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Volume 70 
Part 5 
Page o606  
May 2014  

Received 26 March 2014
Accepted 22 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 14.3
Details
Open access

(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methyl­sulfon­yl)phen­yl]methyl acetate

aSchool of Biological & Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, People's Republic of China, and bNingbo Ocean & Fishery Bureau, Ningbo 315100, People's Republic of China
Correspondence e-mail: chjin641@163.com

The structure of the title compound, C20H21NO6S, is of inter­est with respect to its anti­bacterial properties. The oxazolidine ring makes dihedral angles of 79.63 (14) and 56.16 (12)° with the phenyl and benzene rings, respectively, while the phenyl and benzene rings make a dihedral angle of 64.37 (13)°. In the crystal, non-classical C-H...O hydrogen bonds link adjacent mol­ecules along the c axis.

Related literature

For the original synthesis of the title compound, see: Li et al. (2011[Li, F., Wang, Z. H., Zhao, L., Xiong, F. J., He, Q. Q. & Chen, F. E. (2011). Tetrahedron Asymmetry, 22, 1337-1341.]). For inversion of the configuration of the sulfonyloxy moiety, see: Shi et al. (2010[Shi, X. X., Shen, C. L., Yao, J. Z., Nie, L. D. & Quan, N. (2010). Tetrahedron Asymmetry, 21, 277-284.]). For background to the anti-bacterial properties of thia­mphenicol-like compounds, see: Nagabhushan (1980[Nagabhushan, T. L. (1980). EP14437. Schering Corporation, USA.], 1981[Nagabhushan, T. L. (1981). Chem. Abstr. 94, 139433.]); Jommi et al. (1985[Jommi, G., Pagliarin, R., Chiarino, D. & Fantucci, M. (1985). Gazz. Chim. Ital. 115, 653-658.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21NO6S

  • Mr = 403.44

  • Monoclinic, P 21

  • a = 5.837 (3) Å

  • b = 21.021 (10) Å

  • c = 7.884 (4) Å

  • [beta] = 100.256 (7)°

  • V = 952.0 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.16 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.968

  • 6495 measured reflections

  • 3658 independent reflections

  • 3254 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.02

  • 3658 reflections

  • 255 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1356 Friedel pairs

  • Absolute structure parameter: -0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...O4i 0.97 2.52 3.373 (3) 147
C10-H10...O6i 0.98 2.54 3.384 (3) 144
C13-H13C...O1ii 0.96 2.55 3.305 (3) 135
Symmetry codes: (i) x, y, z+1; (ii) x-1, y, z-1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supporting information for this paper is available from the IUCr electronic archives (Reference: HG5390 ).


Acknowledgements

The authors thank Professor Xiang-shan Wang for his help and advice in the solution of the crystal structure.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Jommi, G., Pagliarin, R., Chiarino, D. & Fantucci, M. (1985). Gazz. Chim. Ital. 115, 653-658.  [ChemPort]
Li, F., Wang, Z. H., Zhao, L., Xiong, F. J., He, Q. Q. & Chen, F. E. (2011). Tetrahedron Asymmetry, 22, 1337-1341.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nagabhushan, T. L. (1980). EP14437. Schering Corporation, USA.
Nagabhushan, T. L. (1981). Chem. Abstr. 94, 139433.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shi, X. X., Shen, C. L., Yao, J. Z., Nie, L. D. & Quan, N. (2010). Tetrahedron Asymmetry, 21, 277-284.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o606  [ doi:10.1107/S1600536814009106 ]

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