2-Amino-2,3-dimethyl­butanamide

Yin, Y.

doi:10.1107/S1600536810015679

Volume 66
Part 6
Page o1258
June 2010

Received 16 April 2010
Accepted 28 April 2010
Online 8 May 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.152
Data-to-parameter ratio = 17.5
Details

2-Amino-2,3-dimethylbutanamide

Yongbiao Yin ^a ^*

^aDepartment of Chemistry, Mudanjiang Teachers College, Mudanjiang 157012, People's Republic of China
Correspondence e-mail: yinyongbiao68@163.com

The title compound, C₆H₁₄N₂O, was synthesized by the reaction between 2-amino-2,3-dimethylbutanonitrile and oil of vitriol (sulfuric acid). A racemic mixture of L- and R-2-amino-2,3-dimethylbutanamide was characterized crystallographically. In the crystal structure, intermolecular N-HO hydrogen bonds link the two enantiomers into a three-dimensional network.

Related literature

2-Amino-2,3-dimethylbutanamide, a common intermediate in the synthesis of imidazolinone compounds, is an excellent weedicide, usually used as racemic mixture of the levo and dextral enantiomers, see: Goatz et al. (1990); Harir et al. (2007).

Experimental

Crystal data

C₆H₁₄N₂O
M_r = 130.19
Monoclinic, P 2₁ /c
a = 12.1766 (8) Å
b = 6.1741 (4) Å
c = 10.2322 (5) Å
= 94.682 (6)°
V = 766.69 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 120 K
0.14 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.991, T_max = 0.993
3390 measured reflections
1503 independent reflections
922 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.152
S = 0.95
1503 reflections
86 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2BO1ⁱ	0.89	2.52	3.364 (2)	158
N1-H1BO1ⁱ	0.86	2.19	3.0295 (19)	165
N1-H1AO1ⁱⁱ	0.86	2.20	3.054 (2)	176
N2-H2CO1ⁱⁱⁱ	0.89	2.51	3.393 (3)	172
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2145 ).

Acknowledgements

The author thanks the Natural Science Foundation of Heilongjiang Province for financial support.

References

Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Goatz, A., Lavy, T. & Gbur, E. (1990). Weed Sci. 38, 421-489.
Harir, M., Gaspar, A., Frommberger, M., Lucio, M., Azzouzi, M. E., Martens, D., Kettrup, A. & Schmitt-Kopplin, P. (2007). J. Agric. Food Chem. 55, 9936-9943.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds