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accessDichloridobis(2-chlorobenzyl)tin(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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![[Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.]](../../../../../../logos/arrows/e_arr.gif "Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.")
). For the of dichloridobis(2-fluorobenzyl)tin(IV), see: Yin & Gao (2006).
![[Scheme 1]](bt5298scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; 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, 2010).
Supporting information
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028072/bt5298sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028072/bt5298Isup2.hkl
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.
Hydrogen atoms were placed in calculated positions (C–H 0.95–0.99 Å) and included in the 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.
Diorganotin(IV) dichlorides have the tin centres in a tetrahedral environment but the 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).
For the synthesis of the title compound, see: Sisido et al. (1961). For the of dichloridobis(2-fluorobenzyl)tin, see: Yin & Gao (2006).
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).
![[Figure 1]](./bt5298fig1thm.gif) | 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. |
| [Sn(C7H6Cl)2Cl2] | F(000) = 856 |
| Mr = 440.73 | Dx = 1.903 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 7518 reflections |
| a = 26.0750 (13) Å | θ = 3.1–28.3° |
| b = 4.7757 (2) Å | µ = 2.34 mm−1 |
| c = 13.3389 (7) Å | T = 100 K |
| β = 112.1538 (5)° | Block, colorless |
| V = 1538.42 (13) Å3 | 0.40 × 0.10 × 0.10 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 1767 independent reflections |
| Radiation source: fine-focus sealed tube | 1674 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| ω scans | θmax = 27.5°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −33→33 |
| Tmin = 0.455, Tmax = 0.800 | k = −6→6 |
| 8736 measured reflections | l = −17→17 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.073 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0414P)2 + 6.0977P] where P = (Fo2 + 2Fc2)/3 |
| 1767 reflections | (Δ/σ)max = 0.001 |
| 87 parameters | Δρmax = 2.12 e Å−3 |
| 0 restraints | Δρmin = −1.03 e Å−3 |
| [Sn(C7H6Cl)2Cl2] | V = 1538.42 (13) Å3 |
| Mr = 440.73 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 26.0750 (13) Å | µ = 2.34 mm−1 |
| b = 4.7757 (2) Å | T = 100 K |
| c = 13.3389 (7) Å | 0.40 × 0.10 × 0.10 mm |
| β = 112.1538 (5)° |
| Bruker SMART APEX diffractometer | 1767 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1674 reflections with I > 2σ(I) |
| Tmin = 0.455, Tmax = 0.800 | Rint = 0.029 |
| 8736 measured reflections |
| R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
| wR(F2) = 0.073 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 2.12 e Å−3 |
| 1767 reflections | Δρmin = −1.03 e Å−3 |
| 87 parameters |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.5000 | 0.53623 (5) | 0.7500 | 0.01430 (10) | |
| Cl1 | 0.53371 (3) | 0.85923 (15) | 0.89559 (5) | 0.02030 (16) | |
| Cl2 | 0.33923 (3) | 0.48153 (16) | 0.55119 (6) | 0.02400 (17) | |
| C1 | 0.42929 (11) | 0.3670 (6) | 0.7750 (2) | 0.0181 (5) | |
| H1A | 0.4121 | 0.2202 | 0.7202 | 0.022* | |
| H1B | 0.4417 | 0.2783 | 0.8473 | 0.022* | |
| C2 | 0.38724 (11) | 0.5857 (6) | 0.7673 (2) | 0.0161 (5) | |
| C3 | 0.38871 (11) | 0.7290 (6) | 0.8594 (2) | 0.0192 (5) | |
| H3 | 0.4171 | 0.6866 | 0.9273 | 0.023* | |
| C4 | 0.34985 (13) | 0.9316 (7) | 0.8546 (3) | 0.0237 (6) | |
| H4 | 0.3516 | 1.0249 | 0.9187 | 0.028* | |
| C5 | 0.30839 (13) | 0.9987 (6) | 0.7564 (3) | 0.0249 (6) | |
| H5 | 0.2820 | 1.1390 | 0.7531 | 0.030* | |
| C6 | 0.30554 (12) | 0.8602 (7) | 0.6627 (3) | 0.0232 (6) | |
| H6 | 0.2772 | 0.9050 | 0.5950 | 0.028* | |
| C7 | 0.34455 (11) | 0.6557 (6) | 0.6692 (2) | 0.0186 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.01278 (15) | 0.01420 (15) | 0.01702 (15) | 0.000 | 0.00688 (10) | 0.000 |
| Cl1 | 0.0189 (3) | 0.0207 (4) | 0.0207 (3) | −0.0001 (2) | 0.0067 (2) | −0.0046 (2) |
| Cl2 | 0.0218 (3) | 0.0308 (4) | 0.0187 (3) | −0.0035 (3) | 0.0068 (3) | −0.0029 (3) |
| C1 | 0.0158 (12) | 0.0176 (13) | 0.0233 (13) | 0.0000 (10) | 0.0100 (10) | 0.0018 (10) |
| C2 | 0.0138 (12) | 0.0148 (12) | 0.0212 (13) | −0.0009 (9) | 0.0084 (10) | 0.0020 (10) |
| C3 | 0.0188 (12) | 0.0217 (14) | 0.0198 (13) | −0.0020 (10) | 0.0104 (10) | 0.0023 (11) |
| C4 | 0.0258 (15) | 0.0219 (15) | 0.0304 (15) | −0.0041 (11) | 0.0185 (13) | −0.0043 (12) |
| C5 | 0.0184 (14) | 0.0220 (14) | 0.0406 (18) | 0.0019 (10) | 0.0182 (13) | 0.0013 (12) |
| C6 | 0.0148 (12) | 0.0244 (15) | 0.0298 (15) | 0.0001 (11) | 0.0077 (11) | 0.0055 (12) |
| C7 | 0.0162 (12) | 0.0213 (14) | 0.0205 (13) | −0.0025 (10) | 0.0093 (10) | −0.0002 (10) |
| Sn1—C1i | 2.151 (3) | C2—C7 | 1.401 (4) |
| Sn1—C1 | 2.151 (3) | C3—C4 | 1.385 (4) |
| Sn1—Cl1 | 2.3740 (7) | C3—H3 | 0.9500 |
| Sn1—Cl1i | 2.3740 (7) | C4—C5 | 1.385 (5) |
| Cl2—C7 | 1.739 (3) | C4—H4 | 0.9500 |
| C1—C2 | 1.489 (4) | C5—C6 | 1.391 (5) |
| C1—H1A | 0.9900 | C5—H5 | 0.9500 |
| C1—H1B | 0.9900 | C6—C7 | 1.389 (4) |
| C2—C3 | 1.395 (4) | C6—H6 | 0.9500 |
| C1i—Sn1—C1 | 135.86 (16) | C4—C3—C2 | 121.7 (3) |
| C1i—Sn1—Cl1 | 107.23 (8) | C4—C3—H3 | 119.2 |
| C1—Sn1—Cl1 | 101.07 (8) | C2—C3—H3 | 119.2 |
| C1i—Sn1—Cl1i | 101.07 (8) | C5—C4—C3 | 120.2 (3) |
| C1—Sn1—Cl1i | 107.23 (8) | C5—C4—H4 | 119.9 |
| Cl1—Sn1—Cl1i | 98.96 (4) | C3—C4—H4 | 119.9 |
| C2—C1—Sn1 | 112.17 (18) | C4—C5—C6 | 119.8 (3) |
| C2—C1—H1A | 109.2 | C4—C5—H5 | 120.1 |
| Sn1—C1—H1A | 109.2 | C6—C5—H5 | 120.1 |
| C2—C1—H1B | 109.2 | C7—C6—C5 | 119.2 (3) |
| Sn1—C1—H1B | 109.2 | C7—C6—H6 | 120.4 |
| H1A—C1—H1B | 107.9 | C5—C6—H6 | 120.4 |
| C3—C2—C7 | 117.0 (3) | C6—C7—C2 | 122.1 (3) |
| C3—C2—C1 | 120.5 (2) | C6—C7—Cl2 | 118.2 (2) |
| C7—C2—C1 | 122.5 (3) | C2—C7—Cl2 | 119.7 (2) |
| Symmetry code: (i) −x+1, y, −z+3/2. |
Experimental details
| Crystal data | |
| Chemical formula | [Sn(C7H6Cl)2Cl2] |
| Mr | 440.73 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 26.0750 (13), 4.7757 (2), 13.3389 (7) |
| β (°) | 112.1538 (5) |
| V (Å3) | 1538.42 (13) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 2.34 |
| Crystal size (mm) | 0.40 × 0.10 × 0.10 |
| Data collection | |
| Diffractometer | Bruker SMART APEX diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.455, 0.800 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 8736, 1767, 1674 |
| Rint | 0.029 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.073, 1.07 |
| No. of reflections | 1767 |
| No. of parameters | 87 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 2.12, −1.03 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank the University of Malaya (RG020/09AFR) for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541. CrossRef Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, H.-D. & Gao, Z.-J. (2006). Huaxue Shiji, 28, 39–40. CAS Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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).