Bis{S-benzyl 3-[(6-methyl­pyridin-2-yl)methyl­idene]dithio­carbazato}nickel(II)

Ravoof, T.B.S.A.; Omar, S.A.; Mohamed Tahir, M.I.; Crouse, K.A.

doi:10.1107/S1600536812017333

Volume 68
Part 5
Page m664
May 2012

Received 16 April 2012
Accepted 19 April 2012
Online 25 April 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.087
Data-to-parameter ratio = 18.5
Details

Bis{S-benzyl 3-[(6-methylpyridin-2-yl)methylidene]dithiocarbazato}nickel(II)

Thahira Begum S. A. Ravoof,^a ^* Siti Aminah Omar,^a Mohamed Ibrahim Mohamed Tahir ^a and Karen A. Crouse ^a

^aDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM, Serdang, Selangor, Malaysia
Correspondence e-mail: thahira.begum@science.upm.edu.my

The asymmetric unit of the title compound, [Ni(C₁₅H₁₄N₃S₂)₂], consists of two independent molecules with similar configurations. Each Ni²⁺ cation is coordinated in a cis-mode by two tridentate N,N',S-chelating Schiff base ligands, creating a distorted octahedron [the smallest angle being 77.57 (7)° and the widest being 168.97 (7)° for one molecule, and 78.04 (7) and 167.55 (7)° for the second molecule]. The dihedral angle between the mean coordination planes of the two ligands is 86.76 (7)° for one and 89.99 (7)° for the second molecule. [pi] - [pi] interactions between neighbouring pyridine rings with plane-to-plane distances of 3.540 (1) and 3.704 (1) Å are observed.

Related literature

For background to the coordination chemistry of hydrazine carbodithioates, see: Ravoof et al. (2010). For the synthesis, see: Ravoof et al. (2004). For related structures, see: Ali et al. (1997, 1999); Omar et al. (2012).

Experimental

Crystal data

[Ni(C₁₅H₁₄N₃S₂)₂]
M_r = 659.57
Triclinic, $[P \overline 1]$
a = 12.3544 (9) Å
b = 15.6411 (6) Å
c = 16.9333 (10) Å
= 69.520 (5)°
= 87.516 (5)°
= 89.446 (5)°
V = 3062.4 (3) Å³
Z = 4
Mo K radiation
= 0.94 mm^-1
T = 150 K
0.16 × 0.13 × 0.11 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.88, T_max = 0.90
23348 measured reflections
13743 independent reflections
11306 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.087
S = 0.97
13696 reflections
739 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.51 e Å^-3

Table 1
Selected bond lengths (Å)

Ni1-N202	2.0139 (18)
Ni1-N102	2.0173 (17)
Ni1-N115	2.1761 (18)
Ni1-N215	2.1881 (18)
Ni1-S105	2.4062 (6)
Ni1-S205	2.4158 (6)
Ni2-N302	2.0085 (18)
Ni2-N402	2.0156 (18)
Ni2-N315	2.1604 (17)
Ni2-N415	2.1770 (18)
Ni2-S405	2.4202 (6)
Ni2-S305	2.4263 (6)

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2622 ).

Acknowledgements

Support for the project came from Universiti Putra Malaysia (UPM) under research University Grant Schemes (RUGS No. 05-01-11-1243RU & RUGS No. 9174000) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01-03-11-986FR). SAO wishes to thank UPM for the award of a Graduate Research Fellowship.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Ali, M. A., Butcher, R. J. & Bryan, J. C. (1999). Inorg. Chim. Acta, 287, 8-13.
Ali, M. A., Majumder, S. M. M., Butcher, R. J., Jasinski, J. P. & Jasinski, J. M. (1997). Polyhedron, 16, 2749-2754.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Omar, S. A., Ravoof, T. B. S. A., Mohamed Tahir, M. I. & Crouse, K. A. (2012). Acta Cryst. E68, m316-m317.
Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., Cowley, A. R. & Ali, M. A. (2004). Polyhedron, 23(16), 2491-2498.
Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871-876.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.

metal-organic compounds