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

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

doi:10.1107/S1600536810054024

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m145

doi:10.1107/S1600536810054024

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{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-κ³N¹,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

(Received 24 November 2010; accepted 24 December 2010; online 8 January 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 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

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
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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. The hydrogen-bonded (dashed lines) tetramer in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

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

Crystal data top

[Sn(C₆H₅)₂(C₁₂H₉N₃OS)(C₆H₅)₂]	Z = 4
M_r = 516.17	F(000) = 1032
Triclinic, P1	D_x = 1.586 Mg m⁻³
a = 10.0228 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9676 (16) Å	Cell parameters from 4687 reflections
c = 19.732 (3) Å	θ = 2.3–26.9°
α = 89.880 (2)°	µ = 1.30 mm⁻¹
β = 88.696 (2)°	T = 298 K
γ = 85.435 (1)°	Block, orange
V = 2161.6 (5) Å³	0.23 × 0.18 × 0.12 mm

Data collection top

Bruker SMART 1000 diffractometer	7339 independent reflections
Radiation source: fine-focus sealed tube	5240 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.754, T_max = 0.860	k = −13→12
10805 measured reflections	l = −23→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0739P)²] where P = (F_o² + 2F_c²)/3
7339 reflections	(Δ/σ)_max = 0.001
541 parameters	Δρ_max = 1.56 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₁₂H₉N₃OS)(C₆H₅)₂]	γ = 85.435 (1)°
M_r = 516.17	V = 2161.6 (5) Å³
Triclinic, P1	Z = 4
a = 10.0228 (14) Å	Mo Kα radiation
b = 10.9676 (16) Å	µ = 1.30 mm⁻¹
c = 19.732 (3) Å	T = 298 K
α = 89.880 (2)°	0.23 × 0.18 × 0.12 mm
β = 88.696 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 1.56 e Å⁻³
7339 reflections	Δρ_min = −0.79 e Å⁻³
541 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.94444 (4)	0.74053 (3)	0.412798 (19)	0.03969 (14)
Sn2	0.00729 (4)	0.23449 (3)	0.106121 (19)	0.04414 (14)
N1	0.8748 (4)	0.8873 (4)	0.4820 (2)	0.0389 (10)
N2	0.9313 (5)	0.8903 (4)	0.5463 (2)	0.0492 (12)
N3	1.0343 (6)	0.7806 (5)	0.6313 (3)	0.0689 (16)
H3A	1.0376	0.8470	0.6540	0.083*
H3B	1.0664	0.7121	0.6479	0.083*
N4	0.0984 (4)	0.0635 (4)	0.0630 (2)	0.0414 (11)
N5	0.0689 (5)	−0.0488 (4)	0.0921 (2)	0.0462 (12)
N6	−0.0081 (6)	−0.1457 (4)	0.1860 (3)	0.0641 (15)
H6A	−0.0010	−0.2137	0.1641	0.077*
H6B	−0.0367	−0.1437	0.2274	0.077*
O1	0.8805 (4)	0.8727 (4)	0.33971 (18)	0.0475 (10)
O2	0.0506 (4)	0.2965 (4)	0.0086 (2)	0.0547 (11)
S1	0.97185 (17)	0.64262 (14)	0.52905 (8)	0.0507 (4)
S2	0.0102 (2)	0.08899 (15)	0.20601 (8)	0.0600 (5)
C1	0.7892 (6)	0.9790 (5)	0.4688 (3)	0.0454 (14)
H1	0.7695	1.0353	0.5035	0.055*
C2	0.7216 (5)	1.0023 (5)	0.4060 (3)	0.0403 (13)
C3	0.7693 (5)	0.9484 (5)	0.3446 (3)	0.0412 (13)
C4	0.7010 (6)	0.9777 (6)	0.2835 (3)	0.0507 (15)
H4	0.7317	0.9409	0.2431	0.061*
C5	0.5912 (6)	1.0589 (6)	0.2838 (3)	0.0584 (17)
H5	0.5494	1.0775	0.2430	0.070*
C6	0.5381 (6)	1.1164 (6)	0.3440 (3)	0.0533 (16)
C7	0.6038 (6)	1.0868 (5)	0.4063 (3)	0.0475 (14)
C8	0.5456 (6)	1.1439 (6)	0.4660 (4)	0.0601 (17)
H8	0.5850	1.1271	0.5076	0.072*
C9	0.4336 (7)	1.2223 (6)	0.4635 (4)	0.072 (2)
H9	0.3978	1.2573	0.5035	0.086*
C10	0.3716 (7)	1.2512 (7)	0.4030 (5)	0.080 (2)
H10	0.2961	1.3062	0.4022	0.096*
C11	0.4231 (6)	1.1975 (7)	0.3439 (4)	0.070 (2)
H11	0.3806	1.2154	0.3033	0.084*
C12	0.9781 (6)	0.7837 (6)	0.5686 (3)	0.0472 (14)
C13	0.8249 (6)	0.6076 (5)	0.3716 (3)	0.0440 (14)
C14	0.7493 (6)	0.5338 (6)	0.4118 (4)	0.0553 (16)
H14	0.7450	0.5456	0.4585	0.066*
C15	0.6798 (7)	0.4425 (6)	0.3832 (4)	0.0681 (19)
H15	0.6307	0.3927	0.4107	0.082*
C16	0.6844 (9)	0.4264 (7)	0.3135 (5)	0.085 (3)
H16	0.6364	0.3669	0.2940	0.102*
C17	0.7581 (10)	0.4965 (8)	0.2743 (4)	0.099 (3)
H17	0.7624	0.4834	0.2277	0.119*
C18	0.8277 (8)	0.5881 (7)	0.3016 (4)	0.075 (2)
H18	0.8766	0.6368	0.2733	0.090*
C19	1.1504 (5)	0.7491 (5)	0.3860 (3)	0.0424 (13)
C20	1.1968 (6)	0.8478 (6)	0.3512 (3)	0.0550 (16)
H20	1.1373	0.9127	0.3384	0.066*
C21	1.3335 (8)	0.8495 (8)	0.3353 (4)	0.076 (2)
H21	1.3650	0.9161	0.3124	0.091*
C22	1.4206 (8)	0.7535 (10)	0.3533 (4)	0.087 (3)
H22	1.5112	0.7554	0.3424	0.104*
C23	1.3769 (7)	0.6546 (9)	0.3871 (4)	0.083 (2)
H23	1.4369	0.5891	0.3985	0.099*
C24	1.2427 (6)	0.6534 (6)	0.4039 (3)	0.0595 (17)
H24	1.2131	0.5872	0.4278	0.071*
C25	0.1833 (6)	0.0530 (6)	0.0113 (3)	0.0483 (15)
H25	0.2173	−0.0257	−0.0004	0.058*
C26	0.2289 (6)	0.1518 (6)	−0.0291 (3)	0.0461 (14)
C27	0.1601 (7)	0.2678 (6)	−0.0279 (3)	0.0548 (16)
C28	0.2088 (8)	0.3617 (7)	−0.0708 (4)	0.072 (2)
H28	0.1634	0.4390	−0.0713	0.087*
C29	0.3204 (9)	0.3383 (8)	−0.1105 (4)	0.082 (3)
H29	0.3500	0.4008	−0.1375	0.099*
C30	0.3926 (7)	0.2236 (8)	−0.1124 (3)	0.0650 (19)
C31	0.3494 (6)	0.1270 (7)	−0.0721 (3)	0.0550 (17)
C32	0.5141 (9)	0.2039 (11)	−0.1522 (4)	0.088 (3)
H32	0.5429	0.2671	−0.1789	0.105*
C33	0.5871 (9)	0.0951 (11)	−0.1514 (4)	0.093 (3)
H33	0.6674	0.0848	−0.1761	0.111*
C34	0.5426 (7)	−0.0016 (8)	−0.1138 (3)	0.076 (2)
H34	0.5912	−0.0774	−0.1148	0.091*
C35	0.4265 (7)	0.0149 (7)	−0.0748 (3)	0.0631 (18)
H35	0.3986	−0.0505	−0.0496	0.076*
C36	0.0259 (6)	−0.0414 (5)	0.1551 (3)	0.0438 (13)
C37	−0.2025 (6)	0.2693 (5)	0.0914 (3)	0.0454 (14)
C38	−0.2527 (7)	0.3028 (6)	0.0285 (3)	0.0628 (18)
H38	−0.1946	0.3020	−0.0089	0.075*
C39	−0.3868 (8)	0.3373 (7)	0.0203 (4)	0.085 (2)
H39	−0.4177	0.3603	−0.0223	0.101*
C40	−0.4757 (8)	0.3378 (7)	0.0752 (5)	0.083 (2)
H40	−0.5662	0.3607	0.0696	0.100*
C41	−0.4287 (7)	0.3043 (7)	0.1376 (4)	0.074 (2)
H41	−0.4872	0.3042	0.1748	0.089*
C42	−0.2932 (7)	0.2704 (6)	0.1452 (4)	0.0622 (18)
H42	−0.2626	0.2477	0.1879	0.075*
C43	0.1128 (5)	0.3726 (5)	0.1536 (3)	0.0421 (13)
C44	0.1418 (7)	0.4771 (6)	0.1197 (3)	0.0599 (17)
H44	0.1222	0.4854	0.0740	0.072*
C45	0.2000 (7)	0.5706 (6)	0.1527 (3)	0.0665 (19)
H45	0.2189	0.6405	0.1287	0.080*
C46	0.2299 (8)	0.5615 (6)	0.2196 (4)	0.068 (2)
H46	0.2675	0.6250	0.2415	0.082*
C47	0.2035 (9)	0.4571 (7)	0.2540 (4)	0.084 (3)
H47	0.2248	0.4493	0.2995	0.100*
C48	0.1457 (8)	0.3634 (6)	0.2221 (4)	0.069 (2)
H48	0.1285	0.2934	0.2464	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0424 (2)	0.0429 (2)	0.0336 (2)	−0.00235 (17)	−0.00036 (16)	0.00203 (17)
Sn2	0.0562 (3)	0.0419 (2)	0.0352 (2)	−0.00743 (18)	−0.00820 (18)	0.00630 (17)
N1	0.043 (3)	0.043 (3)	0.031 (3)	−0.005 (2)	−0.0026 (19)	0.003 (2)
N2	0.064 (3)	0.052 (3)	0.032 (3)	−0.009 (2)	−0.010 (2)	0.004 (2)
N3	0.095 (4)	0.071 (4)	0.042 (3)	−0.006 (3)	−0.020 (3)	0.005 (3)
N4	0.049 (3)	0.047 (3)	0.030 (3)	−0.013 (2)	−0.001 (2)	0.004 (2)
N5	0.065 (3)	0.036 (3)	0.039 (3)	−0.013 (2)	0.002 (2)	0.003 (2)
N6	0.099 (4)	0.041 (3)	0.053 (3)	−0.016 (3)	0.010 (3)	0.006 (3)
O1	0.056 (2)	0.053 (2)	0.031 (2)	0.0045 (19)	0.0030 (17)	0.0068 (18)
O2	0.076 (3)	0.055 (3)	0.033 (2)	−0.007 (2)	−0.004 (2)	0.0133 (19)
S1	0.0669 (10)	0.0478 (9)	0.0364 (8)	0.0019 (7)	−0.0021 (7)	0.0085 (7)
S2	0.1025 (14)	0.0464 (9)	0.0316 (8)	−0.0095 (9)	−0.0022 (8)	0.0068 (7)
C1	0.051 (4)	0.041 (3)	0.043 (3)	0.002 (3)	0.004 (3)	−0.004 (3)
C2	0.045 (3)	0.042 (3)	0.034 (3)	−0.005 (2)	0.001 (2)	0.008 (2)
C3	0.043 (3)	0.039 (3)	0.042 (3)	−0.007 (2)	0.002 (2)	0.005 (2)
C4	0.053 (4)	0.065 (4)	0.035 (3)	−0.010 (3)	−0.001 (3)	0.005 (3)
C5	0.051 (4)	0.074 (4)	0.052 (4)	−0.011 (3)	−0.014 (3)	0.012 (3)
C6	0.044 (3)	0.057 (4)	0.060 (4)	−0.014 (3)	−0.003 (3)	0.018 (3)
C7	0.049 (3)	0.044 (3)	0.050 (4)	−0.006 (3)	0.003 (3)	0.010 (3)
C8	0.063 (4)	0.051 (4)	0.065 (5)	0.006 (3)	0.014 (3)	0.007 (3)
C9	0.071 (5)	0.055 (4)	0.086 (6)	0.008 (4)	0.022 (4)	0.015 (4)
C10	0.044 (4)	0.074 (5)	0.117 (7)	0.012 (3)	0.022 (4)	0.029 (5)
C11	0.046 (4)	0.075 (5)	0.088 (6)	−0.002 (3)	−0.004 (4)	0.027 (4)
C12	0.047 (3)	0.056 (4)	0.039 (3)	−0.003 (3)	−0.007 (3)	0.008 (3)
C13	0.049 (3)	0.033 (3)	0.050 (4)	−0.002 (2)	−0.011 (3)	0.005 (3)
C14	0.046 (4)	0.057 (4)	0.063 (4)	−0.002 (3)	0.002 (3)	0.001 (3)
C15	0.057 (4)	0.060 (4)	0.089 (6)	−0.015 (3)	−0.004 (4)	0.010 (4)
C16	0.104 (6)	0.073 (5)	0.083 (6)	−0.034 (5)	−0.039 (5)	0.005 (5)
C17	0.159 (9)	0.089 (6)	0.058 (5)	−0.054 (6)	−0.031 (6)	0.003 (5)
C18	0.114 (6)	0.073 (5)	0.045 (4)	−0.036 (4)	−0.017 (4)	0.007 (4)
C19	0.041 (3)	0.055 (4)	0.032 (3)	−0.009 (3)	−0.003 (2)	−0.002 (3)
C20	0.060 (4)	0.062 (4)	0.043 (4)	−0.012 (3)	0.001 (3)	−0.001 (3)
C21	0.080 (6)	0.099 (6)	0.054 (5)	−0.043 (5)	0.013 (4)	−0.009 (4)
C22	0.049 (5)	0.146 (9)	0.068 (6)	−0.030 (5)	0.012 (4)	−0.020 (6)
C23	0.044 (4)	0.128 (7)	0.073 (5)	0.015 (4)	−0.007 (4)	−0.007 (5)
C24	0.047 (4)	0.075 (5)	0.055 (4)	0.002 (3)	0.001 (3)	0.005 (3)
C25	0.055 (4)	0.053 (4)	0.038 (3)	−0.011 (3)	−0.003 (3)	0.000 (3)
C26	0.054 (4)	0.064 (4)	0.023 (3)	−0.022 (3)	−0.006 (2)	0.001 (3)
C27	0.076 (5)	0.061 (4)	0.030 (3)	−0.016 (3)	−0.016 (3)	0.009 (3)
C28	0.092 (6)	0.067 (5)	0.061 (5)	−0.029 (4)	−0.011 (4)	0.027 (4)
C29	0.099 (6)	0.103 (7)	0.052 (5)	−0.057 (5)	−0.009 (4)	0.033 (4)
C30	0.075 (5)	0.088 (5)	0.036 (4)	−0.035 (4)	−0.007 (3)	0.010 (4)
C31	0.059 (4)	0.080 (5)	0.030 (3)	−0.032 (4)	−0.010 (3)	0.000 (3)
C32	0.085 (6)	0.143 (8)	0.044 (5)	−0.059 (6)	0.000 (4)	0.018 (5)
C33	0.068 (6)	0.168 (10)	0.048 (5)	−0.044 (6)	0.001 (4)	0.000 (6)
C34	0.062 (5)	0.123 (7)	0.046 (4)	−0.015 (4)	−0.004 (3)	−0.014 (4)
C35	0.059 (4)	0.095 (6)	0.038 (4)	−0.020 (4)	−0.003 (3)	−0.004 (4)
C36	0.050 (3)	0.041 (3)	0.040 (3)	−0.002 (3)	−0.005 (3)	0.009 (3)
C37	0.052 (4)	0.039 (3)	0.046 (4)	−0.006 (3)	−0.007 (3)	−0.003 (3)
C38	0.062 (4)	0.076 (5)	0.051 (4)	−0.007 (3)	−0.009 (3)	0.009 (3)
C39	0.081 (6)	0.095 (6)	0.078 (6)	−0.003 (5)	−0.034 (5)	0.015 (5)
C40	0.067 (5)	0.083 (6)	0.100 (7)	0.003 (4)	−0.021 (5)	0.003 (5)
C41	0.066 (5)	0.082 (5)	0.073 (5)	−0.005 (4)	0.005 (4)	−0.007 (4)
C42	0.067 (5)	0.063 (4)	0.056 (4)	−0.004 (3)	−0.011 (3)	0.000 (3)
C43	0.048 (3)	0.036 (3)	0.043 (3)	−0.005 (2)	−0.003 (3)	0.001 (3)
C44	0.079 (5)	0.057 (4)	0.046 (4)	−0.014 (3)	−0.006 (3)	0.008 (3)
C45	0.099 (6)	0.057 (4)	0.047 (4)	−0.033 (4)	−0.001 (4)	0.005 (3)
C46	0.089 (5)	0.056 (4)	0.063 (5)	−0.025 (4)	−0.012 (4)	−0.002 (4)
C47	0.137 (7)	0.070 (5)	0.050 (4)	−0.035 (5)	−0.035 (5)	0.006 (4)
C48	0.104 (6)	0.054 (4)	0.054 (4)	−0.023 (4)	−0.022 (4)	0.015 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.116 (4)	C17—H17	0.9300
Sn1—C19	2.128 (5)	C18—H18	0.9300
Sn1—C13	2.134 (5)	C19—C20	1.387 (8)
Sn1—N1	2.175 (4)	C19—C24	1.393 (8)
Sn1—S1	2.5420 (16)	C20—C21	1.400 (10)
Sn2—O2	2.088 (4)	C20—H20	0.9300
Sn2—C37	2.134 (6)	C21—C22	1.364 (11)
Sn2—C43	2.144 (5)	C21—H21	0.9300
Sn2—N4	2.185 (5)	C22—C23	1.369 (12)
Sn2—S2	2.5326 (16)	C22—H22	0.9300
N1—C1	1.299 (7)	C23—C24	1.379 (9)
N1—N2	1.401 (6)	C23—H23	0.9300
N2—C12	1.303 (7)	C24—H24	0.9300
N3—C12	1.371 (7)	C25—C26	1.440 (8)
N3—H3A	0.8600	C25—H25	0.9300
N3—H3B	0.8600	C26—C27	1.398 (9)
N4—C25	1.313 (7)	C26—C31	1.468 (9)
N4—N5	1.408 (6)	C27—C28	1.440 (9)
N5—C36	1.307 (7)	C28—C29	1.360 (11)
N6—C36	1.359 (7)	C28—H28	0.9300
N6—H6A	0.8600	C29—C30	1.400 (11)
N6—H6B	0.8600	C29—H29	0.9300
O1—C3	1.337 (6)	C30—C31	1.412 (9)
O2—C27	1.315 (8)	C30—C32	1.436 (11)
S1—C12	1.741 (6)	C31—C35	1.400 (9)
S2—C36	1.744 (6)	C32—C33	1.350 (12)
C1—C2	1.438 (8)	C32—H32	0.9300
C1—H1	0.9300	C33—C34	1.390 (12)
C2—C3	1.407 (7)	C33—H33	0.9300
C2—C7	1.442 (8)	C34—C35	1.380 (9)
C3—C4	1.423 (8)	C34—H34	0.9300
C4—C5	1.360 (8)	C35—H35	0.9300
C4—H4	0.9300	C37—C42	1.381 (9)
C5—C6	1.419 (9)	C37—C38	1.387 (8)
C5—H5	0.9300	C38—C39	1.380 (10)
C6—C11	1.399 (9)	C38—H38	0.9300
C6—C7	1.431 (8)	C39—C40	1.387 (11)
C7—C8	1.427 (8)	C39—H39	0.9300
C8—C9	1.360 (9)	C40—C41	1.367 (11)
C8—H8	0.9300	C40—H40	0.9300
C9—C10	1.383 (11)	C41—C42	1.391 (9)
C9—H9	0.9300	C41—H41	0.9300
C10—C11	1.379 (11)	C42—H42	0.9300
C10—H10	0.9300	C43—C44	1.374 (8)
C11—H11	0.9300	C43—C48	1.400 (8)
C13—C14	1.387 (8)	C44—C45	1.389 (9)
C13—C18	1.397 (9)	C44—H44	0.9300
C14—C15	1.392 (9)	C45—C46	1.362 (9)
C14—H14	0.9300	C45—H45	0.9300
C15—C16	1.387 (11)	C46—C47	1.371 (10)
C15—H15	0.9300	C46—H46	0.9300
C16—C17	1.341 (11)	C47—C48	1.378 (9)
C16—H16	0.9300	C47—H47	0.9300
C17—C18	1.385 (10)	C48—H48	0.9300

O1—Sn1—C19	93.23 (19)	C13—C18—H18	119.9
O1—Sn1—C13	92.32 (19)	C20—C19—C24	118.3 (6)
C19—Sn1—C13	122.7 (2)	C20—C19—Sn1	122.1 (4)
O1—Sn1—N1	81.88 (15)	C24—C19—Sn1	119.6 (4)
C19—Sn1—N1	111.26 (18)	C19—C20—C21	119.9 (7)
C13—Sn1—N1	126.00 (19)	C19—C20—H20	120.1
O1—Sn1—S1	157.99 (11)	C21—C20—H20	120.1
C19—Sn1—S1	98.65 (16)	C22—C21—C20	120.0 (7)
C13—Sn1—S1	96.69 (16)	C22—C21—H21	120.0
N1—Sn1—S1	76.57 (12)	C20—C21—H21	120.0
O2—Sn2—C37	91.4 (2)	C21—C22—C23	121.2 (7)
O2—Sn2—C43	93.16 (19)	C21—C22—H22	119.4
C37—Sn2—C43	118.6 (2)	C23—C22—H22	119.4
O2—Sn2—N4	81.15 (16)	C22—C23—C24	119.0 (8)
C37—Sn2—N4	115.57 (18)	C22—C23—H23	120.5
C43—Sn2—N4	125.61 (18)	C24—C23—H23	120.5
O2—Sn2—S2	157.71 (13)	C23—C24—C19	121.6 (7)
C37—Sn2—S2	101.39 (17)	C23—C24—H24	119.2
C43—Sn2—S2	96.54 (16)	C19—C24—H24	119.2
N4—Sn2—S2	76.88 (12)	N4—C25—C26	126.2 (6)
C1—N1—N2	114.9 (5)	N4—C25—H25	116.9
C1—N1—Sn1	126.3 (4)	C26—C25—H25	116.9
N2—N1—Sn1	118.6 (3)	C27—C26—C25	121.2 (6)
C12—N2—N1	114.2 (5)	C27—C26—C31	120.8 (6)
C12—N3—H3A	120.0	C25—C26—C31	118.1 (6)
C12—N3—H3B	120.0	O2—C27—C26	124.3 (6)
H3A—N3—H3B	120.0	O2—C27—C28	117.3 (6)
C25—N4—N5	114.2 (5)	C26—C27—C28	118.4 (7)
C25—N4—Sn2	126.1 (4)	C29—C28—C27	120.6 (8)
N5—N4—Sn2	119.6 (3)	C29—C28—H28	119.7
C36—N5—N4	114.6 (4)	C27—C28—H28	119.7
C36—N6—H6A	120.0	C28—C29—C30	122.5 (7)
C36—N6—H6B	120.0	C28—C29—H29	118.8
H6A—N6—H6B	120.0	C30—C29—H29	118.8
C3—O1—Sn1	125.5 (3)	C29—C30—C31	119.9 (7)
C27—O2—Sn2	126.7 (4)	C29—C30—C32	121.0 (8)
C12—S1—Sn1	92.4 (2)	C31—C30—C32	119.1 (8)
C36—S2—Sn2	93.7 (2)	C35—C31—C30	117.6 (6)
N1—C1—C2	126.7 (5)	C35—C31—C26	124.5 (6)
N1—C1—H1	116.7	C30—C31—C26	117.9 (7)
C2—C1—H1	116.7	C33—C32—C30	121.0 (8)
C3—C2—C1	122.1 (5)	C33—C32—H32	119.5
C3—C2—C7	119.4 (5)	C30—C32—H32	119.5
C1—C2—C7	118.5 (5)	C32—C33—C34	120.1 (8)
O1—C3—C2	123.1 (5)	C32—C33—H33	119.9
O1—C3—C4	117.1 (5)	C34—C33—H33	119.9
C2—C3—C4	119.8 (5)	C35—C34—C33	120.1 (9)
C5—C4—C3	120.6 (6)	C35—C34—H34	120.0
C5—C4—H4	119.7	C33—C34—H34	120.0
C3—C4—H4	119.7	C34—C35—C31	122.1 (7)
C4—C5—C6	122.4 (6)	C34—C35—H35	119.0
C4—C5—H5	118.8	C31—C35—H35	119.0
C6—C5—H5	118.8	N5—C36—N6	117.8 (5)
C11—C6—C5	121.9 (6)	N5—C36—S2	127.1 (4)
C11—C6—C7	120.1 (6)	N6—C36—S2	115.1 (4)
C5—C6—C7	118.1 (6)	C42—C37—C38	117.0 (6)
C8—C7—C6	116.5 (6)	C42—C37—Sn2	121.3 (5)
C8—C7—C2	123.7 (6)	C38—C37—Sn2	121.4 (5)
C6—C7—C2	119.7 (5)	C39—C38—C37	121.5 (7)
C9—C8—C7	121.4 (7)	C39—C38—H38	119.2
C9—C8—H8	119.3	C37—C38—H38	119.2
C7—C8—H8	119.3	C38—C39—C40	120.4 (7)
C8—C9—C10	121.7 (7)	C38—C39—H39	119.8
C8—C9—H9	119.2	C40—C39—H39	119.8
C10—C9—H9	119.2	C41—C40—C39	119.1 (8)
C11—C10—C9	119.2 (7)	C41—C40—H40	120.4
C11—C10—H10	120.4	C39—C40—H40	120.4
C9—C10—H10	120.4	C40—C41—C42	119.9 (8)
C10—C11—C6	121.2 (7)	C40—C41—H41	120.0
C10—C11—H11	119.4	C42—C41—H41	120.0
C6—C11—H11	119.4	C37—C42—C41	122.1 (7)
N2—C12—N3	117.0 (5)	C37—C42—H42	119.0
N2—C12—S1	127.3 (4)	C41—C42—H42	119.0
N3—C12—S1	115.6 (5)	C44—C43—C48	117.5 (5)
C14—C13—C18	117.9 (6)	C44—C43—Sn2	121.5 (4)
C14—C13—Sn1	122.7 (4)	C48—C43—Sn2	120.8 (4)
C18—C13—Sn1	119.3 (5)	C43—C44—C45	121.0 (6)
C13—C14—C15	120.9 (6)	C43—C44—H44	119.5
C13—C14—H14	119.5	C45—C44—H44	119.5
C15—C14—H14	119.5	C46—C45—C44	121.1 (6)
C16—C15—C14	119.5 (7)	C46—C45—H45	119.5
C16—C15—H15	120.2	C44—C45—H45	119.5
C14—C15—H15	120.2	C45—C46—C47	118.8 (6)
C17—C16—C15	120.0 (7)	C45—C46—H46	120.6
C17—C16—H16	120.0	C47—C46—H46	120.6
C15—C16—H16	120.0	C46—C47—C48	121.0 (7)
C16—C17—C18	121.4 (8)	C46—C47—H47	119.5
C16—C17—H17	119.3	C48—C47—H47	119.5
C18—C17—H17	119.3	C47—C48—C43	120.7 (6)
C17—C18—C13	120.2 (7)	C47—C48—H48	119.7
C17—C18—H18	119.9	C43—C48—H48	119.7

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₁₂H₉N₃OS)(C₆H₅)₂]
M_r	516.17
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.0228 (14), 10.9676 (16), 19.732 (3)
α, β, γ (°)	89.880 (2), 88.696 (2), 85.435 (1)
V (Å³)	2161.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.23 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.754, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	10805, 7339, 5240
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 1.00
No. of reflections	7339
No. of parameters	541
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.56, −0.79

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y+1, −z+1.

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. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sarma, M. S., Mazumder, S., Ghosh, D., Roy, A., Duthie, A. & Tiekink, E. R. T. (2007). Appl. Organomet. Chem. 21, 890–905. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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