[Journal logo]

Volume 69 
Part 11 
Page o1712  
November 2013  

Received 8 October 2013
Accepted 22 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 14.5
Details
Open access

N-(2-Chloro­acet­yl)glycine

aSchool of Materials Science and Engineering, Changzhou University & High Technology, Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China, and bHigh Technology Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China
Correspondence e-mail: zycqyc@hotmail.com

The title compound, C4H6ClNO3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In each mol­ecule, there are N-H...O and N-H...Cl hydrogen bonds. Both mol­ecules are relatively planar, with the mean plane of the acetamide [N-C(=O)C] group being inclined to the mean plane of the acetate group [C-C(=O)O] by 9.23 (13)° in mol­ecule A and 6.23 (12)° in mol­ecule B. In the crystal, adjacent mol­ecules are linked by O-H...O hydrogen bonds and weak C-H...O contacts forming -A-A-A- and -B-B-B- parallel chains propagating along the a-axis direction.

Related literature

For the use of the title compound as an inter­mediate in the synthesis of polydespipeptides and their copolymers, which have a wide range of biomedical properties, see: Feng et al. (2010[Feng, Y., Lu, J., Behl, M. & Lendlein, A. (2010). Macromol. Biosci. 10, 1008-1021.]). For the synthetic procedure, see: Allmendenger et al. (1988[Allmendenger, T., Rihs, G. & Wetter, H. (1988). Helv. Chim. Acta, 71, 395-403.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the crystal structure of (2,2,2-tri­chloro­acte­yl)glycine, see: Dou et al. (1995[Dou, S., Kehrer, A., Ofial, A. R. & Weiss, A. (1995). J. Mol. Struct. 345, 11-29.]).

[Scheme 1]

Experimental

Crystal data
  • C4H6ClNO3

  • Mr = 151.55

  • Monoclinic, P 21 /c

  • a = 18.001 (4) Å

  • b = 7.6371 (17) Å

  • c = 9.372 (2) Å

  • [beta] = 105.025 (3)°

  • V = 1244.4 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.54 mm-1

  • T = 296 K

  • 0.28 × 0.22 × 0.15 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.863, Tmax = 0.923

  • 9419 measured reflections

  • 2419 independent reflections

  • 2143 reflections with I > 2[sigma](I)

  • Rint = 0.044

  • 3 standard reflections every 120 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.07

  • 2419 reflections

  • 167 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1'...Cl1 0.86 2.44 2.9422 (18) 118
N1-H1'...O2 0.86 2.24 2.618 (2) 106
N2-H2'...Cl2 0.86 2.46 2.9450 (18) 116
N2-H2'...O4 0.86 2.22 2.619 (2) 108
O1-H1...O3i 0.82 1.84 2.647 (2) 166
O5-H5...O6ii 0.82 1.85 2.657 (2) 167
C4-H4B...O2ii 0.97 2.57 3.080 (3) 113
C8-H8B...O4i 0.97 2.57 3.099 (3) 114
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2655 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Allmendenger, T., Rihs, G. & Wetter, H. (1988). Helv. Chim. Acta, 71, 395-403.
Dou, S., Kehrer, A., Ofial, A. R. & Weiss, A. (1995). J. Mol. Struct. 345, 11-29.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Feng, Y., Lu, J., Behl, M. & Lendlein, A. (2010). Macromol. Biosci. 10, 1008-1021.  [CrossRef] [ChemPort] [PubMed]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1712  [ doi:10.1107/S1600536813028997 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.