rac-2,3-Dibromo­propionamide

Köppen, R.; Emmerling, F.; Koch, M.

doi:10.1107/S160053681205132X

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 (C-C) = 0.015 Å
R = 0.066
wR = 0.184
Data-to-parameter ratio = 24.3
Details

rac-2,3-Dibromopropionamide

Robert Köppen,^a ^* Franziska Emmerling ^a and Matthias Koch ^a

^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-HO hydrogen bonds, forming chains along the c-axis direction. These chains are linked through N-HO hydrogen bonds, forming an undulating two-dimensional network lying parallel to the bc plane. There are also short BrBr contacts present [3.514 (3) Å].

Related literature

For the crystal structure of the starting material, see: Zhou et al. (2007). For the development and application of acrylamide analysis in food, see: Rosén & Hellenäs (2002); Hashimoto (1976); Nemoto et al. (2002); Cheng et al. (2006); Mizukami et al. (2006), Zhang et al. (2005, 2006). For halogen interactions, see: Pedireddim et al. (1994).

Experimental

Crystal data

C₃H₅Br₂NO
M_r = 230.88
Monoclinic, P 2₁ /c
a = 11.926 (3) Å
b = 6.5911 (14) Å
c = 8.991 (2) Å
= 103.574 (14)°
V = 687.0 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.23, T_max = 0.56
4500 measured reflections
1556 independent reflections
470 reflections with I > 2(I)
R_int = 0.181

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.184
S = 0.77
1556 reflections
64 parameters
H-atom parameters constrained
_max = 0.86 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.55	3.185 (11)	132
N1-H2O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996); 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.
Hashimoto, A. (1976). Analyst, 101, 932-938.
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.
Nemoto, S., Takatsuki, S., Sasaki, K. & Maitani, T. (2002). J. Food Hyg. Soc. Jpn, 43, 371-376.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, Y., Dong, Y., Ren, Y. P. & Zhang, Y. (2006). J. Chromatogr. A, 1116, 209-216.
Zhang, Y., Zhang, G. Y. & Zhang, Y. (2005). J. Chromatogr. A, 1075, 1-21.
Zhou, Q.-L., Zhang, Z.-H. & Jing, Z.-L. (2007). Acta Cryst. E63, o3039.

organic compounds