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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m966.
Published online 2010 July 17. doi:  10.1107/S1600536810028072
PMCID: PMC3007463

Dichloridobis(2-chloro­benz­yl)tin(IV)

Abstract

Mol­ecules of the title compound, [Sn(C7H6Cl)2Cl2], lie on a twofold rotation axis which passes through the Sn atom. The SnIV atom exists in a distorted tetra­hedral geometry. Adjacent mol­ecules are linked by weak Sn(...)Cl contacts [3.703 (1) Å], forming a linear chain motif extending along the b axis.

Related literature

For the synthesis of the title compound, see: Sisido et al. (1961 [triangle]). For the crystal structure of dichloridobis(2-fluoro­benz­yl)tin(IV), see: Yin & Gao (2006 [triangle]).

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Object name is e-66-0m966-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6Cl)2Cl2]
  • M r = 440.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m966-efi1.jpg
  • a = 26.0750 (13) Å
  • b = 4.7757 (2) Å
  • c = 13.3389 (7) Å
  • β = 112.1538 (5)°
  • V = 1538.42 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.34 mm−1
  • T = 100 K
  • 0.40 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.455, T max = 0.800
  • 8736 measured reflections
  • 1767 independent reflections
  • 1674 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.073
  • S = 1.07
  • 1767 reflections
  • 87 parameters
  • H-atom parameters constrained
  • Δρmax = 2.12 e Å−3
  • Δρmin = −1.03 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028072/bt5298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028072/bt5298Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Diorganotin(IV) dichlorides have the tin centres in a tetrahedral environment but the coordination number can raise by tin–chlorine bridging; the bridging interaction can be regarded as a formal coordination bond if the distance is sufficiently short. In di(2-chlorobenzyl)tin dichloride (Scheme I, Fig. 1), as the interaction is 3.703 (1) Å, the geometry is better interpreted as being tetrahedral. The compound is isostructural with the fluorine analog (Yin & Gao, 2006).

Experimental

The compound was synthesized by the reaction of metallic tin with 2-benzyl chloride (Sisido et al., 1961), and crystals were obtained by recrystallization from chloroform.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.99 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). In the final difference Fouier map there is a peak (2.122e/Å3) at 0.96Å from Sn1 and a hole (-1.027e/Å3) at 0.79Å from Sn1.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl2(C7H6Cl)2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C7H6Cl)2Cl2]F(000) = 856
Mr = 440.73Dx = 1.903 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7518 reflections
a = 26.0750 (13) Åθ = 3.1–28.3°
b = 4.7757 (2) ŵ = 2.34 mm1
c = 13.3389 (7) ÅT = 100 K
β = 112.1538 (5)°Block, colorless
V = 1538.42 (13) Å30.40 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1767 independent reflections
Radiation source: fine-focus sealed tube1674 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −33→33
Tmin = 0.455, Tmax = 0.800k = −6→6
8736 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0414P)2 + 6.0977P] where P = (Fo2 + 2Fc2)/3
1767 reflections(Δ/σ)max = 0.001
87 parametersΔρmax = 2.12 e Å3
0 restraintsΔρmin = −1.03 e Å3

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

xyzUiso*/Ueq
Sn10.50000.53623 (5)0.75000.01430 (10)
Cl10.53371 (3)0.85923 (15)0.89559 (5)0.02030 (16)
Cl20.33923 (3)0.48153 (16)0.55119 (6)0.02400 (17)
C10.42929 (11)0.3670 (6)0.7750 (2)0.0181 (5)
H1A0.41210.22020.72020.022*
H1B0.44170.27830.84730.022*
C20.38724 (11)0.5857 (6)0.7673 (2)0.0161 (5)
C30.38871 (11)0.7290 (6)0.8594 (2)0.0192 (5)
H30.41710.68660.92730.023*
C40.34985 (13)0.9316 (7)0.8546 (3)0.0237 (6)
H40.35161.02490.91870.028*
C50.30839 (13)0.9987 (6)0.7564 (3)0.0249 (6)
H50.28201.13900.75310.030*
C60.30554 (12)0.8602 (7)0.6627 (3)0.0232 (6)
H60.27720.90500.59500.028*
C70.34455 (11)0.6557 (6)0.6692 (2)0.0186 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01278 (15)0.01420 (15)0.01702 (15)0.0000.00688 (10)0.000
Cl10.0189 (3)0.0207 (4)0.0207 (3)−0.0001 (2)0.0067 (2)−0.0046 (2)
Cl20.0218 (3)0.0308 (4)0.0187 (3)−0.0035 (3)0.0068 (3)−0.0029 (3)
C10.0158 (12)0.0176 (13)0.0233 (13)0.0000 (10)0.0100 (10)0.0018 (10)
C20.0138 (12)0.0148 (12)0.0212 (13)−0.0009 (9)0.0084 (10)0.0020 (10)
C30.0188 (12)0.0217 (14)0.0198 (13)−0.0020 (10)0.0104 (10)0.0023 (11)
C40.0258 (15)0.0219 (15)0.0304 (15)−0.0041 (11)0.0185 (13)−0.0043 (12)
C50.0184 (14)0.0220 (14)0.0406 (18)0.0019 (10)0.0182 (13)0.0013 (12)
C60.0148 (12)0.0244 (15)0.0298 (15)0.0001 (11)0.0077 (11)0.0055 (12)
C70.0162 (12)0.0213 (14)0.0205 (13)−0.0025 (10)0.0093 (10)−0.0002 (10)

Geometric parameters (Å, °)

Sn1—C1i2.151 (3)C2—C71.401 (4)
Sn1—C12.151 (3)C3—C41.385 (4)
Sn1—Cl12.3740 (7)C3—H30.9500
Sn1—Cl1i2.3740 (7)C4—C51.385 (5)
Cl2—C71.739 (3)C4—H40.9500
C1—C21.489 (4)C5—C61.391 (5)
C1—H1A0.9900C5—H50.9500
C1—H1B0.9900C6—C71.389 (4)
C2—C31.395 (4)C6—H60.9500
C1i—Sn1—C1135.86 (16)C4—C3—C2121.7 (3)
C1i—Sn1—Cl1107.23 (8)C4—C3—H3119.2
C1—Sn1—Cl1101.07 (8)C2—C3—H3119.2
C1i—Sn1—Cl1i101.07 (8)C5—C4—C3120.2 (3)
C1—Sn1—Cl1i107.23 (8)C5—C4—H4119.9
Cl1—Sn1—Cl1i98.96 (4)C3—C4—H4119.9
C2—C1—Sn1112.17 (18)C4—C5—C6119.8 (3)
C2—C1—H1A109.2C4—C5—H5120.1
Sn1—C1—H1A109.2C6—C5—H5120.1
C2—C1—H1B109.2C7—C6—C5119.2 (3)
Sn1—C1—H1B109.2C7—C6—H6120.4
H1A—C1—H1B107.9C5—C6—H6120.4
C3—C2—C7117.0 (3)C6—C7—C2122.1 (3)
C3—C2—C1120.5 (2)C6—C7—Cl2118.2 (2)
C7—C2—C1122.5 (3)C2—C7—Cl2119.7 (2)

Symmetry codes: (i) −x+1, y, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5298).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc.83, 538–541.
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Yin, H.-D. & Gao, Z.-J. (2006). Huaxue Shiji, 28, 39–40.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography