PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1677.
Published online 2009 November 25. doi:  10.1107/S160053680904940X
PMCID: PMC2971998

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

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1677-scheme1.jpg

Experimental

Crystal data

  • (C9H14N)2[SnBr4(C6H4Cl)2]
  • M r = 933.84
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1677-efi1.jpg
  • a = 25.7930 (3) Å
  • b = 9.0937 (1) Å
  • c = 15.8303 (2) Å
  • β = 113.4146 (6)°
  • V = 3407.30 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.62 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.482, T max = 0.756
  • 15816 measured reflections
  • 3916 independent reflections
  • 3427 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.098
  • S = 1.24
  • 3916 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 1.28 e Å−3
  • Δρmin = −1.03 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904940X/xu2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904940X/xu2683Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

(C9H14N)2[SnBr4(C6H4Cl)2]F(000) = 1816
Mr = 933.84Dx = 1.820 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer3916 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

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 = 1.24w = 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 Å3
0 restraintsΔρmin = −1.03 e Å3

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

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
C15—H15C···Br10.962.913.839 (5)163

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2683).

References

  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.
  • Yap, Q. L., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m696. [PMC free article] [PubMed]

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