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Volume 69 
Part 2 
Page o151  
February 2013  

Received 26 October 2012
Accepted 19 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.015 Å
R = 0.066
wR = 0.184
Data-to-parameter ratio = 24.3
Details
Open access

rac-2,3-Dibromopropionamide

aBAM Federal Institute for Materials Research and Testing, Department of Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany
Correspondence e-mail: robert.koeppen@bam.de

The racemic title compound, C3H5Br2NO, was crystallized from methanol. In the crystal, adjacent molecules are linked through N-H...O hydrogen bonds, forming chains along the c-axis direction. These chains are linked through N-H...O hydrogen bonds, forming an undulating two-dimensional network lying parallel to the bc plane. There are also short Br...Br contacts present [3.514 (3) Å].

Related literature

For the crystal structure of the starting material, see: Zhou et al. (2007[Zhou, Q.-L., Zhang, Z.-H. & Jing, Z.-L. (2007). Acta Cryst. E63, o3039.]). For the development and application of acrylamide analysis in food, see: Rosén & Hellenäs (2002[Rosén, J. & Hellenäs, K.-E. (2002). Analyst, 127, 880-882.]); Hashimoto (1976[Hashimoto, A. (1976). Analyst, 101, 932-938.]); Nemoto et al. (2002[Nemoto, S., Takatsuki, S., Sasaki, K. & Maitani, T. (2002). J. Food Hyg. Soc. Jpn, 43, 371-376.]); Cheng et al. (2006[Cheng, W. C., Hsiao, S. W., Chou, S. S., Sun-Hwang, L., Lu, T. J. & Yeh, A. I. (2006). J. Food Drug Anal. 14, 207-214.]); Mizukami et al. (2006[Mizukami, Y., Kohata, K., Yamaguchi, Y., Hayashi, N., Sawai, Y., Chuda, Y., Ono, H., Yada, H. & Yoshida, M. (2006). J. Agric. Food Chem. 54, 7370-7377.]), Zhang et al. (2005[Zhang, Y., Zhang, G. Y. & Zhang, Y. (2005). J. Chromatogr. A, 1075, 1-21.], 2006[Zhang, Y., Dong, Y., Ren, Y. P. & Zhang, Y. (2006). J. Chromatogr. A, 1116, 209-216.]). For halogen interactions, see: Pedireddim et al. (1994[Pedireddim, J., Reddy, D., Goud, B., Craig, D., Rae, A. & Desiraju, G. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.]).

[Scheme 1]

Experimental

Crystal data
  • C3H5Br2NO

  • Mr = 230.88

  • Monoclinic, P 21 /c

  • a = 11.926 (3) Å

  • b = 6.5911 (14) Å

  • c = 8.991 (2) Å

  • [beta] = 103.574 (14)°

  • V = 687.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 11.70 mm-1

  • T = 296 K

  • 0.14 × 0.11 × 0.05 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.23, Tmax = 0.56

  • 4500 measured reflections

  • 1556 independent reflections

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

  • Rint = 0.181

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.184

  • S = 0.77

  • 1556 reflections

  • 64 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.86 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.55 3.185 (11) 132
N1-H2...O1ii 0.86 2.09 2.942 (12) 173
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2488 ).


References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cheng, W. C., Hsiao, S. W., Chou, S. S., Sun-Hwang, L., Lu, T. J. & Yeh, A. I. (2006). J. Food Drug Anal. 14, 207-214.  [ChemPort]
Hashimoto, A. (1976). Analyst, 101, 932-938.  [CrossRef] [PubMed] [ChemPort]
Mizukami, Y., Kohata, K., Yamaguchi, Y., Hayashi, N., Sawai, Y., Chuda, Y., Ono, H., Yada, H. & Yoshida, M. (2006). J. Agric. Food Chem. 54, 7370-7377.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nemoto, S., Takatsuki, S., Sasaki, K. & Maitani, T. (2002). J. Food Hyg. Soc. Jpn, 43, 371-376.  [CrossRef] [ChemPort]
Pedireddim, J., Reddy, D., Goud, B., Craig, D., Rae, A. & Desiraju, G. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.
Rosén, J. & Hellenäs, K.-E. (2002). Analyst, 127, 880-882.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, Y., Dong, Y., Ren, Y. P. & Zhang, Y. (2006). J. Chromatogr. A, 1116, 209-216.  [ISI] [PubMed] [ChemPort]
Zhang, Y., Zhang, G. Y. & Zhang, Y. (2005). J. Chromatogr. A, 1075, 1-21.  [ISI] [PubMed] [ChemPort]
Zhou, Q.-L., Zhang, Z.-H. & Jing, Z.-L. (2007). Acta Cryst. E63, o3039.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o151  [ doi:10.1107/S160053681205132X ]

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