Dipyridinium tribromidochloridobis(4-chloro-phen-yl)stannate(IV).

The tin atom in the substituted ammonium stannate(IV), (C(5)H(6)N)(2)[SnBr(3)(C(6)H(4)Cl)(2)Cl], lies on a center of symmetry in a distorted octa-hedral coordination geometry. Each independent halogen site is occupied by bromine and chlorine anions in an approximate 3:1 ratio. The pyridinium cation forms a hydrogen bond to only one of the halogen atoms.

Related literature

For bis­(4-dimethyl­amino­pyridinium) tetra­halido­diorgano­stannates, see: Lo & Ng (2008a ▶,b ▶); Yap et al. (2008 ▶).

Experimental

Crystal data

(C5H6N)2[SnBr3(C6H4Cl)2Cl]

M = 777.17

Monoclinic,

a = 11.5130 (2) Å

b = 11.7139 (2) Å

c = 18.7748 (3) Å

β = 93.230 (1)°

V = 2527.99 (7) Å3

Z = 4

Mo Kα radiation

μ = 6.08 mm−1

T = 100 K

0.27 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.327, T max = 0.529 (expected range = 0.298–0.482)

11728 measured reflections

2903 independent reflections

2668 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.047

S = 1.02

2903 reflections

146 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016687/bt2945sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016687/bt2945Isup2.hkl

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

(C5H6N)2[SnBr3(C6H4Cl)2Cl]	F(000) = 1488
Mr = 777.17	Dx = 2.042 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6664 reflections
a = 11.5130 (2) Å	θ = 2.5–28.3°
b = 11.7139 (2) Å	µ = 6.08 mm−1
c = 18.7748 (3) Å	T = 100 K
β = 93.230 (1)°	Prism, brown
V = 2527.99 (7) Å3	0.27 × 0.19 × 0.12 mm
Z = 4

Bruker SMART APEX diffractometer	2903 independent reflections
Radiation source: fine-focus sealed tube	2668 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.327, Tmax = 0.529	k = −15→15
11728 measured reflections	l = −23→24

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0246P)2 + 3.4843P] where P = (Fo2 + 2Fc2)/3
2903 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.39 e Å−3
4 restraints	Δρmin = −0.83 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.5000	0.5000	0.5000	0.01196 (6)
Br1	0.308690 (19)	0.509165 (19)	0.578153 (12)	0.01383 (8)	0.7365 (11)
Br2	0.551744 (19)	0.288797 (18)	0.550827 (12)	0.01450 (7)	0.7635 (11)
Cl1'	0.308690 (19)	0.509165 (19)	0.578153 (12)	0.01383 (8)	0.2635 (11)
Cl2'	0.551744 (19)	0.288797 (18)	0.550827 (12)	0.01450 (7)	0.2365 (11)
Cl1	0.83429 (5)	0.71755 (5)	0.76748 (3)	0.02688 (12)
N1	0.15868 (16)	0.59124 (16)	0.43101 (10)	0.0217 (4)
H1	0.2206	0.5891	0.4607	0.026*
C1	0.60325 (16)	0.57206 (16)	0.58772 (10)	0.0129 (4)
C2	0.60187 (18)	0.52532 (17)	0.65598 (11)	0.0165 (4)
H2	0.5522	0.4626	0.6644	0.020*
C3	0.67258 (18)	0.56972 (18)	0.71184 (11)	0.0188 (4)
H3	0.6716	0.5379	0.7584	0.023*
C4	0.74442 (17)	0.66121 (18)	0.69830 (11)	0.0182 (4)
C5	0.74654 (17)	0.70998 (17)	0.63157 (11)	0.0171 (4)
H5	0.7961	0.7729	0.6234	0.021*
C6	0.67469 (17)	0.66515 (17)	0.57641 (11)	0.0155 (4)
H6	0.6745	0.6987	0.5303	0.019*
C7	0.0884 (2)	0.50083 (18)	0.42776 (13)	0.0225 (5)
H7	0.1048	0.4366	0.4575	0.027*
C8	−0.0077 (2)	0.50100 (18)	0.38125 (13)	0.0235 (5)
H8	−0.0579	0.4366	0.3777	0.028*
C9	−0.03042 (19)	0.5968 (2)	0.33953 (12)	0.0238 (5)
H9	−0.0971	0.5988	0.3074	0.029*
C10	0.0440 (2)	0.68937 (19)	0.34465 (12)	0.0231 (5)
H10	0.0290	0.7552	0.3161	0.028*
C11	0.13982 (19)	0.68517 (19)	0.39135 (12)	0.0224 (5)
H11	0.1920	0.7479	0.3955	0.027*

	U11	U22	U33	U12	U13	U23
Sn1	0.01296 (10)	0.01329 (10)	0.00948 (10)	−0.00098 (6)	−0.00070 (7)	0.00034 (7)
Br1	0.01297 (12)	0.01610 (12)	0.01249 (13)	−0.00044 (8)	0.00142 (9)	0.00093 (8)
Br2	0.01749 (12)	0.01242 (11)	0.01334 (12)	0.00098 (8)	−0.00136 (8)	0.00188 (8)
Cl1'	0.01297 (12)	0.01610 (12)	0.01249 (13)	−0.00044 (8)	0.00142 (9)	0.00093 (8)
Cl2'	0.01749 (12)	0.01242 (11)	0.01334 (12)	0.00098 (8)	−0.00136 (8)	0.00188 (8)
Cl1	0.0254 (3)	0.0349 (3)	0.0193 (3)	−0.0073 (2)	−0.0073 (2)	−0.0056 (2)
N1	0.0177 (9)	0.0277 (10)	0.0190 (9)	0.0050 (7)	−0.0038 (7)	−0.0047 (8)
C1	0.0126 (9)	0.0155 (9)	0.0103 (9)	0.0020 (7)	−0.0011 (7)	−0.0014 (7)
C2	0.0160 (9)	0.0177 (9)	0.0156 (10)	−0.0017 (7)	0.0004 (8)	−0.0001 (8)
C3	0.0221 (10)	0.0222 (10)	0.0119 (9)	0.0010 (8)	−0.0016 (8)	0.0022 (8)
C4	0.0153 (10)	0.0237 (10)	0.0150 (10)	0.0002 (8)	−0.0041 (8)	−0.0054 (8)
C5	0.0155 (9)	0.0170 (9)	0.0188 (10)	−0.0028 (7)	0.0002 (8)	−0.0013 (8)
C6	0.0154 (9)	0.0170 (9)	0.0142 (10)	0.0012 (7)	0.0018 (7)	0.0010 (8)
C7	0.0251 (12)	0.0223 (11)	0.0204 (12)	0.0064 (8)	0.0055 (9)	0.0023 (9)
C8	0.0194 (11)	0.0239 (11)	0.0276 (13)	−0.0015 (8)	0.0062 (9)	−0.0024 (9)
C9	0.0173 (10)	0.0332 (12)	0.0204 (11)	0.0049 (9)	−0.0028 (8)	−0.0028 (9)
C10	0.0280 (11)	0.0214 (10)	0.0201 (11)	0.0058 (9)	0.0029 (9)	0.0019 (9)
C11	0.0251 (11)	0.0196 (10)	0.0225 (11)	−0.0018 (8)	0.0034 (9)	−0.0048 (9)

Sn1—C1i	2.149 (2)	C3—C4	1.386 (3)
Sn1—C1	2.149 (2)	C3—H3	0.9500
Sn1—Br1	2.7166 (2)	C4—C5	1.378 (3)
Sn1—Cl2'i	2.7060 (2)	C5—C6	1.391 (3)
Sn1—Br2i	2.7060 (2)	C5—H5	0.9500
Sn1—Br2	2.7060 (2)	C6—H6	0.9500
Sn1—Cl1'i	2.7166 (2)	C7—C8	1.370 (3)
Sn1—Br1i	2.7166 (2)	C7—H7	0.9500
Cl1—C4	1.744 (2)	C8—C9	1.384 (3)
N1—C7	1.332 (3)	C8—H8	0.9500
N1—C11	1.339 (3)	C9—C10	1.383 (3)
N1—H1	0.8800	C9—H9	0.9500
C1—C6	1.389 (3)	C10—C11	1.371 (3)
C1—C2	1.394 (3)	C10—H10	0.9500
C2—C3	1.392 (3)	C11—H11	0.9500
C2—H2	0.9500
C1i—Sn1—C1	180.000 (1)	C6—C1—Sn1	119.86 (14)
C1i—Sn1—Cl2'i	89.29 (5)	C2—C1—Sn1	121.05 (14)
C1—Sn1—Cl2'i	90.71 (5)	C3—C2—C1	120.63 (19)
C1i—Sn1—Br2i	89.29 (5)	C3—C2—H2	119.7
C1—Sn1—Br2i	90.71 (5)	C1—C2—H2	119.7
Cl2'i—Sn1—Br2i	0.000 (13)	C4—C3—C2	118.71 (19)
C1i—Sn1—Br2	90.71 (5)	C4—C3—H3	120.6
C1—Sn1—Br2	89.29 (5)	C2—C3—H3	120.6
Cl2'i—Sn1—Br2	180.0	C5—C4—C3	121.90 (19)
Br2i—Sn1—Br2	180.0	C5—C4—Cl1	118.68 (16)
C1i—Sn1—Cl1'i	90.05 (5)	C3—C4—Cl1	119.41 (17)
C1—Sn1—Cl1'i	89.95 (5)	C4—C5—C6	118.67 (19)
Cl2'i—Sn1—Cl1'i	90.845 (7)	C4—C5—H5	120.7
Br2i—Sn1—Cl1'i	90.845 (7)	C6—C5—H5	120.7
Br2—Sn1—Cl1'i	89.155 (7)	C5—C6—C1	120.98 (19)
C1i—Sn1—Br1i	90.05 (5)	C5—C6—H6	119.5
C1—Sn1—Br1i	89.95 (5)	C1—C6—H6	119.5
Cl2'i—Sn1—Br1i	90.845 (7)	N1—C7—C8	119.7 (2)
Br2i—Sn1—Br1i	90.845 (7)	N1—C7—H7	120.2
Br2—Sn1—Br1i	89.155 (7)	C8—C7—H7	120.2
Cl1'i—Sn1—Br1i	0.000 (8)	C7—C8—C9	118.8 (2)
C1i—Sn1—Br1	89.95 (5)	C7—C8—H8	120.6
C1—Sn1—Br1	90.05 (5)	C9—C8—H8	120.6
Cl2'i—Sn1—Br1	89.155 (7)	C8—C9—C10	120.0 (2)
Br2i—Sn1—Br1	89.155 (7)	C8—C9—H9	120.0
Br2—Sn1—Br1	90.845 (7)	C10—C9—H9	120.0
Cl1'i—Sn1—Br1	180.0	C11—C10—C9	119.3 (2)
Br1i—Sn1—Br1	180.0	C11—C10—H10	120.3
C7—N1—C11	123.26 (19)	C9—C10—H10	120.3
C7—N1—H1	118.4	N1—C11—C10	119.0 (2)
C11—N1—H1	118.4	N1—C11—H11	120.5
C6—C1—C2	119.08 (18)	C10—C11—H11	120.5
Cl2'i—Sn1—C1—C6	−40.72 (15)	C1—C2—C3—C4	−0.1 (3)
Br2i—Sn1—C1—C6	−40.72 (15)	C2—C3—C4—C5	0.9 (3)
Br2—Sn1—C1—C6	139.28 (15)	C2—C3—C4—Cl1	−179.64 (16)
Cl1'i—Sn1—C1—C6	50.12 (15)	C3—C4—C5—C6	−0.4 (3)
Br1i—Sn1—C1—C6	50.12 (15)	Cl1—C4—C5—C6	−179.89 (15)
Br1—Sn1—C1—C6	−129.88 (15)	C4—C5—C6—C1	−0.9 (3)
Cl2'i—Sn1—C1—C2	140.70 (15)	C2—C1—C6—C5	1.7 (3)
Br2i—Sn1—C1—C2	140.70 (15)	Sn1—C1—C6—C5	−176.91 (15)
Br2—Sn1—C1—C2	−39.30 (15)	C11—N1—C7—C8	1.0 (3)
Cl1'i—Sn1—C1—C2	−128.46 (15)	N1—C7—C8—C9	−1.2 (3)
Br1i—Sn1—C1—C2	−128.46 (15)	C7—C8—C9—C10	0.8 (3)
Br1—Sn1—C1—C2	51.54 (15)	C8—C9—C10—C11	−0.1 (3)
C6—C1—C2—C3	−1.2 (3)	C7—N1—C11—C10	−0.3 (3)
Sn1—C1—C2—C3	177.39 (15)	C9—C10—C11—N1	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.88	2.55	3.317 (2)	146

Table 1

Selected bond lengths (Å) (X = Br, Cl)

Sn1—C1	2.149 (2)
Sn1—X1	2.7166 (2)
Sn1—X2	2.7060 (2)