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Acta Cryst. (2009). E65, m714    [ doi:10.1107/S1600536809019722 ]

Trimethylphenylammonium dibromidotriphenylstannate(IV)

Q. L. Yap, K. M. Lo and S. W. Ng

Abstract top

The five-coordinate Sn atom in the title salt, [(CH3)3(C6H6)N][SnBr2(C6H5)3], exists in a distorted trans-C3SnBr2 trigonal-bipyramidal coordination geometry. In the crystal structure no obvious hydrogen bonding is observed.

Related literature top

The are few examples of dihalogenotriarylstannate salts having a counter-ion that does not participate in hydrogen bonding, which appears to assist in stabilizing the salt, see: Beckmann et al. (2002); Harrison et al. (1978); Kuhn et al. (2001); Ng (1995); Wharf & Simard (1991).

Experimental top

Bis(4-dimethylaminopyridinium) dibromidotriphenylstannate (1.0 g, 1.6 mmol) and trimethylphenylammonium bromide (0.34 g, 1.6 mmol) were heated in ethanol for 1 hour. Colorless crystals separated after a few days.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: pubCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [PhMe3N][SnBr2Ph3] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Trimethylphenylammonium dibromidotriphenylstannate(IV) top
Crystal data top
(C9H14N)[SnBr2(C6H5)3]F(000) = 636
Mr = 646.02Dx = 1.646 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9930 reflections
a = 9.0010 (1) Åθ = 2.4–28.3°
b = 16.7778 (2) ŵ = 4.06 mm−1
c = 9.2448 (1) ÅT = 100 K
β = 111.003 (1)°Block, colorless
V = 1303.37 (3) Å30.30 × 0.25 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		5966 independent reflections
Radiation source: fine-focus sealed tube5889 reflections with I > 2σ(I)
graphiteRint = 0.012
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.567, Tmax = 0.746k = −21→21
12525 measured reflectionsl = −12→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.016H-atom parameters constrained
wR(F2) = 0.042 w = 1/[σ2(Fo2) + (0.0283P)2 + 0.211P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5966 reflectionsΔρmax = 0.38 e Å−3
280 parametersΔρmin = −0.22 e Å−3
1 restraintAbsolute structure: Flack (1983), 2872 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.011 (3)
Crystal data top
(C9H14N)[SnBr2(C6H5)3]V = 1303.37 (3) Å3
Mr = 646.02Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.0010 (1) ŵ = 4.06 mm−1
b = 16.7778 (2) ÅT = 100 K
c = 9.2448 (1) Å0.30 × 0.25 × 0.20 mm
β = 111.003 (1)°
Data collection top
Bruker SMART APEX
diffractometer		5966 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5889 reflections with I > 2σ(I)
Tmin = 0.567, Tmax = 0.746Rint = 0.012
12525 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.016H-atom parameters constrained
wR(F2) = 0.042Δρmax = 0.38 e Å−3
S = 1.06Δρmin = −0.22 e Å−3
5966 reflectionsAbsolute structure: Flack (1983), 2872 Friedel pairs
280 parametersFlack parameter: 0.011 (3)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.800735 (16)0.499537 (6)0.968485 (15)0.01425 (4)
Br10.50474 (2)0.441885 (12)0.78666 (2)0.01891 (5)
Br21.10719 (2)0.544697 (12)1.14791 (2)0.01839 (5)
N10.4280 (2)0.36054 (11)1.3067 (2)0.0184 (3)
C10.8550 (2)0.52187 (12)0.7653 (2)0.0173 (4)
C20.7539 (3)0.56900 (13)0.6462 (3)0.0213 (4)
H20.65960.59030.65490.026*
C30.7901 (3)0.58504 (15)0.5146 (3)0.0254 (5)
H30.72090.61750.43460.030*
C40.9258 (3)0.55404 (16)0.4999 (3)0.0273 (5)
H40.94950.56490.40970.033*
C51.0273 (3)0.50715 (18)0.6166 (3)0.0292 (5)
H51.12050.48550.60600.035*
C60.9933 (3)0.49146 (15)0.7499 (3)0.0250 (5)
H61.06450.46000.83040.030*
C70.8524 (2)0.38465 (13)1.0804 (2)0.0157 (4)
C80.8729 (3)0.37779 (14)1.2360 (3)0.0220 (4)
H80.86380.42351.29310.026*
C90.9068 (3)0.30373 (16)1.3081 (3)0.0301 (5)
H90.91670.29851.41350.036*
C100.9261 (3)0.23781 (15)1.2269 (3)0.0315 (6)
H100.94940.18731.27640.038*
C110.9113 (3)0.24555 (14)1.0730 (3)0.0299 (5)
H110.92640.20051.01760.036*
C120.8743 (3)0.31912 (14)0.9998 (3)0.0249 (5)
H120.86410.32430.89440.030*
C130.6992 (2)0.59342 (13)1.0628 (2)0.0159 (4)
C140.7844 (3)0.66346 (13)1.1201 (2)0.0202 (4)
H140.89050.66861.12270.024*
C150.7154 (3)0.72562 (13)1.1732 (3)0.0229 (4)
H150.77470.77281.21200.027*
C160.5604 (3)0.71924 (14)1.1700 (3)0.0253 (5)
H160.51260.76221.20410.030*
C170.4761 (3)0.64944 (15)1.1163 (3)0.0250 (5)
H170.37100.64411.11610.030*
C180.5447 (2)0.58699 (13)1.0626 (2)0.0186 (4)
H180.48550.53961.02560.022*
C190.5292 (2)0.28835 (13)1.3666 (2)0.0175 (4)
C200.6100 (3)0.28234 (14)1.5255 (3)0.0238 (5)
H200.60510.32441.59240.029*
C210.6975 (3)0.21445 (15)1.5849 (3)0.0264 (5)
H210.75360.21001.69330.032*
C220.7040 (3)0.15287 (14)1.4874 (3)0.0242 (4)
H220.76280.10591.52900.029*
C230.6246 (3)0.15991 (13)1.3294 (3)0.0227 (4)
H230.63020.11791.26260.027*
C240.5367 (3)0.22799 (13)1.2673 (3)0.0206 (4)
H240.48260.23301.15860.025*
C250.2875 (3)0.35662 (15)1.3594 (3)0.0265 (5)
H25A0.32570.35341.47270.040*
H25B0.22340.30941.31470.040*
H25C0.22210.40461.32490.040*
C260.3650 (3)0.36554 (15)1.1328 (3)0.0317 (6)
H26A0.45420.36861.09580.048*
H26B0.29850.41321.09970.048*
H26C0.30120.31801.08940.048*
C270.5184 (3)0.43595 (14)1.3676 (3)0.0246 (4)
H27A0.60960.43941.33360.037*
H27B0.55630.43581.48100.037*
H27C0.44840.48191.32780.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01733 (6)0.01231 (6)0.01367 (6)0.00070 (5)0.00626 (4)0.00004 (5)
Br10.01852 (9)0.01789 (10)0.01856 (10)−0.00257 (7)0.00452 (8)−0.00274 (8)
Br20.01643 (9)0.01616 (10)0.01963 (10)−0.00018 (7)0.00289 (7)−0.00003 (8)
N10.0194 (8)0.0184 (9)0.0166 (8)0.0022 (7)0.0056 (7)0.0002 (7)
C10.0205 (9)0.0167 (10)0.0149 (9)−0.0030 (7)0.0064 (7)−0.0023 (7)
C20.0207 (10)0.0206 (10)0.0219 (10)−0.0020 (8)0.0069 (8)0.0007 (8)
C30.0246 (11)0.0295 (12)0.0183 (10)−0.0072 (9)0.0030 (8)0.0035 (9)
C40.0313 (12)0.0360 (13)0.0164 (10)−0.0127 (10)0.0107 (9)−0.0040 (9)
C50.0279 (11)0.0385 (13)0.0262 (11)0.0014 (11)0.0157 (9)−0.0030 (11)
C60.0255 (10)0.0293 (13)0.0206 (10)0.0051 (9)0.0087 (8)0.0017 (9)
C70.0108 (8)0.0177 (9)0.0160 (9)0.0051 (7)0.0014 (7)0.0017 (8)
C80.0217 (10)0.0222 (11)0.0248 (11)0.0014 (8)0.0114 (9)0.0022 (9)
C90.0276 (12)0.0338 (13)0.0323 (13)0.0033 (10)0.0148 (10)0.0152 (11)
C100.0212 (10)0.0212 (11)0.0508 (16)0.0022 (9)0.0113 (11)0.0155 (11)
C110.0252 (11)0.0155 (10)0.0466 (15)0.0006 (9)0.0101 (11)−0.0062 (11)
C120.0246 (11)0.0203 (11)0.0264 (11)−0.0016 (8)0.0048 (9)−0.0052 (9)
C130.0192 (9)0.0152 (9)0.0130 (8)0.0030 (7)0.0054 (7)0.0030 (8)
C140.0229 (10)0.0178 (10)0.0197 (10)−0.0006 (8)0.0072 (8)0.0007 (8)
C150.0329 (12)0.0143 (10)0.0213 (10)−0.0016 (8)0.0095 (9)−0.0023 (8)
C160.0344 (12)0.0202 (11)0.0259 (11)0.0079 (9)0.0165 (10)0.0015 (9)
C170.0263 (11)0.0261 (11)0.0270 (11)0.0056 (9)0.0150 (9)0.0026 (9)
C180.0212 (9)0.0176 (10)0.0181 (9)0.0003 (8)0.0082 (8)0.0013 (8)
C190.0155 (9)0.0171 (10)0.0198 (10)0.0017 (7)0.0061 (8)0.0029 (8)
C200.0291 (11)0.0254 (11)0.0193 (11)0.0052 (9)0.0114 (9)−0.0007 (9)
C210.0307 (12)0.0310 (13)0.0183 (10)0.0081 (10)0.0096 (9)0.0039 (9)
C220.0240 (10)0.0217 (11)0.0273 (11)0.0068 (8)0.0099 (9)0.0046 (9)
C230.0244 (10)0.0167 (10)0.0276 (11)0.0001 (8)0.0099 (9)−0.0028 (9)
C240.0211 (10)0.0184 (10)0.0192 (10)−0.0003 (8)0.0034 (8)−0.0011 (8)
C250.0165 (10)0.0271 (12)0.0373 (13)0.0025 (9)0.0115 (9)0.0040 (10)
C260.0450 (14)0.0278 (13)0.0158 (10)0.0150 (10)0.0029 (10)0.0027 (9)
C270.0257 (10)0.0174 (10)0.0304 (11)−0.0012 (8)0.0094 (9)0.0006 (9)
Geometric parameters (Å, °) top
Sn1—Br12.7657 (2)C13—C181.395 (3)
Sn1—Br22.7667 (2)C13—C141.399 (3)
Sn1—C12.137 (2)C14—C151.390 (3)
Sn1—C72.158 (2)C14—H140.9500
Sn1—C132.156 (2)C15—C161.389 (3)
N1—C271.500 (3)C15—H150.9500
N1—C261.503 (3)C16—C171.387 (4)
N1—C191.497 (3)C16—H160.9500
N1—C251.511 (3)C17—C181.394 (3)
C1—C21.396 (3)C17—H170.9500
C1—C61.399 (3)C18—H180.9500
C2—C31.394 (3)C19—C241.385 (3)
C2—H20.9500C19—C201.390 (3)
C3—C41.378 (4)C20—C211.382 (3)
C3—H30.9500C20—H200.9500
C4—C51.382 (4)C21—C221.386 (3)
C4—H40.9500C21—H210.9500
C5—C61.397 (3)C22—C231.382 (3)
C5—H50.9500C22—H220.9500
C6—H60.9500C23—C241.391 (3)
C7—C121.381 (3)C23—H230.9500
C7—C81.388 (3)C24—H240.9500
C8—C91.391 (3)C25—H25A0.9800
C8—H80.9500C25—H25B0.9800
C9—C101.382 (4)C25—H25C0.9800
C9—H90.9500C26—H26A0.9800
C10—C111.387 (4)C26—H26B0.9800
C10—H100.9500C26—H26C0.9800
C11—C121.389 (3)C27—H27A0.9800
C11—H110.9500C27—H27B0.9800
C12—H120.9500C27—H27C0.9800
C1—Sn1—C7120.02 (8)C18—C13—Sn1120.68 (16)
C1—Sn1—C13119.42 (8)C14—C13—Sn1120.82 (14)
C7—Sn1—C13120.54 (7)C15—C14—C13120.7 (2)
C1—Sn1—Br289.20 (5)C15—C14—H14119.7
C13—Sn1—Br291.91 (5)C13—C14—H14119.7
C7—Sn1—Br287.71 (5)C16—C15—C14120.5 (2)
C1—Sn1—Br190.06 (5)C16—C15—H15119.8
C13—Sn1—Br192.62 (5)C14—C15—H15119.8
C7—Sn1—Br188.51 (5)C15—C16—C17119.3 (2)
Br1—Sn1—Br2175.151 (7)C15—C16—H16120.4
C27—N1—C26107.47 (18)C17—C16—H16120.4
C27—N1—C19111.54 (16)C16—C17—C18120.5 (2)
C26—N1—C19112.77 (17)C16—C17—H17119.8
C27—N1—C25108.64 (17)C18—C17—H17119.8
C26—N1—C25107.97 (18)C17—C18—C13120.6 (2)
C19—N1—C25108.32 (17)C17—C18—H18119.7
C2—C1—C6118.6 (2)C13—C18—H18119.7
C2—C1—Sn1120.17 (15)C24—C19—C20121.1 (2)
C6—C1—Sn1121.19 (15)C24—C19—N1120.93 (18)
C3—C2—C1120.5 (2)C20—C19—N1117.91 (19)
C3—C2—H2119.8C19—C20—C21119.2 (2)
C1—C2—H2119.8C19—C20—H20120.4
C4—C3—C2120.4 (2)C21—C20—H20120.4
C4—C3—H3119.8C22—C21—C20120.4 (2)
C2—C3—H3119.8C22—C21—H21119.8
C5—C4—C3120.0 (2)C20—C21—H21119.8
C5—C4—H4120.0C21—C22—C23119.8 (2)
C3—C4—H4120.0C21—C22—H22120.1
C4—C5—C6120.2 (2)C23—C22—H22120.1
C4—C5—H5119.9C22—C23—C24120.6 (2)
C6—C5—H5119.9C22—C23—H23119.7
C5—C6—C1120.4 (2)C24—C23—H23119.7
C5—C6—H6119.8C19—C24—C23118.8 (2)
C1—C6—H6119.8C19—C24—H24120.6
C12—C7—C8120.1 (2)C23—C24—H24120.6
C12—C7—Sn1120.01 (15)N1—C25—H25A109.5
C8—C7—Sn1119.79 (15)N1—C25—H25B109.5
C9—C8—C7119.7 (2)H25A—C25—H25B109.5
C9—C8—H8120.2N1—C25—H25C109.5
C7—C8—H8120.2H25A—C25—H25C109.5
C10—C9—C8120.2 (2)H25B—C25—H25C109.5
C10—C9—H9119.9N1—C26—H26A109.5
C8—C9—H9119.9N1—C26—H26B109.5
C9—C10—C11119.8 (2)H26A—C26—H26B109.5
C9—C10—H10120.1N1—C26—H26C109.5
C11—C10—H10120.1H26A—C26—H26C109.5
C12—C11—C10120.1 (2)H26B—C26—H26C109.5
C12—C11—H11120.0N1—C27—H27A109.5
C10—C11—H11120.0N1—C27—H27B109.5
C7—C12—C11120.0 (2)H27A—C27—H27B109.5
C7—C12—H12120.0N1—C27—H27C109.5
C11—C12—H12120.0H27A—C27—H27C109.5
C18—C13—C14118.46 (19)H27B—C27—H27C109.5
C13—Sn1—C1—C2−38.04 (19)C10—C11—C12—C70.1 (3)
C7—Sn1—C1—C2143.32 (15)C1—Sn1—C13—C18113.96 (16)
Br2—Sn1—C1—C2−129.79 (16)C7—Sn1—C13—C18−67.41 (18)
Br1—Sn1—C1—C255.01 (16)Br2—Sn1—C13—C18−155.88 (16)
C13—Sn1—C1—C6140.49 (17)Br1—Sn1—C13—C1822.41 (16)
C7—Sn1—C1—C6−38.1 (2)C1—Sn1—C13—C14−63.53 (18)
Br2—Sn1—C1—C648.75 (17)C7—Sn1—C13—C14115.10 (17)
Br1—Sn1—C1—C6−126.46 (17)Br2—Sn1—C13—C1426.62 (16)
C6—C1—C2—C30.2 (3)Br1—Sn1—C13—C14−155.09 (16)
Sn1—C1—C2—C3178.79 (16)C18—C13—C14—C15−1.0 (3)
C1—C2—C3—C40.5 (3)Sn1—C13—C14—C15176.54 (16)
C2—C3—C4—C5−0.4 (4)C13—C14—C15—C16−0.2 (3)
C3—C4—C5—C6−0.4 (4)C14—C15—C16—C171.4 (3)
C4—C5—C6—C11.1 (4)C15—C16—C17—C18−1.5 (3)
C2—C1—C6—C5−1.0 (3)C16—C17—C18—C130.4 (3)
Sn1—C1—C6—C5−179.56 (19)C14—C13—C18—C170.9 (3)
C1—Sn1—C7—C12−19.52 (19)Sn1—C13—C18—C17−176.66 (16)
C13—Sn1—C7—C12161.86 (15)C27—N1—C19—C24−131.5 (2)
Br2—Sn1—C7—C12−107.26 (16)C26—N1—C19—C24−10.4 (3)
Br1—Sn1—C7—C1269.69 (16)C25—N1—C19—C24109.0 (2)
C1—Sn1—C7—C8156.62 (15)C27—N1—C19—C2051.2 (2)
C13—Sn1—C7—C8−22.00 (19)C26—N1—C19—C20172.2 (2)
Br2—Sn1—C7—C868.87 (15)C25—N1—C19—C20−68.3 (2)
Br1—Sn1—C7—C8−114.17 (15)C24—C19—C20—C21−0.8 (3)
C12—C7—C8—C9−3.6 (3)N1—C19—C20—C21176.6 (2)
Sn1—C7—C8—C9−179.74 (16)C19—C20—C21—C22−0.4 (4)
C7—C8—C9—C102.5 (3)C20—C21—C22—C231.1 (4)
C8—C9—C10—C11−0.1 (3)C21—C22—C23—C24−0.7 (4)
C9—C10—C11—C12−1.2 (4)C20—C19—C24—C231.1 (3)
C8—C7—C12—C112.3 (3)N1—C19—C24—C23−176.13 (19)
Sn1—C7—C12—C11178.46 (17)C22—C23—C24—C19−0.4 (3)
Acknowledgements top

We thank the University of Malaya (RG020/09AFR) for supporting this study.

references
References top

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

Beckmann, J., Dakternieks, D., Duthie, A. & Tiekink, E. R. T. (2002). J. Organomet. Chem. 648, 204–208.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Harrison, P. G., Molloy, K. & Phillips, R. C. (1978). J. Organomet. Chem. 160, 421–434.

Kuhn, N., Steinmann, M. & Walker, M. (2001). Z. Naturforsch. Teil B, 56, 129–136.

Ng, S. W. (1995). Acta Cryst. C51, 1124–1125.

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.

Wharf, I. & Simard, M. G. (1991). Acta Cryst. C47, 1605–1609.