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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 [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.114
Data-to-parameter ratio = 11.9
Details
Open access

N-([beta]-Carboxyethyl)-[alpha]-isoleucine

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-H...O and O-H...N hydrogen bonds.

Related literature

For toxicological investigations on acrylamide, see: Besaratinia & Pfeifer (2007[Besaratinia, A. & Pfeifer, G. P. (2007). Carcinogenesis, 28, 519-528.]); Parzefall (2008[Parzefall, W. (2008). Food Chem. Toxicol. 46, 1360-1364.]); Bowyer et al. (2009[Bowyer, J. F., Latendresse, J. R. & Delongchamp, R. R. (2009). Toxicol. Appl. Pharmacol. 240, 401-411.]); Wang et al. (2010[Wang, R.-S., McDaniel, L. P. & Manjanatha, M. (2010). Toxicol. Sci. 117, 72-80.]); Mei et al. (2010[Mei, N., McDaniel, L. P. & Dobrovolsky, V. N. (2010). Toxicol. Sci. 115, 412-421.]); Koyama et al. (2011[Koyama, N., Yasui, M. & &Kimura, A. (2011). Mutagenesis, 26, 545-549.]); Lee et al. (2012[Lee, T., Manjanatha, M. & Aidoo, A. (2012). J. Toxicol. Environ. Health, A75, 324-339.]); Nixon et al. (2012[Nixon, B., Stanger, S. J. & Nixon, B. (2012). Toxicol. Sci. 129, 135-145.]); Rice (2005[Rice, J. M. (2005). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 580, 3-20.]). For directives on monitoring acrylamide in drinking water, see: EU (2000[EU (2000). Directive 2000/60/EC of the European Parliament and of the Council establishing a framework for the Community action in the field of water policy.]). For the determination of acrylamide in different media, see: Zangrando et al. (2012[Zangrando, R., Gambaro, A. & De Pieri, S. (2012). Int. J. Environ. Anal. Chem. 92, 1150-1150.]); Marin et al. (2006[Marin, J. M., Pozo, O. J. & Sancho, J. V. (2006). J. Mass Spectrom. 41, 1041-1048.]); Lucentini et al. (2009[Lucentini, L., Ferretti, E. & Veschetti, E. (2009). J. AOAC Int. 92, 263-270.]); Keramat et al. (2011[Keramat, J., LeBail, A. & Prost, C. (2011). Food Bioprocess Technol. 4, 340-363.]); Tareke et al. (2002[Tareke, E., Rydberg, P. & Karlsson, P. (2002). J. Agric. Food Chem. 50, 4998-5006.]); Pittet et al. (2004[Pittet, A., Perisset, A. & Oberson, J. M. (2004). J. Chromatogr. A, 1035, 123-130.]); Castle & Eriksson (2005[Castle, L. & Eriksson, S. (2005). J. AOAC Int. 88, 274-284.]); Mizukami et al. (2006[Mizukami, Y., Kohate, K., Katsunori, Y. & Yamaguchi, Y. (2006). J. Agric. Food Chem. 54, 7370-7377.]); Dias Soares et al. (2009[Dias Soares, C. M. & Fernandes, J. O. (2009). Food Anal. Methods, 2, 197-203.]); Alpmann & Morlock (2008[Alpmann, A. & Morlock, G. (2008). J. Sep. Sci. 31, 71-77.]); Preston et al. (2009[Preston, A., Fodey, T. & Douglas, A. (2009). J. Immunol. Methods, 341, 19-29.]); Perez & Osterman-Golkar (2003[Perez, H. L. & Osterman-Golkar, S. (2003). Analyst, 128, 1033-1036.]).

[Scheme 1]

Experimental

Crystal data
  • C9H18N2O3

  • Mr = 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[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.944, Tmax = 0.994

  • 7386 measured reflections

  • 1516 independent reflections

  • 1124 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.114

  • S = 0.95

  • 1516 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.17 2.982 (3) 159
N1-H1B...O1ii 0.86 2.33 3.097 (4) 149
O2-H21...N5iii 0.82 1.89 2.708 (2) 176
N5-H51...O3iv 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[Bruker (2001). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SADABS and SAINT. 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: BG2493 ).


References

Alpmann, A. & Morlock, G. (2008). J. Sep. Sci. 31, 71-77.  [ISI] [CrossRef] [PubMed] [ChemPort]
Besaratinia, A. & Pfeifer, G. P. (2007). Carcinogenesis, 28, 519-528.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bowyer, J. F., Latendresse, J. R. & Delongchamp, R. R. (2009). Toxicol. Appl. Pharmacol. 240, 401-411.  [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Castle, L. & Eriksson, S. (2005). J. AOAC Int. 88, 274-284.  [PubMed] [ChemPort]
Dias Soares, C. M. & Fernandes, J. O. (2009). Food Anal. Methods, 2, 197-203.
EU (2000). Directive 2000/60/EC of the European Parliament and of the Council establishing a framework for the Community action in the field of water policy.
Keramat, J., LeBail, A. & Prost, C. (2011). Food Bioprocess Technol. 4, 340-363.  [CrossRef] [ChemPort]
Koyama, N., Yasui, M. & &Kimura, A. (2011). Mutagenesis, 26, 545-549.  [ISI] [CrossRef] [ChemPort] [PubMed]
Lee, T., Manjanatha, M. & Aidoo, A. (2012). J. Toxicol. Environ. Health, A75, 324-339.  [CrossRef]
Lucentini, L., Ferretti, E. & Veschetti, E. (2009). J. AOAC Int. 92, 263-270.  [PubMed] [ChemPort]
Marin, J. M., Pozo, O. J. & Sancho, J. V. (2006). J. Mass Spectrom. 41, 1041-1048.  [ISI] [PubMed] [ChemPort]
Mei, N., McDaniel, L. P. & Dobrovolsky, V. N. (2010). Toxicol. Sci. 115, 412-421.  [ISI] [CrossRef] [ChemPort] [PubMed]
Mizukami, Y., Kohate, K., Katsunori, Y. & Yamaguchi, Y. (2006). J. Agric. Food Chem. 54, 7370-7377.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nixon, B., Stanger, S. J. & Nixon, B. (2012). Toxicol. Sci. 129, 135-145.  [ISI] [CrossRef] [ChemPort] [PubMed]
Parzefall, W. (2008). Food Chem. Toxicol. 46, 1360-1364.  [ISI] [PubMed] [ChemPort]
Perez, H. L. & Osterman-Golkar, S. (2003). Analyst, 128, 1033-1036.  [PubMed]
Pittet, A., Perisset, A. & Oberson, J. M. (2004). J. Chromatogr. A, 1035, 123-130.  [ISI] [PubMed] [ChemPort]
Preston, A., Fodey, T. & Douglas, A. (2009). J. Immunol. Methods, 341, 19-29.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rice, J. M. (2005). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 580, 3-20.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tareke, E., Rydberg, P. & Karlsson, P. (2002). J. Agric. Food Chem. 50, 4998-5006.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wang, R.-S., McDaniel, L. P. & Manjanatha, M. (2010). Toxicol. Sci. 117, 72-80.  [ISI] [CrossRef] [ChemPort] [PubMed]
Zangrando, R., Gambaro, A. & De Pieri, S. (2012). Int. J. Environ. Anal. Chem. 92, 1150-1150.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o172-o173   [ doi:10.1107/S160053681205146X ]

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