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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1334.
Published online 2010 September 30. doi:  10.1107/S1600536810038122
PMCID: PMC2983377

Bis(benzyl­triethyl­ammonium) hexa­chloridostannate(IV)

Abstract

The reaction between benzyl­triethyl­ammonium chloride and dimethyl­tin dichloride yields the title salt, [(C6H5CH2)(C2H5)3N]2[SnCl6]. The SnIV atom, located on a center of inversion, exists in an octa­hedral coordination environment. The cation links with the anion via weak C—H(...)Cl hydrogen bonding.

Related literature

For bis­(tetra­methyl­ammonium) hexa­chloridostannate(IV), see: Furukawa et al. (1982 [triangle]). For bis­(tetra-n-propyl­ammonium) hexa­chloridostannate(IV), see: James et al. (1992 [triangle]). For bis­(tetraethyl­ammonium) hexa­chloridostannate(IV), see: Sowa et al. (1981 [triangle]).

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Object name is e-66-m1334-scheme1.jpg

Experimental

Crystal data

  • (C13H22N)2[SnCl6]
  • M r = 716.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1334-efi1.jpg
  • a = 11.2096 (6) Å
  • b = 11.2306 (6) Å
  • c = 12.9796 (7) Å
  • β = 90.872 (1)°
  • V = 1633.82 (15) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.29 mm−1
  • T = 295 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.698, T max = 0.882
  • 15028 measured reflections
  • 3756 independent reflections
  • 3276 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.059
  • S = 1.01
  • 3756 reflections
  • 160 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.39 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]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038122/xu5035sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038122/xu5035Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The reaction of dimethyltin dichloride with ammonium halides sometimes leads to tin-carbon cleave to result in the formation of a hexahalogenostannate. Tin-methyl cleavage was noted in the reaction of dimethyltin dichloride with and benzyltriethylammonium chloride; the resulting the title salt (Scheme I, Fig. 1) consists of ammonium cations and hexachloridostannate anions. The reported ammonium hexachloridostannates all have symmetrically substituted ammonium cations.

Experimental

Dimethyltin(IV) dichloride (0.219 g, 1 mmol) and benzyltriethylammonium chloride (0.455 g, 2 mmol) were dissolved in methanol and the solution kept at 333 K. Crystals were isolated after several days; m.p. 452–454 K.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the 2(C6H5CH2)(C2H5)3N+ SnCl62- salt at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C13H22N)2[SnCl6]F(000) = 732
Mr = 716.02Dx = 1.455 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8245 reflections
a = 11.2096 (6) Åθ = 2.4–28.2°
b = 11.2306 (6) ŵ = 1.29 mm1
c = 12.9796 (7) ÅT = 295 K
β = 90.872 (1)°Prism, colorless
V = 1633.82 (15) Å30.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer3756 independent reflections
Radiation source: fine-focus sealed tube3276 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→13
Tmin = 0.698, Tmax = 0.882k = −14→14
15028 measured reflectionsl = −16→16

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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.032P)2 + 0.4848P] where P = (Fo2 + 2Fc2)/3
3756 reflections(Δ/σ)max = 0.001
160 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.39 e Å3

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

xyzUiso*/Ueq
Sn10.50000.50000.50000.03041 (6)
Cl10.53546 (4)0.67877 (4)0.60050 (3)0.04330 (11)
Cl20.45054 (4)0.39111 (4)0.65796 (3)0.04483 (12)
Cl30.70731 (4)0.44472 (5)0.52383 (4)0.04963 (13)
N10.10908 (13)0.22025 (14)0.56788 (12)0.0390 (3)
C10.1030 (2)0.3475 (2)0.60638 (18)0.0534 (5)
H1A0.17620.36490.64430.064*
H1B0.09970.40020.54720.064*
C2−0.0015 (2)0.3758 (2)0.6748 (2)0.0659 (7)
H2A0.00270.45760.69580.099*
H2B0.00130.32540.73450.099*
H2C−0.07480.36220.63730.099*
C3−0.00149 (17)0.1864 (2)0.50650 (16)0.0519 (5)
H3A−0.06800.18160.55330.062*
H3B0.01030.10750.47790.062*
C4−0.0354 (2)0.2704 (3)0.41919 (19)0.0744 (8)
H4A−0.10660.24210.38530.112*
H4B0.02830.27360.37070.112*
H4C−0.04920.34860.44640.112*
C50.11816 (18)0.13332 (19)0.65726 (15)0.0460 (5)
H5A0.12950.05390.62960.055*
H5B0.04290.13360.69320.055*
C60.2178 (2)0.1584 (3)0.73500 (17)0.0627 (6)
H6A0.21810.09790.78730.094*
H6B0.20510.23480.76620.094*
H6C0.29300.15830.70070.094*
C70.22048 (17)0.21310 (18)0.50080 (15)0.0436 (4)
H7A0.21220.27100.44570.052*
H7B0.28910.23630.54260.052*
C80.24596 (17)0.09404 (19)0.45360 (15)0.0429 (4)
C90.3185 (3)0.0112 (2)0.5036 (2)0.0660 (7)
H90.34920.02840.56890.079*
C100.3458 (3)−0.0965 (3)0.4577 (2)0.0798 (8)
H100.3933−0.15150.49270.096*
C110.3032 (3)−0.1225 (2)0.3612 (2)0.0713 (7)
H110.3217−0.19490.33060.086*
C120.2334 (2)−0.0415 (3)0.3098 (2)0.0632 (6)
H120.2049−0.05870.24380.076*
C130.2049 (2)0.0659 (2)0.35541 (16)0.0524 (5)
H130.15740.12020.31950.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.02733 (9)0.03422 (10)0.02977 (9)−0.00209 (6)0.00331 (6)0.00222 (6)
Cl10.0462 (3)0.0419 (2)0.0420 (2)−0.0050 (2)0.00723 (19)−0.00544 (19)
Cl20.0483 (3)0.0508 (3)0.0354 (2)−0.0082 (2)0.00231 (18)0.00960 (19)
Cl30.0344 (2)0.0550 (3)0.0595 (3)0.0041 (2)0.0010 (2)0.0053 (2)
N10.0344 (8)0.0408 (8)0.0418 (8)−0.0066 (6)0.0041 (6)0.0081 (7)
C10.0606 (14)0.0438 (11)0.0561 (12)−0.0041 (10)0.0122 (10)0.0042 (9)
C20.0721 (16)0.0610 (15)0.0650 (15)0.0120 (13)0.0182 (12)0.0052 (12)
C30.0346 (10)0.0675 (15)0.0536 (12)−0.0047 (9)−0.0041 (9)0.0039 (10)
C40.0640 (16)0.101 (2)0.0578 (14)0.0305 (15)−0.0091 (12)0.0077 (14)
C50.0429 (11)0.0497 (11)0.0454 (10)−0.0070 (9)0.0037 (8)0.0154 (9)
C60.0511 (13)0.0902 (19)0.0467 (12)−0.0049 (12)−0.0053 (10)0.0124 (12)
C70.0375 (10)0.0483 (11)0.0453 (10)−0.0073 (8)0.0074 (8)0.0075 (8)
C80.0348 (10)0.0498 (11)0.0443 (10)−0.0025 (8)0.0033 (8)0.0071 (8)
C90.0628 (16)0.0793 (19)0.0554 (14)0.0197 (13)−0.0120 (12)0.0016 (12)
C100.081 (2)0.0746 (19)0.084 (2)0.0352 (16)−0.0011 (15)0.0087 (15)
C110.0777 (18)0.0575 (15)0.0793 (18)0.0054 (13)0.0182 (14)−0.0086 (13)
C120.0640 (15)0.0723 (16)0.0535 (13)−0.0050 (13)0.0044 (11)−0.0103 (12)
C130.0502 (12)0.0615 (14)0.0453 (11)0.0037 (10)−0.0008 (9)0.0070 (10)

Geometric parameters (Å, °)

Sn1—Cl3i2.4207 (5)C4—H4C0.9600
Sn1—Cl32.4207 (5)C5—C61.520 (3)
Sn1—Cl12.4237 (5)C5—H5A0.9700
Sn1—Cl1i2.4237 (5)C5—H5B0.9700
Sn1—Cl2i2.4579 (4)C6—H6A0.9600
Sn1—Cl22.4579 (4)C6—H6B0.9600
N1—C31.512 (2)C6—H6C0.9600
N1—C11.515 (3)C7—C81.500 (3)
N1—C51.518 (2)C7—H7A0.9700
N1—C71.535 (2)C7—H7B0.9700
C1—C21.515 (3)C8—C131.385 (3)
C1—H1A0.9700C8—C91.390 (3)
C1—H1B0.9700C9—C101.386 (4)
C2—H2A0.9600C9—H90.9300
C2—H2B0.9600C10—C111.364 (4)
C2—H2C0.9600C10—H100.9300
C3—C41.519 (3)C11—C121.367 (4)
C3—H3A0.9700C11—H110.9300
C3—H3B0.9700C12—C131.384 (4)
C4—H4A0.9600C12—H120.9300
C4—H4B0.9600C13—H130.9300
Cl3i—Sn1—Cl3180.0H4A—C4—H4B109.5
Cl3i—Sn1—Cl190.320 (18)C3—C4—H4C109.5
Cl3—Sn1—Cl189.680 (18)H4A—C4—H4C109.5
Cl3i—Sn1—Cl1i89.680 (18)H4B—C4—H4C109.5
Cl3—Sn1—Cl1i90.320 (18)N1—C5—C6115.36 (17)
Cl1—Sn1—Cl1i180.0N1—C5—H5A108.4
Cl3i—Sn1—Cl2i89.662 (17)C6—C5—H5A108.4
Cl3—Sn1—Cl2i90.338 (17)N1—C5—H5B108.4
Cl1—Sn1—Cl2i89.974 (17)C6—C5—H5B108.4
Cl1i—Sn1—Cl2i90.026 (17)H5A—C5—H5B107.5
Cl3i—Sn1—Cl290.338 (17)C5—C6—H6A109.5
Cl3—Sn1—Cl289.662 (17)C5—C6—H6B109.5
Cl1—Sn1—Cl290.026 (17)H6A—C6—H6B109.5
Cl1i—Sn1—Cl289.974 (17)C5—C6—H6C109.5
Cl2i—Sn1—Cl2180.00 (2)H6A—C6—H6C109.5
C3—N1—C1111.75 (17)H6B—C6—H6C109.5
C3—N1—C5106.60 (15)C8—C7—N1116.09 (15)
C1—N1—C5110.92 (16)C8—C7—H7A108.3
C3—N1—C7110.82 (15)N1—C7—H7A108.3
C1—N1—C7106.10 (14)C8—C7—H7B108.3
C5—N1—C7110.73 (15)N1—C7—H7B108.3
C2—C1—N1115.49 (18)H7A—C7—H7B107.4
C2—C1—H1A108.4C13—C8—C9117.5 (2)
N1—C1—H1A108.4C13—C8—C7121.09 (19)
C2—C1—H1B108.4C9—C8—C7121.3 (2)
N1—C1—H1B108.4C10—C9—C8121.0 (2)
H1A—C1—H1B107.5C10—C9—H9119.5
C1—C2—H2A109.5C8—C9—H9119.5
C1—C2—H2B109.5C11—C10—C9120.3 (3)
H2A—C2—H2B109.5C11—C10—H10119.8
C1—C2—H2C109.5C9—C10—H10119.8
H2A—C2—H2C109.5C10—C11—C12119.7 (3)
H2B—C2—H2C109.5C10—C11—H11120.1
N1—C3—C4115.5 (2)C12—C11—H11120.1
N1—C3—H3A108.4C11—C12—C13120.4 (2)
C4—C3—H3A108.4C11—C12—H12119.8
N1—C3—H3B108.4C13—C12—H12119.8
C4—C3—H3B108.4C8—C13—C12121.1 (2)
H3A—C3—H3B107.5C8—C13—H13119.4
C3—C4—H4A109.5C12—C13—H13119.4
C3—C4—H4B109.5
C3—N1—C1—C258.9 (2)C5—N1—C7—C859.4 (2)
C5—N1—C1—C2−59.9 (2)N1—C7—C8—C1393.4 (2)
C7—N1—C1—C2179.8 (2)N1—C7—C8—C9−91.3 (3)
C1—N1—C3—C452.4 (2)C13—C8—C9—C10−1.7 (4)
C5—N1—C3—C4173.76 (19)C7—C8—C9—C10−177.2 (3)
C7—N1—C3—C4−65.7 (2)C8—C9—C10—C111.1 (5)
C3—N1—C5—C6−174.68 (19)C9—C10—C11—C120.0 (5)
C1—N1—C5—C6−52.8 (2)C10—C11—C12—C13−0.5 (4)
C7—N1—C5—C664.7 (2)C9—C8—C13—C121.2 (3)
C3—N1—C7—C8−58.7 (2)C7—C8—C13—C12176.7 (2)
C1—N1—C7—C8179.82 (17)C11—C12—C13—C8−0.1 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2B···Cl1ii0.962.743.685 (3)169

Symmetry codes: (ii) −x+1/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5035).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Furukawa, Y., Prabhumirashi, L. S., Ikeda, R. & Nakamura, D. (1982). Bull. Chem. Soc. Jpn, 55, 995–998.
  • James, M. A., Knop, O. & Cameron, T. S. (1992). Can. J. Chem.70, 1795–1821.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sowa, H., Druck, U. & Kutoglu, A. (1981). Cryst. Struct. Commun.10, 699–702.
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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