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Volume 64 
Part 12 
Page o2422  
December 2008  

Received 10 November 2008
Accepted 14 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.014 Å
R = 0.078
wR = 0.166
Data-to-parameter ratio = 16.2
Details
Open access

1-(3-Bromopropoxy)-4-chlorobenzene

aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: chemywg@126.com

In the molecule of the title compound, C8H8BrClO, the Cl atom lies slightly out of the aromatic ring plane [displacement = 0.072 (3) Å]. In the crystal structure, a [pi]-[pi] contact between the phenyl rings [centroid-centroid distance = 3.699 (3) Å] may stabilize the structure. There also exists a C-H...[pi] contact between the methylene group and the chlorophenyl ring.

Related literature

For general background, see: Zirngibl et al. (1988[Zirngibl, L., Fischer, J., Jahn, U. & Thiele, K. (1988). Ann. N. Y. Acad. Sci. 54, 63-73.]). For related structures, see: Menini & Gusevskaya (2006[Menini, L. & Gusevskaya, E. V. (2006). Appl. Catal. A Gen. 309, 122-128.]); Baggaley & Watts (1982[Baggaley, K. H. & Watts, E. A. (1982). European Patent Application EP0049060.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8BrClO

  • Mr = 235.50

  • Monoclinic, P 21 /c

  • a = 9.0680 (18) Å

  • b = 9.781 (2) Å

  • c = 10.238 (2) Å

  • [beta] = 98.01 (3)°

  • V = 899.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.81 mm-1

  • T = 294 (2) K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.327, Tmax = 0.382

  • 1726 measured reflections

  • 1620 independent reflections

  • 769 reflections with I > 2[sigma](I)

  • Rint = 0.060

  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.078

  • wR(F2) = 0.166

  • S = 1.00

  • 1620 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...Cg1i 0.97 2.88 3.665 (3) 138
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]. Cg1 is the centroid of the C3-C8 ring.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2572 ).


Acknowledgements

This research was financially supported by the Department of Science and Technology of Jiangsu Province (grant No. BE200830457) and the `863' project (grant No. 2007 A A02Z211) of the Ministry of Science and Technology of the People's Republic of China.

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.
Baggaley, K. H. & Watts, E. A. (1982). European Patent Application EP0049060.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Menini, L. & Gusevskaya, E. V. (2006). Appl. Catal. A Gen. 309, 122-128.  [CrossRef] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [CrossRef] [details]
Zirngibl, L., Fischer, J., Jahn, U. & Thiele, K. (1988). Ann. N. Y. Acad. Sci. 54, 63-73.  [CrossRef]


Acta Cryst (2008). E64, o2422  [ doi:10.1107/S1600536808037896 ]

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