(E)-1-Phenyl-2-({5-[(1E)-(2-phenyl­hydrazin-1-yl­idene)meth­yl]-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/S1600536810003302

Volume 66
Part 3
Pages o504-o505
March 2010

Received 26 January 2010
Accepted 27 January 2010
Online 3 February 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.006 Å
R = 0.050
wR = 0.108
Data-to-parameter ratio = 17.2
Details

(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]-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, C₁₈H₁₆N₄S, adopts a U-shape with the aromatic groups lying syn and orientated in the same direction as the thiophene S atom. The conformation about each of the C=N bonds is E. Overall, the molecule is curved as seen in the dihedral angle of 30.26 (19)° formed between the terminal benzene rings. In the crystal, supramolecular chains along the c axis are formed by a combination of N-HN hydrogen bonds and N-H [pi] interactions.

Related literature

For specific uses of 2-substituted-thiophenes as materials, see: Michaleviciute et al. (2007, 2009); Kwon et al. (2009). For their specific uses as biological agents, see: Sonar & Crooks (2009); Mellado & Cortes (2009); Satyanarayana et al. (2008); Lourenço et al. (2007). For the preparation of hydrazones of thiophenecarbaldehydes, see: Kwon, et al. (2009); Wardell et al. (2007); Vaysse & Pastour (1964); Novitskii et al. (1961). For related structures, see: Wardell et al. (2007, 2010); Ferreira et al. (2009); Nogueira et al. (2010); de Lima et al. (2010).

Experimental

Crystal data

C₁₈H₁₆N₄S
M_r = 320.41
Trigonal, P 3₂
a = 15.6495 (6) Å
c = 5.9335 (10) Å
V = 1258.5 (2) Å³
Z = 3
Mo K radiation
= 0.20 mm^-1
T = 120 K
0.42 × 0.06 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.767, T_max = 1.000
11400 measured reflections
3675 independent reflections
3287 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.108
S = 1.04
3675 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1748 Friedel pairs
Flack parameter: 0.04 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6-C11 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2nN4ⁱ	0.88 (4)	2.58 (5)	3.398 (4)	155 (4)
C12-H12N2ⁱⁱ	0.95	2.57	3.463 (5)	157
N4-H4NCgⁱⁱ	0.89 (4)	2.81 (5)	3.415 (4)	126 (3)
Symmetry codes: (i) $[-x+y+1, -x+2, z+{\script{1\over 3}}]$ ; (ii) $[-y+2, x-y+1, z+{\script{2\over 3}}]$ .

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: HG2637 ).

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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