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

Madeley, L.G.; Lemmerer, A.; Michael, J.P.

doi:10.1107/S1600536812043498

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 (C-C) = 0.003 Å
R = 0.030
wR = 0.077
Data-to-parameter ratio = 15.7
Details

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

Lee G. Madeley,^a Andreas Lemmerer ^a and Joseph P. Michael ^a ^*

^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-HS interactions, forming infinite chains along the b-axis direction.

Related literature

For related synthesis, see: Tamaru et al. (1978); Schroth et al. (2000).

Experimental

Crystal data

C₁₀H₁₆N₂S₂
M_r = 228.37
Monoclinic, C 2/c
a = 20.520 (3) Å
b = 5.7237 (7) Å
c = 11.220 (2) Å
= 122.009 (5)°
V = 1117.4 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.827, T_max = 0.933
1759 measured reflections
1022 independent reflections
957 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.077
S = 1.09
1022 reflections
65 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5BS1ⁱ	0.98	2.98	3.8373 (18)	146
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Schroth, W., Spitzner, R., Felicetti, M., Wagner, C. & Bruhn, C. (2000). Eur. J. Org. Chem. pp. 3093-3012.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tamaru, Y., Harada, T. & Yoshida, Z.-I. (1978). J. Am. Chem. Soc. 100, 1923-1925.

organic compounds