(3aR*,6S*,7S*,7aR*)-2-(4-Methoxy­benz­yl)-7-(4-nitro­phen­yl)-6-phenyl-3a,6,7,7a-tetra­hydro­isoindolin-1-one

Zhao, J.; Wu, J.-L.

doi:10.1107/S1600536810017010

Volume 66
Part 6
Page o1387
June 2010

Received 27 April 2010
Accepted 10 May 2010
Online 19 May 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.123
Data-to-parameter ratio = 17.1
Details

(3aR,6S,7S,7aR)-2-(4-Methoxybenzyl)-7-(4-nitrophenyl)-6-phenyl-3a,6,7,7a-tetrahydroisoindolin-1-one

Jian Zhao ^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

The title compound, C₂₈H₂₆N₂O₄, crystallizes as a racemate with four stereogenic centers. In the molecule, the pyrrolidone ring adopts an envelope conformation and the cyclohexene ring has a twisted envelope conformation. In the crystal structure, molecules are linked by weak intermolecular C-HO hydrogen bonds.

Related literature

For bioactive compounds, see: Walling et al. (1988); Liu et al. (2006, 2008). For microwave-assisted intramolecular Diels-Alder cycloaddition, see: Wang et al. (2009); Wu et al. (2006, 2007). For the synthesis of title compound, see: Wu et al. (2009).

Experimental

Crystal data

C₂₈H₂₆N₂O₄
M_r = 454.51
Triclinic, $[P \overline 1]$
a = 5.4369 (4) Å
b = 12.2662 (7) Å
c = 18.149 (1) Å
= 79.633 (1)°
= 84.036 (2)°
= 80.325 (2)°
V = 1170.25 (13) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.37 × 0.31 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.967, T_max = 0.985
11469 measured reflections
5285 independent reflections
3402 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.123
S = 1.01
5285 reflections
309 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AO3ⁱ	0.97	2.63	3.239 (2)	122
C28-H28AO1ⁱⁱ	0.96	2.55	3.242 (2)	129
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2150 ).

Acknowledgements

This work was supported by a research grant from the Natural Science Foundation of China (grant No. 20572092). Professor Wei-Min Dai is thanked for his valuable suggestions on this work. Mr Jianming Gu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structural analysis.

References

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Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.
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