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Acta Cryst. (2009). E65, m1602-m1603    [ doi:10.1107/S1600536809048090 ]

Chlorido(dimethyl sulfoxide-[kappa]O)triphenyltin(IV)

S. Kumar, S. M. Shadab and M. Idrees

Abstract top

In the title compound, [Sn(C6H5)3Cl(C2H6OS)], the SnIV atom is coordinated by three phenyl groups, a chloride ion and a dimethyl sulfoxide molecule in a distorted trigonal-bipyramidal geometry. In the crystal, adjacent molecules are linked through intermolecular C-H...Cl hydrogen bonds, weak C-H...[pi] interactions and [pi]-[pi] interactions [centroid-centroid distance = 3.934 (3) Å. An intramolecular C-H...[pi] interaction is also observed.

Comment top

Triorganotin(IV) complexes are well known for their biological activities as well as industrial applications (Willem et al., 1997; Gielen et al., 2000; Tian et al., 2005). Owing to wide spread applications of organotin compounds, their synthesis and characterization with O–containing ligands have been a continuing subject in recent years (Lo & Ng, 2009, Ng & Kumar Das, 1997). There are very rare examples of the triorganotin(IV) complexes with solvent molecules (Lo & Ng, 2009), in which solvent molecule acts as a chelator ligand.

The bond lengths and bond angles in the molecules are within normal ranges (Allen et al. 1987). The SnIV atom is coordinated by three phenyl groups, one chloride ion and one solvent molecule (DMSO) in a distorted trigonal biyramidal geometry (Fig. 1). The three phenyl groups are attached in a plane to the Sn atom and seemed like as three pedal of ceiling fan. The one chloride and one solvent molecule are located at axial positions and three phenyl groups are located at equatorial positions. Each phenyl group of the one compound is interacted with another phenyl group of another molecule by a π–π interaction and further interacted by a C—H···π interaction. The neighboring molecules are bound by C—H···Cl, C—H···π (Table 2) and a π–π interaction with a centroid-centroid distance of 3.934 (3) Å (Fig. 2).

Related literature top

For general background to the biological activity and industrial applications of triorganotin(IV) complexes, see: Willem et al. (1997); Gielen et al. (2000); Tian et al. (2005). For bond-length data, see: Allen et al. (1987). For some unusual examples of adducts with orxygen-donor ligands, see: Lo & Ng (2009); Ng & Kumar Das (1997). Cg1 and Cg3 are the centroids of the C1–C6 and C13–C18 rings, respectively.

Experimental top

Triphenyltinchloride (0.385 g, 1 mmol) was dissolved in DMSO (4 ml) and heated until the reactant dissolved completely. The solution was filtered and solvent allowed evaporating slowly. Fine colorless crystal produced after 3 days. Crystals are stable at room temperature. Analysis calc. for C20H21SOClSn: C 51.81, H 4.57, S 6.92. Found: C 51.68, H 4.56, S 6.95.

Refinement top

All of the hydrogen atoms were placed in calculated positions (C–H = 0.93 or 0.96 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The highest residual electron density peak is located 0.87 Å from atom Sn1. The Hooft parameter value is -0.045 (17).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. An ORTEP diagram of the title compound, with displacement ellipsoids drawn at the 50% probability level for non-hydrogen atoms.
[Figure 2] Fig. 2. In the packing diagram, molecules are bounded by weak intermolecular weak hydrogen bonds.
Chlorido(dimethyl sulfoxide-κO)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3Cl(C2H6OS)]F(000) = 928
Mr = 463.57Dx = 1.562 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 6343 reflections
a = 10.417 (5) Åθ = 2.4–28.3°
b = 13.235 (5) ŵ = 1.54 mm−1
c = 14.302 (5) ÅT = 293 K
V = 1971.8 (14) Å3Prism, colorless
Z = 40.26 × 0.24 × 0.22 mm
Data collection top
Bruker SMART CCD
diffractometer		4052 independent reflections
Radiation source: fine-focus sealed tube3877 reflections with I > 2σ(I)
graphiteRint = 0.048
φ and ω scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −13→12
Tmin = 0.677, Tmax = 0.712k = −16→15
11203 measured reflectionsl = −15→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)] = 0.031H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0344P)2 + 2.3774P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
4052 reflectionsΔρmax = 1.18 e Å−3
217 parametersΔρmin = −0.86 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1732 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.07 (3)
Crystal data top
[Sn(C6H5)3Cl(C2H6OS)]V = 1971.8 (14) Å3
Mr = 463.57Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.417 (5) ŵ = 1.54 mm−1
b = 13.235 (5) ÅT = 293 K
c = 14.302 (5) Å0.26 × 0.24 × 0.22 mm
Data collection top
Bruker SMART CCD
diffractometer		4052 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		3877 reflections with I > 2σ(I)
Tmin = 0.677, Tmax = 0.712Rint = 0.048
11203 measured reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.085Δρmax = 1.18 e Å−3
S = 1.15Δρmin = −0.86 e Å−3
4052 reflectionsAbsolute structure: Flack (1983), 1732 Friedel pairs
217 parametersFlack parameter: −0.07 (3)
0 restraints
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 > σ(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
Sn10.65650 (3)0.90124 (2)0.76810 (2)0.01581 (9)
Cl10.70946 (11)1.06792 (8)0.69548 (9)0.0215 (2)
S10.60492 (11)0.71709 (9)0.93706 (8)0.0203 (2)
O10.6043 (3)0.7472 (2)0.8339 (2)0.0212 (7)
C170.5280 (5)1.0132 (4)1.0442 (4)0.0253 (11)
H170.55861.01121.10530.030*
C140.4365 (4)1.0183 (4)0.8606 (4)0.0227 (10)
H140.40601.02030.79950.027*
C31.0216 (5)0.7334 (4)0.7804 (3)0.0295 (12)
H31.04610.66620.77350.035*
C20.8928 (5)0.7602 (4)0.7732 (4)0.0246 (10)
H20.83190.71040.76140.030*
C90.3759 (5)0.7531 (4)0.5849 (4)0.0287 (12)
H90.30230.71440.59390.034*
C180.5971 (5)0.9694 (3)0.9717 (3)0.0211 (10)
H180.67510.93840.98510.025*
C130.5538 (4)0.9702 (3)0.8800 (3)0.0179 (9)
C120.5932 (5)0.8685 (4)0.5590 (3)0.0198 (10)
H120.66610.90780.54970.024*
C80.4438 (4)0.7872 (4)0.6612 (4)0.0227 (10)
H80.41630.77050.72110.027*
C70.5534 (4)0.8467 (3)0.6496 (3)0.0185 (10)
C190.6133 (5)0.5836 (4)0.9315 (4)0.0279 (11)
H19A0.69750.56360.91140.042*
H19B0.55060.55900.88780.042*
H19C0.59630.55570.99220.042*
C100.4154 (5)0.7756 (4)0.4954 (4)0.0256 (11)
H100.36870.75270.44430.031*
C200.4428 (5)0.7303 (4)0.9743 (4)0.0265 (11)
H20A0.42260.80070.98090.040*
H20B0.43160.69691.03330.040*
H20C0.38680.70040.92870.040*
C110.5260 (5)0.8328 (4)0.4823 (4)0.0249 (11)
H110.55470.84700.42210.030*
C41.1127 (5)0.8061 (4)0.7976 (4)0.0310 (12)
H41.19880.78830.80230.037*
C60.9465 (4)0.9331 (4)0.8018 (4)0.0233 (10)
H60.92231.00020.81010.028*
C10.8536 (4)0.8603 (3)0.7833 (3)0.0187 (9)
C160.4115 (5)1.0605 (4)1.0232 (4)0.0262 (11)
H160.36401.09061.07060.031*
C51.0761 (5)0.9062 (5)0.8081 (4)0.0313 (12)
H51.13780.95560.81920.038*
C150.3661 (5)1.0628 (4)0.9314 (4)0.0293 (12)
H150.28841.09420.91790.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01343 (14)0.01702 (14)0.01697 (15)0.00044 (12)0.00008 (12)0.00061 (12)
Cl10.0183 (5)0.0193 (5)0.0268 (6)−0.0005 (4)−0.0006 (5)0.0046 (4)
S10.0192 (5)0.0212 (6)0.0205 (6)−0.0035 (5)−0.0025 (5)0.0022 (5)
O10.0262 (16)0.0221 (17)0.0152 (16)0.0020 (14)0.0026 (14)0.0018 (13)
C170.033 (3)0.023 (2)0.020 (3)−0.004 (2)0.003 (2)−0.001 (2)
C140.018 (2)0.025 (2)0.025 (3)0.002 (2)0.000 (2)−0.001 (2)
C30.030 (3)0.039 (3)0.020 (3)0.020 (2)0.000 (2)−0.007 (2)
C20.022 (2)0.028 (2)0.025 (2)0.0069 (19)−0.004 (2)−0.002 (2)
C90.020 (3)0.026 (3)0.040 (3)−0.002 (2)−0.006 (2)−0.006 (2)
C180.021 (2)0.014 (2)0.029 (3)−0.0012 (19)0.000 (2)−0.001 (2)
C130.018 (2)0.019 (2)0.017 (2)−0.0021 (19)0.0027 (19)−0.0019 (18)
C120.021 (2)0.023 (2)0.015 (2)−0.0004 (19)0.0012 (19)−0.0036 (18)
C80.017 (2)0.025 (2)0.026 (3)−0.002 (2)0.001 (2)0.000 (2)
C70.016 (2)0.018 (2)0.022 (2)0.0074 (18)−0.0002 (19)0.0010 (19)
C190.035 (3)0.020 (3)0.028 (3)0.004 (2)−0.004 (2)0.006 (2)
C100.029 (3)0.025 (3)0.024 (3)0.005 (2)−0.009 (2)−0.008 (2)
C200.027 (3)0.036 (3)0.017 (2)−0.007 (2)0.002 (2)0.002 (2)
C110.033 (3)0.022 (2)0.020 (2)0.006 (2)0.003 (2)0.0051 (19)
C40.021 (2)0.052 (3)0.020 (2)0.012 (2)0.001 (2)0.004 (2)
C60.017 (2)0.029 (3)0.024 (2)0.0002 (19)−0.001 (2)0.003 (2)
C10.015 (2)0.025 (2)0.016 (2)0.0042 (18)−0.001 (2)0.0016 (17)
C160.024 (3)0.029 (3)0.025 (3)−0.005 (2)0.005 (2)−0.011 (2)
C50.018 (2)0.046 (3)0.029 (3)−0.001 (2)0.003 (2)0.010 (3)
C150.017 (3)0.033 (3)0.038 (3)0.002 (2)0.003 (2)−0.005 (2)
Geometric parameters (Å, °) top
Sn1—Cl12.4999 (14)C12—C111.384 (7)
Sn1—O12.311 (3)C12—C71.391 (7)
Sn1—C12.134 (5)C12—H120.9300
Sn1—C72.132 (5)C8—C71.397 (7)
Sn1—C132.131 (5)C8—H80.9300
S1—O11.529 (3)C19—H19A0.9600
S1—C191.771 (5)C19—H19B0.9600
S1—C201.779 (5)C19—H19C0.9600
C17—C181.389 (7)C10—C111.391 (7)
C17—C161.399 (8)C10—H100.9300
C17—H170.9300C20—H20A0.9600
C14—C151.382 (7)C20—H20B0.9600
C14—C131.405 (7)C20—H20C0.9600
C14—H140.9300C11—H110.9300
C3—C41.374 (8)C4—C51.387 (8)
C3—C21.391 (7)C4—H40.9300
C3—H30.9300C6—C11.392 (7)
C2—C11.394 (6)C6—C51.398 (7)
C2—H20.9300C6—H60.9300
C9—C101.377 (8)C16—C151.395 (8)
C9—C81.376 (7)C16—H160.9300
C9—H90.9300C5—H50.9300
C18—C131.387 (7)C15—H150.9300
C18—H180.9300
C13—Sn1—C7119.29 (18)C7—C8—H8119.6
C13—Sn1—C1121.03 (17)C12—C7—C8118.1 (4)
C7—Sn1—C1118.63 (17)C12—C7—Sn1121.4 (3)
C13—Sn1—O187.39 (15)C8—C7—Sn1120.6 (4)
C7—Sn1—O184.62 (15)S1—C19—H19A109.5
C1—Sn1—O187.74 (15)S1—C19—H19B109.5
C13—Sn1—Cl192.56 (13)H19A—C19—H19B109.5
C7—Sn1—Cl194.58 (13)S1—C19—H19C109.5
C1—Sn1—Cl193.10 (12)H19A—C19—H19C109.5
O1—Sn1—Cl1179.04 (9)H19B—C19—H19C109.5
O1—S1—C19102.5 (2)C9—C10—C11119.4 (5)
O1—S1—C20105.1 (2)C9—C10—H10120.3
C19—S1—C2099.1 (3)C11—C10—H10120.3
S1—O1—Sn1128.46 (19)S1—C20—H20A109.5
C18—C17—C16118.4 (5)S1—C20—H20B109.5
C18—C17—H17120.8H20A—C20—H20B109.5
C16—C17—H17120.8S1—C20—H20C109.5
C15—C14—C13120.7 (5)H20A—C20—H20C109.5
C15—C14—H14119.7H20B—C20—H20C109.5
C13—C14—H14119.7C12—C11—C10119.8 (5)
C4—C3—C2120.1 (5)C12—C11—H11120.1
C4—C3—H3120.0C10—C11—H11120.1
C2—C3—H3120.0C3—C4—C5119.9 (5)
C3—C2—C1121.2 (5)C3—C4—H4120.1
C3—C2—H2119.4C5—C4—H4120.1
C1—C2—H2119.4C1—C6—C5120.5 (5)
C10—C9—C8120.8 (5)C1—C6—H6119.8
C10—C9—H9119.6C5—C6—H6119.8
C8—C9—H9119.6C6—C1—C2118.3 (4)
C13—C18—C17122.3 (5)C6—C1—Sn1120.8 (3)
C13—C18—H18118.8C2—C1—Sn1120.9 (3)
C17—C18—H18118.8C15—C16—C17120.4 (5)
C18—C13—C14118.2 (4)C15—C16—H16119.8
C18—C13—Sn1122.9 (3)C17—C16—H16119.8
C14—C13—Sn1118.9 (3)C4—C5—C6120.1 (5)
C11—C12—C7121.1 (5)C4—C5—H5119.9
C11—C12—H12119.4C6—C5—H5119.9
C7—C12—H12119.4C14—C15—C16120.0 (5)
C9—C8—C7120.7 (5)C14—C15—H15120.0
C9—C8—H8119.6C16—C15—H15120.0
C19—S1—O1—Sn1−159.5 (3)Cl1—Sn1—C7—C1237.2 (4)
C20—S1—O1—Sn197.4 (3)C13—Sn1—C7—C8−47.5 (4)
C13—Sn1—O1—S1−41.8 (3)C1—Sn1—C7—C8120.9 (4)
C7—Sn1—O1—S1−161.5 (3)O1—Sn1—C7—C836.4 (4)
C1—Sn1—O1—S179.4 (3)Cl1—Sn1—C7—C8−143.1 (4)
C4—C3—C2—C1−0.1 (8)C8—C9—C10—C110.5 (8)
C16—C17—C18—C13−0.6 (7)C7—C12—C11—C101.2 (7)
C17—C18—C13—C140.7 (7)C9—C10—C11—C12−1.5 (7)
C17—C18—C13—Sn1−178.9 (4)C2—C3—C4—C50.2 (8)
C15—C14—C13—C18−0.5 (7)C5—C6—C1—C21.4 (7)
C15—C14—C13—Sn1179.1 (4)C5—C6—C1—Sn1−177.5 (4)
C7—Sn1—C13—C18152.0 (4)C3—C2—C1—C6−0.7 (8)
C1—Sn1—C13—C18−16.1 (5)C3—C2—C1—Sn1178.2 (4)
O1—Sn1—C13—C1869.7 (4)C13—Sn1—C1—C6−61.1 (4)
Cl1—Sn1—C13—C18−111.3 (4)C7—Sn1—C1—C6130.6 (4)
C7—Sn1—C13—C14−27.5 (4)O1—Sn1—C1—C6−146.7 (4)
C1—Sn1—C13—C14164.3 (3)Cl1—Sn1—C1—C633.7 (4)
O1—Sn1—C13—C14−109.9 (4)C13—Sn1—C1—C2120.0 (4)
Cl1—Sn1—C13—C1469.2 (4)C7—Sn1—C1—C2−48.2 (4)
C10—C9—C8—C70.9 (8)O1—Sn1—C1—C234.4 (4)
C11—C12—C7—C80.2 (7)Cl1—Sn1—C1—C2−145.1 (4)
C11—C12—C7—Sn1179.9 (4)C18—C17—C16—C150.3 (8)
C9—C8—C7—C12−1.3 (7)C3—C4—C5—C60.5 (8)
C9—C8—C7—Sn1179.0 (4)C1—C6—C5—C4−1.3 (8)
C13—Sn1—C7—C12132.8 (4)C13—C14—C15—C160.2 (8)
C1—Sn1—C7—C12−58.8 (4)C17—C16—C15—C14−0.2 (8)
O1—Sn1—C7—C12−143.3 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20C···Cl1i0.962.693.610 (6)161
C20—H20A···Cg30.962.943.813 (6)151
C20—H20B···Cg1ii0.962.613.490 (6)153
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+2.
Table 1
Selected geometric parameters (Å) top
Sn1—Cl12.4999 (14)Sn1—C72.132 (5)
Sn1—O12.311 (3)Sn1—C132.131 (5)
Sn1—C12.134 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20C···Cl1i0.962.693.610 (6)161
C20—H20A···Cg30.962.943.813 (6)151
C20—H20B···Cg1ii0.962.613.490 (6)153
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+2.
Acknowledgements top

SMS is grateful to the Council of Science and Technology, UP (CST, UP), India, for providing grants under the Young Scientists Scheme [ref No. CST/SERPD/D-3505.2008].

references
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