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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1391.
Published online 2008 October 11. doi:  10.1107/S1600536808032248
PMCID: PMC2959668

4-(Dimethyl­amino)pyridinium dibromido(4-bromo­phen­yl)dimethyl­stannate(IV)

Abstract

The anion in the title compound, (C7H11N2)[SnBr2(CH3)2(C6H4Br)], is five-coordinate within a distorted trans-C3SnBr2 trigonal–bipyramidal geometry. The cation and anion are linked by an N—H(...)Br hydrogen bond.

Related literature

For the crystal structure of 4-(dimethyl­amino)­pyridinium dibromidotriphenyl­stannate(IV), see: Norhafiza et al. (2008 [triangle]).

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Object name is e-64-m1391-scheme1.jpg

Experimental

Crystal data

  • (C7H11N2)[SnBr2(CH3)2(C6H4Br)]
  • M r = 587.76
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1391-efi1.jpg
  • a = 7.3397 (1) Å
  • b = 11.1034 (2) Å
  • c = 12.2270 (2) Å
  • α = 100.038 (1)°
  • β = 102.472 (1)°
  • γ = 94.679 (1)°
  • V = 950.65 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 7.64 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.208, T max = 0.862
  • 8826 measured reflections
  • 4346 independent reflections
  • 3718 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.096
  • S = 1.13
  • 4346 reflections
  • 194 parameters
  • H-atom parameters constrained
  • Δρmax = 1.07 e Å−3
  • Δρmin = −1.24 e Å−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, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032248/tk2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032248/tk2315Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (grant No. FS339/2008A).

supplementary crystallographic information

Experimental

Bis(4-bromophenyl)dimethyltin (0.10 g, 0.2 mmol) [which was prepared by the reaction between dimethyltin dichloride and 4-bromophenylmagnesium bromide] and 4-dimethylaminopyridine hydrobromide perbromide (0.08 g, 0.2 mmol) were heated in chloroform (100 ml) for 3 h. The solution was filtered and the solvent allow to evaporate to give colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The ammonium H-atom was similarly treated [(N—H 0.88 Å; U(H) = 1.2Ueq(N)]. The final difference Fourier map had a large peak at 1 Å and a deep hole at about 1 Å from the Sn1 atom.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [C7H11N2][SnBr2(CH3)2(C6H4Br)] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C7H11N2)[SnBr2(CH3)2(C6H4Br)]Z = 2
Mr = 587.76F(000) = 560
Triclinic, P1Dx = 2.053 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3397 (1) ÅCell parameters from 5297 reflections
b = 11.1034 (2) Åθ = 2.3–28.3°
c = 12.2270 (2) ŵ = 7.64 mm1
α = 100.038 (1)°T = 100 K
β = 102.472 (1)°Plate, colourless
γ = 94.679 (1)°0.30 × 0.20 × 0.02 mm
V = 950.65 (3) Å3

Data collection

Bruker SMART APEX diffractometer4346 independent reflections
Radiation source: fine-focus sealed tube3718 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.208, Tmax = 0.862k = −14→14
8826 measured reflectionsl = −15→15

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) = 0.096H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.0496P)2 + 0.4605P] where P = (Fo2 + 2Fc2)/3
4346 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 1.07 e Å3
0 restraintsΔρmin = −1.24 e Å3

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

xyzUiso*/Ueq
Sn10.38417 (3)0.25338 (2)0.773249 (19)0.01548 (9)
Br10.74942 (5)0.26874 (4)0.91216 (3)0.01853 (11)
Br20.02956 (5)0.24575 (4)0.63868 (3)0.01814 (11)
Br30.36372 (6)−0.36881 (4)0.72001 (4)0.03322 (13)
N10.8504 (5)0.0064 (3)0.7756 (3)0.0221 (7)
H10.84380.08620.78720.027*
N20.8761 (5)−0.3667 (3)0.7213 (2)0.0199 (7)
C10.3068 (6)0.3599 (4)0.9145 (3)0.0251 (9)
H1A0.17400.33570.91120.038*
H1B0.32630.44750.91150.038*
H1C0.38450.34560.98590.038*
C20.5034 (5)0.3149 (4)0.6446 (3)0.0198 (8)
H2A0.43130.27140.56900.030*
H2B0.63430.29760.65530.030*
H2C0.49940.40370.65070.030*
C30.3607 (5)0.0584 (4)0.7558 (3)0.0164 (7)
C40.3542 (5)0.0007 (4)0.8482 (3)0.0208 (8)
H40.35110.04960.91960.025*
C50.3520 (5)−0.1260 (4)0.8384 (3)0.0227 (8)
H50.3462−0.16370.90180.027*
C60.3585 (5)−0.1962 (4)0.7338 (3)0.0201 (8)
C70.3613 (5)−0.1437 (4)0.6397 (3)0.0238 (8)
H70.3632−0.19330.56850.029*
C80.3611 (6)−0.0170 (4)0.6514 (3)0.0217 (8)
H80.36110.01950.58660.026*
C90.8666 (6)−0.0529 (4)0.6733 (3)0.0237 (8)
H90.8744−0.00760.61500.028*
C100.8721 (5)−0.1769 (4)0.6517 (3)0.0191 (8)
H100.8787−0.21760.57780.023*
C110.8680 (5)−0.2459 (4)0.7390 (3)0.0179 (8)
C120.8551 (5)−0.1788 (4)0.8470 (3)0.0205 (8)
H120.8542−0.21990.90890.025*
C130.8440 (5)−0.0552 (4)0.8610 (3)0.0232 (8)
H130.8315−0.01150.93250.028*
C140.8600 (6)−0.4359 (4)0.6050 (3)0.0236 (9)
H14A0.9550−0.39860.57150.035*
H14B0.7343−0.43370.55810.035*
H14C0.8799−0.52170.60780.035*
C150.8821 (6)−0.4367 (4)0.8132 (3)0.0244 (9)
H15A0.9843−0.39780.87880.037*
H15B0.9039−0.52150.78580.037*
H15C0.7622−0.43770.83620.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01676 (15)0.01707 (15)0.01403 (14)0.00355 (11)0.00520 (10)0.00423 (10)
Br10.0172 (2)0.0208 (2)0.01645 (19)0.00236 (15)0.00153 (14)0.00369 (15)
Br20.0158 (2)0.0221 (2)0.01817 (19)0.00498 (15)0.00386 (14)0.00728 (15)
Br30.0257 (2)0.0189 (2)0.0537 (3)0.00577 (17)0.0064 (2)0.0061 (2)
N10.0209 (17)0.0167 (16)0.0251 (16)0.0044 (14)−0.0002 (14)0.0005 (13)
N20.0215 (17)0.0251 (18)0.0133 (14)0.0041 (14)0.0044 (13)0.0033 (13)
C10.021 (2)0.035 (2)0.0181 (18)0.0055 (18)0.0048 (16)0.0007 (17)
C20.0186 (19)0.025 (2)0.0178 (17)0.0023 (16)0.0069 (15)0.0064 (15)
C30.0104 (17)0.0211 (19)0.0173 (17)0.0010 (14)0.0017 (14)0.0047 (15)
C40.0190 (19)0.027 (2)0.0184 (18)0.0039 (16)0.0047 (15)0.0083 (16)
C50.0160 (19)0.031 (2)0.0216 (19)0.0047 (17)0.0023 (15)0.0092 (17)
C60.0133 (18)0.0131 (18)0.033 (2)0.0031 (14)0.0044 (16)0.0037 (16)
C70.018 (2)0.028 (2)0.0228 (19)0.0056 (17)0.0033 (16)−0.0019 (17)
C80.024 (2)0.024 (2)0.0183 (17)0.0051 (16)0.0055 (15)0.0061 (16)
C90.020 (2)0.028 (2)0.0218 (19)0.0023 (17)0.0000 (16)0.0076 (17)
C100.0155 (18)0.024 (2)0.0183 (17)0.0041 (15)0.0034 (15)0.0038 (15)
C110.0113 (17)0.025 (2)0.0187 (17)0.0056 (15)0.0047 (14)0.0048 (15)
C120.020 (2)0.024 (2)0.0188 (18)0.0052 (16)0.0057 (15)0.0048 (16)
C130.0167 (19)0.029 (2)0.0241 (19)0.0082 (17)0.0055 (16)0.0022 (17)
C140.033 (2)0.022 (2)0.0182 (18)0.0088 (18)0.0084 (17)0.0027 (16)
C150.030 (2)0.024 (2)0.0202 (18)0.0065 (18)0.0052 (17)0.0087 (16)

Geometric parameters (Å, °)

Sn1—C12.127 (4)C4—H40.9500
Sn1—C22.139 (3)C5—C61.390 (6)
Sn1—C32.127 (4)C5—H50.9500
Sn1—Br12.8211 (4)C6—C71.380 (6)
Sn1—Br22.7486 (4)C7—C81.390 (6)
Br3—C61.899 (4)C7—H70.9500
N1—C91.343 (5)C8—H80.9500
N1—C131.351 (5)C9—C101.361 (6)
N1—H10.8800C9—H90.9500
N2—C111.329 (5)C10—C111.422 (5)
N2—C151.469 (5)C10—H100.9500
N2—C141.469 (5)C11—C121.426 (5)
C1—H1A0.9800C12—C131.364 (6)
C1—H1B0.9800C12—H120.9500
C1—H1C0.9800C13—H130.9500
C2—H2A0.9800C14—H14A0.9800
C2—H2B0.9800C14—H14B0.9800
C2—H2C0.9800C14—H14C0.9800
C3—C41.400 (5)C15—H15A0.9800
C3—C81.400 (5)C15—H15B0.9800
C4—C51.390 (6)C15—H15C0.9800
C1—Sn1—C2128.9 (2)C7—C6—C5121.7 (4)
C1—Sn1—C3118.8 (2)C7—C6—Br3119.2 (3)
C2—Sn1—C3112.1 (1)C5—C6—Br3119.1 (3)
C1—Sn1—Br290.82 (11)C6—C7—C8118.7 (3)
C3—Sn1—Br292.78 (10)C6—C7—H7120.7
C2—Sn1—Br289.98 (10)C8—C7—H7120.7
C1—Sn1—Br188.38 (11)C7—C8—C3121.8 (4)
C3—Sn1—Br188.88 (10)C7—C8—H8119.1
C2—Sn1—Br189.39 (10)C3—C8—H8119.1
Br1—Sn1—Br2178.33 (1)N1—C9—C10121.1 (4)
C9—N1—C13120.7 (3)N1—C9—H9119.4
C9—N1—H1119.7C10—C9—H9119.4
C13—N1—H1119.7C9—C10—C11120.4 (3)
C11—N2—C15121.9 (3)C9—C10—H10119.8
C11—N2—C14119.9 (3)C11—C10—H10119.8
C15—N2—C14117.9 (3)N2—C11—C10122.0 (3)
Sn1—C1—H1A109.5N2—C11—C12121.5 (3)
Sn1—C1—H1B109.5C10—C11—C12116.5 (4)
H1A—C1—H1B109.5C13—C12—C11119.6 (3)
Sn1—C1—H1C109.5C13—C12—H12120.2
H1A—C1—H1C109.5C11—C12—H12120.2
H1B—C1—H1C109.5N1—C13—C12121.6 (3)
Sn1—C2—H2A109.5N1—C13—H13119.2
Sn1—C2—H2B109.5C12—C13—H13119.2
H2A—C2—H2B109.5N2—C14—H14A109.5
Sn1—C2—H2C109.5N2—C14—H14B109.5
H2A—C2—H2C109.5H14A—C14—H14B109.5
H2B—C2—H2C109.5N2—C14—H14C109.5
C4—C3—C8117.4 (4)H14A—C14—H14C109.5
C4—C3—Sn1122.0 (3)H14B—C14—H14C109.5
C8—C3—Sn1120.5 (3)N2—C15—H15A109.5
C5—C4—C3121.9 (4)N2—C15—H15B109.5
C5—C4—H4119.1H15A—C15—H15B109.5
C3—C4—H4119.1N2—C15—H15C109.5
C4—C5—C6118.4 (4)H15A—C15—H15C109.5
C4—C5—H5120.8H15B—C15—H15C109.5
C6—C5—H5120.8
C1—Sn1—C3—C4−20.4 (4)C6—C7—C8—C30.9 (6)
C2—Sn1—C3—C4156.0 (3)C4—C3—C8—C7−2.1 (6)
Br2—Sn1—C3—C4−112.9 (3)Sn1—C3—C8—C7174.7 (3)
Br1—Sn1—C3—C467.2 (3)C13—N1—C9—C101.7 (6)
C1—Sn1—C3—C8162.9 (3)N1—C9—C10—C11−2.4 (6)
C2—Sn1—C3—C8−20.6 (3)C15—N2—C11—C10176.6 (4)
Br2—Sn1—C3—C870.5 (3)C14—N2—C11—C10−9.5 (6)
Br1—Sn1—C3—C8−109.5 (3)C15—N2—C11—C12−3.3 (6)
C8—C3—C4—C51.3 (6)C14—N2—C11—C12170.6 (3)
Sn1—C3—C4—C5−175.5 (3)C9—C10—C11—N2−179.0 (4)
C3—C4—C5—C60.7 (6)C9—C10—C11—C120.9 (5)
C4—C5—C6—C7−2.0 (6)N2—C11—C12—C13−178.9 (4)
C4—C5—C6—Br3178.0 (3)C10—C11—C12—C131.2 (5)
C5—C6—C7—C81.2 (6)C9—N1—C13—C120.5 (6)
Br3—C6—C7—C8−178.8 (3)C11—C12—C13—N1−1.9 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.563.319 (3)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2315).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Norhafiza, I., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m720. [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. (2008). publCIF In preparation.

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