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Volume 64 
Part 4 
Page o690  
April 2008  

Received 24 February 2008
Accepted 6 March 2008
Online 12 March 2008


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Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.005 Å
R = 0.052
wR = 0.140
Data-to-parameter ratio = 13.3
Details

4-{[(1,3-Benzothiazolium-2-yl)hydrazono](phenyl)methyl}-3-methyl-1-phenyl-1H-pyrazol-5-olate monohydrate

Yi-Feng Suna,b* and Yi-Ping Cuia

aAdvanced Photonics Center, School of Electronic Science and Engineering, Southeast University, 210096 Nanjing, Jiangsu, People's Republic of China, and bDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China
Correspondence e-mail: sunyf50@hotmail.com

The title compound, C24H19N5OS·H2O, was synthesized by the reaction of 4-benzoyl-3-methyl-1-phenylpyrazol-5-one and 2-hydrazino-1,3-benzothiazole. Proton transfer leads to the formation of a zwitterionic structure and the molecule exists in the enolate form. The pyrazolone ring makes dihedral angles of 35.4 (3), 69.7 (3) and 40.1 (3)° with the 1-phenyl, indirectly bound phenyl and benzothiazole ring systems, respectively. The molecules are linked into one-dimensional chains by a combination of N-H...O, O-H...N and O-H...O hydrogen bonds.

Related literature

For related literature, see: Akama & Tong (1996[Akama, Y. & Tong, A. (1996). Microchem. J. 53, 34-41.]); Eller & Holzer (2004[Eller, G. A. & Holzer, W. (2004). Heterocycles, 63, 2537-2555.]); Morakot et al. (2008[Morakot, N., Ngeontae, W., Aeungmaitrepirom, W. & Tuntulani, T. (2008). Bull. Korean Chem. Soc. 29, 221-224.]); Rana et al. (2007[Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian J. Pharm. Sci. 69, 10-17.]); Sieron (2007[Sieron, L. (2007). Acta Cryst. E63, m598-m600.]); Kim et al. (2005[Kim, Y. H., Youk, J. S., Kim, S. H. & Chang, S. K. (2005). Bull. Korean Chem. Soc. 26, 47-50.]); Costa et al. (2006[Costa, S. P. G., Batista, R. M. F., Sousa, A. M. R. C. & Raposo, M. M. M. (2006). Mater. Sci. Forum, 514-516, 147-151.]); Usman et al. (2003[Usman, A., Fun, H.-K., Chantrapromma, S., Zhang, M., Chen, Z.-F., Tang, Y.-Z., Shi, S.-M. & Liang, H. (2003). Acta Cryst. E59, m41-m43.]). Two related compounds we have previously reported exist in the enamine-keto tautomeric form (Sun et al., 2006[Sun, Y., Zhang, D., Gao, H., Wang, H. & Tao, R. (2006). Anal. Sci. X, 22, x289-x290.], 2007[Sun, Y.-F., Sun, X.-Z., Zhang, D.-D. & Cui, Y.-P. (2007). Acta Cryst. E63, o2005-o2006.]).

[Scheme 1]

Experimental

Crystal data

  • C24H19N5OS·H2O

  • Mr = 443.52

  • Triclinic, [P \overline 1]

  • a = 7.1059 (16) Å

  • b = 12.906 (3) Å

  • c = 13.439 (3) Å

  • [alpha] = 67.173 (4)°

  • [beta] = 85.597 (4)°

  • [gamma] = 76.226 (4)°

  • V = 1103.1 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 273 (2) K

  • 0.15 × 0.12 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.982

  • 5750 measured reflections

  • 3850 independent reflections

  • 3210 reflections with I > 2[sigma](I)

  • Rint = 0.018
Refinement

  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.139

  • S = 1.09

  • 3850 reflections

  • 290 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H25...N5i 0.85 1.97 2.815 (3) 178
O2-H26...O1ii 0.85 2.00 2.829 (3) 166
N1-H1...O2 0.86 1.81 2.662 (3) 173
N2-H2...O1 0.86 1.78 2.541 (3) 146
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, 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: LH2599 ).

Acknowledgements

This project was supported by the Jiangsu Planned Projects for Postdoctoral Research Funds (No. 0701001B).

References

Akama, Y. & Tong, A. (1996). Microchem. J. 53, 34-41.
Bruker (1997). SMART, SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Costa, S. P. G., Batista, R. M. F., Sousa, A. M. R. C. & Raposo, M. M. M. (2006). Mater. Sci. Forum, 514-516, 147-151.
Eller, G. A. & Holzer, W. (2004). Heterocycles, 63, 2537-2555.
Kim, Y. H., Youk, J. S., Kim, S. H. & Chang, S. K. (2005). Bull. Korean Chem. Soc. 26, 47-50.
Morakot, N., Ngeontae, W., Aeungmaitrepirom, W. & Tuntulani, T. (2008). Bull. Korean Chem. Soc. 29, 221-224.
Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian J. Pharm. Sci. 69, 10-17.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sieron, L. (2007). Acta Cryst. E63, m598-m600.
Sun, Y.-F., Sun, X.-Z., Zhang, D.-D. & Cui, Y.-P. (2007). Acta Cryst. E63, o2005-o2006.
Sun, Y., Zhang, D., Gao, H., Wang, H. & Tao, R. (2006). Anal. Sci. X, 22, x289-x290.
Usman, A., Fun, H.-K., Chantrapromma, S., Zhang, M., Chen, Z.-F., Tang, Y.-Z., Shi, S.-M. & Liang, H. (2003). Acta Cryst. E59, m41-m43.

Acta Cryst (2008). E64, o690  [ doi:10.1107/S1600536808006193 ]

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