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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1039.
Published online 2009 August 8. doi:  10.1107/S1600536809030232
PMCID: PMC2970020

Bis[4-(dimethyl­amino)pyridinium] tetra­bromidobis(4-chloro­phen­yl)stannate(IV)–4-bromo­chloro­benzene (1/1)

Abstract

In the title compound, (C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrCl, the SnIV atom in the tetra­bromidobis(4-chloro­phen­yl)stannate(IV) anion lies on a centre of inversion. The distances between the 4-(dimethyl­amino)pyridinium N atom and the Br atoms of the anion are 3.450 (2) and 3.452 (2) Å, suggesting weak hydrogen bonding. The 4-bromo­chloro­benzene solvent mol­ecule, which is a bromination by-product from the reaction, is disordered about a twofold rotation axis with approximately equal occupancy.

Related literature

For related structures, see Lo & Ng (2009 [triangle]); Koon et al. (2009 [triangle]); Yap et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1039-scheme1.jpg

Experimental

Crystal data

  • (C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrCl
  • M r = 1099.22
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1039-efi1.jpg
  • a = 8.7692 (18) Å
  • b = 10.128 (2) Å
  • c = 11.407 (2) Å
  • α = 111.16 (3)°
  • β = 93.38 (3)°
  • γ = 92.85 (3)°
  • V = 940.4 (3) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 6.23 mm−1
  • T = 100 K
  • 0.45 × 0.26 × 0.19 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.169, T max = 0.384 (expected range = 0.135–0.306)
  • 7255 measured reflections
  • 4265 independent reflections
  • 3919 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.062
  • S = 1.05
  • 4265 reflections
  • 207 parameters
  • H-atom parameters constrained
  • Δρmax = 0.77 e Å−3
  • Δρmin = −1.12 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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030232/hg2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030232/hg2523Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant Nos. PS072/2007C and PS320/2008C) for supporting this study.

supplementary crystallographic information

Experimental

Tetra(4-chlorophenyl)tin (0.57 g, 1 mmol) and 4-dimethylaminopyridine hydrobromide perbromide (0.40 g, 1 mmol) was dissolved in absolute ethanol (25 ml) and refluxed for six hours. The solution was filtered and colourless crystals were isolated upon cooling.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95 to 0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times U(C,N). N—H was refined and placed in the calculated position of N—H 0.88 ± 0.01 Å.

Figures

Fig. 1.
The molecular structure of bis[4-(dimethylamino)pyridinium] tetrabromidobis(4-chlorophenyl)stannate(IV) 4-bromochlorobenzene, showing 50% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres of arbitrary radius. ...

Crystal data

(C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrClZ = 1
Mr = 1099.22F(000) = 530
Triclinic, P1Dx = 1.941 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7692 (18) ÅCell parameters from 6036 reflections
b = 10.128 (2) Åθ = 2.2–30.5°
c = 11.407 (2) ŵ = 6.23 mm1
α = 111.16 (3)°T = 100 K
β = 93.38 (3)°Block, colourless
γ = 92.85 (3)°0.45 × 0.26 × 0.19 mm
V = 940.4 (3) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer4265 independent reflections
Radiation source: fine-focus sealed tube3919 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→8
Tmin = 0.169, Tmax = 0.384k = −13→13
7255 measured reflectionsl = −14→13

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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0323P)2 + 0.8768P] where P = (Fo2 + 2Fc2)/3
4265 reflections(Δ/σ)max = 0.001
207 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = −1.12 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/UeqOcc. (<1)
Sn10.50000.50000.50000.01198 (6)
Br10.43772 (3)0.21868 (2)0.45713 (2)0.01709 (7)
Br20.75993 (3)0.43138 (3)0.38027 (2)0.01756 (7)
Br30.77314 (5)0.20503 (4)0.97712 (4)0.02952 (10)0.50
Cl20.77314 (5)0.20503 (4)0.97712 (4)0.02952 (10)0.50
Cl10.13889 (10)0.39025 (9)−0.06015 (7)0.03579 (19)
N1−0.1837 (3)0.2294 (2)0.5641 (2)0.0186 (4)
H1−0.25250.26750.52940.022*
N20.1383 (3)0.0420 (2)0.7154 (2)0.0210 (5)
C10.3775 (3)0.4724 (2)0.3230 (2)0.0151 (5)
C20.4409 (3)0.5295 (3)0.2416 (2)0.0184 (5)
H20.53680.58380.26580.022*
C30.3651 (3)0.5080 (3)0.1248 (3)0.0229 (6)
H30.40780.54820.06940.027*
C40.2268 (3)0.4272 (3)0.0906 (2)0.0240 (6)
C50.1589 (3)0.3723 (3)0.1713 (3)0.0242 (6)
H50.06230.31930.14720.029*
C60.2349 (3)0.3965 (3)0.2886 (2)0.0194 (5)
H60.18910.36090.34570.023*
C7−0.2277 (3)0.1231 (3)0.6020 (3)0.0202 (5)
H7−0.33310.09150.59280.024*
C8−0.1239 (3)0.0602 (3)0.6534 (2)0.0188 (5)
H8−0.1573−0.01460.67970.023*
C90.0341 (3)0.1054 (3)0.6681 (2)0.0159 (5)
C100.0741 (3)0.2198 (3)0.6290 (2)0.0173 (5)
H100.17810.25580.63830.021*
C11−0.0357 (3)0.2780 (3)0.5785 (2)0.0182 (5)
H11−0.00730.35450.55280.022*
C120.3025 (3)0.0848 (3)0.7299 (3)0.0281 (6)
H12A0.32740.12240.66480.042*
H12B0.36100.00230.72120.042*
H12C0.32890.15830.81340.042*
C130.0909 (4)−0.0632 (3)0.7687 (3)0.0308 (7)
H13A0.0393−0.01690.84530.046*
H13B0.1812−0.10620.78960.046*
H13C0.0204−0.13710.70700.046*
C140.5185 (4)0.1403 (3)1.0834 (3)0.0282 (6)
H140.53170.23641.13960.034*
C150.6185 (4)0.0876 (3)0.9901 (3)0.0249 (6)
C160.5999 (4)−0.0512 (3)0.9068 (3)0.0276 (6)
H160.6685−0.08530.84290.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01253 (12)0.01045 (11)0.01205 (11)0.00037 (8)−0.00207 (8)0.00356 (8)
Br10.01696 (13)0.01231 (11)0.02127 (13)−0.00079 (9)−0.00159 (9)0.00599 (9)
Br20.01604 (13)0.01762 (12)0.01965 (13)0.00199 (9)0.00089 (9)0.00756 (10)
Br30.0333 (2)0.0299 (2)0.0258 (2)−0.00401 (17)−0.00423 (17)0.01252 (17)
Cl20.0333 (2)0.0299 (2)0.0258 (2)−0.00401 (17)−0.00423 (17)0.01252 (17)
Cl10.0435 (5)0.0421 (4)0.0144 (3)0.0164 (3)−0.0097 (3)0.0016 (3)
N10.0168 (11)0.0179 (10)0.0218 (11)0.0034 (8)−0.0034 (9)0.0087 (9)
N20.0219 (12)0.0216 (11)0.0209 (11)0.0057 (9)−0.0017 (9)0.0094 (9)
C10.0183 (12)0.0117 (10)0.0125 (11)0.0033 (9)−0.0015 (9)0.0012 (9)
C20.0183 (12)0.0189 (12)0.0178 (12)0.0046 (10)0.0002 (10)0.0063 (10)
C30.0261 (14)0.0282 (14)0.0164 (12)0.0111 (11)0.0038 (11)0.0092 (11)
C40.0275 (15)0.0252 (13)0.0137 (12)0.0118 (11)−0.0050 (10)0.0003 (10)
C50.0222 (14)0.0218 (13)0.0231 (14)0.0012 (11)−0.0085 (11)0.0032 (11)
C60.0188 (13)0.0193 (12)0.0179 (12)−0.0006 (10)−0.0035 (10)0.0052 (10)
C70.0176 (13)0.0194 (12)0.0216 (13)−0.0016 (10)−0.0003 (10)0.0060 (10)
C80.0229 (14)0.0158 (11)0.0178 (12)−0.0011 (10)0.0010 (10)0.0066 (10)
C90.0206 (13)0.0141 (11)0.0114 (11)0.0054 (9)0.0000 (9)0.0025 (9)
C100.0165 (12)0.0172 (11)0.0187 (12)−0.0010 (9)0.0004 (10)0.0075 (10)
C110.0209 (13)0.0161 (11)0.0181 (12)−0.0012 (10)−0.0009 (10)0.0075 (10)
C120.0196 (14)0.0363 (16)0.0294 (15)0.0120 (12)−0.0009 (12)0.0124 (13)
C130.0401 (18)0.0283 (15)0.0313 (16)0.0090 (13)−0.0012 (13)0.0192 (13)
C140.0389 (17)0.0190 (12)0.0208 (14)0.0096 (12)−0.0056 (12)0.0004 (10)
C150.0312 (15)0.0216 (13)0.0192 (13)0.0061 (11)−0.0089 (11)0.0055 (11)
C160.0338 (16)0.0253 (14)0.0197 (13)0.0110 (12)−0.0019 (12)0.0028 (11)

Geometric parameters (Å, °)

Sn1—C1i2.148 (3)C5—H50.9500
Sn1—C12.148 (3)C6—H60.9500
Sn1—Br2i2.7172 (9)C7—C81.357 (4)
Sn1—Br22.7172 (8)C7—H70.9500
Sn1—Br12.7319 (7)C8—C91.418 (4)
Sn1—Br1i2.7319 (7)C8—H80.9500
Br3—C151.807 (3)C9—C101.420 (3)
Cl1—C41.744 (3)C10—C111.357 (4)
N1—C111.344 (3)C10—H100.9500
N1—C71.346 (3)C11—H110.9500
N1—H10.8800C12—H12A0.9800
N2—C91.337 (3)C12—H12B0.9800
N2—C131.460 (4)C12—H12C0.9800
N2—C121.465 (4)C13—H13A0.9800
C1—C21.386 (4)C13—H13B0.9800
C1—C61.392 (4)C13—H13C0.9800
C2—C31.392 (4)C14—C16ii1.378 (5)
C2—H20.9500C14—C151.389 (4)
C3—C41.382 (4)C14—H140.9500
C3—H30.9500C15—C161.379 (4)
C4—C51.383 (4)C16—C14ii1.378 (5)
C5—C61.391 (4)C16—H160.9500
C1i—Sn1—C1180.0C1—C6—H6119.7
C1i—Sn1—Br2i89.62 (7)N1—C7—C8121.0 (2)
C1—Sn1—Br2i90.38 (7)N1—C7—H7119.5
C1i—Sn1—Br290.38 (7)C8—C7—H7119.5
C1—Sn1—Br289.62 (7)C7—C8—C9120.5 (2)
Br2i—Sn1—Br2180.0C7—C8—H8119.8
C1i—Sn1—Br189.88 (7)C9—C8—H8119.8
C1—Sn1—Br190.12 (7)N2—C9—C8121.3 (2)
Br2i—Sn1—Br191.55 (3)N2—C9—C10122.5 (2)
Br2—Sn1—Br188.45 (3)C8—C9—C10116.2 (2)
C1i—Sn1—Br1i90.12 (7)C11—C10—C9120.2 (2)
C1—Sn1—Br1i89.88 (7)C11—C10—H10119.9
Br2i—Sn1—Br1i88.45 (3)C9—C10—H10119.9
Br2—Sn1—Br1i91.55 (3)N1—C11—C10121.3 (2)
Br1—Sn1—Br1i180.0N1—C11—H11119.4
C11—N1—C7120.7 (2)C10—C11—H11119.4
C11—N1—H1119.6N2—C12—H12A109.5
C7—N1—H1119.6N2—C12—H12B109.5
C9—N2—C13120.7 (2)H12A—C12—H12B109.5
C9—N2—C12122.5 (2)N2—C12—H12C109.5
C13—N2—C12116.4 (2)H12A—C12—H12C109.5
C2—C1—C6119.5 (2)H12B—C12—H12C109.5
C2—C1—Sn1120.03 (18)N2—C13—H13A109.5
C6—C1—Sn1120.51 (19)N2—C13—H13B109.5
C1—C2—C3120.5 (3)H13A—C13—H13B109.5
C1—C2—H2119.7N2—C13—H13C109.5
C3—C2—H2119.7H13A—C13—H13C109.5
C4—C3—C2118.9 (3)H13B—C13—H13C109.5
C4—C3—H3120.6C16ii—C14—C15119.1 (3)
C2—C3—H3120.6C16ii—C14—H14120.4
C3—C4—C5121.8 (3)C15—C14—H14120.4
C3—C4—Cl1118.7 (2)C16—C15—C14121.1 (3)
C5—C4—Cl1119.5 (2)C16—C15—Br3119.9 (2)
C4—C5—C6118.6 (3)C14—C15—Br3119.0 (2)
C4—C5—H5120.7C14ii—C16—C15119.7 (3)
C6—C5—H5120.7C14ii—C16—H16120.1
C5—C6—C1120.6 (3)C15—C16—H16120.1
C5—C6—H6119.7
C1i—Sn1—C1—C219 (100)C2—C1—C6—C52.8 (4)
Br2i—Sn1—C1—C2134.73 (19)Sn1—C1—C6—C5−176.7 (2)
Br2—Sn1—C1—C2−45.27 (19)C11—N1—C7—C8−1.4 (4)
Br1—Sn1—C1—C2−133.72 (19)N1—C7—C8—C90.0 (4)
Br1i—Sn1—C1—C246.28 (19)C13—N2—C9—C8−8.1 (4)
C1i—Sn1—C1—C6−161 (100)C12—N2—C9—C8179.0 (2)
Br2i—Sn1—C1—C6−45.7 (2)C13—N2—C9—C10172.4 (2)
Br2—Sn1—C1—C6134.3 (2)C12—N2—C9—C10−0.5 (4)
Br1—Sn1—C1—C645.8 (2)C7—C8—C9—N2−178.2 (2)
Br1i—Sn1—C1—C6−134.2 (2)C7—C8—C9—C101.3 (4)
C6—C1—C2—C3−1.9 (4)N2—C9—C10—C11178.2 (2)
Sn1—C1—C2—C3177.68 (19)C8—C9—C10—C11−1.3 (4)
C1—C2—C3—C4−0.9 (4)C7—N1—C11—C101.4 (4)
C2—C3—C4—C52.8 (4)C9—C10—C11—N10.0 (4)
C2—C3—C4—Cl1−175.6 (2)C16ii—C14—C15—C160.7 (5)
C3—C4—C5—C6−1.8 (4)C16ii—C14—C15—Br3179.7 (2)
Cl1—C4—C5—C6176.5 (2)C14—C15—C16—C14ii−0.7 (5)
C4—C5—C6—C1−1.0 (4)Br3—C15—C16—C14ii−179.7 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2523).

References

  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Koon, Y. C., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m663. [PMC free article] [PubMed]
  • Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m630. [PMC free article] [PubMed]
  • 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]

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