (14)	0.0005 (10)	0.0012 (10)	−0.0017 (10)
C4	0.0209 (15)	0.0175 (13)	0.0188 (14)	−0.0002 (11)	0.0062 (11)	0.0010 (11)
C5	0.0193 (14)	0.0162 (13)	0.0243 (15)	0.0012 (11)	0.0036 (11)	0.0024 (11)
C6	0.0161 (14)	0.0181 (13)	0.0269 (15)	0.0005 (11)	0.0049 (11)	0.0008 (11)
C7	0.0216 (16)	0.0241 (16)	0.0305 (18)	0.0036 (12)	0.0085 (13)	−0.0015 (12)

Br1—C1	1.900 (3)	C5—C6	1.527 (4)
O1—C3	1.366 (3)	C5—H5A	0.9700
O1—C4	1.441 (3)	C5—H5B	0.9700
C1—C2	1.384 (4)	C6—C7	1.523 (4)
C1—C3i	1.386 (4)	C6—H6A	0.9700
C2—C3	1.397 (4)	C6—H6B	0.9700
C2—H2	0.9300	C7—H7A	0.9600
C4—C5	1.511 (4)	C7—H7B	0.9600
C4—H4A	0.9700	C7—H7C	0.9600
C4—H4B	0.9700
C3—O1—C4	117.5 (2)	C4—C5—H5A	109.2
C2—C1—C3i	122.2 (3)	C6—C5—H5A	109.2
C2—C1—Br1	118.7 (2)	C4—C5—H5B	109.2
C3i—C1—Br1	119.1 (2)	C6—C5—H5B	109.2
C1—C2—C3	120.0 (3)	H5A—C5—H5B	107.9
C1—C2—H2	120.0	C7—C6—C5	111.5 (2)
C3—C2—H2	120.0	C7—C6—H6A	109.3
O1—C3—C1i	117.8 (2)	C5—C6—H6A	109.3
O1—C3—C2	124.3 (3)	C7—C6—H6B	109.3
C1i—C3—C2	117.8 (3)	C5—C6—H6B	109.3
O1—C4—C5	107.3 (2)	H6A—C6—H6B	108.0
O1—C4—H4A	110.3	C6—C7—H7A	109.5
C5—C4—H4A	110.3	C6—C7—H7B	109.5
O1—C4—H4B	110.3	H7A—C7—H7B	109.5
C5—C4—H4B	110.3	C6—C7—H7C	109.5
H4A—C4—H4B	108.5	H7A—C7—H7C	109.5
C4—C5—C6	112.0 (2)	H7B—C7—H7C	109.5