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Volume 68 
Part 3 
Page o609  
March 2012  

Received 19 January 2012
Accepted 31 January 2012
Online 4 February 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 15.4
Details
Open access

1-(2-Methoxyphenyl)-2-{[2-(2-methoxyphenyl)hydrazinylidene](nitro)methyl}diazene

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: veschwkg@ufs.ac.za

In the title compound, C15H15N5O4, a nitroformazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204 (6) Å and adopts a closed syn,s-cis configuration with an intramolecular N-H...N hydrogen bond. The formazan plane makes dihedral angles of 4.32 (5) and 24.35 (5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58 (8)°. In the crystal, C-H...O interactions connect the molecules into an inversion dimer.

Related literature

For synthetic background, see: Pelkis et al. (1957[Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR (Engl. Transl.), 27, 2190-2194.]). For applications of formazans, see: Irving (1977[Irving, H. M. N. H. (1977). Dithizone. Analytical Sciences Monographs, No. 5. London: The Chemical Society.]). For related structures, see: Gilroy et al. (2008[Gilroy, J. B., Otieno, P. O., Ferguson, M. J., McDonald, R. & Hicks, R. G. (2008). Inorg. Chem. 47, 1279-1286.]); 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.]); von Eschwege et al. (2011[Eschwege, K. G. von, Conradie, J. & Kuhn, A. (2011). J. Phys. Chem. A, 115, 14637-14646.], 2012[Eschwege, K. G. von, Muller, F. & Hosten, E. C. (2012). Acta Cryst. E68, o199-o200.]); von Eschwege & Swarts (2010[Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15N5O4

  • Mr = 329.32

  • Triclinic, [P \overline 1]

  • a = 7.2025 (5) Å

  • b = 10.9574 (8) Å

  • c = 11.2190 (9) Å

  • [alpha] = 117.188 (2)°

  • [beta] = 91.416 (2)°

  • [gamma] = 107.251 (2)°

  • V = 738.66 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.25 × 0.21 × 0.06 mm

Data collection
  • Bruker X8 APEXII 4K KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.]) Tmin = 0.668, Tmax = 0.746

  • 10250 measured reflections

  • 3431 independent reflections

  • 2824 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.11

  • S = 1.04

  • 3431 reflections

  • 223 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...N2 1.10 (3) 1.73 (3) 2.6117 (15) 134 (3)
C17-H17B...O1i 0.98 2.47 3.3325 (16) 146
C27-H27C...O2i 0.98 2.65 3.3907 (17) 133
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.]); data reduction: SAINT-Plus; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5057 ).


Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Eschwege, K. G. von, Conradie, J. & Kuhn, A. (2011). J. Phys. Chem. A, 115, 14637-14646.  [PubMed]
Eschwege, K. G. von, Muller, F. & Hosten, E. C. (2012). Acta Cryst. E68, o199-o200.  [CSD] [CrossRef] [details]
Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [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.
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 (Engl. Transl.), 27, 2190-2194.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o609  [ doi:10.1107/S1600536812004175 ]

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