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Volume 68 
Part 1 
Pages o199-o200  
January 2012  

Received 9 December 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.086
Data-to-parameter ratio = 18.1
Details
Open access

(E)-1-[2-(Methylsulfanyl)phenyl]-2-({(E)-2-[2-(methylsulfanyl)phenyl]hydrazinylidene}(nitro)methyl)diazene

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa, and bDepartment of Chemistry, Nelson Mandela Metropolitan University, PO Box 77000, Port Elizabeth 6031, South Africa
Correspondence e-mail: veschwkg@ufs.ac.za

In the title compound, C15H15N5O2S2, the phenyl rings make dihedral angles of 4.03 (4) and 9.77 (5)° with the plane defined by the central N-N-C-N-N atoms (r.m.s. deviation = 0.010 Å). The C-S-C-C torsion angles of the methylsulfanyl groups with their respective phenyl rings are -7.47 (13) and -72.07 (13)°. The shortest centroid-centroid distance of 3.707 Å occurs between the two [pi]-systems N-N-C-N-N and the benzene ring in the diazene 1-position. The H atom bound to the N atom is involved in intramolecular N-H...N and N-H...S contacts, while the nitro O atoms are involved in intermolecular C-H...O contacts.

Related literature

For the chemistry of dithizone, see: Irving (1977[Irving, H. M. N. H. (1977). Dithizone. Analytical Sciences Monographs No. 5. London: The Chemical Society.]). For related structures, see: Laing (1977[Laing, M. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 1248-1252.]); Mito et al. (1997[Mito, M., Takeda, K., Mukai, K., Azuma, N., Gleiter, M. R., Krieger, C. & Neugebaue, F. A. (1997). J. Phys. Chem. B, 101, 9517-9524.]); Gilroy et al. (2008[Gilroy, J. B., Otieno, P. O., Ferguson, M. J., McDonald, R. & Hicks, R. G. (2008). Inorg. Chem. 47, 1279-1286.]). For the synthesis of nitroformazans, see: Pelkis et al. (1957[Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR, 27, 2190-2194.]). For DFT and electrochemistry studies of dithizone, see: von Eschwege & Swarts (2010[Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.]); von Eschwege, Conradie & Kuhn (2011[Eschwege, K. G. von, Conradie, J. & Kuhn, A. (2011). J. Phys. Chem. A. doi:10.1021/jp208212e.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15N5O2S2

  • Mr = 361.44

  • Monoclinic, P 21 /c

  • a = 4.7283 (2) Å

  • b = 17.9791 (10) Å

  • c = 19.3865 (8) Å

  • [beta] = 103.646 (2)°

  • V = 1601.54 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 200 K

  • 0.79 × 0.21 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 1.000

  • 14965 measured reflections

  • 3960 independent reflections

  • 3301 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.086

  • S = 1.04

  • 3960 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...S2 0.88 2.60 3.0248 (13) 110
N4-H4...N1 0.88 1.99 2.6229 (16) 128
C2-H2B...O1i 0.98 2.36 3.253 (2) 151
C25-H25...O2ii 0.95 2.45 3.1901 (19) 134
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and 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: ZQ2147 ).


Acknowledgements

The research funds of the University of the Free State, the Nelson Mandela Metropolitan University and the National Research Foundation are gratefully acknowledged.

References

Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Eschwege, K. G. von, Conradie, J. & Kuhn, A. (2011). J. Phys. Chem. A. doi:10.1021/jp208212e.
Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gilroy, J. B., Otieno, P. O., Ferguson, M. J., McDonald, R. & Hicks, R. G. (2008). Inorg. Chem. 47, 1279-1286.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Irving, H. M. N. H. (1977). Dithizone. Analytical Sciences Monographs No. 5. London: The Chemical Society.
Laing, M. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 1248-1252.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mito, M., Takeda, K., Mukai, K., Azuma, N., Gleiter, M. R., Krieger, C. & Neugebaue, F. A. (1997). J. Phys. Chem. B, 101, 9517-9524.  [CSD] [CrossRef] [ChemPort]
Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR, 27, 2190-2194.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o199-o200   [ doi:10.1107/S1600536811054080 ]

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