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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 [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.115
Data-to-parameter ratio = 15.1
Details
Open access

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

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-H...N(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[Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.], 2010[Tarafder, M. T. H., Khan, S. S., Islam, M. A. A. A. A., Lorenzi, L. & Zangrando, E. (2010). Acta Cryst. E66, o2851.]). For the corresponding metal complexes, see: Reza et al. (2012[Reza, M. S., Islam, M. A. A. A. A., Tarafder, M. T. H., Sheikh, M. C. & Zangrando, E. (2012). Acta Cryst. E68, m976-m977.]); Liu et al. (2009[Liu, Y.-H., Ye, J., Liu, X.-L. & Guo, R. (2009). J. Coord. Chem. 62, 3488-3499.]). For the biological activity of similar sulfur-nitrogen-containing Schiff base derivatives, see: Maia et al. (2010[Maia, P. I. D. S., Fernandes, A. G. D. A., Silva, J. J. N., Andricopulo, A. D., Lemos, S. S., Lang, E. S., Abram, U. & Deflon, V. M. (2010). J. Inorg. Biochem. 104, 1276-1282.]); Pavan et al. (2010[Pavan, F. R., Maia, P. I., d, S., Leite, S. R. A., Deflon, V. M., Batista, A. A., Sato, D. N., Franzblau, S. G. & Leite, C. Q. F. (2010). Eur. J. Med. Chem. 45, 1898-1905.]); Zhu et al. (2009[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.]). For the synthesis, see: Crouse et al. (2004[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.]); Khoo (2008[Khoo, T. J. (2008). PhD thesis, Universiti Putra Malaysia, Malaysia.]); Tarafder et al. (2008[Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.], 2010[Tarafder, M. T. H., Khan, S. S., Islam, M. A. A. A. A., Lorenzi, L. & Zangrando, E. (2010). Acta Cryst. E66, o2851.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3S2

  • Mr = 313.43

  • Triclinic, [P \overline 1]

  • a = 5.3784 (5) Å

  • b = 10.1570 (9) Å

  • c = 14.5488 (17) Å

  • [alpha] = 77.315 (9)°

  • [beta] = 84.735 (9)°

  • [gamma] = 78.193 (8)°

  • V = 758.06 (13) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.83, Tmax = 0.97

  • 15664 measured reflections

  • 2918 independent reflections

  • 2469 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
N1-H1n...N3i 0.88 (2) 2.02 (2) 2.897 (3) 172 (2)
C8-H8...Cg1ii 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khoo, T. J. (2008). PhD thesis, Universiti Putra Malaysia, Malaysia.
Liu, Y.-H., Ye, J., Liu, X.-L. & Guo, R. (2009). J. Coord. Chem. 62, 3488-3499.  [ISI] [CSD] [CrossRef] [ChemPort]
Maia, P. I. D. S., Fernandes, A. G. D. A., Silva, J. J. N., Andricopulo, A. D., Lemos, S. S., Lang, E. S., Abram, U. & Deflon, V. M. (2010). J. Inorg. Biochem. 104, 1276-1282.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Pavan, F. R., Maia, P. I., d, S., Leite, S. R. A., Deflon, V. M., Batista, A. A., Sato, D. N., Franzblau, S. G. & Leite, C. Q. F. (2010). Eur. J. Med. Chem. 45, 1898-1905.  [ISI] [CrossRef] [ChemPort] [PubMed]
Reza, M. S., Islam, M. A. A. A. A., Tarafder, M. T. H., Sheikh, M. C. & Zangrando, E. (2012). Acta Cryst. E68, m976-m977.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.  [CSD] [CrossRef] [ChemPort] [details]
Tarafder, M. T. H., Khan, S. S., Islam, M. A. A. A. A., Lorenzi, L. & Zangrando, E. (2010). Acta Cryst. E66, o2851.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o167-o168   [ doi:10.1107/S1600536812051537 ]

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