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Acta Cryst. (2010). E66, m1334    [ doi:10.1107/S1600536810038122 ]

Bis(benzyltriethylammonium) hexachloridostannate(IV)

E. Najafi, M. M. Amini and S. W. Ng

Abstract top

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.

Comment top

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.

Related literature top

For bis(tetramethylammonium) hexachloridostannate, see: Furukawa et al. (1982). For bis(tetra-n-propylammonium) hexachloridostannate, see: James et al. (1992). For bis(tetra-ethylammonium) hexachloridostannate, see: Sowa et al. (1981).

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] 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.
Bis(benzyltriethylammonium) hexachloridostannate(IV) top
Crystal data top
(C13H22N)2[SnCl6]F(000) = 732
Mr = 716.02Dx = 1.455 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		3756 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 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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.01 w = 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 Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
(C13H22N)2[SnCl6]V = 1633.82 (15) Å3
Mr = 716.02Z = 2
Monoclinic, P21/nMo Kα radiation
a = 11.2096 (6) ŵ = 1.29 mm−1
b = 11.2306 (6) ÅT = 295 K
c = 12.9796 (7) Å0.30 × 0.20 × 0.10 mm
β = 90.872 (1)°
Data collection top
Bruker SMART APEX
diffractometer		3756 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3276 reflections with I > 2σ(I)
Tmin = 0.698, Tmax = 0.882Rint = 0.022
15028 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.059Δρmax = 0.41 e Å−3
S = 1.01Δρmin = −0.39 e Å−3
3756 reflectionsAbsolute structure: ?
160 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···Cl1i0.962.743.685 (3)169
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2.
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Sowa, H., Druck, U. & Kutoglu, A. (1981). Cryst. Struct. Commun. 10, 699–702.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.