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Volume 68 
Part 11 
Pages o3146-o3147  
November 2012  

Received 18 September 2012
Accepted 6 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.095
Data-to-parameter ratio = 7.5
Details
Open access

3-tert-Butyl 5-methyl (2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,3-oxazolidine-3,5-dicarboxylate

aBenemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, Puebla, Pue. 72570, Mexico,bUniversidad Autónoma de Nuevo León, UANL, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico, and cInstitut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91190 Gif-sur-Yvette, France
Correspondence e-mail: sylvain_bernes@hotmail.com

The title molecule, C23H26N2O8, was synthesized in three steps starting from m-nitrocinnamic acid. The central oxazolidine ring adopts an almost perfect envelope conformation with the O atom as the flap [puckering parameter [varphi] = 0.3 (6)°]. The dihedral angle formed by the benzene rings is 61.81 (9)°. In the crystal, molecules are connected into double chains parallel to [010] by C-H...O hydrogen bonds. The absolute configuration was assigned from the synthetic procedure.

Related literature

For the Sharpless asymmetric aminohydroxylation, see: Rudolph et al. (1996[Rudolph, J., Sennhenn, P. C., Vlaar, C. P. & Sharpless, K. B. (1996). Angew. Chem. Int. Ed. 35, 2810-2813.]). For the synthesis of the phenylisoserine precursor of the title molecule, see: Montiel-Smith et al. (2002[Montiel-Smith, S., Cervantes-Mejía, V., Dubois, J., Guénard, D., Guéritte, F. & Sandoval-Ramírez, J. (2002). Eur. J. Org. Chem. pp. 2260-2264.]). For the stereocontrolled formation of the oxazolidine in the title molecule, see: Denis et al. (1994[Denis, J.-N., Kanazawa, A. M. & Green, A. E. (1994). Tetrahedron Lett. 35, 105-108.]). For the structure of a related chiral N-Boc-protected oxazolidine, see: Tinant et al. (1996[Tinant, B., Declercq, J. P. & Cagnon, J. R. (1996). Bull. Soc. Chim. Belg. 105, 325-328.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H26N2O8

  • Mr = 458.46

  • Monoclinic, P 21

  • a = 10.383 (1) Å

  • b = 6.0303 (6) Å

  • c = 18.7366 (17) Å

  • [beta] = 95.591 (4)°

  • V = 1167.57 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.60 × 0.16 × 0.16 mm

Data collection
  • Siemens P4 diffractometer

  • 3169 measured reflections

  • 2275 independent reflections

  • 1628 reflections with I > 2[sigma](I)

  • Rint = 0.024

  • 3 standard reflections every 97 reflections intensity decay: 0.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.095

  • S = 1.02

  • 2275 reflections

  • 304 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...O15i 0.98 2.50 3.400 (4) 153
C5-H5A...O28ii 0.98 2.59 3.387 (4) 138
C26-H26A...O1iii 0.93 2.59 3.252 (4) 128
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z]; (iii) x, y-1, z.

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5008 ).


Acknowledgements

This work was supported by the France-Mexico ECOS-ANUIES (M97-E02) agreement.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Denis, J.-N., Kanazawa, A. M. & Green, A. E. (1994). Tetrahedron Lett. 35, 105-108.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Montiel-Smith, S., Cervantes-Mejía, V., Dubois, J., Guénard, D., Guéritte, F. & Sandoval-Ramírez, J. (2002). Eur. J. Org. Chem. pp. 2260-2264.
Rudolph, J., Sennhenn, P. C., Vlaar, C. P. & Sharpless, K. B. (1996). Angew. Chem. Int. Ed. 35, 2810-2813.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Tinant, B., Declercq, J. P. & Cagnon, J. R. (1996). Bull. Soc. Chim. Belg. 105, 325-328.  [ChemPort]


Acta Cryst (2012). E68, o3146-o3147   [ doi:10.1107/S160053681204192X ]

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