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

Eschwege, K.G. von; Muller, F.; Hosten, E.C.

doi:10.1107/S1600536811054080

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 (C-C) = 0.002 Å
R = 0.031
wR = 0.086
Data-to-parameter ratio = 18.1
Details

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

Karel G. von Eschwege,^a ^* Fabian Muller ^a and Eric C. Hosten ^b

^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-HN and N-HS contacts, while the nitro O atoms are involved in intermolecular C-HO contacts.

Related literature

For the chemistry of dithizone, see: Irving (1977). For related structures, see: Laing (1977); Mito et al. (1997); Gilroy et al. (2008). For the synthesis of nitroformazans, see: Pelkis et al. (1957). For DFT and electrochemistry studies of dithizone, see: von Eschwege & Swarts (2010); von Eschwege, Conradie & Kuhn (2011).

Experimental

Crystal data

C₁₅H₁₅N₅O₂S₂
M_r = 361.44
Monoclinic, P 2₁ /c
a = 4.7283 (2) Å
b = 17.9791 (10) Å
c = 19.3865 (8) Å
= 103.646 (2)°
V = 1601.54 (13) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.870, T_max = 1.000
14965 measured reflections
3960 independent reflections
3301 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.086
S = 1.04
3960 reflections
219 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4S2	0.88	2.60	3.0248 (13)	110
N4-H4N1	0.88	1.99	2.6229 (16)	128
C2-H2BO1ⁱ	0.98	2.36	3.253 (2)	151
C25-H25O2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

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Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.
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organic compounds