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Acta Cryst. (2009). E65, m596    [ doi:10.1107/S160053680901513X ]

Dibenzyldichloridotin(IV)

K. M. Lo and S. W. Ng

Abstract top

The title compound, [Sn(C7H7)2Cl2], exists as a monomeric tetrahedral molecule. The Sn atom lies on a special position of site symmetry 2. Adjacent molecules are linked into a linear chain running along the b axis of the monoclinic unit cell by Sn...Cl bridges of 3.7275 (4) Å.

Related literature top

For the synthesis of dibenzyltin dichloride by the direct reaction of benzyl chloride and metallic tin, see: Shishido et al. (1961). For an overview of crystallographic and theoretical structures of diorganotin dichlorides, see: Buntine et al. (2003).

Experimental top

Dibenzyltin dichloride was synthesized from benzyl chloride and metallic tin by a literature method (Shishido et al., 1961). Crystals were obtained by recrystallization from chloroform.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2U(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of part of the supramolecular chain in (C6H5CH2)2SnCl2 drawn at the 70% probability level. Dashed lines denote the Sn···Cl bridges. Hydrogen atoms are drawn as spheres of arbitrary radius. Unlabelled atoms within the partially labelled molecule are related by the symmetry operation: -x+1, y, -z+1/2.
Dibenzyldichloridotin(IV) top
Crystal data top
[Sn(C7H7)2Cl2]F(000) = 728
Mr = 371.84Dx = 1.793 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5461 reflections
a = 23.7710 (3) Åθ = 2.5–28.3°
b = 4.8019 (1) ŵ = 2.22 mm−1
c = 12.0808 (2) ÅT = 123 K
β = 92.560 (1)°Block, colorless
V = 1377.60 (4) Å30.35 × 0.30 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		1580 independent reflections
Radiation source: fine-focus sealed tube1527 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −30→30
Tmin = 0.511, Tmax = 0.732k = −6→6
6090 measured reflectionsl = −15→15
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)] = 0.014Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.041H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0238P)2 + 1.6061P]
where P = (Fo2 + 2Fc2)/3
1580 reflections(Δ/σ)max = 0.001
78 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.60 e Å−3
Crystal data top
[Sn(C7H7)2Cl2]V = 1377.60 (4) Å3
Mr = 371.84Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.7710 (3) ŵ = 2.22 mm−1
b = 4.8019 (1) ÅT = 123 K
c = 12.0808 (2) Å0.35 × 0.30 × 0.15 mm
β = 92.560 (1)°
Data collection top
Bruker SMART APEX
diffractometer		1580 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1527 reflections with I > 2σ(I)
Tmin = 0.511, Tmax = 0.732Rint = 0.021
6090 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.014H-atom parameters constrained
wR(F2) = 0.041Δρmax = 0.27 e Å−3
S = 1.03Δρmin = −0.60 e Å−3
1580 reflectionsAbsolute structure: ?
78 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.49246 (2)0.25000.01354 (6)
Cl10.473226 (16)0.81293 (8)0.38720 (3)0.01976 (9)
C10.57846 (6)0.3263 (3)0.31462 (14)0.0206 (3)
H1A0.57160.21460.38160.025*
H1B0.59420.20080.25880.025*
C20.62055 (7)0.5502 (3)0.34383 (14)0.0175 (3)
C30.65796 (6)0.6448 (3)0.26657 (13)0.0197 (3)
H30.65630.56940.19380.024*
C40.69765 (7)0.8477 (3)0.29468 (14)0.0225 (3)
H40.72280.91110.24110.027*
C50.70071 (8)0.9580 (3)0.40082 (17)0.0253 (4)
H50.72821.09520.42040.030*
C60.66358 (7)0.8673 (4)0.47815 (14)0.0260 (3)
H60.66540.94360.55080.031*
C70.62366 (7)0.6650 (3)0.44994 (13)0.0222 (3)
H70.59830.60440.50350.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01130 (9)0.01254 (9)0.01666 (9)0.000−0.00051 (6)0.000
Cl10.02142 (18)0.02114 (18)0.01692 (16)−0.00076 (14)0.00309 (13)−0.00308 (13)
C10.0153 (7)0.0142 (7)0.0318 (8)0.0000 (6)−0.0049 (6)0.0023 (6)
C20.0129 (7)0.0138 (6)0.0254 (8)0.0020 (6)−0.0044 (6)0.0025 (6)
C30.0168 (7)0.0191 (7)0.0232 (7)0.0026 (6)0.0001 (6)−0.0025 (6)
C40.0145 (7)0.0216 (7)0.0316 (8)−0.0003 (6)0.0022 (6)0.0026 (6)
C50.0195 (8)0.0193 (7)0.0361 (10)−0.0029 (6)−0.0081 (7)−0.0010 (7)
C60.0271 (8)0.0281 (8)0.0222 (8)0.0000 (7)−0.0075 (6)−0.0023 (6)
C70.0204 (8)0.0249 (8)0.0210 (7)−0.0011 (6)−0.0016 (6)0.0051 (6)
Geometric parameters (Å, °) top
Sn1—Cl1i3.7275 (4)C3—C41.388 (2)
Sn1—C1ii2.143 (2)C3—H30.9500
Sn1—C12.143 (2)C4—C51.386 (3)
Sn1—Cl12.3695 (4)C4—H40.9500
Sn1—Cl1ii2.3695 (4)C5—C61.384 (3)
C1—C21.500 (2)C5—H50.9500
C1—H1A0.9900C6—C71.390 (2)
C1—H1B0.9900C6—H60.9500
C2—C31.394 (2)C7—H70.9500
C2—C71.394 (2)
C1ii—Sn1—C1136.30 (8)C4—C3—C2120.80 (15)
C1ii—Sn1—Cl1103.88 (4)C4—C3—H3119.6
C1—Sn1—Cl1104.09 (4)C2—C3—H3119.6
C1ii—Sn1—Cl1ii104.09 (4)C5—C4—C3120.11 (15)
C1—Sn1—Cl1ii103.88 (4)C5—C4—H4119.9
Cl1—Sn1—Cl1ii99.001 (18)C3—C4—H4119.9
C2—C1—Sn1112.29 (10)C6—C5—C4119.69 (16)
C2—C1—H1A109.1C6—C5—H5120.2
Sn1—C1—H1A109.1C4—C5—H5120.2
C2—C1—H1B109.1C5—C6—C7120.24 (16)
Sn1—C1—H1B109.1C5—C6—H6119.9
H1A—C1—H1B107.9C7—C6—H6119.9
C3—C2—C7118.52 (15)C6—C7—C2120.63 (15)
C3—C2—C1120.99 (15)C6—C7—H7119.7
C7—C2—C1120.48 (15)C2—C7—H7119.7
C1ii—Sn1—C1—C2177.45 (13)C2—C3—C4—C50.4 (2)
Cl1—Sn1—C1—C2−54.18 (12)C3—C4—C5—C6−0.8 (3)
Cl1ii—Sn1—C1—C249.01 (12)C4—C5—C6—C70.5 (3)
Sn1—C1—C2—C3−90.75 (16)C5—C6—C7—C20.2 (3)
Sn1—C1—C2—C790.34 (15)C3—C2—C7—C6−0.6 (2)
C7—C2—C3—C40.3 (2)C1—C2—C7—C6178.31 (15)
C1—C2—C3—C4−178.60 (14)
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y, −z+1/2.
Acknowledgements top

We thank the University of Malaya (FS339/2008A) for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Buntine, M. A., Kosovel, F. J. & Tiekink, E. R. T. (2003). CrystEngComm, 5, 331–338.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Shishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc. 83, 538–541.

Westrip, S. P. (2009). publCIF. In preparation.