rac-2,3-Dibromo-propionamide.

The racemic title compound, C(3)H(5)Br(2)NO, was crystallized from methanol. In the crystal, adjacent mol-ecules 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 ▶). 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 = 230.88

Monoclinic,

a = 11.926 (3) Å

b = 6.5911 (14) Å

c = 8.991 (2) Å

β = 103.574 (14)°

V = 687.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.181

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.184

S = 0.77

1556 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.50 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681205132X/bg2488sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205132X/bg2488Isup2.mol

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205132X/bg2488Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205132X/bg2488Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H5Br2NO	F(000) = 432
Mr = 230.88	Dx = 2.232 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 756 reflections
a = 11.926 (3) Å	θ = 2.5–20.6°
b = 6.5911 (14) Å	µ = 11.70 mm−1
c = 8.991 (2) Å	T = 296 K
β = 103.574 (14)°	Block, colourless
V = 687.0 (3) Å3	0.14 × 0.11 × 0.05 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	1556 independent reflections
Radiation source: fine-focus sealed tube	470 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.181
ω/2θ scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.23, Tmax = 0.56	k = −8→8
4500 measured reflections	l = −10→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 0.77	w = 1/[σ2(Fo2) + (0.0796P)2] where P = (Fo2 + 2Fc2)/3
1556 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.40891 (12)	0.3123 (3)	0.39780 (17)	0.1139 (8)
Br2	0.19816 (12)	−0.1953 (2)	0.11104 (17)	0.1065 (7)
O1	0.1347 (5)	0.0988 (12)	0.3970 (9)	0.067 (2)
N1	0.0718 (7)	0.2806 (13)	0.1819 (10)	0.072 (3)
H1	0.0110	0.3215	0.2088	0.087*
H2	0.0844	0.3184	0.0957	0.087*
C1	0.3463 (10)	0.030 (2)	0.3142 (14)	0.107 (5)
H4	0.3995	−0.0396	0.2652	0.129*
H5	0.3291	−0.0550	0.3939	0.129*
C2	0.2455 (8)	0.0907 (19)	0.2077 (12)	0.077 (3)
H3	0.2622	0.1865	0.1325	0.092*
C3	0.1452 (8)	0.1613 (15)	0.2720 (13)	0.054 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.1008 (11)	0.1465 (16)	0.1073 (13)	−0.0630 (10)	0.0505 (9)	−0.0552 (10)
Br2	0.1118 (12)	0.0981 (12)	0.1182 (13)	−0.0294 (8)	0.0443 (9)	−0.0549 (9)
O1	0.070 (5)	0.080 (5)	0.059 (5)	0.007 (4)	0.034 (4)	0.011 (4)
N1	0.067 (6)	0.082 (7)	0.071 (6)	0.025 (5)	0.022 (5)	0.021 (5)
C1	0.085 (9)	0.163 (15)	0.088 (10)	0.048 (9)	0.048 (8)	0.029 (9)
C2	0.050 (6)	0.115 (10)	0.069 (8)	0.019 (6)	0.021 (6)	0.023 (7)
C3	0.063 (7)	0.057 (8)	0.050 (7)	0.001 (5)	0.031 (6)	−0.003 (6)

Br1—C1	2.077 (15)	C1—C2	1.407 (14)
Br2—C2	2.097 (12)	C1—H4	0.9700
O1—C3	1.231 (10)	C1—H5	0.9700
N1—C3	1.307 (12)	C2—C3	1.518 (13)
N1—H1	0.8597	C2—H3	0.9800
N1—H2	0.8604
C3—N1—H1	120.1	C1—C2—C3	116.9 (10)
C3—N1—H2	119.9	C1—C2—Br2	97.5 (9)
H1—N1—H2	120.0	C3—C2—Br2	105.9 (7)
C2—C1—Br1	99.8 (9)	C1—C2—H3	111.8
C2—C1—H4	111.8	C3—C2—H3	111.8
Br1—C1—H4	111.8	Br2—C2—H3	111.8
C2—C1—H5	111.8	O1—C3—N1	124.8 (9)
Br1—C1—H5	111.8	O1—C3—C2	120.2 (10)
H4—C1—H5	109.5	N1—C3—C2	114.9 (10)
Br1—C1—C2—C3	−74.1 (11)	Br2—C2—C3—O1	80.6 (10)
Br1—C1—C2—Br2	173.7 (4)	C1—C2—C3—N1	156.6 (12)
C1—C2—C3—O1	−26.7 (17)	Br2—C2—C3—N1	−96.1 (9)

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

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) ; (ii) .