(E)-1-(3-Nitro­phen­yl)-2-({5-[(1E)-2-(3-nitro­phen­yl)hydrazin-1-ylidenemeth­yl]-2-thien­yl}methyl­idene)hydrazine

Lima, G.M. de; Harrison, W.T.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536810002771

Volume 66
Part 2
Pages o457-o458
February 2010

Received 21 January 2010
Accepted 22 January 2010
Online 27 January 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 15.6
Details

(E)-1-(3-Nitrophenyl)-2-({5-[(1E)-2-(3-nitrophenyl)hydrazin-1-ylidenemethyl]-2-thienyl}methylidene)hydrazine

Geraldo M. de Lima,^a William T. A. Harrison,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ⁺ and Solange M. S. V. Wardell ^e

^aDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil,^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia,^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
Correspondence e-mail: edward.tiekink@gmail.com

The title molecule, C₁₈H₁₄N₆O₄S, adopts a U-shape with the aromatic groups lying syn and oriented in the same direction as the thiophene S atom. Twists away from planarity are evident with the maximum deviation being found for a terminal nitro group: C/C/N/O = 19.0 (3)°. The conformation about each of the C=N bonds is E. In the crystal, centrosymmetrically related molecules are connected via N-HO_nitro hydrogen bonds, forming 14-membered {HNC₃NO}₂ synthons. These are linked into layers via C-HO_nitro interactions with the primary interactions between layers being of the type C-H [pi] , where the [pi] -system is the thiophene ring.

Related literature

For the preparation of hydrazones of thiophenecarbaldehydes, see: Kwon et al. (2009); Wardell et al. (2007); Vaysse & Pastour (1964). For general uses of 2-substituted-thiophenes, see: Campaigne (1984). For their specific uses as materials, see: Michaleviciute et al. (2007, 2009); Kwon et al. (2009). For their specific uses as pharmacological agents, see: Kleemann et al. (2006); Sonar & Crooks (2009); Mellado et al. (2009); Satyanarayana et al. (2008); Lourenço et al. (2007). For related structures, see: Wardell et al. (2007, 2010); Ferreira et al. (2009); Nogueira et al. (2010).

Experimental

Crystal data

C₁₈H₁₄N₆O₄S
M_r = 410.41
Monoclinic, P 2₁ /c
a = 11.1790 (5) Å
b = 20.6993 (9) Å
c = 8.0334 (2) Å
= 100.513 (2)°
V = 1827.70 (12) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 120 K
0.62 × 0.10 × 0.06 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.668, T_max = 0.746
21780 measured reflections
4183 independent reflections
3001 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.133
S = 1.08
4183 reflections
268 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nO2ⁱ	0.89 (2)	2.27 (2)	3.103 (2)	156 (2)
C2-H2O3ⁱⁱ	0.95	2.46	3.278 (3)	145
C18-H18O4ⁱⁱⁱ	0.95	2.48	3.241 (3)	137
C12-H12Cg1^iv	0.95	2.58	3.323 (2)	135
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x-1, y, z+1; (iii) x, y, z+1; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2635 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

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