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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m714.
Published online 2009 June 6. doi:  10.1107/S1600536809019722
PMCID: PMC2969208

Trimethyl­phenyl­ammonium dibromidotriphenyl­stannate(IV)

Abstract

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

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 [triangle]); Harrison et al. (1978 [triangle]); Kuhn et al. (2001 [triangle]); Ng (1995 [triangle]); Wharf & Simard (1991 [triangle]).

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Object name is e-65-0m714-scheme1.jpg

Experimental

Crystal data

  • (C9H14N)[SnBr2(C6H5)3]
  • M r = 646.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m714-efi1.jpg
  • a = 9.0010 (1) Å
  • b = 16.7778 (2) Å
  • c = 9.2448 (1) Å
  • β = 111.003 (1)°
  • V = 1303.37 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 4.06 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.567, T max = 0.746 (expected range = 0.337–0.444)
  • 12525 measured reflections
  • 5966 independent reflections
  • 5889 reflections with I > 2σ(I)
  • R int = 0.012

Refinement

  • R[F 2 > 2σ(F 2)] = 0.016
  • wR(F 2) = 0.042
  • S = 1.06
  • 5966 reflections
  • 280 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.22 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2872 Friedel pairs
  • Flack parameter: 0.011 (3)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019722/tk2456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019722/tk2456Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [PhMe3N][SnBr2Ph3] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C9H14N)[SnBr2(C6H5)3]F(000) = 636
Mr = 646.02Dx = 1.646 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer5966 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

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) = 0.042w = 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 Å3
280 parametersΔρmin = −0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 2872 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.011 (3)

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2456).

References

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