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Volume 69 
Part 5 
Page o774  
May 2013  

Received 31 March 2013
Accepted 13 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.084
Data-to-parameter ratio = 18.7
Details
Open access

2,2'-(Carbonothioyldisulfanediyl)bis(2-methylpropanoic acid)

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,bPrograma de Ingenieria Agroindustrial, Universidad San Buenaventura, AA 7154, Santiago de Cali, Colombia,cCase Western Reserve University, Department of Macromolecular Science and Engineering, 2100 Adelbert Road, Kent Hale Smith Bldg., Cleveland, Ohio 44106, USA, and dInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

The molecular structure of the title compound, C9H14O4S3, exhibits intramolecular C-H...S hydrogen bonds. In the crystal, pairs of O-H...O hydrogen bonds lead to the formation of centrosymmetric dimers, which are in turn connected by weak C-H...O interactions. The combination of these interactions generates edge-fused R22(8) and R22(20) rings running along [211].

Related literature

For pharmaceutical properties of trithiocarbonates, see: Dehmel et al. (2007[Dehmel, F., Ciossek, T., Maier, T., Weinbrenner, S., Schmidt, B., Zoche, M. & Beckers, T. (2007). Bioorg. Med. Chem. Lett. 17, 4746-4752.]). For trithiocarbonates as intermediates in organic synthesis, see: Metzner (1996[Metzner, P. (1996). Pure & Appl. Chem. 68, 863-868.]). For the control of polymerization reactions of trithiocarbonates, see: Harrisson & Wooley (2005[Harrisson, S. & Wooley, K. L. (2005). Chem. Commun. pp. 3259-3261.]); Bilalis et al. (2006[Bilalis, P., Pitsikalis, M. & Hadjichristidis, N. (2006). J. Polym. Sci. Part A Polym. Chem. 44, 659-665.]); Millard et al. (2006[Millard, P. E., Barner, L., Stenzel, M. H., Davis, T. P., Barner-Kowollik, C. & Muller, A. H. E. (2006). Macromol. Rapid Commun. 27, 821-828.]). For radical polymerization with RAFT reactions, see: Moad et al. (2005[Moad, G., Chong, Y. K., Postma, A., Rizzardo, E. & Thang, S. H. (2005). Polymer, 46, 8458-8468.]). For related structures, see: El-khateeb & Roller (2007[El-khateeb, M. & Roller, A. (2007). Polyhedron, 26, 3920-3924.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For graph-set motifs, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). For the synthesis, see: Lai et al. (2002[Lai, J. T., Filla, D. & Shea, R. (2002). Macromolecules, 35, 6754-6756.]).

[Scheme 1]

Experimental

Crystal data
  • C9H14O4S3

  • Mr = 282.41

  • Monoclinic, P 21 /c

  • a = 10.4044 (2) Å

  • b = 10.4947 (2) Å

  • c = 13.7744 (3) Å

  • [beta] = 117.363 (1)°

  • V = 1335.76 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.55 mm-1

  • T = 295 K

  • 0.34 × 0.29 × 0.23 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 5423 measured reflections

  • 2825 independent reflections

  • 2273 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.084

  • S = 1.05

  • 2825 reflections

  • 151 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8B...S1 0.96 2.85 3.506 (2) 127
C5-H5A...S1 0.96 2.83 3.4955 (19) 127
O1-H1...O4i 0.82 1.84 2.6549 (17) 178
O3-H3...O2i 0.82 1.81 2.6321 (15) 178
C6-H6C...O4ii 0.96 2.69 3.518 (2) 144
Symmetry codes: (i) -x, -y+1, -z; (ii) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2200 ).


Acknowledgements

RMF thanks the Universidad del Valle, Colombia, and CG thanks the Universidad San Buenaventura, Cali, Colombia, for partial financial support.

References

Bilalis, P., Pitsikalis, M. & Hadjichristidis, N. (2006). J. Polym. Sci. Part A Polym. Chem. 44, 659-665.  [CrossRef] [ChemPort]
Dehmel, F., Ciossek, T., Maier, T., Weinbrenner, S., Schmidt, B., Zoche, M. & Beckers, T. (2007). Bioorg. Med. Chem. Lett. 17, 4746-4752.  [CrossRef] [PubMed] [ChemPort]
El-khateeb, M. & Roller, A. (2007). Polyhedron, 26, 3920-3924.  [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harrisson, S. & Wooley, K. L. (2005). Chem. Commun. pp. 3259-3261.  [CrossRef]
Lai, J. T., Filla, D. & Shea, R. (2002). Macromolecules, 35, 6754-6756.  [ISI] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Metzner, P. (1996). Pure & Appl. Chem. 68, 863-868.  [CrossRef] [ChemPort]
Millard, P. E., Barner, L., Stenzel, M. H., Davis, T. P., Barner-Kowollik, C. & Muller, A. H. E. (2006). Macromol. Rapid Commun. 27, 821-828.  [ISI] [CrossRef] [ChemPort]
Moad, G., Chong, Y. K., Postma, A., Rizzardo, E. & Thang, S. H. (2005). Polymer, 46, 8458-8468.  [CrossRef] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o774  [ doi:10.1107/S1600536813010179 ]

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