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Volume 69 
Part 2 
Page o316  
February 2013  

Received 29 December 2012
Accepted 25 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.048
wR = 0.127
Data-to-parameter ratio = 11.6
Details
Open access

(1S,3aS,4S,7aS)-Ethyl 1-benzyl-2-(4-methoxybenzyl)-6,7-dimethyl-3-oxo-2,3,3a,4,5,7a-hexahydro-1H-isoindole-4-carboxylate dichloromethane monosolvate

aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
Correspondence e-mail: wyz@zju.edu.cn

In the title compound, C28H33NO4·CH2Cl2, the pyrrolidone ring adopts a twisted envelope conformation and the cyclohexene has a half-chair conformation. In the crystal, weak C-H...O hydrogen bonds link the components into chains along [100].

Related literature

For isoindolin-1-one derivatives in cytochalasins, see: Liu et al. (2006[Liu, R., Gu, Q., Zhu, W., Cui, C., Fan, G., Fang, Y., Zhu, T. & Liu, H. (2006). J. Nat. Prod. 69, 871-875.]); Cox et al. (1983[Cox, R. H., Cutler, H. G., Hurd, R. E. & Cole, R. J. (1983). J. Agric. Food Chem. 31, 405-408.]).

[Scheme 1]

Experimental

Crystal data
  • C28H33NO4·CH2Cl2

  • Mr = 532.48

  • Monoclinic, P 21

  • a = 9.6864 (5) Å

  • b = 15.5706 (8) Å

  • c = 9.7460 (6) Å

  • [beta] = 109.221 (7)°

  • V = 1387.99 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.32 × 0.26 × 0.23 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.919, Tmax = 0.941

  • 6260 measured reflections

  • 3844 independent reflections

  • 2990 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.127

  • S = 1.07

  • 3844 reflections

  • 330 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1789 Friedel pairs

  • Flack parameter: -0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C29-H29B...O2i 0.97 2.42 3.313 (7) 153
C6-H6...O3ii 0.93 2.65 3.562 (5) 166
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5380 ).


Acknowledgements

This work was supported by a research grant from the Natural Science Foundation of China (grant No. 21172191). The authors gratefully acknowledge Mr Jiyong Liu and Jianming Gu of Zhejiang University for their kind assistance in the crystal structure analysis and for useful dicussions.

References

Cox, R. H., Cutler, H. G., Hurd, R. E. & Cole, R. J. (1983). J. Agric. Food Chem. 31, 405-408.  [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Liu, R., Gu, Q., Zhu, W., Cui, C., Fan, G., Fang, Y., Zhu, T. & Liu, H. (2006). J. Nat. Prod. 69, 871-875.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o316  [ doi:10.1107/S1600536813002560 ]

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