{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-κ3N1,O,S}diphenyl­tin(IV)

Cui, J.; Ruan, H.; Qiao, Y.; Yin, H.

doi:10.1107/S1600536810054024

Volume 67
Part 2
Page m145
February 2011

Received 24 November 2010
Accepted 24 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 13.6
Details

{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-³N¹,O,S}diphenyltin(IV)

Jichun Cui,^a Hong Ruan,^a Yanling Qiao ^a and Handong Yin ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: handongyin@163.com

The asymmetric unit of the title compound, [Sn(C₆H₅)₂(C₁₂H₉N₃OS)], contains two independent molecules with almost identical configurations. In each molecule, the Sn^IV atom is coordinated by O, N and S atoms from a (2-oxido-1-naphthaldehyde)thiosemicarbazonato ligand and two C atoms from phenyl rings in a distorted trigonal-bipyramidal geometry. Weak intermolecular N-HO and N-HS hydrogen bonds link four molecules into a centrosymmetric tetramer. The crystal packing exhibits short intermolecular SS contacts of 3.335 (3) Å.

Related literature

For related organotin(IV) complexes with salicylaldehydethiosemicarbazones, see: Sarma et al. (2007).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₁₂H₉N₃OS)]
M_r = 516.17
Triclinic, $[P \overline 1]$
a = 10.0228 (14) Å
b = 10.9676 (16) Å
c = 19.732 (3) Å
= 89.880 (2)°
= 88.696 (2)°
= 85.435 (1)°
V = 2161.6 (5) Å³
Z = 4
Mo K radiation
= 1.30 mm^-1
T = 298 K
0.23 × 0.18 × 0.12 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.754, T_max = 0.860
10805 measured reflections
7339 independent reflections
5240 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.133
S = 1.00
7339 reflections
541 parameters
H-atom parameters constrained
_max = 1.56 e Å^-3
_min = -0.79 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N6-H6BO1ⁱ	0.86	2.35	3.209 (6)	177
N3-H3AS2ⁱⁱ	0.86	2.87	3.522 (6)	134
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5008 ).

Acknowledgements

We acknowledge the National Natural Foundation of China (grant No. 20771053) and the Students Science and Technology Innovation Fund of Liaocheng University (grant No. SRT10064HX2).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sarma, M. S., Mazumder, S., Ghosh, D., Roy, A., Duthie, A. & Tiekink, E. R. T. (2007). Appl. Organomet. Chem. 21, 890-905.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

metal-organic compounds

{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-3N1,O,S}diphenyltin(IV)