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Volume 64 
Part 2 
Page o424  
February 2008  

Received 14 December 2007
Accepted 7 January 2008
Online 11 January 2008

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Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.071
Data-to-parameter ratio = 18.7
Details
Open access

1,3,5-Trichloro-2-methoxybenzene

Sanjay Telu,a Sean Parkin,b Larry W. Robertsona and Hans-Joachim Lehmlera*

aDepartment of Occupational and Environmental Health, University of Iowa, 100 Oakdale Campus, 124 IREH, Iowa City, IA 52242-5000, USA, and bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USA
Correspondence e-mail: hans-joachim-lehmler@uiowa.edu

The methoxy group of the title compound, C7H5Cl3O, is rotated out of the plane of the aromatic ring system, with a dihedral angle of 84.11 (13)°, due to the two bulky ortho-chloro substituents.

Related literature

For similar structures of anisoles with two ortho-chloro substituents, see: Rissanen et al. (1987[Rissanen, K., Valkonen, J. & Knuutinen, J. (1987). Acta Cryst. C43, 1966-1968.]); Weller & Gerstner (1995[Weller, F. & Gerstner, E. (1995). Z. Kristallogr. 210, 629-629.]); Wieczorek (1980[Wieczorek, M. W. (1980). Acta Cryst. B36, 1515-1517.]). For other related literature, see: Brownlee et al. (1993[Brownlee, B. G., MacInnis, G. A. & Noton, L. R. (1993). Environ. Sci. Technol. 27, 2450-2455.]); Curtis et al. (1972[Curtis, R. F., Land, D. G., Griffiths, N. M., Gee, M., Robinson, D., Peel, J. L., Dennis, C. & Gee, J. M. (1972). Nature (London), 235, 223-224.]); Iimura et al. (1984[Iimura, Y., Sakurai, T., Asahi, K.-I., Takahashi, N. & Oka, H. (1984). Acta Cryst. C40, 2058-2061.]); Kolehmainen & Knuutinen (1983[Kolehmainen, E. & Knuutinen, J. (1983). Org. Magn. Reson. 21, 388-390.]); Oswald et al. (2005[Oswald, I. D. H., Allan, D. R., Day, G. M., Motherwell, W. D. S. & Parsons, S. (2005). Cryst. Growth Des. 5, 1055-1071.]); Pereira et al. (2000[Pereira, C. S., Marques, J. J. F. & San Romao, M. V. (2000). Crit. Rev. Microbiol. 26, 147-162.]); Rissanen et al. (1988[Rissanen, K., Valkonen, J. & Mannila, B. (1988). Acta Cryst. C44, 684-686.]); Vlachos et al. (2007[Vlachos, P., Kampioti, A., Kornaros, M. & Lyberatos, G. (2007). Eur. Food Res. Technol. 225, 653-663.]); Zhang et al. (2006[Zhang, L., Hu, R. & Yang, Z. (2006). Water Sci. Technol. 54, 335-344.]).

[Scheme 1]

Experimental

Crystal data

  • C7H5Cl3O

  • Mr = 211.46

  • Monoclinic, P 21 /n

  • a = 14.7538 (5) Å

  • b = 3.9846 (2) Å

  • c = 15.4810 (7) Å

  • [beta] = 115.5031 (19)°

  • V = 821.42 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.05 mm-1

  • T = 90.0 (2) K

  • 0.25 × 0.25 × 0.12 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.780, Tmax = 0.885

  • 13489 measured reflections

  • 1888 independent reflections

  • 1558 reflections with I > 2[sigma](I)

  • Rint = 0.020
Refinement

  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.070

  • S = 1.13

  • 1888 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: XP in SHELXTL (Sheldrick, 1994[Sheldrick, G. M. (1994). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELX97 and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2200 ).

Acknowledgements

This research was supported by grant Nos. ES05605, ES012475 and ES013661 from the National Institute of Environmental Health Sciences, NIH.

References

Brownlee, B. G., MacInnis, G. A. & Noton, L. R. (1993). Environ. Sci. Technol. 27, 2450-2455.  [CrossRef] [ChemPort]
Curtis, R. F., Land, D. G., Griffiths, N. M., Gee, M., Robinson, D., Peel, J. L., Dennis, C. & Gee, J. M. (1972). Nature (London), 235, 223-224.  [CrossRef] [ChemPort] [ISI]
Iimura, Y., Sakurai, T., Asahi, K.-I., Takahashi, N. & Oka, H. (1984). Acta Cryst. C40, 2058-2061.  [CrossRef] [details]
Kolehmainen, E. & Knuutinen, J. (1983). Org. Magn. Reson. 21, 388-390.  [CrossRef] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Oswald, I. D. H., Allan, D. R., Day, G. M., Motherwell, W. D. S. & Parsons, S. (2005). Cryst. Growth Des. 5, 1055-1071.  [CrossRef] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pereira, C. S., Marques, J. J. F. & San Romao, M. V. (2000). Crit. Rev. Microbiol. 26, 147-162.  [CrossRef] [PubMed]
Rissanen, K., Valkonen, J. & Knuutinen, J. (1987). Acta Cryst. C43, 1966-1968.  [CrossRef] [details]
Rissanen, K., Valkonen, J. & Mannila, B. (1988). Acta Cryst. C44, 684-686.  [CrossRef] [details]
Sheldrick, G. M. (1994). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vlachos, P., Kampioti, A., Kornaros, M. & Lyberatos, G. (2007). Eur. Food Res. Technol. 225, 653-663.  [ISI] [CrossRef] [ChemPort]
Weller, F. & Gerstner, E. (1995). Z. Kristallogr. 210, 629-629.  [ChemPort]
Wieczorek, M. W. (1980). Acta Cryst. B36, 1515-1517.  [CrossRef] [details] [ISI]
Zhang, L., Hu, R. & Yang, Z. (2006). Water Sci. Technol. 54, 335-344.  [PubMed] [ChemPort]

Acta Cryst (2008). E64, o424  [ doi:10.1107/S160053680800055X ]

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