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

Franzel, C.; Purdy, A.; Butcher, R.J.

doi:10.1107/S1600536813003292

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 (C-C) = 0.004 Å
Some non-H atoms missing,
R = 0.044
wR = 0.116
Data-to-parameter ratio = 20.5
Details

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

Christine Franzel,^a ⁺ Andrew Purdy ^a ^* and Ray J. Butcher ^b

^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-HO 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). Acta Cryst. D65, 148-155].

Related literature

For N-substituted 1,3-thiazolidine-2-thione and for further synthetic details, see: Evans & Thomson (2005). For the definition of amide twist angles, see: Yamada et al. (1993). For details of the use of SQUEEZE, see: van der Sluis & Spek (1990).

Experimental

Crystal data

C₉H₁₂N₂OS₄·0.5C₆H₅Cl
M_r = 348.72
Monoclinic, P 2₁ /n
a = 8.59506 (18) Å
b = 9.4435 (2) Å
c = 18.2640 (4) Å
= 92.614 (2)°
V = 1480.90 (6) Å³
Z = 4
Cu K radiation
= 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), based on expressions derived by Clark & Reid (1995)] T_min = 0.757, T_max = 1.000
5329 measured reflections
2971 independent reflections
2486 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.116
S = 1.05
2971 reflections
145 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9AO1ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Evans, D. & Thomson, R. (2005). J. Am. Chem. Soc. 157, 10506-10507.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. A46, 194-201.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yamada, S. (1993). Angew. Chem. Int. Ed. Engl. 32, 1083-1085.

organic compounds