(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

Lin, B.; Wu, J.-L.

doi:10.1107/S1600536813002560

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 (C-C) = 0.007 Å
R = 0.048
wR = 0.127
Data-to-parameter ratio = 11.6
Details

(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

Benguo Lin ^a and Jin-Long Wu ^a ^*

^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-HO hydrogen bonds link the components into chains along [100].

Related literature

For isoindolin-1-one derivatives in cytochalasins, see: Liu et al. (2006); Cox et al. (1983).

Experimental

Crystal data

C₂₈H₃₃NO₄·CH₂Cl₂
M_r = 532.48
Monoclinic, P 2₁
a = 9.6864 (5) Å
b = 15.5706 (8) Å
c = 9.7460 (6) Å
= 109.221 (7)°
V = 1387.99 (14) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.919, T_max = 0.941
6260 measured reflections
3844 independent reflections
2990 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.127
S = 1.07
3844 reflections
330 parameters
1 restraint
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1789 Friedel pairs
Flack parameter: -0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C29-H29BO2ⁱ	0.97	2.42	3.313 (7)	153
C6-H6O3ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Liu, R., Gu, Q., Zhu, W., Cui, C., Fan, G., Fang, Y., Zhu, T. & Liu, H. (2006). J. Nat. Prod. 69, 871-875.
Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds