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Volume 69 
Part 6 
Page o893  
June 2013  

Received 6 May 2013
Accepted 9 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.026
wR = 0.073
Data-to-parameter ratio = 12.5
Details
Open access

4-(2-Hydroxyphenyl)-3,5-dithiaheptanedioic acid

aDepartment of Physics, Kandaswami Kandar's College, Velur, Namakkal 638 182, India,bInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic,cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and dCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the crystal of the title compound, C11H12O5S2, molecules are linked by O-H...O hydrogen bonds and C-H...O interactions, forming a three-dimensional network.

Related literature

For related structures, see: Guo et al. (2010[Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538-8539.]); Yu et al. (2010[Yu, G.-M., Zhao, L., Guo, Y.-N., Xu, G.-F., Zou, L.-F., Tang, J.-K. & Li, Y.-H. (2010). J. Mol. Struct. 982, 139-144.]); Rollas & Kucukguzel (2007[Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12O5S2

  • Mr = 288.33

  • Triclinic, [P \overline 1]

  • a = 7.2465 (1) Å

  • b = 7.6533 (1) Å

  • c = 12.0141 (2) Å

  • [alpha] = 101.094 (2)°

  • [beta] = 99.129 (1)°

  • [gamma] = 102.390 (2)°

  • V = 624.57 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.916, Tmax = 0.929

  • 2746 measured reflections

  • 2180 independent reflections

  • 1918 reflections with I > 2[sigma](I)

  • Rint = 0.008

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.073

  • S = 1.06

  • 2180 reflections

  • 175 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 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
C2-H2...O3i 0.93 2.58 3.395 (2) 146
O1-H1...O4ii 0.75 (2) 1.97 (2) 2.7143 (19) 173 (3)
C8-H8B...O5iii 0.97 2.53 3.429 (2) 154
O2-H2A...O1iv 0.81 (3) 1.92 (3) 2.706 (2) 163 (2)
O5-H5A...O3v 0.79 (3) 1.97 (3) 2.7459 (19) 165 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) -x+2, -y+1, -z; (iii) x, y+1, z; (iv) -x+1, -y+1, -z; (v) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]); software used to prepare material for publication: SHELXL97 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: BT6906 ).


Acknowledgements

The authors thank the TBI Consultancy, University of Madras, India, for the data collection. KR also thanks the management of Kandaswami Kandars College, Velur, Namakkal, Tamilnadu, India.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538-8539.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Yu, G.-M., Zhao, L., Guo, Y.-N., Xu, G.-F., Zou, L.-F., Tang, J.-K. & Li, Y.-H. (2010). J. Mol. Struct. 982, 139-144.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o893  [ doi:10.1107/S1600536813012737 ]

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