{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-κ3 N 1,O,S}diphenyl­tin(IV)

Jichun Cui; Hong Ruan; Yanling Qiao; Handong Yin

doi:10.1107/S1600536810054024

. 2011 Jan 8;67(Pt 2):m145. doi: 10.1107/S1600536810054024

{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-κ³ N ¹,O,S}diphenyltin(IV)

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

PMCID: PMC3051660 PMID: 21522829

Abstract

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—H⋯O and N—H⋯S hydrogen bonds link four molecules into a centrosymmetric tetramer. The crystal packing exhibits short intermolecular S⋯S 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,
a = 10.0228 (14) Å
b = 10.9676 (16) Å
c = 19.732 (3) Å
α = 89.880 (2)°
β = 88.696 (2)°
γ = 85.435 (1)°
V = 2161.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.133
S = 1.00
7339 reflections
541 parameters
H-atom parameters constrained
Δρ_max = 1.56 e Å⁻³
Δρ_min = −0.79 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054024/cv5008sup1.cif

e-67-0m145-sup1.cif^{(26.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054024/cv5008Isup2.hkl

e-67-0m145-Isup2.hkl^{(359.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6B⋯O1ⁱ	0.86	2.35	3.209 (6)	177
N3—H3A⋯S2ⁱⁱ	0.86	2.87	3.522 (6)	134

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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).

supplementary crystallographic information

Comment

Recently, some organotin(IV) complexes of salicylaldehyde- thiosemicarbazones have been reported (Sarma et al., 2007). As an extension of the work on the organotin(IV) thiosemicarbazones chemistry, the title compound, (I), is reported here (Fig. 1).

In both independent molecules of the title compound, (I), the Sn atom has distorted trigonal-bipyramidal geometry, with atoms O and S in axial positions [O1—Sn1—S1 = 157.99 (11)°, O2—Sn2—S2 = 157.71 (13)°] and the atoms C, C and N in equatorial positions. The sum of the equatorial angles is 359.96 ° and 359.78 °, indicating approximate coplanarity for these atoms in two molecules. The Sn1—N1 (Sn2—N4) bond length is 2.175 (4) Å (2.185 (5) Å) close to the sum of the non-polar covalent radii 2.15 Å, indicating a strong Sn—N interaction.

Weak intermolecular N—H···O and N—H···S hydrogen bonds (Table 1) link four molecules into centrosymmetric tetramer (Fig. 2). The crystal packing exhibits short intermolecular S···S contacts of 3.335 (3) Å.

Experimental

The reaction was carried out under nitrogen atmosphere. 2-hydroxy-1-naphthaldehydethiosemicarbazone (1 mmol) and sodium ethoxide (1.1 mmol) were added to the solution of benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Diphenyltin dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirredfor 4 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1) to yield orange blocks of the title compound (yield 73%).