Bis[4-(dimethyl-amino)pyridinium] tetra-bromidobis(4-chloro-phen-yl)stannate(IV)-4-bromo-chloro-benzene (1/1).

In the title compound, (C(7)H(11)N(2))(2)[SnBr(4)(C(6)H(4)Cl)(2)]·C(6)H(4)BrCl, the Sn(IV) atom in the tetra-bromidobis(4-chloro-phen-yl)stannate(IV) anion lies on a centre of inversion. The distances between the 4-(dimethyl-amino)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-bromo-chloro-benzene solvent mol-ecule, 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 = 1099.22

Triclinic,

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[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.062

S = 1.05

4265 reflections

207 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −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 ▶).

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

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

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

(C7H11N2)2[SnBr4(C6H4Cl)2]·C6H4BrCl	Z = 1
Mr = 1099.22	F(000) = 530
Triclinic, P1	Dx = 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

Bruker APEXII CCD area-detector diffractometer	4265 independent reflections
Radiation source: fine-focus sealed tube	3919 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→8
Tmin = 0.169, Tmax = 0.384	k = −13→13
7255 measured reflections	l = −14→13

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(Fo2) + (0.0323P)2 + 0.8768P] where P = (Fo2 + 2Fc2)/3
4265 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −1.12 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)