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

Gowda, B.T.; Foro, S.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536810001467

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 (C-C) = 0.009 Å
R = 0.027
wR = 0.066
Data-to-parameter ratio = 12.6
Details

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

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^a and Hartmut Fuess ^b

^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-HBr and N-HCl contacts occur.

Related literature

For preparation of the title compound, see: Gowda et al. (2003). 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, 2009). For the conformations of other amides, see: Brown (1966).

Experimental

Crystal data

C₈H₅Br₃ClNO
M_r = 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 radiation
= 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.098, T_max = 0.120
4524 measured reflections
1645 independent reflections
1491 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(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
_max = 0.77 e Å^-3
_min = -0.56 e Å^-3
Absolute structure: Flack (1983), 416 Friedel pairs
Flack parameter: 0.049 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NBr1	0.85 (3)	2.78 (8)	3.155 (6)	109 (6)
N1-H1NCl1	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o3242.
Gowda, B. T., Svoboda, I. & Fuess, H. (2007). Acta Cryst. E63, o3267.
Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds