1,4-Dibromo-2,5-bis­(hex­yloxy)benzene

Li, Y.-F.; Xu, C.; Cen, F.-F.; Wang, Z.-Q.; Zhang, Y.-Q.

doi:10.1107/S1600536808028730

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1930

doi:10.1107/S1600536808028730

Open

access

1,4-Dibromo-2,5-bis(hexyloxy)benzene

Ying-Fei Li,^a Chen Xu,^b ^* Fei-Fei Cen,^a Zhi-Qiang Wang ^b and Yu-Qing Zhang ^a ^*

^aChemical Engineering and Pharmaceutics School, Henan University of Science and Technology, Luoyang 471003, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
^*Correspondence e-mail: xubohan@163.com, zhangyq8@126.com

(Received 14 August 2008; accepted 8 September 2008; online 13 September 2008)

In the centrosymmetric title compound, C₁₈H₂₈Br₂O₂, 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. Intermolecular Br⋯Br interactions [3.410 (3) Å] are present, resulting in a one-dimensional supramolecular 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_r = 436.22
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.063
S = 1.06
1818 reflections
101 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Noncovalent interactions play an important role in designing superstructures (Brammer, 2004). Among these weak forces, the intermolecular interactions between halogen atoms have been a subject of interest (Desiraju et al., 1989). In order to gain more insight into the structure-regulating ability of intermolecular Br···Br interactions, herein we report the crystal structure of the title compound.

A view of the centrosymmetric molecular structure of the title compound is given in Fig.1. The alkyl chains are in the fully extended all-trans conformation and each of them is almost perfectly planar. The C—C—O—C torsion angles of 3.4 (4)^o, indicate that the two alkyl chains are coplanar with the benzene ring. The crystal structure of the titile compound reveals the presence of a near linear C—Br···Br fragment[C—Br···Br=155.6 (3)^o], the Br···Br distance (3.410 Å) is shorter than the sum of van der Waals radii(3.72 Å) and those in the other compound [3.634 (4)–3.9527 (9) Å](Kuriger et al., 2008; Ali et al., 2008). Owing to the intermolecular Br···Br interactions, the crystal structure of the title compound is extended to a one-dimensional chain structure. The chains are intercalated by van der Waals forces (Fig.2).

Related literature top

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

Experimental top

The title compound was prepared as described in literature (Maruyama & Kawanishi 2002) and recrystallized from dichloromethane-ethanol at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level. Inversion related atoms are labelled with an A. (Symmetry code: -x, 1 - y, -z).
	Fig. 2. Partial view of the crystal packing showing the formation of the infinite chains of molecules formed by the intermolecular Br···Br interactions. Intercalated neighboring chains complete the sheets in the structure running parallel to (100). H atoms have been omitted for clarity.

1,4-Dibromo-2,5-bis(hexyloxy)benzene top

Crystal data top

C₁₈H₂₈Br₂O₂	Z = 1
M_r = 436.22	F(000) = 222
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0346P)² + 0.0096P] where P = (F_o² + 2F_c²)/3
1818 reflections	(Δ/σ)_max = 0.001
101 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₂₈Br₂O₂	γ = 99.193 (2)°
M_r = 436.22	V = 493.11 (15) Å³
Triclinic, P1	Z = 1
a = 6.9638 (12) Å	Mo Kα radiation
b = 8.2581 (14) Å	µ = 4.12 mm⁻¹
c = 9.7321 (17) Å	T = 295 K
α = 107.012 (2)°	0.28 × 0.27 × 0.07 mm
β = 106.981 (2)°

Data collection top

Bruker SMART CCD diffractometer	1818 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1567 reflections with I > 2σ(I)
T_min = 0.391, T_max = 0.764	R_int = 0.018
3675 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
1818 reflections	Δρ_min = −0.23 e Å⁻³
101 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₈Br₂O₂
M_r	436.22
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.9638 (12), 8.2581 (14), 9.7321 (17)
α, β, γ (°)	107.012 (2), 106.981 (2), 99.193 (2)
V (Å³)	493.11 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.12
Crystal size (mm)	0.28 × 0.27 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.391, 0.764
No. of measured, independent and observed [I > 2σ(I)] reflections	3675, 1818, 1567
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.063, 1.06
No. of reflections	1818
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Doctoral Foundation of Luoyang Normal University.

References

Ali, B. F., Al-Far, R. H. & Haddad, S. F. (2008). Acta Cryst. E64, m751–m752. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brammer, L. (2004). Chem. Soc. Rev. 33, 476–489. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. & Parthasarathy, R. (1989). J. Am. Chem. Soc. 111, 8725–8726. CrossRef CAS Web of Science Google Scholar
Kuriger, T. M., Moratti, S. C. & Simpson, J. (2008). Acta Cryst. E64, o709. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maruyama, S. & Kawanishi, Y. (2002). J. Mater. Chem. 12, 2245–2249. Web of Science CrossRef CAS 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