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Volume 67 
Part 6 
Page o1483  
June 2011  

Received 20 April 2011
Accepted 12 May 2011
Online 20 May 2011

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.047
wR = 0.112
Data-to-parameter ratio = 8.4
Details
Open access

2-{(1R,2R)-2-[Bis(4-methylbenzyl)amino]cyclohexyl}isoindoline-1,3-dione

Chao Li,a Xiang-Kai Fu,a* Chuan-Long Wua and Jing Huanga

aCollege of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry, Southwest University, The Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing 400715, People's Republic of China
Correspondence e-mail: fxk@swu.edu.cn

In the title molecule, C30H32N2O2, the two tolyl rings form dihedral angles of 65.8 (1) and 6.6 (1)° with the isoindole-1,3-dione mean plane. The cyclohexane ring adopts a chair conformation.

Related literature

For applications of chiral tertiary amines as catalysts for direct aldol reactions, see: Paradowska et al. (2009[Paradowska, J., Rogozinóska, M. & Mlynarski, J. (2009). Tetrahedron Lett. 50, 1639-1641.]). For details of the synthesis, see: Kaik & Gawronski (2003[Kaik, M. & Gawronski, J. (2003). Tetrahedron Asymmetry, 14, 1559-1563.]); Gawronski et al. (1998[Gawronski, J., Kazmierczak, F., Gawronska, K., Rychlewska, U., Nordén, B. & Holmén, A. (1998). J. Am. Chem. Soc. 120, 12083-12091.]).

[Scheme 1]

Experimental

Crystal data

  • C30H32N2O2

  • Mr = 452.58

  • Monoclinic, P 21

  • a = 12.472 (2) Å

  • b = 9.2853 (17) Å

  • c = 12.505 (2) Å

  • [beta] = 115.305 (2)°

  • V = 1309.1 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 298 K

  • 0.38 × 0.24 × 0.24 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 6901 measured reflections

  • 2597 independent reflections

  • 2042 reflections with I > 2[sigma](I)

  • Rint = 0.022
Refinement

  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.112

  • S = 1.11

  • 2597 reflections

  • 309 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.10 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. 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: CV5079 ).

Acknowledgements

The authors are grateful to the Southwest University of China for financial support.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gawronski, J., Kazmierczak, F., Gawronska, K., Rychlewska, U., Nordén, B. & Holmén, A. (1998). J. Am. Chem. Soc. 120, 12083-12091.  [ChemPort]
Kaik, M. & Gawronski, J. (2003). Tetrahedron Asymmetry, 14, 1559-1563.  [ChemPort]
Paradowska, J., Rogozinóska, M. & Mlynarski, J. (2009). Tetrahedron Lett. 50, 1639-1641.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2011). E67, o1483  [ doi:10.1107/S1600536811018101 ]

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