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Volume 68 
Part 11 
Page o3211  
November 2012  

Received 17 October 2012
Accepted 19 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.077
Data-to-parameter ratio = 15.7
Details
Open access

(±)-(rel-3R,3'R)-1,1'-Dimethyl-3,3'-bipyrrolidine-2,2'-dithione

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO Wits, 2050 Johannesburg, South Africa
Correspondence e-mail: joseph.michael@wits.ac.za

The asymmetric unit of the racemic title compound, C10H16N2S2, a C2-symmetric bis(thiolactam), contains one half-molecule, the complete molecule being generated by a twofold axis symmetry operation. The five-membered ring is nearly planar, with a maximum deviation of 0.025 (1) Å. In the crystal, the molecules are linked via weak C-H...S interactions, forming infinite chains along the b-axis direction.

Related literature

For related synthesis, see: Tamaru et al. (1978[Tamaru, Y., Harada, T. & Yoshida, Z.-I. (1978). J. Am. Chem. Soc. 100, 1923-1925.]); Schroth et al. (2000[Schroth, W., Spitzner, R., Felicetti, M., Wagner, C. & Bruhn, C. (2000). Eur. J. Org. Chem. pp. 3093-3012.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16N2S2

  • Mr = 228.37

  • Monoclinic, C 2/c

  • a = 20.520 (3) Å

  • b = 5.7237 (7) Å

  • c = 11.220 (2) Å

  • [beta] = 122.009 (5)°

  • V = 1117.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 173 K

  • 0.45 × 0.42 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.827, Tmax = 0.933

  • 1759 measured reflections

  • 1022 independent reflections

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

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.077

  • S = 1.09

  • 1022 reflections

  • 65 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5B...S1i 0.98 2.98 3.8373 (18) 146
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6851 ).


Acknowledgements

This work was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work. Dr R. B. Katz is thanked for performing the preliminary syntheses.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Schroth, W., Spitzner, R., Felicetti, M., Wagner, C. & Bruhn, C. (2000). Eur. J. Org. Chem. pp. 3093-3012.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tamaru, Y., Harada, T. & Yoshida, Z.-I. (1978). J. Am. Chem. Soc. 100, 1923-1925.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, o3211  [ doi:10.1107/S1600536812043498 ]

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