[Journal logo]

Volume 65 
Part 10 
Page o2389  
October 2009  

Received 21 August 2009
Accepted 2 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.119
Data-to-parameter ratio = 13.8
Details
Open access

trans-4,5-Dihydroxy-1,3-diphenylimidazolidine-2-thione

aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China, and bCollege of Chemistry, Luoyang Normal University, Xinxiang 453007, People's Republic of China
Correspondence e-mail: zzf5188@sohu.com

In the title compound, C15H14N2O2S, the five-membered ring adopts an envelope conformation and the two hydroxy groups lie on opposite sides of the ring. The six-membered rings are oriented at a dihedral angle of 22.63 (3)°. In the crystal structure, intermolecular O-H...S and O-H...O hydrogen bonds link the molecules into a two-dimensional network.

Related literature

For the biological activity of imidazolidine-2-one derivatives, see: Lam et al. (1994[Lam, P. Y. S., Jadhav, P. K., Eyermann, C. J., Hodge, C. N., Ru, Y., Bacheler, L. T., Meek, J. L., Otto, M. J., Rayner, M. M., Wong, Y. N., Chang, C.-H., Weber, P. C., Jackson, D. A., Sharpe, T. R. & Erickson-Viitanen, S. (1994). Science, 263, 380-384.]); Lenzen & Ahmad (2001[Lenzen, S. & Ahmad, R. (2001). Ger. Offen. DE10012401.]); Perronnet & Teche (1973[Perronnet, J. & Teche, A. (1973). US Patent 3 905 996.]). For related structures, see: Enders et al. (1979[Enders, E., Ebbighausen, V., Gau, W., Wunsche, C. & Stendel, W. (1979). US Patent 4 173 645.]); Zhang et al. (2007[Zhang, Z.-F., Zhang, J.-M., Guo, J.-P. & Qu, G.-R. (2007). Acta Cryst. E63, o2821-o2823.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O2S

  • Mr = 286.34

  • Orthorhombic, P c a 21

  • a = 20.5119 (4) Å

  • b = 7.1020 (4) Å

  • c = 9.6659 (3) Å

  • V = 1408.09 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 294 K

  • 0.35 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.923, Tmax = 0.944

  • 7542 measured reflections

  • 2521 independent reflections

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

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.119

  • S = 1.09

  • 2521 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1123 Friedel pairs

  • Flack parameter: 0.16 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...S1i 0.91 2.41 3.261 (2) 156
O2-H2...O1ii 0.82 2.13 2.930 (3) 167
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. 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: 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: HK2762 ).


Acknowledgements

Financial support from Henan Normal University and the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (grant No. 2008IRTSTHN002) is gratefully acknowledged. The authors also thank the Physiochemical Analysis Measurement Laboratory, College of Chemistry, Luoyang Normal University, for performing the X-ray analysis.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Enders, E., Ebbighausen, V., Gau, W., Wunsche, C. & Stendel, W. (1979). US Patent 4 173 645.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Lam, P. Y. S., Jadhav, P. K., Eyermann, C. J., Hodge, C. N., Ru, Y., Bacheler, L. T., Meek, J. L., Otto, M. J., Rayner, M. M., Wong, Y. N., Chang, C.-H., Weber, P. C., Jackson, D. A., Sharpe, T. R. & Erickson-Viitanen, S. (1994). Science, 263, 380-384.  [CrossRef] [ChemPort] [PubMed] [ISI]
Lenzen, S. & Ahmad, R. (2001). Ger. Offen. DE10012401.
Perronnet, J. & Teche, A. (1973). US Patent 3 905 996.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, Z.-F., Zhang, J.-M., Guo, J.-P. & Qu, G.-R. (2007). Acta Cryst. E63, o2821-o2823.  [CSD] [CrossRef] [details]


Acta Cryst (2009). E65, o2389  [ doi:10.1107/S160053680903548X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.