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Acta Cryst. (2007). E63, m2959    [ doi:10.1107/S1600536807055560 ]

(4-Amino-3-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)triphenyltin(IV)

Q. Wang, R. Zhang and L. Du

Abstract top

In the title complex, [Sn(C6H5)3(C8H7N4S)], all bond lengths and angles show normal values. The Sn centre is four-coordinated by three C atoms [Sn-C 2.119 (6)-2.133 (6) Å] and one N atom [Sn-N 2.107 (5) Å] in a distorted tetrahedral geometry. The crystal packing exhibits no classical intermolecular hydrogen bonds.

Comment top

In recent years, organotin complexes have been attracting more and more attention for their wide industrial applications and biological activities (Dubey & Roy, 2003). In order to explore the relationships between the properties and structures, a large number of organotin complexes have been prepared (Gielen, 2002). We report here the structure of the title mononuclear Sn(IV) complex, (I).

The molecular structure of complex (I) is shown in Fig. 1. Sn1 is four-coordinated in a distorted tetrahedron geometry. The Sn—N bond distance is comparable to that found in [phenyl-tris(pyrimidine-2-thiolato)tin(IV)] (Li et al., 2005). The bond angles at the Sn1 atom range from 99.9 (2) to 110.7 (2)°. The crystal packing exhibits no classical intermolecular hydrogen bonds.

Related literature top

For related literature, see: Dubey & Roy (2003); Gielen (2002); Li et al. (2005). [Reference required for normal values?]

Experimental top

The reaction was carried out under nitrogen atmoshpere. 4-Amino-5-phenyl-4H-1,2,4-triazole-3-thiol (0.192 g, 1 mmol) was added to the solution of benzene (30 ml) with sodium ethoxide (0.68 g, 1 mmol) in a Schlenk flask. After stirring for 10 min, triphenyltin chloride (0.385 g, 1 mmol) was added to the mixture. The mixture was kept at 313 K for 12 h. After cooling down to the room temperature, the solution was filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from diethyl ether. Colourless single crystals of the title complex were obtained after one week. Yield, 87%. Analysis calculated for C26H22N4S1Sn1: C 57.70, H 4.10, N, 10.35; found: C 57.91, H 4.29, N, 10.09. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93 Å and N—H = 0.86 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq of the parent atom.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms omitted for clarity.
Triphenyl(4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol-κN2)tin(IV) top
Crystal data top
[Sn(C6H5)3(C8H7N4S)]Z = 2
Mr = 541.23F000 = 544
Triclinic, P1Dx = 1.511 Mg m−3
Hall symbol: -P1Mo Kα radiation
λ = 0.71073 Å
a = 8.964 (8) ÅCell parameters from 2210 reflections
b = 9.656 (8) Åθ = 2.4–23.8º
c = 15.481 (13) ŵ = 1.18 mm−1
α = 84.423 (10)ºT = 293 (2) K
β = 86.911 (10)ºBlock, colourless
γ = 63.110 (8)º0.60 × 0.54 × 0.48 mm
V = 1189.4 (18) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer		4066 independent reflections
Radiation source: fine-focus sealed tube2892 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.043
T = 293(2) Kθmax = 25.0º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→10
Tmin = 0.537, Tmax = 0.601k = −11→11
5879 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0477P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4066 reflectionsΔρmax = 1.09 e Å−3
289 parametersΔρmin = −0.92 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sn(C6H5)3(C8H7N4S)]γ = 63.110 (8)º
Mr = 541.23V = 1189.4 (18) Å3
Triclinic, P1Z = 2
a = 8.964 (8) ÅMo Kα
b = 9.656 (8) ŵ = 1.18 mm−1
c = 15.481 (13) ÅT = 293 (2) K
α = 84.423 (10)º0.60 × 0.54 × 0.48 mm
β = 86.911 (10)º
Data collection top
Siemens SMART CCD area-detector
diffractometer		4066 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2892 reflections with I > 2σ(I)
Tmin = 0.537, Tmax = 0.601Rint = 0.043
5879 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511 restraint
wR(F2) = 0.122H-atom parameters constrained
S = 1.00Δρmax = 1.09 e Å−3
4066 reflectionsΔρmin = −0.92 e Å−3
289 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.23422 (6)0.73462 (6)0.79295 (3)0.03700 (19)
N10.1773 (7)0.6966 (6)0.6698 (3)0.0366 (13)
N20.2770 (7)0.5565 (6)0.6339 (3)0.0416 (14)
N30.0812 (7)0.7134 (6)0.5445 (3)0.0364 (13)
N4−0.0199 (8)0.7765 (7)0.4711 (3)0.0560 (18)
H4A−0.00010.72300.42690.067*
H4B−0.10180.86870.47020.067*
S1−0.0960 (2)0.9684 (2)0.63727 (13)0.0499 (5)
C10.0562 (8)0.7946 (8)0.6174 (4)0.0348 (16)
C20.2143 (8)0.5715 (8)0.5573 (4)0.0375 (16)
C30.2865 (9)0.4439 (8)0.4994 (4)0.0416 (17)
C40.2067 (10)0.4278 (9)0.4301 (4)0.053 (2)
H40.10010.50520.41580.063*
C50.2786 (12)0.3024 (11)0.3821 (5)0.061 (2)
H50.22300.29810.33420.073*
C60.4307 (13)0.1835 (10)0.4034 (6)0.070 (3)
H60.47760.09560.37220.084*
C70.5135 (12)0.1961 (10)0.4718 (6)0.073 (3)
H70.61900.11730.48670.088*
C80.4400 (11)0.3256 (9)0.5185 (5)0.060 (2)
H80.49780.33210.56480.072*
C90.0375 (8)0.7371 (7)0.8760 (4)0.0331 (15)
C10−0.0341 (9)0.6419 (9)0.8663 (5)0.053 (2)
H10−0.00050.57830.82050.064*
C11−0.1562 (9)0.6389 (10)0.9236 (6)0.066 (2)
H11−0.20370.57300.91630.079*
C12−0.2080 (10)0.7327 (11)0.9915 (6)0.068 (2)
H12−0.29000.73041.03030.082*
C13−0.1382 (11)0.8281 (11)1.0009 (5)0.070 (3)
H13−0.17300.89251.04630.084*
C14−0.0169 (9)0.8311 (8)0.9445 (4)0.0459 (18)
H140.02990.89740.95230.055*
C150.2901 (7)0.9268 (7)0.7841 (4)0.0302 (15)
C160.1941 (9)1.0706 (8)0.7417 (5)0.0481 (19)
H160.09261.09060.71780.058*
C170.2463 (10)1.1841 (9)0.7344 (5)0.061 (2)
H170.17961.28030.70560.073*
C180.3940 (11)1.1589 (10)0.7684 (5)0.064 (2)
H180.42901.23650.76290.077*
C190.4886 (10)1.0189 (11)0.8105 (6)0.064 (2)
H190.58931.00070.83450.077*
C200.4395 (8)0.9031 (9)0.8184 (5)0.0486 (19)
H200.50750.80740.84730.058*
C210.4577 (8)0.5244 (7)0.8192 (4)0.0346 (16)
C220.4786 (9)0.4393 (9)0.8978 (5)0.0482 (19)
H220.39580.47410.94040.058*
C230.6228 (11)0.3018 (10)0.9135 (6)0.071 (3)
H230.63600.24260.96620.085*
C240.7458 (10)0.2530 (11)0.8516 (7)0.075 (3)
H240.84370.16150.86260.089*
C250.7260 (10)0.3372 (10)0.7739 (6)0.068 (2)
H250.80970.30240.73170.081*
C260.5835 (8)0.4730 (9)0.7575 (5)0.051 (2)
H260.57140.53100.70440.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0371 (3)0.0410 (3)0.0347 (3)−0.0189 (2)0.0001 (2)−0.0043 (2)
N10.042 (3)0.041 (4)0.027 (3)−0.019 (3)−0.002 (3)−0.006 (3)
N20.048 (4)0.037 (4)0.035 (3)−0.015 (3)−0.006 (3)0.000 (3)
N30.045 (4)0.040 (4)0.027 (3)−0.022 (3)−0.009 (3)0.004 (3)
N40.080 (5)0.050 (4)0.032 (3)−0.022 (4)−0.020 (3)−0.002 (3)
S10.0490 (12)0.0419 (12)0.0570 (12)−0.0176 (10)−0.0044 (9)−0.0086 (10)
C10.042 (4)0.041 (4)0.031 (4)−0.028 (4)0.000 (3)0.001 (3)
C20.046 (4)0.036 (4)0.035 (4)−0.023 (4)0.000 (3)−0.002 (3)
C30.050 (5)0.044 (5)0.036 (4)−0.026 (4)0.010 (3)−0.007 (3)
C40.067 (5)0.067 (6)0.043 (5)−0.046 (5)0.010 (4)−0.014 (4)
C50.091 (7)0.077 (7)0.044 (5)−0.062 (6)0.022 (5)−0.026 (5)
C60.113 (8)0.053 (6)0.059 (6)−0.050 (6)0.036 (6)−0.028 (5)
C70.081 (6)0.053 (6)0.069 (6)−0.014 (5)0.014 (5)−0.021 (5)
C80.076 (6)0.057 (6)0.051 (5)−0.031 (5)0.007 (4)−0.017 (4)
C90.037 (4)0.031 (4)0.029 (4)−0.014 (3)−0.009 (3)0.004 (3)
C100.044 (5)0.063 (5)0.061 (5)−0.031 (4)0.004 (4)−0.012 (4)
C110.047 (5)0.078 (7)0.091 (7)−0.047 (5)0.001 (5)0.004 (5)
C120.051 (5)0.083 (7)0.073 (6)−0.036 (5)0.016 (5)0.004 (5)
C130.066 (6)0.083 (7)0.056 (6)−0.029 (5)0.027 (5)−0.022 (5)
C140.047 (5)0.049 (5)0.047 (5)−0.026 (4)0.008 (4)−0.011 (4)
C150.025 (3)0.037 (4)0.030 (4)−0.014 (3)0.007 (3)−0.012 (3)
C160.042 (4)0.045 (5)0.059 (5)−0.019 (4)−0.015 (4)−0.004 (4)
C170.075 (6)0.043 (5)0.070 (6)−0.032 (5)−0.016 (5)0.007 (4)
C180.087 (7)0.065 (6)0.066 (6)−0.055 (6)−0.004 (5)−0.009 (5)
C190.050 (5)0.076 (7)0.081 (6)−0.039 (5)−0.014 (5)−0.012 (5)
C200.041 (4)0.049 (5)0.061 (5)−0.024 (4)−0.012 (4)−0.002 (4)
C210.031 (4)0.033 (4)0.043 (4)−0.018 (3)−0.003 (3)−0.004 (3)
C220.042 (4)0.059 (5)0.036 (4)−0.016 (4)−0.004 (3)0.003 (4)
C230.076 (7)0.069 (6)0.052 (5)−0.023 (5)−0.024 (5)0.024 (5)
C240.042 (5)0.069 (6)0.084 (7)−0.001 (5)−0.014 (5)0.006 (6)
C250.043 (5)0.063 (6)0.072 (6)−0.005 (4)0.004 (4)0.003 (5)
C260.035 (4)0.051 (5)0.054 (5)−0.011 (4)0.007 (4)0.007 (4)
Geometric parameters (Å, °) top
Sn1—N12.107 (5)C11—C121.375 (11)
Sn1—C92.119 (6)C11—H110.9300
Sn1—C152.120 (6)C12—C131.349 (11)
Sn1—C212.133 (6)C12—H120.9300
N1—C11.322 (8)C13—C141.366 (10)
N1—N21.391 (7)C13—H130.9300
N2—C21.307 (8)C14—H140.9300
N3—C21.354 (8)C15—C161.379 (9)
N3—C11.387 (7)C15—C201.380 (9)
N3—N41.401 (7)C16—C171.366 (10)
N4—H4A0.860C16—H160.9300
N4—H4B0.860C17—C181.360 (11)
S1—C11.660 (7)C17—H170.9300
C2—C31.474 (9)C18—C191.350 (11)
C3—C81.357 (10)C18—H180.9300
C3—C41.379 (9)C19—C201.368 (10)
C4—C51.360 (9)C19—H190.9300
C4—H40.9300C20—H200.9300
C5—C61.358 (12)C21—C221.371 (9)
C5—H50.9300C21—C261.379 (9)
C6—C71.371 (11)C22—C231.383 (10)
C6—H60.9300C22—H220.9300
C7—C81.378 (10)C23—C241.364 (11)
C7—H70.9300C23—H230.9300
C8—H80.9300C24—C251.356 (12)
C9—C101.360 (9)C24—H240.9300
C9—C141.384 (8)C25—C261.369 (10)
C10—C111.381 (10)C25—H250.9300
C10—H100.9300C26—H260.9300
N1—Sn1—C9105.3 (2)C12—C11—H11119.7
N1—Sn1—C15110.6 (2)C10—C11—H11119.7
C9—Sn1—C15119.5 (2)C13—C12—C11118.9 (7)
N1—Sn1—C2199.9 (2)C13—C12—H12120.5
C9—Sn1—C21110.3 (3)C11—C12—H12120.5
C15—Sn1—C21109.4 (2)C12—C13—C14120.8 (8)
C1—N1—N2112.5 (5)C12—C13—H13119.6
C1—N1—Sn1127.6 (4)C14—C13—H13119.6
N2—N1—Sn1119.8 (4)C13—C14—C9121.2 (7)
C2—N2—N1105.0 (5)C13—C14—H14119.4
C2—N3—C1109.3 (5)C9—C14—H14119.4
C2—N3—N4128.1 (5)C16—C15—C20117.3 (6)
C1—N3—N4122.5 (6)C16—C15—Sn1125.1 (4)
N3—N4—H4A120.0C20—C15—Sn1117.4 (5)
N3—N4—H4B120.0C17—C16—C15120.8 (6)
H4A—N4—H4B120.0C17—C16—H16119.6
N1—C1—N3103.4 (6)C15—C16—H16119.6
N1—C1—S1127.9 (5)C18—C17—C16121.2 (8)
N3—C1—S1128.6 (5)C18—C17—H17119.4
N2—C2—N3109.8 (5)C16—C17—H17119.4
N2—C2—C3121.0 (6)C19—C18—C17118.5 (7)
N3—C2—C3129.2 (6)C19—C18—H18120.7
C8—C3—C4116.2 (7)C17—C18—H18120.7
C8—C3—C2118.0 (6)C18—C19—C20121.4 (7)
C4—C3—C2125.6 (7)C18—C19—H19119.3
C5—C4—C3122.2 (8)C20—C19—H19119.3
C5—C4—H4118.9C19—C20—C15120.7 (7)
C3—C4—H4118.9C19—C20—H20119.6
C6—C5—C4120.7 (8)C15—C20—H20119.6
C6—C5—H5119.6C22—C21—C26119.2 (6)
C4—C5—H5119.6C22—C21—Sn1120.5 (5)
C5—C6—C7118.5 (7)C26—C21—Sn1120.3 (5)
C5—C6—H6120.8C21—C22—C23120.0 (7)
C7—C6—H6120.8C21—C22—H22120.0
C6—C7—C8119.9 (9)C23—C22—H22120.0
C6—C7—H7120.1C24—C23—C22119.9 (8)
C8—C7—H7120.1C24—C23—H23120.1
C3—C8—C7122.5 (8)C22—C23—H23120.1
C3—C8—H8118.8C25—C24—C23120.3 (8)
C7—C8—H8118.8C25—C24—H24119.8
C10—C9—C14117.9 (6)C23—C24—H24119.8
C10—C9—Sn1121.3 (5)C24—C25—C26120.3 (8)
C14—C9—Sn1120.7 (5)C24—C25—H25119.8
C9—C10—C11120.7 (7)C26—C25—H25119.8
C9—C10—H10119.7C25—C26—C21120.2 (7)
C11—C10—H10119.7C25—C26—H26119.9
C12—C11—C10120.5 (7)C21—C26—H26119.9
C9—Sn1—N1—C171.0 (6)C15—Sn1—C9—C14−21.9 (6)
C15—Sn1—N1—C1−59.4 (6)C21—Sn1—C9—C14106.2 (6)
C21—Sn1—N1—C1−174.6 (5)C14—C9—C10—C11−0.5 (11)
C9—Sn1—N1—N2−111.5 (5)Sn1—C9—C10—C11176.6 (6)
C15—Sn1—N1—N2118.1 (5)C9—C10—C11—C120.3 (12)
C21—Sn1—N1—N22.9 (5)C10—C11—C12—C130.3 (13)
C1—N1—N2—C20.4 (7)C11—C12—C13—C14−0.5 (14)
Sn1—N1—N2—C2−177.5 (4)C12—C13—C14—C90.2 (13)
N2—N1—C1—N3−0.5 (7)C10—C9—C14—C130.3 (11)
Sn1—N1—C1—N3177.1 (4)Sn1—C9—C14—C13−176.9 (6)
N2—N1—C1—S1175.9 (5)N1—Sn1—C15—C1648.9 (6)
Sn1—N1—C1—S1−6.4 (9)C9—Sn1—C15—C16−73.5 (6)
C2—N3—C1—N10.5 (7)C21—Sn1—C15—C16158.0 (5)
N4—N3—C1—N1−179.0 (5)N1—Sn1—C15—C20−126.6 (5)
C2—N3—C1—S1−176.0 (5)C9—Sn1—C15—C20111.0 (5)
N4—N3—C1—S14.5 (9)C21—Sn1—C15—C20−17.5 (6)
N1—N2—C2—N3−0.1 (7)C20—C15—C16—C170.1 (10)
N1—N2—C2—C3−179.2 (6)Sn1—C15—C16—C17−175.5 (5)
C1—N3—C2—N2−0.2 (7)C15—C16—C17—C180.0 (12)
N4—N3—C2—N2179.3 (6)C16—C17—C18—C19−0.4 (13)
C1—N3—C2—C3178.8 (6)C17—C18—C19—C200.6 (13)
N4—N3—C2—C3−1.7 (11)C18—C19—C20—C15−0.5 (12)
N2—C2—C3—C8−14.5 (10)C16—C15—C20—C190.2 (10)
N3—C2—C3—C8166.6 (7)Sn1—C15—C20—C19176.0 (5)
N2—C2—C3—C4160.5 (7)N1—Sn1—C21—C22−132.2 (5)
N3—C2—C3—C4−18.4 (11)C9—Sn1—C21—C22−21.7 (6)
C8—C3—C4—C5−1.5 (11)C15—Sn1—C21—C22111.7 (5)
C2—C3—C4—C5−176.6 (7)N1—Sn1—C21—C2648.3 (6)
C3—C4—C5—C63.0 (12)C9—Sn1—C21—C26158.8 (5)
C4—C5—C6—C7−3.0 (13)C15—Sn1—C21—C26−67.8 (6)
C5—C6—C7—C81.6 (13)C26—C21—C22—C23−1.6 (10)
C4—C3—C8—C70.1 (12)Sn1—C21—C22—C23178.9 (6)
C2—C3—C8—C7175.6 (7)C21—C22—C23—C241.6 (12)
C6—C7—C8—C3−0.1 (14)C22—C23—C24—C25−1.2 (14)
N1—Sn1—C9—C1036.1 (6)C23—C24—C25—C260.9 (14)
C15—Sn1—C9—C10161.1 (5)C24—C25—C26—C21−0.9 (12)
C21—Sn1—C9—C10−70.9 (6)C22—C21—C26—C251.3 (10)
N1—Sn1—C9—C14−146.9 (5)Sn1—C21—C26—C25−179.2 (6)
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20271025) for financial support.

references
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