metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 SnIV 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[Sarma, M. S., Mazumder, S., Ghosh, D., Roy, A., Duthie, A. & Tiekink, E. R. T. (2007). Appl. Organomet. Chem. 21, 890-905.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)2(C12H9N3OS)]

  • Mr = 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.754, Tmax = 0.860

  • 10805 measured reflections

  • 7339 independent reflections

  • 5240 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.133

  • S = 1.00

  • 7339 reflections

  • 541 parameters

  • H-atom parameters constrained

  • Δρmax = 1.56 e Å−3

  • Δρmin = −0.79 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%).

Refinement top

All H atoms were positioned geometrically (C—H 0.93 Å, N—H 0.86 Å), and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, N).

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] 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
Mr = 516.17F(000) = 1032
Triclinic, P1Dx = 1.586 Mg m3
a = 10.0228 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9676 (16) ÅCell parameters from 4687 reflections
c = 19.732 (3) Åθ = 2.3–26.9°
α = 89.880 (2)°µ = 1.30 mm1
β = 88.696 (2)°T = 298 K
γ = 85.435 (1)°Block, orange
V = 2161.6 (5) Å30.23 × 0.18 × 0.12 mm
Data collection top
Bruker SMART 1000
diffractometer
7339 independent reflections
Radiation source: fine-focus sealed tube5240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.754, Tmax = 0.860k = 1312
10805 measured reflectionsl = 2317
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0739P)2]
where P = (Fo2 + 2Fc2)/3
7339 reflections(Δ/σ)max = 0.001
541 parametersΔρmax = 1.56 e Å3
0 restraintsΔρmin = 0.79 e Å3
Crystal data top
[Sn(C6H5)2(C12H9N3OS)(C6H5)2]γ = 85.435 (1)°
Mr = 516.17V = 2161.6 (5) Å3
Triclinic, P1Z = 4
a = 10.0228 (14) ÅMo Kα radiation
b = 10.9676 (16) ŵ = 1.30 mm1
c = 19.732 (3) ÅT = 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)
Tmin = 0.754, Tmax = 0.860Rint = 0.032
10805 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.00Δρmax = 1.56 e Å3
7339 reflectionsΔρmin = 0.79 e Å3
541 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.94444 (4)0.74053 (3)0.412798 (19)0.03969 (14)
Sn20.00729 (4)0.23449 (3)0.106121 (19)0.04414 (14)
N10.8748 (4)0.8873 (4)0.4820 (2)0.0389 (10)
N20.9313 (5)0.8903 (4)0.5463 (2)0.0492 (12)
N31.0343 (6)0.7806 (5)0.6313 (3)0.0689 (16)
H3A1.03760.84700.65400.083*
H3B1.06640.71210.64790.083*
N40.0984 (4)0.0635 (4)0.0630 (2)0.0414 (11)
N50.0689 (5)0.0488 (4)0.0921 (2)0.0462 (12)
N60.0081 (6)0.1457 (4)0.1860 (3)0.0641 (15)
H6A0.00100.21370.16410.077*
H6B0.03670.14370.22740.077*
O10.8805 (4)0.8727 (4)0.33971 (18)0.0475 (10)
O20.0506 (4)0.2965 (4)0.0086 (2)0.0547 (11)
S10.97185 (17)0.64262 (14)0.52905 (8)0.0507 (4)
S20.0102 (2)0.08899 (15)0.20601 (8)0.0600 (5)
C10.7892 (6)0.9790 (5)0.4688 (3)0.0454 (14)
H10.76951.03530.50350.055*
C20.7216 (5)1.0023 (5)0.4060 (3)0.0403 (13)
C30.7693 (5)0.9484 (5)0.3446 (3)0.0412 (13)
C40.7010 (6)0.9777 (6)0.2835 (3)0.0507 (15)
H40.73170.94090.24310.061*
C50.5912 (6)1.0589 (6)0.2838 (3)0.0584 (17)
H50.54941.07750.24300.070*
C60.5381 (6)1.1164 (6)0.3440 (3)0.0533 (16)
C70.6038 (6)1.0868 (5)0.4063 (3)0.0475 (14)
C80.5456 (6)1.1439 (6)0.4660 (4)0.0601 (17)
H80.58501.12710.50760.072*
C90.4336 (7)1.2223 (6)0.4635 (4)0.072 (2)
H90.39781.25730.50350.086*
C100.3716 (7)1.2512 (7)0.4030 (5)0.080 (2)
H100.29611.30620.40220.096*
C110.4231 (6)1.1975 (7)0.3439 (4)0.070 (2)
H110.38061.21540.30330.084*
C120.9781 (6)0.7837 (6)0.5686 (3)0.0472 (14)
C130.8249 (6)0.6076 (5)0.3716 (3)0.0440 (14)
C140.7493 (6)0.5338 (6)0.4118 (4)0.0553 (16)
H140.74500.54560.45850.066*
C150.6798 (7)0.4425 (6)0.3832 (4)0.0681 (19)
H150.63070.39270.41070.082*
C160.6844 (9)0.4264 (7)0.3135 (5)0.085 (3)
H160.63640.36690.29400.102*
C170.7581 (10)0.4965 (8)0.2743 (4)0.099 (3)
H170.76240.48340.22770.119*
C180.8277 (8)0.5881 (7)0.3016 (4)0.075 (2)
H180.87660.63680.27330.090*
C191.1504 (5)0.7491 (5)0.3860 (3)0.0424 (13)
C201.1968 (6)0.8478 (6)0.3512 (3)0.0550 (16)
H201.13730.91270.33840.066*
C211.3335 (8)0.8495 (8)0.3353 (4)0.076 (2)
H211.36500.91610.31240.091*
C221.4206 (8)0.7535 (10)0.3533 (4)0.087 (3)
H221.51120.75540.34240.104*
C231.3769 (7)0.6546 (9)0.3871 (4)0.083 (2)
H231.43690.58910.39850.099*
C241.2427 (6)0.6534 (6)0.4039 (3)0.0595 (17)
H241.21310.58720.42780.071*
C250.1833 (6)0.0530 (6)0.0113 (3)0.0483 (15)
H250.21730.02570.00040.058*
C260.2289 (6)0.1518 (6)0.0291 (3)0.0461 (14)
C270.1601 (7)0.2678 (6)0.0279 (3)0.0548 (16)
C280.2088 (8)0.3617 (7)0.0708 (4)0.072 (2)
H280.16340.43900.07130.087*
C290.3204 (9)0.3383 (8)0.1105 (4)0.082 (3)
H290.35000.40080.13750.099*
C300.3926 (7)0.2236 (8)0.1124 (3)0.0650 (19)
C310.3494 (6)0.1270 (7)0.0721 (3)0.0550 (17)
C320.5141 (9)0.2039 (11)0.1522 (4)0.088 (3)
H320.54290.26710.17890.105*
C330.5871 (9)0.0951 (11)0.1514 (4)0.093 (3)
H330.66740.08480.17610.111*
C340.5426 (7)0.0016 (8)0.1138 (3)0.076 (2)
H340.59120.07740.11480.091*
C350.4265 (7)0.0149 (7)0.0748 (3)0.0631 (18)
H350.39860.05050.04960.076*
C360.0259 (6)0.0414 (5)0.1551 (3)0.0438 (13)
C370.2025 (6)0.2693 (5)0.0914 (3)0.0454 (14)
C380.2527 (7)0.3028 (6)0.0285 (3)0.0628 (18)
H380.19460.30200.00890.075*
C390.3868 (8)0.3373 (7)0.0203 (4)0.085 (2)
H390.41770.36030.02230.101*
C400.4757 (8)0.3378 (7)0.0752 (5)0.083 (2)
H400.56620.36070.06960.100*
C410.4287 (7)0.3043 (7)0.1376 (4)0.074 (2)
H410.48720.30420.17480.089*
C420.2932 (7)0.2704 (6)0.1452 (4)0.0622 (18)
H420.26260.24770.18790.075*
C430.1128 (5)0.3726 (5)0.1536 (3)0.0421 (13)
C440.1418 (7)0.4771 (6)0.1197 (3)0.0599 (17)
H440.12220.48540.07400.072*
C450.2000 (7)0.5706 (6)0.1527 (3)0.0665 (19)
H450.21890.64050.12870.080*
C460.2299 (8)0.5615 (6)0.2196 (4)0.068 (2)
H460.26750.62500.24150.082*
C470.2035 (9)0.4571 (7)0.2540 (4)0.084 (3)
H470.22480.44930.29950.100*
C480.1457 (8)0.3634 (6)0.2221 (4)0.069 (2)
H480.12850.29340.24640.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0424 (2)0.0429 (2)0.0336 (2)0.00235 (17)0.00036 (16)0.00203 (17)
Sn20.0562 (3)0.0419 (2)0.0352 (2)0.00743 (18)0.00820 (18)0.00630 (17)
N10.043 (3)0.043 (3)0.031 (3)0.005 (2)0.0026 (19)0.003 (2)
N20.064 (3)0.052 (3)0.032 (3)0.009 (2)0.010 (2)0.004 (2)
N30.095 (4)0.071 (4)0.042 (3)0.006 (3)0.020 (3)0.005 (3)
N40.049 (3)0.047 (3)0.030 (3)0.013 (2)0.001 (2)0.004 (2)
N50.065 (3)0.036 (3)0.039 (3)0.013 (2)0.002 (2)0.003 (2)
N60.099 (4)0.041 (3)0.053 (3)0.016 (3)0.010 (3)0.006 (3)
O10.056 (2)0.053 (2)0.031 (2)0.0045 (19)0.0030 (17)0.0068 (18)
O20.076 (3)0.055 (3)0.033 (2)0.007 (2)0.004 (2)0.0133 (19)
S10.0669 (10)0.0478 (9)0.0364 (8)0.0019 (7)0.0021 (7)0.0085 (7)
S20.1025 (14)0.0464 (9)0.0316 (8)0.0095 (9)0.0022 (8)0.0068 (7)
C10.051 (4)0.041 (3)0.043 (3)0.002 (3)0.004 (3)0.004 (3)
C20.045 (3)0.042 (3)0.034 (3)0.005 (2)0.001 (2)0.008 (2)
C30.043 (3)0.039 (3)0.042 (3)0.007 (2)0.002 (2)0.005 (2)
C40.053 (4)0.065 (4)0.035 (3)0.010 (3)0.001 (3)0.005 (3)
C50.051 (4)0.074 (4)0.052 (4)0.011 (3)0.014 (3)0.012 (3)
C60.044 (3)0.057 (4)0.060 (4)0.014 (3)0.003 (3)0.018 (3)
C70.049 (3)0.044 (3)0.050 (4)0.006 (3)0.003 (3)0.010 (3)
C80.063 (4)0.051 (4)0.065 (5)0.006 (3)0.014 (3)0.007 (3)
C90.071 (5)0.055 (4)0.086 (6)0.008 (4)0.022 (4)0.015 (4)
C100.044 (4)0.074 (5)0.117 (7)0.012 (3)0.022 (4)0.029 (5)
C110.046 (4)0.075 (5)0.088 (6)0.002 (3)0.004 (4)0.027 (4)
C120.047 (3)0.056 (4)0.039 (3)0.003 (3)0.007 (3)0.008 (3)
C130.049 (3)0.033 (3)0.050 (4)0.002 (2)0.011 (3)0.005 (3)
C140.046 (4)0.057 (4)0.063 (4)0.002 (3)0.002 (3)0.001 (3)
C150.057 (4)0.060 (4)0.089 (6)0.015 (3)0.004 (4)0.010 (4)
C160.104 (6)0.073 (5)0.083 (6)0.034 (5)0.039 (5)0.005 (5)
C170.159 (9)0.089 (6)0.058 (5)0.054 (6)0.031 (6)0.003 (5)
C180.114 (6)0.073 (5)0.045 (4)0.036 (4)0.017 (4)0.007 (4)
C190.041 (3)0.055 (4)0.032 (3)0.009 (3)0.003 (2)0.002 (3)
C200.060 (4)0.062 (4)0.043 (4)0.012 (3)0.001 (3)0.001 (3)
C210.080 (6)0.099 (6)0.054 (5)0.043 (5)0.013 (4)0.009 (4)
C220.049 (5)0.146 (9)0.068 (6)0.030 (5)0.012 (4)0.020 (6)
C230.044 (4)0.128 (7)0.073 (5)0.015 (4)0.007 (4)0.007 (5)
C240.047 (4)0.075 (5)0.055 (4)0.002 (3)0.001 (3)0.005 (3)
C250.055 (4)0.053 (4)0.038 (3)0.011 (3)0.003 (3)0.000 (3)
C260.054 (4)0.064 (4)0.023 (3)0.022 (3)0.006 (2)0.001 (3)
C270.076 (5)0.061 (4)0.030 (3)0.016 (3)0.016 (3)0.009 (3)
C280.092 (6)0.067 (5)0.061 (5)0.029 (4)0.011 (4)0.027 (4)
C290.099 (6)0.103 (7)0.052 (5)0.057 (5)0.009 (4)0.033 (4)
C300.075 (5)0.088 (5)0.036 (4)0.035 (4)0.007 (3)0.010 (4)
C310.059 (4)0.080 (5)0.030 (3)0.032 (4)0.010 (3)0.000 (3)
C320.085 (6)0.143 (8)0.044 (5)0.059 (6)0.000 (4)0.018 (5)
C330.068 (6)0.168 (10)0.048 (5)0.044 (6)0.001 (4)0.000 (6)
C340.062 (5)0.123 (7)0.046 (4)0.015 (4)0.004 (3)0.014 (4)
C350.059 (4)0.095 (6)0.038 (4)0.020 (4)0.003 (3)0.004 (4)
C360.050 (3)0.041 (3)0.040 (3)0.002 (3)0.005 (3)0.009 (3)
C370.052 (4)0.039 (3)0.046 (4)0.006 (3)0.007 (3)0.003 (3)
C380.062 (4)0.076 (5)0.051 (4)0.007 (3)0.009 (3)0.009 (3)
C390.081 (6)0.095 (6)0.078 (6)0.003 (5)0.034 (5)0.015 (5)
C400.067 (5)0.083 (6)0.100 (7)0.003 (4)0.021 (5)0.003 (5)
C410.066 (5)0.082 (5)0.073 (5)0.005 (4)0.005 (4)0.007 (4)
C420.067 (5)0.063 (4)0.056 (4)0.004 (3)0.011 (3)0.000 (3)
C430.048 (3)0.036 (3)0.043 (3)0.005 (2)0.003 (3)0.001 (3)
C440.079 (5)0.057 (4)0.046 (4)0.014 (3)0.006 (3)0.008 (3)
C450.099 (6)0.057 (4)0.047 (4)0.033 (4)0.001 (4)0.005 (3)
C460.089 (5)0.056 (4)0.063 (5)0.025 (4)0.012 (4)0.002 (4)
C470.137 (7)0.070 (5)0.050 (4)0.035 (5)0.035 (5)0.006 (4)
C480.104 (6)0.054 (4)0.054 (4)0.023 (4)0.022 (4)0.015 (3)
Geometric parameters (Å, º) top
Sn1—O12.116 (4)C17—H170.9300
Sn1—C192.128 (5)C18—H180.9300
Sn1—C132.134 (5)C19—C201.387 (8)
Sn1—N12.175 (4)C19—C241.393 (8)
Sn1—S12.5420 (16)C20—C211.400 (10)
Sn2—O22.088 (4)C20—H200.9300
Sn2—C372.134 (6)C21—C221.364 (11)
Sn2—C432.144 (5)C21—H210.9300
Sn2—N42.185 (5)C22—C231.369 (12)
Sn2—S22.5326 (16)C22—H220.9300
N1—C11.299 (7)C23—C241.379 (9)
N1—N21.401 (6)C23—H230.9300
N2—C121.303 (7)C24—H240.9300
N3—C121.371 (7)C25—C261.440 (8)
N3—H3A0.8600C25—H250.9300
N3—H3B0.8600C26—C271.398 (9)
N4—C251.313 (7)C26—C311.468 (9)
N4—N51.408 (6)C27—C281.440 (9)
N5—C361.307 (7)C28—C291.360 (11)
N6—C361.359 (7)C28—H280.9300
N6—H6A0.8600C29—C301.400 (11)
N6—H6B0.8600C29—H290.9300
O1—C31.337 (6)C30—C311.412 (9)
O2—C271.315 (8)C30—C321.436 (11)
S1—C121.741 (6)C31—C351.400 (9)
S2—C361.744 (6)C32—C331.350 (12)
C1—C21.438 (8)C32—H320.9300
C1—H10.9300C33—C341.390 (12)
C2—C31.407 (7)C33—H330.9300
C2—C71.442 (8)C34—C351.380 (9)
C3—C41.423 (8)C34—H340.9300
C4—C51.360 (8)C35—H350.9300
C4—H40.9300C37—C421.381 (9)
C5—C61.419 (9)C37—C381.387 (8)
C5—H50.9300C38—C391.380 (10)
C6—C111.399 (9)C38—H380.9300
C6—C71.431 (8)C39—C401.387 (11)
C7—C81.427 (8)C39—H390.9300
C8—C91.360 (9)C40—C411.367 (11)
C8—H80.9300C40—H400.9300
C9—C101.383 (11)C41—C421.391 (9)
C9—H90.9300C41—H410.9300
C10—C111.379 (11)C42—H420.9300
C10—H100.9300C43—C441.374 (8)
C11—H110.9300C43—C481.400 (8)
C13—C141.387 (8)C44—C451.389 (9)
C13—C181.397 (9)C44—H440.9300
C14—C151.392 (9)C45—C461.362 (9)
C14—H140.9300C45—H450.9300
C15—C161.387 (11)C46—C471.371 (10)
C15—H150.9300C46—H460.9300
C16—C171.341 (11)C47—C481.378 (9)
C16—H160.9300C47—H470.9300
C17—C181.385 (10)C48—H480.9300
O1—Sn1—C1993.23 (19)C13—C18—H18119.9
O1—Sn1—C1392.32 (19)C20—C19—C24118.3 (6)
C19—Sn1—C13122.7 (2)C20—C19—Sn1122.1 (4)
O1—Sn1—N181.88 (15)C24—C19—Sn1119.6 (4)
C19—Sn1—N1111.26 (18)C19—C20—C21119.9 (7)
C13—Sn1—N1126.00 (19)C19—C20—H20120.1
O1—Sn1—S1157.99 (11)C21—C20—H20120.1
C19—Sn1—S198.65 (16)C22—C21—C20120.0 (7)
C13—Sn1—S196.69 (16)C22—C21—H21120.0
N1—Sn1—S176.57 (12)C20—C21—H21120.0
O2—Sn2—C3791.4 (2)C21—C22—C23121.2 (7)
O2—Sn2—C4393.16 (19)C21—C22—H22119.4
C37—Sn2—C43118.6 (2)C23—C22—H22119.4
O2—Sn2—N481.15 (16)C22—C23—C24119.0 (8)
C37—Sn2—N4115.57 (18)C22—C23—H23120.5
C43—Sn2—N4125.61 (18)C24—C23—H23120.5
O2—Sn2—S2157.71 (13)C23—C24—C19121.6 (7)
C37—Sn2—S2101.39 (17)C23—C24—H24119.2
C43—Sn2—S296.54 (16)C19—C24—H24119.2
N4—Sn2—S276.88 (12)N4—C25—C26126.2 (6)
C1—N1—N2114.9 (5)N4—C25—H25116.9
C1—N1—Sn1126.3 (4)C26—C25—H25116.9
N2—N1—Sn1118.6 (3)C27—C26—C25121.2 (6)
C12—N2—N1114.2 (5)C27—C26—C31120.8 (6)
C12—N3—H3A120.0C25—C26—C31118.1 (6)
C12—N3—H3B120.0O2—C27—C26124.3 (6)
H3A—N3—H3B120.0O2—C27—C28117.3 (6)
C25—N4—N5114.2 (5)C26—C27—C28118.4 (7)
C25—N4—Sn2126.1 (4)C29—C28—C27120.6 (8)
N5—N4—Sn2119.6 (3)C29—C28—H28119.7
C36—N5—N4114.6 (4)C27—C28—H28119.7
C36—N6—H6A120.0C28—C29—C30122.5 (7)
C36—N6—H6B120.0C28—C29—H29118.8
H6A—N6—H6B120.0C30—C29—H29118.8
C3—O1—Sn1125.5 (3)C29—C30—C31119.9 (7)
C27—O2—Sn2126.7 (4)C29—C30—C32121.0 (8)
C12—S1—Sn192.4 (2)C31—C30—C32119.1 (8)
C36—S2—Sn293.7 (2)C35—C31—C30117.6 (6)
N1—C1—C2126.7 (5)C35—C31—C26124.5 (6)
N1—C1—H1116.7C30—C31—C26117.9 (7)
C2—C1—H1116.7C33—C32—C30121.0 (8)
C3—C2—C1122.1 (5)C33—C32—H32119.5
C3—C2—C7119.4 (5)C30—C32—H32119.5
C1—C2—C7118.5 (5)C32—C33—C34120.1 (8)
O1—C3—C2123.1 (5)C32—C33—H33119.9
O1—C3—C4117.1 (5)C34—C33—H33119.9
C2—C3—C4119.8 (5)C35—C34—C33120.1 (9)
C5—C4—C3120.6 (6)C35—C34—H34120.0
C5—C4—H4119.7C33—C34—H34120.0
C3—C4—H4119.7C34—C35—C31122.1 (7)
C4—C5—C6122.4 (6)C34—C35—H35119.0
C4—C5—H5118.8C31—C35—H35119.0
C6—C5—H5118.8N5—C36—N6117.8 (5)
C11—C6—C5121.9 (6)N5—C36—S2127.1 (4)
C11—C6—C7120.1 (6)N6—C36—S2115.1 (4)
C5—C6—C7118.1 (6)C42—C37—C38117.0 (6)
C8—C7—C6116.5 (6)C42—C37—Sn2121.3 (5)
C8—C7—C2123.7 (6)C38—C37—Sn2121.4 (5)
C6—C7—C2119.7 (5)C39—C38—C37121.5 (7)
C9—C8—C7121.4 (7)C39—C38—H38119.2
C9—C8—H8119.3C37—C38—H38119.2
C7—C8—H8119.3C38—C39—C40120.4 (7)
C8—C9—C10121.7 (7)C38—C39—H39119.8
C8—C9—H9119.2C40—C39—H39119.8
C10—C9—H9119.2C41—C40—C39119.1 (8)
C11—C10—C9119.2 (7)C41—C40—H40120.4
C11—C10—H10120.4C39—C40—H40120.4
C9—C10—H10120.4C40—C41—C42119.9 (8)
C10—C11—C6121.2 (7)C40—C41—H41120.0
C10—C11—H11119.4C42—C41—H41120.0
C6—C11—H11119.4C37—C42—C41122.1 (7)
N2—C12—N3117.0 (5)C37—C42—H42119.0
N2—C12—S1127.3 (4)C41—C42—H42119.0
N3—C12—S1115.6 (5)C44—C43—C48117.5 (5)
C14—C13—C18117.9 (6)C44—C43—Sn2121.5 (4)
C14—C13—Sn1122.7 (4)C48—C43—Sn2120.8 (4)
C18—C13—Sn1119.3 (5)C43—C44—C45121.0 (6)
C13—C14—C15120.9 (6)C43—C44—H44119.5
C13—C14—H14119.5C45—C44—H44119.5
C15—C14—H14119.5C46—C45—C44121.1 (6)
C16—C15—C14119.5 (7)C46—C45—H45119.5
C16—C15—H15120.2C44—C45—H45119.5
C14—C15—H15120.2C45—C46—C47118.8 (6)
C17—C16—C15120.0 (7)C45—C46—H46120.6
C17—C16—H16120.0C47—C46—H46120.6
C15—C16—H16120.0C46—C47—C48121.0 (7)
C16—C17—C18121.4 (8)C46—C47—H47119.5
C16—C17—H17119.3C48—C47—H47119.5
C18—C17—H17119.3C47—C48—C43120.7 (6)
C17—C18—C13120.2 (7)C47—C48—H48119.7
C17—C18—H18119.9C43—C48—H48119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6B···O1i0.862.353.209 (6)177
N3—H3A···S2ii0.862.873.522 (6)134
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2(C12H9N3OS)(C6H5)2]
Mr516.17
Crystal system, space groupTriclinic, 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)
V3)2161.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.30
Crystal size (mm)0.23 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.754, 0.860
No. of measured, independent and
observed [I > 2σ(I)] reflections
10805, 7339, 5240
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.133, 1.00
No. of reflections7339
No. of parameters541
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N6—H6B···O1i0.862.353.209 (6)177
N3—H3A···S2ii0.862.873.522 (6)134
Symmetry codes: (i) x1, y1, 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

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSarma, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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