(Pyridin-4-yl)methyl N′-(3-phenyl­allyl­idene)hydrazinecarbodithio­ate

Low, M.L.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S1600536812051537

Volume 69
Part 2
Pages o167-o168
February 2013

Received 20 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.115
Data-to-parameter ratio = 15.1
Details

(Pyridin-4-yl)methyl N'-(3-phenylallylidene)hydrazinecarbodithioate

May Lee Low,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ⁺ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C₁₆H₁₅N₃S₂, the central C₂N₂S₂ residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the molecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supramolecular chains along [1-10] are stabilized by N-HN(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C-H [pi] (pyridine) interactions.

Related literature

For background to related Schiff bases of S-substituted dithiocarbazates with cinnamaldehyde, see: Tarafder et al. (2008, 2010). For the corresponding metal complexes, see: Reza et al. (2012); Liu et al. (2009). For the biological activity of similar sulfur-nitrogen-containing Schiff base derivatives, see: Maia et al. (2010); Pavan et al. (2010); Zhu et al. (2009). For the synthesis, see: Crouse et al. (2004); Khoo (2008); Tarafder et al. (2008, 2010).

Experimental

Crystal data

C₁₆H₁₅N₃S₂
M_r = 313.43
Triclinic, $[P \overline 1]$
a = 5.3784 (5) Å
b = 10.1570 (9) Å
c = 14.5488 (17) Å
= 77.315 (9)°
= 84.735 (9)°
= 78.193 (8)°
V = 758.06 (13) Å³
Z = 2
Cu K radiation
= 3.14 mm^-1
T = 100 K
0.13 × 0.06 × 0.01 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.83, T_max = 0.97
15664 measured reflections
2918 independent reflections
2469 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.115
S = 1.05
2918 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.42 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3,C12-C15 pyridyl ring.

D-HA	D-H	HA	DA	D-HA
N1-H1nN3ⁱ	0.88 (2)	2.02 (2)	2.897 (3)	172 (2)
C8-H8Cg1ⁱⁱ	0.95	2.92	3.701 (3)	141
Symmetry codes: (i) x+1, y-1, z; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) 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: QM2090 ).

Acknowledgements

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS 9174000) and the Malaysian Ministry of Science Technology and Innovation (MOSTI 09-02-04-9752EA001) and the Malaysian Fundamental Research Grant Scheme (FRGS 01-13-11-986FR). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Crouse, K. A., Chew, K.-B., Tarafder, M. T. H., Kasbollah, A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2004). Polyhedron, 23, 161-168.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Khoo, T. J. (2008). PhD thesis, Universiti Putra Malaysia, Malaysia.
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Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.
Tarafder, M. T. H., Khan, S. S., Islam, M. A. A. A. A., Lorenzi, L. & Zangrando, E. (2010). Acta Cryst. E66, o2851.
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Zhu, Y.-J., Song, K.-K., Ll, Z.-C., Pan, Z.-Z., Guo, Y.-J., Zhou, J.-J., Wang, Q., Liu, B. & Chen, Q.-X. (2009). J. Agric. Food Chem. 57, 5518-5523.

organic compounds