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Acta Cryst. (2008). E64, m1391    [ doi:10.1107/S1600536808032248 ]

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

C. K. Yau, K. M. Lo and S. W. Ng

Abstract top

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 top

For the crystal structure of 4-dimethylaminopyridinium dibromidotriphenylstannate, see: Norhafiza et al. (2008).

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] 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.
4-(Dimethylamino)pyridinium dibromido(4-bromophenyl)dimethylstannate(IV) top
Crystal data top
(C7H11N2)[SnBr2(CH3)2(C6H4Br)]Z = 2
Mr = 587.76F(000) = 560
Triclinic, P1Dx = 2.053 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		4346 independent reflections
Radiation source: fine-focus sealed tube3718 reflections with I > 2σ(I)
graphiteRint = 0.029
φ 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 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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.13 w = 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 Å−3
0 restraintsΔρmin = −1.24 e Å−3
Crystal data top
(C7H11N2)[SnBr2(CH3)2(C6H4Br)]γ = 94.679 (1)°
Mr = 587.76V = 950.65 (3) Å3
Triclinic, P1Z = 2
a = 7.3397 (1) ÅMo Kα radiation
b = 11.1034 (2) ŵ = 7.64 mm−1
c = 12.2270 (2) ÅT = 100 K
α = 100.038 (1)°0.30 × 0.20 × 0.02 mm
β = 102.472 (1)°
Data collection top
Bruker SMART APEX
diffractometer		4346 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3718 reflections with I > 2σ(I)
Tmin = 0.208, Tmax = 0.862Rint = 0.029
8826 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.096Δρmax = 1.07 e Å−3
S = 1.13Δρmin = −1.24 e Å−3
4346 reflectionsAbsolute structure: ?
194 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.563.319 (3)146
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.563.319 (3)146
Acknowledgements top

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

references
References top

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.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.