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Volume 69 
Part 5 
Pages o703-o704  
May 2013  

Received 2 April 2013
Accepted 5 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.040
wR = 0.085
Data-to-parameter ratio = 18.3
Details
Open access

3-(4-Methoxyphenyl)-1,3-selenazolo[2,3-b][1,3]benzothiazol-4-ium hydrogen sulfate

aBaku State University, Z. Khalilov St 23, Baku, AZ-1148, Azerbaijan,bR.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St, Nizhny Novgorod, 603950, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: gunka479@mail.ru

The title compound, C16H12NOSSe+·HSO4-, was obtained from a mixture of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride and potassium hydrogen sulfate. In the cation, the benzene ring is twisted by 71.62 (7)° from the tricycle mean plane. In the crystal, O-H...O hydrogen bonds link the anions into chains along [100]. The anions in adjacent chains are linked via weak C-H...O hydrogen bonds. The crystal packing exhibits short intermolecular contacts between the chalcogen unit and the O atoms: Se...O(anion) 2.713 (3), Se...O(cation) 2.987 (3) and S...O(anion) 2.958 (3) Å.

Related literature

For details of the synthesis and the biological properties of selenium- and nitrogen-containing heterocycles, see: Back (2009[Back, T. G. (2009). Can. J. Chem. 87, 1657-1674.]); Mlochowski & Giurg (2009[Mlochowski, J. & Giurg, M. (2009). In Topics in Heterocyclic Chemistry, edited by R. R. Gupta, Vol. 19, pp. 287-340. Berlin, Heidelberg: Springer-Verlag.]); Mukherjee et al. (2010[Mukherjee, A. J., Zade, S. S., Singh, H. B. & Sunoj, R. B. (2010). Chem. Rev. 110, 4357-4416.]); Selvakumar et al. (2010[Selvakumar, K., Singh, H. B. & Butcher, R. J. (2010). Chem. Eur. J. 16, 10576-10591.]). For the synthesis of the starting compound, 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride, see: Borisov et al. (2012[Borisov, A. V., Matsulevich, Zh. V., Osmanov, V. K. & Borisova, G. N. (2012). Chem. Heterocycl. Compd, 48, 1428-1429.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12NOSSe+·HO4S-

  • Mr = 442.35

  • Monoclinic, P 21

  • a = 4.6408 (8) Å

  • b = 18.263 (3) Å

  • c = 9.4482 (16) Å

  • [beta] = 94.294 (3)°

  • V = 798.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.64 mm-1

  • T = 100 K

  • 0.30 × 0.18 × 0.02 mm

Data collection
  • Bruker SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.505, Tmax = 0.949

  • 8638 measured reflections

  • 4145 independent reflections

  • 3555 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.085

  • S = 0.97

  • 4145 reflections

  • 227 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -0.99 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2075 Friedel pairs

  • Flack parameter: 0.038 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5O...O4i 0.91 1.80 2.610 (4) 147
C6-H6...O4ii 0.95 2.54 3.494 (5) 178
C8-H8...O2iii 0.95 2.26 3.022 (5) 137
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) x, y, z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5401 ).


Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help in this work.

References

Back, T. G. (2009). Can. J. Chem. 87, 1657-1674.  [ISI] [CrossRef] [ChemPort]
Borisov, A. V., Matsulevich, Zh. V., Osmanov, V. K. & Borisova, G. N. (2012). Chem. Heterocycl. Compd, 48, 1428-1429.  [ISI] [CrossRef] [ChemPort]
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Mlochowski, J. & Giurg, M. (2009). In Topics in Heterocyclic Chemistry, edited by R. R. Gupta, Vol. 19, pp. 287-340. Berlin, Heidelberg: Springer-Verlag.
Mukherjee, A. J., Zade, S. S., Singh, H. B. & Sunoj, R. B. (2010). Chem. Rev. 110, 4357-4416.  [ISI] [CrossRef] [ChemPort] [PubMed]
Selvakumar, K., Singh, H. B. & Butcher, R. J. (2010). Chem. Eur. J. 16, 10576-10591.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o703-o704   [ doi:10.1107/S1600536813009288 ]

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