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Volume 68 
Part 1 
Page o208  
January 2012  

Received 14 December 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.061
wR = 0.161
Data-to-parameter ratio = 15.9
Details
Open access

3a,11b-Dihydroxy-3a,11b-dihydro-1H-imidazo[4,5-f][1,10]phenanthroline-2(3H)-thione

aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hljuhouyanjun@163.com

The title compound, C13H10N4O2S, was prepared through a cyclization reaction of 1,10-phenanthroline-5,6-dione and thiourea. The dihedral angle between the pyridine rings is 8.22 (2)°. In the crystal, molecules are connected by N-H...O, O-H...N, N-H...S and O-H...S hydrogen bonds, forming a three-dimensional network.

Related literature

For related structures, see: Liu et al. (2008[Liu, G. X., Huang, R. Y., Xu, H., Kong, X. J., Huang, L. F., Zhu, K. & Ren, X. M. (2008). Polyhedron, 27, 2327-2336.]); Wang et al. (2011[Wang, X. L., Gao, Q., Liu, G. C., Lin, H. Y., Tian, A. X. & Li, J. (2011). Inorg. Chem. Commun., 14, 745-748.]); Cong et al. (2009[Cong, F.-D., Yu, F.-Y., Wei, Z. & Ng, S. W. (2009). Acta Cryst. E65, m1544.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N4O2S

  • Mr = 286.31

  • Monoclinic, P 21 /c

  • a = 11.259 (4) Å

  • b = 12.815 (4) Å

  • c = 8.565 (3) Å

  • [beta] = 100.382 (5)°

  • V = 1215.6 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.18 × 0.14 × 0.12 mm

Data collection
  • Bruker SMART APEXII CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.952, Tmax = 0.968

  • 9690 measured reflections

  • 3035 independent reflections

  • 1325 reflections with I > 2[sigma](I)

  • Rint = 0.107

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.161

  • S = 0.94

  • 3035 reflections

  • 191 parameters

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...O1i 0.93 (4) 2.08 (4) 2.980 (4) 162 (3)
O2-H2O...S1ii 0.82 2.49 3.276 (3) 160
N4-H4N...S1iii 0.90 (4) 2.48 (4) 3.365 (4) 166 (3)
O1-H1O...N1iv 0.82 2.33 2.930 (4) 130
O1-H1O...N2iv 0.82 2.26 3.032 (4) 158
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2329 ).


Acknowledgements

We thank the National Natural Science Foundation of China (No. 20872030), the Foundation of Heilongjiang Education Committee (No. 12511383), the Key Laboratory of Chemical Engineering Process and Technology for High-Efficiency Conversion, the College of Heilongjiang Province and Heilongjiang University, China, for supporting this study.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cong, F.-D., Yu, F.-Y., Wei, Z. & Ng, S. W. (2009). Acta Cryst. E65, m1544.  [CSD] [CrossRef] [details]
Liu, G. X., Huang, R. Y., Xu, H., Kong, X. J., Huang, L. F., Zhu, K. & Ren, X. M. (2008). Polyhedron, 27, 2327-2336.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, X. L., Gao, Q., Liu, G. C., Lin, H. Y., Tian, A. X. & Li, J. (2011). Inorg. Chem. Commun., 14, 745-748.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o208  [ doi:10.1107/S1600536811053967 ]

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