N-(β-Carb­oxy­eth­yl)-α-isoleucine

Nehls, I.; Hanebeck, O.; Becker, R.; Emmerling, F.

doi:10.1107/S160053681205146X

Volume 69
Part 2
Pages o172-o173
February 2013

Received 27 November 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.043
wR = 0.114
Data-to-parameter ratio = 11.9
Details

N-(-Carboxyethyl)--isoleucine

Irene Nehls,^a Olaf Hanebeck,^b Roland Becker ^a and Franziska Emmerling ^a ^*

^aFederal Institute for Materials Research and Testing (BAM), Richard-Willstaetter-Strasse 11, D-12489 Berlin, Germany, and ^bSGS Institut Fresenius GmbH, Tegeler Weg 33, D-10589 Berlin, Germany
Correspondence e-mail: franziska.emmerling@bam.de

The title compound, {2-[(2-carbamoylethyl)amino]-3-methylpentanoic acid}, C₉H₁₈N₂O₃, is of interest with respect to its biological activity. It was formed during an addition reaction between acrylamide and the amino acid isoleucine. The crystal structure is a three-dimensional network built up by intermolecular N-HO and O-HN hydrogen bonds.

Related literature

For toxicological investigations on acrylamide, see: Besaratinia & Pfeifer (2007); Parzefall (2008); Bowyer et al. (2009); Wang et al. (2010); Mei et al. (2010); Koyama et al. (2011); Lee et al. (2012); Nixon et al. (2012); Rice (2005). For directives on monitoring acrylamide in drinking water, see: EU (2000). For the determination of acrylamide in different media, see: Zangrando et al. (2012); Marin et al. (2006); Lucentini et al. (2009); Keramat et al. (2011); Tareke et al. (2002); Pittet et al. (2004); Castle & Eriksson (2005); Mizukami et al. (2006); Dias Soares et al. (2009); Alpmann & Morlock (2008); Preston et al. (2009); Perez & Osterman-Golkar (2003).

Experimental

Crystal data

C₉H₁₈N₂O₃
M_r = 202.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.2989 (17) Å
b = 9.024 (3) Å
c = 23.268 (7) Å
V = 1112.6 (6) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.64 × 0.06 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.944, T_max = 0.994
7386 measured reflections
1516 independent reflections
1124 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.114
S = 0.95
1516 reflections
127 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.86	2.17	2.982 (3)	159
N1-H1BO1ⁱⁱ	0.86	2.33	3.097 (4)	149
O2-H21N5ⁱⁱⁱ	0.82	1.89	2.708 (2)	176
N5-H51O3^iv	0.98	1.91	2.783 (3)	147
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) x+1, y, z; (iii) x-1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: BG2493 ).

References

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organic compounds