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

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

doi:10.1107/S1600536809030232

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1039

doi:10.1107/S1600536809030232

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

See Mun Lee,^a Kong Mun Lo,^a ^* Hapipah Mohd Ali ^a and Ward T. Robinson ^a

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

(Received 8 June 2009; accepted 30 July 2009; online 8 August 2009)

In the title compound, (C₇H₁₁N₂)₂[SnBr₄(C₆H₄Cl)₂]·C₆H₄BrCl, the Sn^IV 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 ); Koon et al. (2009 ); Yap et al. (2008 ).

Experimental

Crystal data

(C₇H₁₁N₂)₂[SnBr₄(C₆H₄Cl)₂]·C₆H₄BrCl
M_r = 1099.22
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.023
wR(F²) = 0.062
S = 1.05
4265 reflections
207 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −1.12 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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.

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

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]·C₆H₄BrCl	Z = 1
M_r = 1099.22	F(000) = 530
Triclinic, P1	D_x = 1.941 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7692 (18) Å	Cell parameters from 6036 reflections
b = 10.128 (2) Å	θ = 2.2–30.5°
c = 11.407 (2) Å	µ = 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 tube	3919 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→8
T_min = 0.169, T_max = 0.384	k = −13→13
7255 measured reflections	l = −14→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0323P)² + 0.8768P] where P = (F_o² + 2F_c²)/3
4265 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

(C₇H₁₁N₂)₂[SnBr₄(C₆H₄Cl)₂]·C₆H₄BrCl	γ = 92.85 (3)°
M_r = 1099.22	V = 940.4 (3) Å³
Triclinic, P1	Z = 1
a = 8.7692 (18) Å	Mo Kα radiation
b = 10.128 (2) Å	µ = 6.23 mm⁻¹
c = 11.407 (2) Å	T = 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)
T_min = 0.169, T_max = 0.384	R_int = 0.019
7255 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	Δρ_max = 0.77 e Å⁻³
4265 reflections	Δρ_min = −1.12 e Å⁻³
207 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.5000	0.5000	0.5000	0.01198 (6)
Br1	0.43772 (3)	0.21868 (2)	0.45713 (2)	0.01709 (7)
Br2	0.75993 (3)	0.43138 (3)	0.38027 (2)	0.01756 (7)
Br3	0.77314 (5)	0.20503 (4)	0.97712 (4)	0.02952 (10)	0.50
Cl2	0.77314 (5)	0.20503 (4)	0.97712 (4)	0.02952 (10)	0.50
Cl1	0.13889 (10)	0.39025 (9)	−0.06015 (7)	0.03579 (19)
N1	−0.1837 (3)	0.2294 (2)	0.5641 (2)	0.0186 (4)
H1	−0.2525	0.2675	0.5294	0.022*
N2	0.1383 (3)	0.0420 (2)	0.7154 (2)	0.0210 (5)
C1	0.3775 (3)	0.4724 (2)	0.3230 (2)	0.0151 (5)
C2	0.4409 (3)	0.5295 (3)	0.2416 (2)	0.0184 (5)
H2	0.5368	0.5838	0.2658	0.022*
C3	0.3651 (3)	0.5080 (3)	0.1248 (3)	0.0229 (6)
H3	0.4078	0.5482	0.0694	0.027*
C4	0.2268 (3)	0.4272 (3)	0.0906 (2)	0.0240 (6)
C5	0.1589 (3)	0.3723 (3)	0.1713 (3)	0.0242 (6)
H5	0.0623	0.3193	0.1472	0.029*
C6	0.2349 (3)	0.3965 (3)	0.2886 (2)	0.0194 (5)
H6	0.1891	0.3609	0.3457	0.023*
C7	−0.2277 (3)	0.1231 (3)	0.6020 (3)	0.0202 (5)
H7	−0.3331	0.0915	0.5928	0.024*
C8	−0.1239 (3)	0.0602 (3)	0.6534 (2)	0.0188 (5)
H8	−0.1573	−0.0146	0.6797	0.023*
C9	0.0341 (3)	0.1054 (3)	0.6681 (2)	0.0159 (5)
C10	0.0741 (3)	0.2198 (3)	0.6290 (2)	0.0173 (5)
H10	0.1781	0.2558	0.6383	0.021*
C11	−0.0357 (3)	0.2780 (3)	0.5785 (2)	0.0182 (5)
H11	−0.0073	0.3545	0.5528	0.022*
C12	0.3025 (3)	0.0848 (3)	0.7299 (3)	0.0281 (6)
H12A	0.3274	0.1224	0.6648	0.042*
H12B	0.3610	0.0023	0.7212	0.042*
H12C	0.3289	0.1583	0.8134	0.042*
C13	0.0909 (4)	−0.0632 (3)	0.7687 (3)	0.0308 (7)
H13A	0.0393	−0.0169	0.8453	0.046*
H13B	0.1812	−0.1062	0.7896	0.046*
H13C	0.0204	−0.1371	0.7070	0.046*
C14	0.5185 (4)	0.1403 (3)	1.0834 (3)	0.0282 (6)
H14	0.5317	0.2364	1.1396	0.034*
C15	0.6185 (4)	0.0876 (3)	0.9901 (3)	0.0249 (6)
C16	0.5999 (4)	−0.0512 (3)	0.9068 (3)	0.0276 (6)
H16	0.6685	−0.0853	0.8429	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01253 (12)	0.01045 (11)	0.01205 (11)	0.00037 (8)	−0.00207 (8)	0.00356 (8)
Br1	0.01696 (13)	0.01231 (11)	0.02127 (13)	−0.00079 (9)	−0.00159 (9)	0.00599 (9)
Br2	0.01604 (13)	0.01762 (12)	0.01965 (13)	0.00199 (9)	0.00089 (9)	0.00756 (10)
Br3	0.0333 (2)	0.0299 (2)	0.0258 (2)	−0.00401 (17)	−0.00423 (17)	0.01252 (17)
Cl2	0.0333 (2)	0.0299 (2)	0.0258 (2)	−0.00401 (17)	−0.00423 (17)	0.01252 (17)
Cl1	0.0435 (5)	0.0421 (4)	0.0144 (3)	0.0164 (3)	−0.0097 (3)	0.0016 (3)
N1	0.0168 (11)	0.0179 (10)	0.0218 (11)	0.0034 (8)	−0.0034 (9)	0.0087 (9)
N2	0.0219 (12)	0.0216 (11)	0.0209 (11)	0.0057 (9)	−0.0017 (9)	0.0094 (9)
C1	0.0183 (12)	0.0117 (10)	0.0125 (11)	0.0033 (9)	−0.0015 (9)	0.0012 (9)
C2	0.0183 (12)	0.0189 (12)	0.0178 (12)	0.0046 (10)	0.0002 (10)	0.0063 (10)
C3	0.0261 (14)	0.0282 (14)	0.0164 (12)	0.0111 (11)	0.0038 (11)	0.0092 (11)
C4	0.0275 (15)	0.0252 (13)	0.0137 (12)	0.0118 (11)	−0.0050 (10)	0.0003 (10)
C5	0.0222 (14)	0.0218 (13)	0.0231 (14)	0.0012 (11)	−0.0085 (11)	0.0032 (11)
C6	0.0188 (13)	0.0193 (12)	0.0179 (12)	−0.0006 (10)	−0.0035 (10)	0.0052 (10)
C7	0.0176 (13)	0.0194 (12)	0.0216 (13)	−0.0016 (10)	−0.0003 (10)	0.0060 (10)
C8	0.0229 (14)	0.0158 (11)	0.0178 (12)	−0.0011 (10)	0.0010 (10)	0.0066 (10)
C9	0.0206 (13)	0.0141 (11)	0.0114 (11)	0.0054 (9)	0.0000 (9)	0.0025 (9)
C10	0.0165 (12)	0.0172 (11)	0.0187 (12)	−0.0010 (9)	0.0004 (10)	0.0075 (10)
C11	0.0209 (13)	0.0161 (11)	0.0181 (12)	−0.0012 (10)	−0.0009 (10)	0.0075 (10)
C12	0.0196 (14)	0.0363 (16)	0.0294 (15)	0.0120 (12)	−0.0009 (12)	0.0124 (13)
C13	0.0401 (18)	0.0283 (15)	0.0313 (16)	0.0090 (13)	−0.0012 (13)	0.0192 (13)
C14	0.0389 (17)	0.0190 (12)	0.0208 (14)	0.0096 (12)	−0.0056 (12)	0.0004 (10)
C15	0.0312 (15)	0.0216 (13)	0.0192 (13)	0.0061 (11)	−0.0089 (11)	0.0055 (11)
C16	0.0338 (16)	0.0253 (14)	0.0197 (13)	0.0110 (12)	−0.0019 (12)	0.0028 (11)

Geometric parameters (Å, º) top

Sn1—C1ⁱ	2.148 (3)	C5—H5	0.9500
Sn1—C1	2.148 (3)	C6—H6	0.9500
Sn1—Br2ⁱ	2.7172 (9)	C7—C8	1.357 (4)
Sn1—Br2	2.7172 (8)	C7—H7	0.9500
Sn1—Br1	2.7319 (7)	C8—C9	1.418 (4)
Sn1—Br1ⁱ	2.7319 (7)	C8—H8	0.9500
Br3—C15	1.807 (3)	C9—C10	1.420 (3)
Cl1—C4	1.744 (3)	C10—C11	1.357 (4)
N1—C11	1.344 (3)	C10—H10	0.9500
N1—C7	1.346 (3)	C11—H11	0.9500
N1—H1	0.8800	C12—H12A	0.9800
N2—C9	1.337 (3)	C12—H12B	0.9800
N2—C13	1.460 (4)	C12—H12C	0.9800
N2—C12	1.465 (4)	C13—H13A	0.9800
C1—C2	1.386 (4)	C13—H13B	0.9800
C1—C6	1.392 (4)	C13—H13C	0.9800
C2—C3	1.392 (4)	C14—C16ⁱⁱ	1.378 (5)
C2—H2	0.9500	C14—C15	1.389 (4)
C3—C4	1.382 (4)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.379 (4)
C4—C5	1.383 (4)	C16—C14ⁱⁱ	1.378 (5)
C5—C6	1.391 (4)	C16—H16	0.9500

C1ⁱ—Sn1—C1	180.0	C1—C6—H6	119.7
C1ⁱ—Sn1—Br2ⁱ	89.62 (7)	N1—C7—C8	121.0 (2)
C1—Sn1—Br2ⁱ	90.38 (7)	N1—C7—H7	119.5
C1ⁱ—Sn1—Br2	90.38 (7)	C8—C7—H7	119.5
C1—Sn1—Br2	89.62 (7)	C7—C8—C9	120.5 (2)
Br2ⁱ—Sn1—Br2	180.0	C7—C8—H8	119.8
C1ⁱ—Sn1—Br1	89.88 (7)	C9—C8—H8	119.8
C1—Sn1—Br1	90.12 (7)	N2—C9—C8	121.3 (2)
Br2ⁱ—Sn1—Br1	91.55 (3)	N2—C9—C10	122.5 (2)
Br2—Sn1—Br1	88.45 (3)	C8—C9—C10	116.2 (2)
C1ⁱ—Sn1—Br1ⁱ	90.12 (7)	C11—C10—C9	120.2 (2)
C1—Sn1—Br1ⁱ	89.88 (7)	C11—C10—H10	119.9
Br2ⁱ—Sn1—Br1ⁱ	88.45 (3)	C9—C10—H10	119.9
Br2—Sn1—Br1ⁱ	91.55 (3)	N1—C11—C10	121.3 (2)
Br1—Sn1—Br1ⁱ	180.0	N1—C11—H11	119.4
C11—N1—C7	120.7 (2)	C10—C11—H11	119.4
C11—N1—H1	119.6	N2—C12—H12A	109.5
C7—N1—H1	119.6	N2—C12—H12B	109.5
C9—N2—C13	120.7 (2)	H12A—C12—H12B	109.5
C9—N2—C12	122.5 (2)	N2—C12—H12C	109.5
C13—N2—C12	116.4 (2)	H12A—C12—H12C	109.5
C2—C1—C6	119.5 (2)	H12B—C12—H12C	109.5
C2—C1—Sn1	120.03 (18)	N2—C13—H13A	109.5
C6—C1—Sn1	120.51 (19)	N2—C13—H13B	109.5
C1—C2—C3	120.5 (3)	H13A—C13—H13B	109.5
C1—C2—H2	119.7	N2—C13—H13C	109.5
C3—C2—H2	119.7	H13A—C13—H13C	109.5
C4—C3—C2	118.9 (3)	H13B—C13—H13C	109.5
C4—C3—H3	120.6	C16ⁱⁱ—C14—C15	119.1 (3)
C2—C3—H3	120.6	C16ⁱⁱ—C14—H14	120.4
C3—C4—C5	121.8 (3)	C15—C14—H14	120.4
C3—C4—Cl1	118.7 (2)	C16—C15—C14	121.1 (3)
C5—C4—Cl1	119.5 (2)	C16—C15—Br3	119.9 (2)
C4—C5—C6	118.6 (3)	C14—C15—Br3	119.0 (2)
C4—C5—H5	120.7	C14ⁱⁱ—C16—C15	119.7 (3)
C6—C5—H5	120.7	C14ⁱⁱ—C16—H16	120.1
C5—C6—C1	120.6 (3)	C15—C16—H16	120.1
C5—C6—H6	119.7

C1ⁱ—Sn1—C1—C2	19 (100)	C2—C1—C6—C5	2.8 (4)
Br2ⁱ—Sn1—C1—C2	134.73 (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—C9	0.0 (4)
Br1ⁱ—Sn1—C1—C2	46.28 (19)	C13—N2—C9—C8	−8.1 (4)
C1ⁱ—Sn1—C1—C6	−161 (100)	C12—N2—C9—C8	179.0 (2)
Br2ⁱ—Sn1—C1—C6	−45.7 (2)	C13—N2—C9—C10	172.4 (2)
Br2—Sn1—C1—C6	134.3 (2)	C12—N2—C9—C10	−0.5 (4)
Br1—Sn1—C1—C6	45.8 (2)	C7—C8—C9—N2	−178.2 (2)
Br1ⁱ—Sn1—C1—C6	−134.2 (2)	C7—C8—C9—C10	1.3 (4)
C6—C1—C2—C3	−1.9 (4)	N2—C9—C10—C11	178.2 (2)
Sn1—C1—C2—C3	177.68 (19)	C8—C9—C10—C11	−1.3 (4)
C1—C2—C3—C4	−0.9 (4)	C7—N1—C11—C10	1.4 (4)
C2—C3—C4—C5	2.8 (4)	C9—C10—C11—N1	0.0 (4)
C2—C3—C4—Cl1	−175.6 (2)	C16ⁱⁱ—C14—C15—C16	0.7 (5)
C3—C4—C5—C6	−1.8 (4)	C16ⁱⁱ—C14—C15—Br3	179.7 (2)
Cl1—C4—C5—C6	176.5 (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.

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)₂[SnBr₄(C₆H₄Cl)₂]·C₆H₄BrCl
M_r	1099.22
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.7692 (18), 10.128 (2), 11.407 (2)
α, β, γ (°)	111.16 (3), 93.38 (3), 92.85 (3)
V (Å³)	940.4 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	6.23
Crystal size (mm)	0.45 × 0.26 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.169, 0.384
No. of measured, independent and observed [I > 2σ(I)] reflections	7255, 4265, 3919
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.062, 1.05
No. of reflections	4265
No. of parameters	207
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −1.12

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).

Acknowledgements

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

References

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