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

Zhang, Z.; Wei, M.; Wang, J.; Zhang, G.

doi:10.1107/S160053680903548X

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 (C-C) = 0.004 Å
R = 0.037
wR = 0.119
Data-to-parameter ratio = 13.8
Details

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

Zhenfeng Zhang,^a ^* Meilin Wei,^a Jiange Wang ^b and Guisheng Zhang ^a

^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-HS and O-HO 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); Lenzen & Ahmad (2001); Perronnet & Teche (1973). For related structures, see: Enders et al. (1979); Zhang et al. (2007).

Experimental

Crystal data

C₁₅H₁₄N₂O₂S
M_r = 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 radiation
= 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) T_min = 0.923, T_max = 0.944
7542 measured reflections
2521 independent reflections
2273 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.119
S = 1.09
2521 reflections
183 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.40 e Å^-3
Absolute structure: Flack (1983), 1123 Friedel pairs
Flack parameter: 0.16 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1S1ⁱ	0.91	2.41	3.261 (2)	156
O2-H2O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: 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.
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, 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.
Zhang, Z.-F., Zhang, J.-M., Guo, J.-P. & Qu, G.-R. (2007). Acta Cryst. E63, o2821-o2823.

organic compounds