[Journal logo]

Volume 69 
Part 4 
Page o601  
April 2013  

Received 24 January 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 124 K
Mean [sigma](C-C) = 0.002 Å
R = 0.026
wR = 0.069
Data-to-parameter ratio = 10.4
Details
Open access

(3R,4S)-1-(4-Methoxyphenyl)-2-oxo-4-(3-vinylphenyl)azetidin-3-yl acetate

aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, People's Republic of China
Correspondence e-mail: sunxunf@shmu.edu.cn

In the title compound, C20H19NO4, the absolute configuration (3R,4S) for the two chiral centres of the molecule has been determined.

Related literature

For the preparation of the title compound, an intermediate in the synthesis of C-4 to C-3' bridged paclitaxel analogues, see: Ganesh et al. (2007[Ganesh, T., Yang, C., Norris, A., Glass, T., Bane, S., Ravindra, R., Banerjee, A., Metaferia, B., Thomas, S. L. & Giannakakou, P. (2007). J. Med. Chem. 50, 713-725.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19NO4

  • Mr = 337.36

  • Monoclinic, C 2

  • a = 20.7448 (4) Å

  • b = 6.3930 (1) Å

  • c = 15.7434 (3) Å

  • [beta] = 124.309 (1)°

  • V = 1724.64 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 124 K

  • 0.20 × 0.18 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.866, Tmax = 0.923

  • 6072 measured reflections

  • 2374 independent reflections

  • 2330 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.069

  • S = 1.06

  • 2374 reflections

  • 228 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 730 Friedel pairs

  • Flack parameter: 0.01 (15)

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: 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: MW2104 ).


Acknowledgements

The work was supported financially by the National Natural Science Foundation of China (No. 81172920), the Shanghai Municipal Committee of Science and Technology (No. 10431903100) and the National Basic Research Program of China (973 Program, No. 2010CB912603). We would like to thank Dr Jie Sun for the single-crystal X-ray determination.

References

Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ganesh, T., Yang, C., Norris, A., Glass, T., Bane, S., Ravindra, R., Banerjee, A., Metaferia, B., Thomas, S. L. & Giannakakou, P. (2007). J. Med. Chem. 50, 713-725.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o601  [ doi:10.1107/S1600536813007897 ]

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.