metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 6 October 2008; accepted 7 October 2008; online 11 October 2008)

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[Norhafiza, I., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m720.]).

[Scheme 1]

Experimental

Crystal data
  • (C7H11N2)[SnBr2(CH3)2(C6H4Br)]

  • Mr = 587.76

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.208, Tmax = 0.862

  • 8826 measured reflections

  • 4346 independent reflections

  • 3718 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯Br1 0.88 2.56 3.319 (3) 146

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


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 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 top
Bruker SMART APEX
diffractometer
4346 independent reflections
Radiation source: fine-focus sealed tube3718 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.208, Tmax = 0.862k = 1414
8826 measured reflectionsl = 1515
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 Å3
0 restraintsΔρmin = 1.24 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.13Δρmax = 1.07 e Å3
4346 reflectionsΔρmin = 1.24 e Å3
194 parameters
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)
H50.34620.16370.90180.027*
C60.3585 (5)0.1962 (4)0.7338 (3)0.0201 (8)
C70.3613 (5)0.1437 (4)0.6397 (3)0.0238 (8)
H70.36320.19330.56850.029*
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)
H90.87440.00760.61500.028*
C100.8721 (5)0.1769 (4)0.6517 (3)0.0191 (8)
H100.87870.21760.57780.023*
C110.8680 (5)0.2459 (4)0.7390 (3)0.0179 (8)
C120.8551 (5)0.1788 (4)0.8470 (3)0.0205 (8)
H120.85420.21990.90890.025*
C130.8440 (5)0.0552 (4)0.8610 (3)0.0232 (8)
H130.83150.01150.93250.028*
C140.8600 (6)0.4359 (4)0.6050 (3)0.0236 (9)
H14A0.95500.39860.57150.035*
H14B0.73430.43370.55810.035*
H14C0.87990.52170.60780.035*
C150.8821 (6)0.4367 (4)0.8132 (3)0.0244 (9)
H15A0.98430.39780.87880.037*
H15B0.90390.52150.78580.037*
H15C0.76220.43770.83620.037*
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, º) 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—C420.4 (4)C6—C7—C8—C30.9 (6)
C2—Sn1—C3—C4156.0 (3)C4—C3—C8—C72.1 (6)
Br2—Sn1—C3—C4112.9 (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—C112.4 (6)
C2—Sn1—C3—C820.6 (3)C15—N2—C11—C10176.6 (4)
Br2—Sn1—C3—C870.5 (3)C14—N2—C11—C109.5 (6)
Br1—Sn1—C3—C8109.5 (3)C15—N2—C11—C123.3 (6)
C8—C3—C4—C51.3 (6)C14—N2—C11—C12170.6 (3)
Sn1—C3—C4—C5175.5 (3)C9—C10—C11—N2179.0 (4)
C3—C4—C5—C60.7 (6)C9—C10—C11—C120.9 (5)
C4—C5—C6—C72.0 (6)N2—C11—C12—C13178.9 (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—C8178.8 (3)C11—C12—C13—N11.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.563.319 (3)146

Experimental details

Crystal data
Chemical formula(C7H11N2)[SnBr2(CH3)2(C6H4Br)]
Mr587.76
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.3397 (1), 11.1034 (2), 12.2270 (2)
α, β, γ (°)100.038 (1), 102.472 (1), 94.679 (1)
V3)950.65 (3)
Z2
Radiation typeMo Kα
µ (mm1)7.64
Crystal size (mm)0.30 × 0.20 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.208, 0.862
No. of measured, independent and
observed [I > 2σ(I)] reflections
8826, 4346, 3718
Rint0.029
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.096, 1.13
No. of reflections4346
No. of parameters194
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.07, 1.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.563.319 (3)146
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNorhafiza, I., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m720.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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