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Acta Cryst. (2009). E65, m1039    [ doi:10.1107/S1600536809030232 ]

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

S. M. Lee, K. M. Lo, H. Mohd Ali and W. T. Robinson

Abstract top

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 top

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

Experimental top

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 top

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.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] 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.
Bis[4-(dimethylamino)pyridinium] tetrabromidobis(4-chlorophenyl)stannate(IV)–4-bromochlorobenzene (1/1) top
Crystal data top
(C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrClZ = 1
Mr = 1099.22F(000) = 530
Triclinic, P1Dx = 1.941 Mg m−3
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 mm−1
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 top
Bruker APEXII CCD area-detector
diffractometer		4265 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 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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.05 w = 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 Å−3
0 restraintsΔρmin = −1.12 e Å−3
Crystal data top
(C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrClγ = 92.85 (3)°
Mr = 1099.22V = 940.4 (3) Å3
Triclinic, P1Z = 1
a = 8.7692 (18) ÅMo Kα radiation
b = 10.128 (2) ŵ = 6.23 mm−1
c = 11.407 (2) ÅT = 100 K
α = 111.16 (3)°0.45 × 0.26 × 0.19 mm
β = 93.38 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		4265 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3919 reflections with I > 2σ(I)
Tmin = 0.169, Tmax = 0.384Rint = 0.019
7255 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.77 e Å−3
S = 1.05Δρmin = −1.12 e Å−3
4265 reflectionsAbsolute structure: ?
207 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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.
Acknowledgements top

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

references
References top

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.

Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m630.

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.