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Acta Cryst. (2009). E65, m1677    [ doi:10.1107/S160053680904940X ]

Bis(trimethylphenylammonium) tetrabromidobis(4-chlorophenyl)stannate(IV)

K. M. Lo and S. W. Ng

Abstract top

The SnIV atom in the title salt, [N(CH3)3(C6H5)]2[SnBr4(C6H4Cl)2], exists in a distorted all-trans SnC2Br4 octahedral geometry. The SnIV atom lies on a center of inversion. Weak intermolecular C-H...Br hydrogen bonding is observed between trimethylphenylammonium cations and the Sn complex anion in the crystal structure.

Related literature top

For bis(4-dimethylaminopyridinium) tetrabromidodiphenylstannate, see: Yap et al. (2008).

Experimental top

In an attempt to cleave a tin-carbon bond in a tetraorganotin compound, tetrakis(4-chlorophenyl)tin (0.57 g, 1 mmol) and trimethylphenylammonium tribromide (0.38 g, 1 mmol) were heated in ethanol for six hours. Colorless crystals of the stannate separated from the solution after a few days.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The final difference Fourier map had peak near Sn1 and a hole near Br2.

The refinement program suggested a rather larger second parameter for the weighting scheme. The scheme was arbitrarily selected as (0.05 5.00), which led to a satisfactory, albeit somewhat large, goodness-of-fit.

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 the two independent formula units of 2[N(CH3)3(C6H5)] [SnBr4(C6H4Cl)2] at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Bis(trimethylphenylammonium) tetrabromidobis(4-chlorophenyl)stannate(IV) top
Crystal data top
(C9H14N)2[SnBr4(C6H4Cl)2]F(000) = 1816
Mr = 933.84Dx = 1.820 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 946 reflections
a = 25.7930 (3) Åθ = 2.4–28.2°
b = 9.0937 (1) ŵ = 5.62 mm−1
c = 15.8303 (2) ÅT = 293 K
β = 113.4146 (6)°Block, colorless
V = 3407.30 (7) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		3916 independent reflections
Radiation source: fine-focus sealed tube3427 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −33→33
Tmin = 0.482, Tmax = 0.756k = −11→11
15816 measured reflectionsl = −20→20
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.05P)2 + 5.0P]
where P = (Fo2 + 2Fc2)/3
3916 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 1.28 e Å−3
0 restraintsΔρmin = −1.03 e Å−3
Crystal data top
(C9H14N)2[SnBr4(C6H4Cl)2]V = 3407.30 (7) Å3
Mr = 933.84Z = 4
Monoclinic, C2/cMo Kα radiation
a = 25.7930 (3) ŵ = 5.62 mm−1
b = 9.0937 (1) ÅT = 293 K
c = 15.8303 (2) Å0.30 × 0.25 × 0.20 mm
β = 113.4146 (6)°
Data collection top
Bruker SMART APEX
diffractometer		3916 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3427 reflections with I > 2σ(I)
Tmin = 0.482, Tmax = 0.756Rint = 0.025
15816 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.098Δρmax = 1.28 e Å−3
S = 1.24Δρmin = −1.03 e Å−3
3916 reflectionsAbsolute structure: ?
181 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.25000.75000.50000.02955 (10)
Br10.183541 (17)0.69102 (4)0.59433 (3)0.04572 (12)
Br20.292712 (17)0.99167 (4)0.60875 (3)0.04584 (12)
Cl10.45173 (6)0.34442 (18)0.80689 (10)0.0818 (4)
N10.13915 (14)0.2207 (3)0.5931 (2)0.0400 (7)
C10.31591 (13)0.6149 (3)0.5957 (2)0.0295 (6)
C20.30386 (17)0.4780 (4)0.6223 (3)0.0422 (8)
H20.26700.44260.59640.051*
C30.34514 (18)0.3939 (4)0.6858 (3)0.0466 (9)
H30.33660.30280.70370.056*
C40.39961 (17)0.4473 (5)0.7226 (3)0.0473 (9)
C50.41310 (16)0.5804 (5)0.6971 (3)0.0518 (10)
H50.45020.61410.72220.062*
C60.37092 (15)0.6646 (4)0.6334 (3)0.0420 (8)
H60.37980.75560.61580.050*
C70.08627 (16)0.2803 (4)0.5981 (2)0.0383 (8)
C80.0346 (2)0.2255 (6)0.5397 (4)0.0658 (13)
H80.03250.15010.49880.079*
C9−0.0136 (2)0.2830 (8)0.5424 (5)0.0817 (17)
H9−0.04850.24690.50220.098*
C10−0.0121 (2)0.3909 (6)0.6018 (4)0.0702 (14)
H10−0.04540.42900.60260.084*
C110.0390 (3)0.4433 (6)0.6607 (4)0.0732 (15)
H110.04030.51610.70270.088*
C120.0888 (2)0.3908 (5)0.6594 (3)0.0564 (11)
H120.12330.42910.69900.068*
C130.1911 (2)0.2531 (7)0.6789 (3)0.0683 (14)
H13A0.19600.35750.68670.102*
H13B0.22360.21070.67310.102*
H13C0.18670.21150.73130.102*
C140.1361 (2)0.0572 (5)0.5795 (5)0.0728 (15)
H14A0.10590.03370.52180.109*
H14B0.12920.01110.62860.109*
H14C0.17120.02220.57950.109*
C150.1479 (2)0.2913 (6)0.5144 (3)0.0573 (11)
H15A0.11710.26600.45770.086*
H15B0.18270.25700.51290.086*
H15C0.14940.39610.52210.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02499 (16)0.03104 (17)0.03048 (17)0.00219 (11)0.00875 (12)0.00523 (11)
Br10.0450 (2)0.0460 (2)0.0533 (2)0.00187 (16)0.02717 (18)0.00690 (16)
Br20.0481 (2)0.0417 (2)0.0424 (2)−0.00224 (16)0.01229 (17)−0.00120 (15)
Cl10.0651 (8)0.0921 (9)0.0723 (8)0.0379 (7)0.0105 (6)0.0363 (7)
N10.0452 (18)0.0404 (15)0.0392 (16)−0.0008 (13)0.0219 (14)0.0015 (12)
C10.0289 (15)0.0301 (14)0.0286 (14)0.0038 (12)0.0105 (12)0.0032 (11)
C20.040 (2)0.0401 (18)0.0415 (19)−0.0019 (16)0.0111 (16)0.0051 (15)
C30.055 (2)0.0371 (18)0.043 (2)0.0073 (17)0.0149 (18)0.0098 (15)
C40.044 (2)0.053 (2)0.0394 (19)0.0212 (18)0.0114 (16)0.0108 (17)
C50.0280 (18)0.062 (3)0.057 (2)0.0037 (18)0.0080 (17)0.010 (2)
C60.0301 (17)0.0438 (19)0.048 (2)0.0015 (15)0.0110 (15)0.0100 (16)
C70.040 (2)0.0405 (18)0.0363 (18)−0.0006 (15)0.0168 (16)0.0021 (14)
C80.049 (3)0.081 (3)0.058 (3)−0.008 (2)0.012 (2)−0.021 (2)
C90.039 (3)0.102 (4)0.089 (4)−0.008 (3)0.010 (3)−0.007 (3)
C100.053 (3)0.069 (3)0.099 (4)0.012 (2)0.041 (3)0.016 (3)
C110.083 (4)0.055 (3)0.098 (4)0.009 (3)0.053 (3)−0.009 (3)
C120.051 (2)0.051 (2)0.068 (3)−0.005 (2)0.024 (2)−0.014 (2)
C130.047 (3)0.105 (4)0.047 (2)0.016 (3)0.013 (2)−0.003 (2)
C140.082 (4)0.040 (2)0.120 (5)0.001 (2)0.065 (4)−0.001 (3)
C150.070 (3)0.064 (3)0.051 (2)−0.006 (2)0.038 (2)0.004 (2)
Geometric parameters (Å, °) top
Sn1—C1i2.156 (3)C7—C121.380 (6)
Sn1—C12.156 (3)C7—C81.380 (6)
Sn1—Br12.7368 (4)C8—C91.365 (8)
Sn1—Br1i2.7368 (4)C8—H80.9300
Sn1—Br2i2.7386 (4)C9—C101.349 (8)
Sn1—Br22.7386 (4)C9—H90.9300
Cl1—C41.743 (4)C10—C111.362 (8)
N1—C141.499 (5)C10—H100.9300
N1—C151.495 (5)C11—C121.377 (7)
N1—C71.499 (5)C11—H110.9300
N1—C131.510 (6)C12—H120.9300
C1—C61.379 (5)C13—H13A0.9600
C1—C21.389 (5)C13—H13B0.9600
C2—C31.371 (5)C13—H13C0.9600
C2—H20.9300C14—H14A0.9600
C3—C41.378 (6)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C4—C51.364 (6)C15—H15A0.9600
C5—C61.384 (5)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—H60.9300
C1i—Sn1—C1180.000 (1)C1—C6—H6119.7
C1i—Sn1—Br190.29 (8)C12—C7—C8119.8 (4)
C1—Sn1—Br189.71 (8)C12—C7—N1120.8 (4)
C1i—Sn1—Br1i89.71 (8)C8—C7—N1119.4 (4)
C1—Sn1—Br1i90.29 (8)C9—C8—C7119.4 (5)
Br1—Sn1—Br1i180.0C9—C8—H8120.3
C1i—Sn1—Br2i90.43 (8)C7—C8—H8120.3
C1—Sn1—Br2i89.57 (8)C8—C9—C10121.7 (5)
Br1—Sn1—Br2i90.173 (13)C8—C9—H9119.1
Br1i—Sn1—Br2i89.827 (12)C10—C9—H9119.1
C1i—Sn1—Br289.57 (8)C11—C10—C9118.9 (5)
C1—Sn1—Br290.43 (8)C11—C10—H10120.5
Br1—Sn1—Br289.827 (12)C9—C10—H10120.5
Br1i—Sn1—Br290.173 (13)C10—C11—C12121.5 (5)
Br2i—Sn1—Br2180.000 (10)C10—C11—H11119.2
C14—N1—C15108.9 (4)C12—C11—H11119.2
C14—N1—C7111.7 (3)C11—C12—C7118.6 (5)
C15—N1—C7109.3 (3)C11—C12—H12120.7
C14—N1—C13107.4 (4)C7—C12—H12120.7
C15—N1—C13107.0 (4)N1—C13—H13A109.5
C7—N1—C13112.5 (3)N1—C13—H13B109.5
C6—C1—C2118.6 (3)H13A—C13—H13B109.5
C6—C1—Sn1120.4 (2)N1—C13—H13C109.5
C2—C1—Sn1121.0 (3)H13A—C13—H13C109.5
C3—C2—C1121.4 (4)H13B—C13—H13C109.5
C3—C2—H2119.3N1—C14—H14A109.5
C1—C2—H2119.3N1—C14—H14B109.5
C2—C3—C4118.6 (4)H14A—C14—H14B109.5
C2—C3—H3120.7N1—C14—H14C109.5
C4—C3—H3120.7H14A—C14—H14C109.5
C5—C4—C3121.6 (3)H14B—C14—H14C109.5
C5—C4—Cl1119.5 (3)N1—C15—H15A109.5
C3—C4—Cl1118.8 (3)N1—C15—H15B109.5
C4—C5—C6119.2 (4)H15A—C15—H15B109.5
C4—C5—H5120.4N1—C15—H15C109.5
C6—C5—H5120.4H15A—C15—H15C109.5
C5—C6—C1120.6 (4)H15B—C15—H15C109.5
C5—C6—H6119.7
Br1—Sn1—C1—C6−133.2 (3)C2—C1—C6—C5−0.7 (6)
Br1i—Sn1—C1—C646.8 (3)Sn1—C1—C6—C5177.9 (3)
Br2i—Sn1—C1—C6136.6 (3)C14—N1—C7—C12140.8 (5)
Br2—Sn1—C1—C6−43.4 (3)C15—N1—C7—C12−98.7 (5)
Br1—Sn1—C1—C245.3 (3)C13—N1—C7—C1220.0 (5)
Br1i—Sn1—C1—C2−134.7 (3)C14—N1—C7—C8−40.4 (6)
Br2i—Sn1—C1—C2−44.8 (3)C15—N1—C7—C880.2 (5)
Br2—Sn1—C1—C2135.2 (3)C13—N1—C7—C8−161.2 (4)
C6—C1—C2—C31.2 (6)C12—C7—C8—C90.9 (8)
Sn1—C1—C2—C3−177.4 (3)N1—C7—C8—C9−178.0 (5)
C1—C2—C3—C4−0.8 (6)C7—C8—C9—C10−1.0 (10)
C2—C3—C4—C5−0.2 (6)C8—C9—C10—C11−0.1 (10)
C2—C3—C4—Cl1177.4 (3)C9—C10—C11—C121.4 (9)
C3—C4—C5—C60.7 (7)C10—C11—C12—C7−1.5 (8)
Cl1—C4—C5—C6−176.9 (3)C8—C7—C12—C110.3 (7)
C4—C5—C6—C1−0.2 (7)N1—C7—C12—C11179.2 (4)
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C15—H15C···Br10.962.913.839 (5)163
Table 1
Selected geometric parameters (Å) top
Sn1—C12.156 (3)Sn1—Br22.7386 (4)
Sn1—Br12.7368 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C15—H15C···Br10.962.913.839 (5)163
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
References top

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

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

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

Westrip, S. P. (2009). publCIF. In preparation.

Yap, Q. L., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m696.