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Volume 69 
Part 8 
Page o1282  
August 2013  

Received 4 June 2013
Accepted 11 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.100
Data-to-parameter ratio = 24.8
Details
Open access

2-(10',10'-Dimethyl-3'-sulfanylidene-4'-azatricyclo[5.2.1.01,5]decan-2'-yl)-10,10-dimethyl-4-azatricyclo[5.2.1.01,5]decane-3-thione

aSchool of Chemistry, Monash University, Clayton, Victoria 3800, Australia
Correspondence e-mail: craig.forsyth@sci.monash.edu.au

The title compound, C28H40N2O2S2, was obtained as a minor product from an anti-aldol reaction between the corresponding N-propionylthiolactam and benzaldehyde. The asymmetric unit contains one half-molecule, which is completed by inversion symmetry. The molecule displays a nearly eclipsed conformation along the central C-C bond with a C-C-C-C- torsion angle of 20.4 (3)°.

Related literature

For chiral auxiliaries providing control over the sterochemical outcome of chemical transformations, see: Valezquez & Olivo (2002[Valezquez, F. & Olivo, H. F. (2002) Curr. Org. Chem. 6, 303-340.]). For a related synthesis, see: Tamaru et al. (1978[Tamaru, Y., Harada, T. & Yoshida, Z. (1978). J. Am. Chem. Soc. 100, 1923-1925.]).

[Scheme 1]

Experimental

Crystal data
  • C28H40N2O2S2

  • Mr = 500.74

  • Tetragonal, P 41 21 2

  • a = 13.8159 (3) Å

  • c = 13.5221 (6) Å

  • V = 2581.09 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 123 K

  • 0.20 × 0.15 × 0.08 mm

Data collection
  • Bruker X8 APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.94, Tmax = 0.98

  • 18157 measured reflections

  • 3814 independent reflections

  • 3601 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.100

  • S = 1.19

  • 3814 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

  • Absolute structure: Parsons & Flack (2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.]); Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]

  • Absolute structure parameter: 0.04 (4)

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 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: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: CIFTAB (Sheldrick, 1997[Sheldrick, G. M. (1997). CIFTAB. University of Göttingen, Germany.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2136 ).


Acknowledgements

We acknowledge support from Monash University and the Australian Research Council for funding this work.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (1997). CIFTAB. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tamaru, Y., Harada, T. & Yoshida, Z. (1978). J. Am. Chem. Soc. 100, 1923-1925.  [CrossRef] [ChemPort] [Web of Science]
Valezquez, F. & Olivo, H. F. (2002) Curr. Org. Chem. 6, 303-340.


Acta Cryst (2013). E69, o1282  [ doi:10.1107/S1600536813019211 ]

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