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Volume 69 
Part 5 
Page o727  
May 2013  

Received 13 March 2013
Accepted 1 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 25.5
Details
Open access

3-(4-Methylphenyl)-4-[(thiosemicarbazono)methyl]-1,2,3-oxadiazol-3-ium-5-olate 1,4-dioxane hemisolvate

aDepartment of PG Studies in Chemistry, Government Science College, Hassan 573 201, India, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

The asymmetric unit of the title compound, C11H11N5O2S·0.5C4H8O2, contains one 3-(p-tolyl)sydnone 4-thiosemicarbazone molecule and a half molecule of 1,4-dioxane, which lies abount an inversion centre. The sydnone ring is almost planar, with a maximum deviation of 0.002 (1) Å, and forms a dihedral angle of 46.31 (5)° with the benzene ring. In the crystal, the two components are linked into a tape along [01-1] by N-H...O and N-H...S hydrogen bonds. The crystal structure is further stabilized by C-H...O and C-H...[pi] interactions, forming a three-dimensional network.

Related literature

For the biological acitivity of sydnones, see: Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.]); Jyothi et al. (2008[Jyothi, C. H., Girisha, K. S., Adithya, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831-2834.]); Nithinchandra et al. (2012[Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.]); Kalluraya et al. (2001[Kalluraya, B., Rahiman, A. M. & David, B. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 263-268.]). For a related structure, see: Fun et al. (2011[Fun, H.-K., Quah, C. K., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o1005-o1006.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11N5O2S·0.5C4H8O2

  • Mr = 321.36

  • Triclinic, [P \overline 1]

  • a = 7.7463 (1) Å

  • b = 9.3776 (1) Å

  • c = 10.4449 (2) Å

  • [alpha] = 79.689 (1)°

  • [beta] = 87.168 (1)°

  • [gamma] = 87.461 (1)°

  • V = 745.09 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 100 K

  • 0.35 × 0.29 × 0.24 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.921, Tmax = 0.944

  • 19865 measured reflections

  • 5407 independent reflections

  • 4782 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 1.08

  • 5407 reflections

  • 212 parameters

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
N4-H1N4...O3i 0.872 (17) 2.040 (17) 2.8624 (12) 156.8 (14)
N5-H1N5...S1ii 0.872 (18) 2.613 (18) 3.4754 (9) 170.2 (14)
C5-H5A...O2iii 0.95 2.31 3.2215 (13) 162
C9-H9A...O3i 0.95 2.34 3.1394 (12) 141
C12-H12B...O2iv 0.99 2.56 3.2626 (14) 128
C11-H11A...Cg1v 0.98 2.94 3.5736 (12) 123
Symmetry codes: (i) x+1, y, z-1; (ii) -x+2, -y+1, -z-1; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5258 ).


Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fun, H.-K., Quah, C. K., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o1005-o1006.
Jyothi, C. H., Girisha, K. S., Adithya, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831-2834.  [ISI] [PubMed]
Kalluraya, B., Rahiman, A. M. & David, B. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 263-268.  [CrossRef] [ChemPort]
Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.  [ISI] [CrossRef] [ChemPort] [PubMed]
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.  [ISI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o727  [ doi:10.1107/S1600536813008805 ]

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