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Volume 69 
Part 5 
Page o783  
May 2013  

Received 8 April 2013
Accepted 16 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.001 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 38.7
Details
Open access

(4S)-4-[(R)-Chloro(4-nitrophenyl)methyl]-1,3-oxazolidin-2-one

aUMR 990, INSERM, Université d'Auvergne, Laboratoire de Chimie Physique, Faculté de Pharmacie, 63001 Clermont-Ferrand, France,bLaboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université d'Auvergne, 63001 Clermont-Ferrand, France, and cSamara State University, 433011 Samara, Russian Federation
Correspondence e-mail: vincent.gaumet@udamail.fr

In the title compound, C10H9ClN2O4, the oxazolidinone ring adopts a near-planar conformation, with mean and maximum deviations of 0.0204 (8) and 0.0328 (8) Å, respectively. The nitro group is twisted slightly from the plane of the benzene ring, making a dihedral angle of 6.79 (3)°. The dihedral angle between the mean oxazolidinone plane and the benzene ring is 56.21 (3)°. In the crystal, N-H...O hydrogen bonds and N-O...[pi] interactions [O...centroid distances = 3.478 (1) and 3.238 (1) Å] dominate the packing, forming infinite zigzag chains along the b-axis direction. Neighbouring chains are linked together through C-H...O and C-H...Cl interactions. The absolute configuration of the two stereogenic centres was determined using the anomalous dispersion of the Cl atom.

Related literature

For the biological activity of oxazolidinone derivatives, see: Michalska et al. (2012[Michalska, K., Karpiuk, I., Król, M. & Tyski, S. (2012). Bioorg. Med. Chem. 21, 577-591.]); Mathur et al. (2013[Mathur, T., Kalia, V., Barman, T. K., Singhal, S., Khan, S., Upadhyay, D. J., Rattan, A. & Raj, V. S. (2013). Int. J. Antimicrob. Agents, 41, 36-40.]); Jindal et al. (2013[Jindal, A., Mahesh, R. & Kumar, B. (2013). Prog. NeuroPsychopharmacol. Biol. Psychiatry, 40, 47-53.]). For related structures, see: Bach et al. (2001[Bach, T., Schlummer, B. & Harms, K. (2001). Chem. Eur. J. 7, 2581-2594.]); Tsui et al. (2013[Tsui, G. C., Ninnemann, N. M., Hosotani, A. & Lautens, M. (2013). Org. Lett. 15, 1064-1067.]). For detailed of the synthesis, see: Madesclaire et al. (2013[Madesclaire, M., Coudert, P., Leal, F., Tarrit, S., Zaitseva, J. V. & Zaitsev, V. P. (2013). Chem. Heterocycl. Compd. In preparation.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9ClN2O4

  • Mr = 256.64

  • Monoclinic, P 21

  • a = 7.2372 (1) Å

  • b = 6.6726 (1) Å

  • c = 11.7126 (2) Å

  • [beta] = 106.715 (1)°

  • V = 541.71 (1) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 296 K

  • 0.52 × 0.49 × 0.34 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.915, Tmax = 1.000

  • 12895 measured reflections

  • 6114 independent reflections

  • 5384 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.06

  • 6114 reflections

  • 158 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2348 Friedel pairs

  • Flack parameter: -0.03 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O15i 0.77 (2) 2.32 (2) 3.095 (1) 179 (2)
C6-H6...O16ii 0.98 2.46 3.309 (2) 145
C11-H11...Cl17iii 0.93 2.83 3.582 (1) 139
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x, y-{\script{1\over 2}}, -z]; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2451 ).


References

Bach, T., Schlummer, B. & Harms, K. (2001). Chem. Eur. J. 7, 2581-2594.  [CrossRef] [PubMed] [ChemPort]
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Jindal, A., Mahesh, R. & Kumar, B. (2013). Prog. NeuroPsychopharmacol. Biol. Psychiatry, 40, 47-53.  [CrossRef] [ChemPort] [PubMed]
Madesclaire, M., Coudert, P., Leal, F., Tarrit, S., Zaitseva, J. V. & Zaitsev, V. P. (2013). Chem. Heterocycl. Compd. In preparation.
Mathur, T., Kalia, V., Barman, T. K., Singhal, S., Khan, S., Upadhyay, D. J., Rattan, A. & Raj, V. S. (2013). Int. J. Antimicrob. Agents, 41, 36-40.  [ISI] [CrossRef] [ChemPort] [PubMed]
Michalska, K., Karpiuk, I., Król, M. & Tyski, S. (2012). Bioorg. Med. Chem. 21, 577-591.  [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Tsui, G. C., Ninnemann, N. M., Hosotani, A. & Lautens, M. (2013). Org. Lett. 15, 1064-1067.  [ISI] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o783  [ doi:10.1107/S1600536813010398 ]

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