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Volume 67 
Part 7 
Pages o1743-o1744  
July 2011  

Received 11 December 2010
Accepted 15 March 2011
Online 18 June 2011

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
H completeness 96%
Disorder in solvent or counterion
R = 0.071
wR = 0.204
Data-to-parameter ratio = 14.8
Details
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(6aS,11aR,11cS)-8-Sulfanylidene-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate

Liang Wang,a Chun-Mei Zhang,b Jun-Xiang Guo,b Qiu-Ye Wub and Hong-Gang Hub*

aSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China, and bDepartment of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China
Correspondence e-mail: huhonggang_fox@msn.com

The title compound, C15H23N2S+·Cl-·0.5H2O, was prepared from (6aS,11aR,11cS)-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracene-8-one (sophocarpine) and Lawesson's reagent. The thione-substituted ring is in an envelope conformation and the three other six-membered rings are in chair conformations. In the crystal, anions and cations are linked by N-H...Cl and weak C-H...Cl hydrogen bonds. One 0.5-occupancy solvent water molecule lies on a twofold rotation axis and another 0.25-occupancy solvent water molecule is in a general position. The H atoms of these water molecules were not located or included in the refinement.

Related literature

For background to the medicinal uses of sophocarpine natural products, see: Gao et al. (2009[Gao, Y. L., Li, G. S., Li, C. M., Zhu, X. Y., Li, M., Fu, C. L. & Li, B. F. J. (2009). Ethnopharmacology, 125, 324-329.]); Jiang et al. (2007[Jiang, H., Hou, C., Zhang, S., Xie, H., Zhou, W., Jin, Q., Cheng, X., Qian, R. & Zhang, X. (2007). Eur. J. Pharmacol. 559, 98-108.]); Liu et al. (2007[Liu, J. Y., Hu, J. H., Zhu, Q. G., Li, F. Q., Wang, J. & Sun, H. J. (2007). Int. Immunopharmacol. 7, 816-823.]). For related structures, see: Ding et al. (2005[Ding, P. L., Liao, Z. X., Huang, H., Zhou, P. & Chen, D. F. (2005). Bioorg Med. Chem. Lett. pp. 1231-1235.]); Khan et al. (1992[Khan, M. A., Burrows, G. E. & Holt, E. M. (1992). Acta Cryst. C48, 2051-2053.]). For the synthesis, see: Kaleta et al. (2006[Kaleta, Z., Makowski, B. T., Soos, T. & Dembinski, R. (2006). Org. Lett. 8, 1625-1628.]).

[Scheme 1]

Experimental

Crystal data

  • C15H23N2S+·Cl-·0.5H2O

  • Mr = 306.87

  • Tetragonal, P 41 21 2

  • a = 7.793 (5) Å

  • c = 52.59 (5) Å

  • V = 3194 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.18 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.915, Tmax = 0.937

  • 11100 measured reflections

  • 2816 independent reflections

  • 2489 reflections with I > 2[sigma](I)

  • Rint = 0.043
Refinement

  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.204

  • S = 1.23

  • 2816 reflections

  • 190 parameters

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

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1023 Friedel pairs

  • Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...Cl1 1.10 (9) 2.01 (8) 3.019 (6) 151 (6)
C4-H4A...Cl1i 0.97 2.82 3.726 (7) 155
Symmetry code: (i) y, x, -z.

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: LH5190 ).

Acknowledgements

The authors are grateful to Weng Linhong and Dr Cheng of the Department of Chemistry of Fudan University for the data acquisition and interpretation. This work was supported by grants from the National Natural Science Foundation (No. 20902109) and the Science & Technology Commission of Shanghai Municipality (No. 08JC1405500)

References

Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Ding, P. L., Liao, Z. X., Huang, H., Zhou, P. & Chen, D. F. (2005). Bioorg Med. Chem. Lett. pp. 1231-1235.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gao, Y. L., Li, G. S., Li, C. M., Zhu, X. Y., Li, M., Fu, C. L. & Li, B. F. J. (2009). Ethnopharmacology, 125, 324-329.  [PubMed] [ChemPort]
Jiang, H., Hou, C., Zhang, S., Xie, H., Zhou, W., Jin, Q., Cheng, X., Qian, R. & Zhang, X. (2007). Eur. J. Pharmacol. 559, 98-108.  [ISI] [PubMed] [ChemPort]
Kaleta, Z., Makowski, B. T., Soos, T. & Dembinski, R. (2006). Org. Lett. 8, 1625-1628.  [ISI] [CrossRef] [PubMed] [ChemPort]
Khan, M. A., Burrows, G. E. & Holt, E. M. (1992). Acta Cryst. C48, 2051-2053.  [CrossRef] [details]
Liu, J. Y., Hu, J. H., Zhu, Q. G., Li, F. Q., Wang, J. & Sun, H. J. (2007). Int. Immunopharmacol. 7, 816-823.  [ISI] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2011). E67, o1743-o1744   [ doi:10.1107/S160053681100972X ]

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