1,4-Bis(3-chloro­prop­oxy)benzene

Wang, Y.

doi:10.1107/S1600536810050348

Volume 67
Part 1
Page o42
January 2011

Received 18 November 2010
Accepted 1 December 2010
Online 8 December 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.078
Data-to-parameter ratio = 20.6
Details

1,4-Bis(3-chloropropoxy)benzene

Yufei Wang ^a ^*

^aFaculty of Science, Rm No 207, Carslow Building F07, The University of Sydney, NSW 2006, Australia
Correspondence e-mail: wyuf2010@126.com

The molecule of the title compound, C₁₂H₁₆Cl₂O₂, has a center of inversion at the centroid of the benzene ring and the asymmetric unit contains one half-molecule. Intermolecular C-H [pi] interactions stabilize the crystal structure.

Related literature

For general background to the use of alkoxybenzene derivatives as intermediates in organic synthesis, see: Dudones & Pearson et al. (2000); Chen & Chao (1996); Jin et al. (2010; Rabindranath et al. (2006); Zhang & Tieke (2008); Zhu et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₂H₁₆Cl₂O₂
M_r = 263.15
Monoclinic, P 2₁ /c
a = 4.9813 (8) Å
b = 8.3200 (14) Å
c = 15.273 (2) Å
= 93.156 (6)°
V = 632.02 (17) Å³
Z = 2
Mo K radiation
= 0.50 mm^-1
T = 113 K
0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) T_min = 0.899, T_max = 0.916
5847 measured reflections
1502 independent reflections
1273 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.078
S = 1.07
1502 reflections
73 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl ring.

D-HA	D-H	HA	DA	D-HA
C4-H4ACg1ⁱ	0.99	2.74	3.577 (2)	143
Symmetry code: (i) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2000); 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: CrystalStructure (Rigaku, 2000); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2255 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Chen, S. A. & Chao, C. I. (1996). Synth. Met. 79, 93-96.
Dudones, J. D. & Pearson, A. J. (2000). Tetrahedron Lett. 41, 8037-8040.
Jin, Y., Xu, Y., Qiao, Z., Peng, J., Wang, B. & Cao, D. (2010). Polymer, 51, 5726-5733.
Rabindranath, A. R., Zhu, Y., Heim, I. & Tieke, B. (2006). Macromolecules, 39, 8250-8256.
Rigaku (2000). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, K. & Tieke, B. (2008). Macromolecules, 41, 7287-7295.
Zhu, Y., Rabindranath, A. R., Beyerlein, T. & Tieke, B. (2007). Macromolecules, 40, 6981-6989.

organic compounds