[Journal logo]

Volume 66 
Part 2 
Page o386  
February 2010  

Received 10 January 2010
Accepted 12 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean [sigma](C-C) = 0.009 Å
R = 0.027
wR = 0.066
Data-to-parameter ratio = 12.6
Details
Open access

2,2,2-Tribromo-N-(2-chlorophenyl)acetamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C8H5Br3ClNO, the conformation of the N-H bond is syn to the 2-chloro substituent in the benzene ring. There are no classical intermolecular hydrogen bonds, but intramolecular N-H...Br and N-H...Cl contacts occur.

Related literature

For preparation of the title compound, see: Gowda et al. (2003[Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.]). For background to our studies on the effect of the ring and the side-chain substituents on the crystal structures of N-aromatic amides, see: Gowda et al. (2007[Gowda, B. T., Svoboda, I. & Fuess, H. (2007). Acta Cryst. E63, o3267.], 2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o3242.]). For the conformations of other amides, see: Brown (1966[Brown, C. J. (1966). Acta Cryst. 21, 442-445.]).

[Scheme 1]

Experimental

Crystal data
  • C8H5Br3ClNO

  • Mr = 406.31

  • Orthorhombic, P n a 21

  • a = 9.1947 (6) Å

  • b = 12.9645 (7) Å

  • c = 9.5213 (6) Å

  • V = 1134.98 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 10.86 mm-1

  • T = 299 K

  • 0.40 × 0.40 × 0.34 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.098, Tmax = 0.120

  • 4524 measured reflections

  • 1645 independent reflections

  • 1491 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.066

  • S = 1.07

  • 1645 reflections

  • 131 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.77 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 416 Friedel pairs

  • Flack parameter: 0.049 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...Br1 0.85 (3) 2.78 (8) 3.155 (6) 109 (6)
N1-H1N...Cl1 0.85 (3) 2.59 (7) 2.961 (5) 107 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5167 ).


Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

Brown, C. J. (1966). Acta Cryst. 21, 442-445.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o3242.  [CSD] [CrossRef] [details]
Gowda, B. T., Svoboda, I. & Fuess, H. (2007). Acta Cryst. E63, o3267.  [CSD] [CrossRef] [details]
Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2010). E66, o386  [ doi:10.1107/S1600536810001467 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.