PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m596.
Published online 2009 April 30. doi:  10.1107/S160053680901513X
PMCID: PMC2977632

Dibenzyl­dichloridotin(IV)

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m596-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H7)2Cl2]
  • M r = 371.84
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m596-efi2.jpg
  • a = 23.7710 (3) Å
  • b = 4.8019 (1) Å
  • c = 12.0808 (2) Å
  • β = 92.560 (1)°
  • V = 1377.60 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.22 mm−1
  • T = 123 K
  • 0.35 × 0.30 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.511, T max = 0.732
  • 6090 measured reflections
  • 1580 independent reflections
  • 1527 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.014
  • wR(F 2) = 0.041
  • S = 1.03
  • 1580 reflections
  • 78 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901513X/tk2438sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901513X/tk2438Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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. ...

Crystal data

[Sn(C7H7)2Cl2]F(000) = 728
Mr = 371.84Dx = 1.793 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer1580 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

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 = 1.03w = 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 Å3
0 restraintsΔρmin = −0.60 e Å3

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

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2438).

References

  • 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. [PubMed]
  • Shishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc.83, 538–541.
  • Westrip, S. P. (2009). publCIF In preparation.

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