metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­benzyl­di­chloridotin(IV)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 21 April 2009; accepted 23 April 2009; online 30 April 2009)

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[Shishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc. 83, 538-541.]). For an overview of crystallographic and theoretical structures of diorganotin dichlorides, see: Buntine et al. (2003[Buntine, M. A., Kosovel, F. J. & Tiekink, E. R. T. (2003). CrystEngComm, 5, 331-338.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C7H7)2Cl2]

  • Mr = 371.84

  • Monoclinic, C 2/c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.511, Tmax = 0.732

  • 6090 measured reflections

  • 1580 independent reflections

  • 1527 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.014

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 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 top
Bruker SMART APEX
diffractometer
1580 independent reflections
Radiation source: fine-focus sealed tube1527 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3030
Tmin = 0.511, Tmax = 0.732k = 66
6090 measured reflectionsl = 1515
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 Å3
0 restraintsΔρmin = 0.60 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0140 restraints
wR(F2) = 0.041H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
1580 reflectionsΔρmin = 0.60 e Å3
78 parameters
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)0.0000.00051 (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, º) 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—C254.18 (12)C3—C4—C5—C60.8 (3)
Cl1ii—Sn1—C1—C249.01 (12)C4—C5—C6—C70.5 (3)
Sn1—C1—C2—C390.75 (16)C5—C6—C7—C20.2 (3)
Sn1—C1—C2—C790.34 (15)C3—C2—C7—C60.6 (2)
C7—C2—C3—C40.3 (2)C1—C2—C7—C6178.31 (15)
C1—C2—C3—C4178.60 (14)
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(C7H7)2Cl2]
Mr371.84
Crystal system, space groupMonoclinic, C2/c
Temperature (K)123
a, b, c (Å)23.7710 (3), 4.8019 (1), 12.0808 (2)
β (°) 92.560 (1)
V3)1377.60 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.22
Crystal size (mm)0.35 × 0.30 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.511, 0.732
No. of measured, independent and
observed [I > 2σ(I)] reflections
6090, 1580, 1527
Rint0.021
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.014, 0.041, 1.03
No. of reflections1580
No. of parameters78
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.60

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBuntine, M. A., Kosovel, F. J. & Tiekink, E. R. T. (2003). CrystEngComm, 5, 331–338.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc. 83, 538–541.  CAS Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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COMMUNICATIONS
ISSN: 2056-9890
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