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Volume 69 
Part 3 
Page o375  
March 2013  

Received 24 November 2012
Accepted 31 January 2013
Online 13 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
Some non-H atoms missing,
R = 0.044
wR = 0.116
Data-to-parameter ratio = 20.5
Details
Open access

3,3'-(1-Oxopropane-1,3-diyl)bis(1,3-thiazolidine-2-thione) chlorobenzene hemisolvate

aNaval Research Laboratory, Chemistry Division, code 6100, 4555 Overlook Av, SW, Washington, DC 20375, USA, and bHoward University, Chemistry Dept, Washington, DC 20059, USA
Correspondence e-mail: andrew.purdy@nrl.navy.mil

The title compound, C9H12N2OS4·0.5C6H5Cl, which contains two 1,3-thiazolidine-2-thione rings, is a by-product of the synthesis of 3-acryloyl-1,3-thiazolidine-2-thione. The dihedral angle between these rings is 79.95 (9)°, with both rings displaying a twisted conformation. The twist angle of the amide group is 5.6 (1)°. In the crystal, the molecules are linked into [001] chains by C-H...O interactions. The chlorobenzene solvent molecule was found to show unresolvable disorder about a centre of inversion and its contribution to the scattering was removed with the SQUEEZE option in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155].

Related literature

For N-substituted 1,3-thiazolidine-2-thione and for further synthetic details, see: Evans & Thomson (2005[Evans, D. & Thomson, R. (2005). J. Am. Chem. Soc. 157, 10506-10507.]). For the definition of amide twist angles, see: Yamada et al. (1993[Yamada, S. (1993). Angew. Chem. Int. Ed. Engl. 32, 1083-1085.]). For details of the use of SQUEEZE, see: van der Sluis & Spek (1990[Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. A46, 194-201.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12N2OS4·0.5C6H5Cl

  • Mr = 348.72

  • Monoclinic, P 21 /n

  • a = 8.59506 (18) Å

  • b = 9.4435 (2) Å

  • c = 18.2640 (4) Å

  • [beta] = 92.614 (2)°

  • V = 1480.90 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 6.68 mm-1

  • T = 123 K

  • 0.45 × 0.25 × 0.14 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.757, Tmax = 1.000

  • 5329 measured reflections

  • 2971 independent reflections

  • 2486 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.05

  • 2971 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9A...O1i 0.99 2.55 3.340 (4) 137
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: HB7002 ).


Acknowledgements

We thank The Office Of Naval Research for financial support. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Evans, D. & Thomson, R. (2005). J. Am. Chem. Soc. 157, 10506-10507.  [ISI] [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. A46, 194-201.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yamada, S. (1993). Angew. Chem. Int. Ed. Engl. 32, 1083-1085.  [CrossRef] [ISI]


Acta Cryst (2013). E69, o375  [ doi:10.1107/S1600536813003292 ]

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