Bis(trimethyl-phenyl-ammonium) tetra-bromidobis(4-chloro-phen-yl)stannate(IV).

The Sn(IV) atom in the title salt, [N(CH(3))(3)(C(6)H(5))](2)[SnBr(4)(C(6)H(4)Cl)(2)], exists in a distorted all-trans SnC(2)Br(4) octa-hedral geometry. The Sn(IV) atom lies on a center of inversion. Weak inter-molecular C-H⋯Br hydrogen bonding is observed between trimethyl-phenyl-ammonium cations and the Sn complex anion in the crystal structure.

Related literature

For bis­(4-dimethyl­amino­pyridinium) tetra­bromidodiphenyl­stannate, see: Yap et al. (2008 ▶).

Experimental

Crystal data

(C9H14N)2[SnBr4(C6H4Cl)2]

M = 933.84

Monoclinic,

a = 25.7930 (3) Å

b = 9.0937 (1) Å

c = 15.8303 (2) Å

β = 113.4146 (6)°

V = 3407.30 (7) Å3

Z = 4

Mo Kα radiation

μ = 5.62 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.482, T max = 0.756

15816 measured reflections

3916 independent reflections

3427 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.098

S = 1.24

3916 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −1.03 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904940X/xu2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904940X/xu2683Isup2.hkl

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

(C9H14N)2[SnBr4(C6H4Cl)2]	F(000) = 1816
Mr = 933.84	Dx = 1.820 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 946 reflections
a = 25.7930 (3) Å	θ = 2.4–28.2°
b = 9.0937 (1) Å	µ = 5.62 mm−1
c = 15.8303 (2) Å	T = 293 K
β = 113.4146 (6)°	Block, colorless
V = 3407.30 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	3427 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→33
Tmin = 0.482, Tmax = 0.756	k = −11→11
15816 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.24	w = 1/[σ2(Fo2) + (0.05P)2 + 5.0P] where P = (Fo2 + 2Fc2)/3
3916 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 1.28 e Å−3
0 restraints	Δρmin = −1.03 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.2500	0.7500	0.5000	0.02955 (10)
Br1	0.183541 (17)	0.69102 (4)	0.59433 (3)	0.04572 (12)
Br2	0.292712 (17)	0.99167 (4)	0.60875 (3)	0.04584 (12)
Cl1	0.45173 (6)	0.34442 (18)	0.80689 (10)	0.0818 (4)
N1	0.13915 (14)	0.2207 (3)	0.5931 (2)	0.0400 (7)
C1	0.31591 (13)	0.6149 (3)	0.5957 (2)	0.0295 (6)
C2	0.30386 (17)	0.4780 (4)	0.6223 (3)	0.0422 (8)
H2	0.2670	0.4426	0.5964	0.051*
C3	0.34514 (18)	0.3939 (4)	0.6858 (3)	0.0466 (9)
H3	0.3366	0.3028	0.7037	0.056*
C4	0.39961 (17)	0.4473 (5)	0.7226 (3)	0.0473 (9)
C5	0.41310 (16)	0.5804 (5)	0.6971 (3)	0.0518 (10)
H5	0.4502	0.6141	0.7222	0.062*
C6	0.37092 (15)	0.6646 (4)	0.6334 (3)	0.0420 (8)
H6	0.3798	0.7556	0.6158	0.050*
C7	0.08627 (16)	0.2803 (4)	0.5981 (2)	0.0383 (8)
C8	0.0346 (2)	0.2255 (6)	0.5397 (4)	0.0658 (13)
H8	0.0325	0.1501	0.4988	0.079*
C9	−0.0136 (2)	0.2830 (8)	0.5424 (5)	0.0817 (17)
H9	−0.0485	0.2469	0.5022	0.098*
C10	−0.0121 (2)	0.3909 (6)	0.6018 (4)	0.0702 (14)
H10	−0.0454	0.4290	0.6026	0.084*
C11	0.0390 (3)	0.4433 (6)	0.6607 (4)	0.0732 (15)
H11	0.0403	0.5161	0.7027	0.088*
C12	0.0888 (2)	0.3908 (5)	0.6594 (3)	0.0564 (11)
H12	0.1233	0.4291	0.6990	0.068*
C13	0.1911 (2)	0.2531 (7)	0.6789 (3)	0.0683 (14)
H13A	0.1960	0.3575	0.6867	0.102*
H13B	0.2236	0.2107	0.6731	0.102*
H13C	0.1867	0.2115	0.7313	0.102*
C14	0.1361 (2)	0.0572 (5)	0.5795 (5)	0.0728 (15)
H14A	0.1059	0.0337	0.5218	0.109*
H14B	0.1292	0.0111	0.6286	0.109*
H14C	0.1712	0.0222	0.5795	0.109*
C15	0.1479 (2)	0.2913 (6)	0.5144 (3)	0.0573 (11)
H15A	0.1171	0.2660	0.4577	0.086*
H15B	0.1827	0.2570	0.5129	0.086*
H15C	0.1494	0.3961	0.5221	0.086*

	U11	U22	U33	U12	U13	U23
Sn1	0.02499 (16)	0.03104 (17)	0.03048 (17)	0.00219 (11)	0.00875 (12)	0.00523 (11)
Br1	0.0450 (2)	0.0460 (2)	0.0533 (2)	0.00187 (16)	0.02717 (18)	0.00690 (16)
Br2	0.0481 (2)	0.0417 (2)	0.0424 (2)	−0.00224 (16)	0.01229 (17)	−0.00120 (15)
Cl1	0.0651 (8)	0.0921 (9)	0.0723 (8)	0.0379 (7)	0.0105 (6)	0.0363 (7)
N1	0.0452 (18)	0.0404 (15)	0.0392 (16)	−0.0008 (13)	0.0219 (14)	0.0015 (12)
C1	0.0289 (15)	0.0301 (14)	0.0286 (14)	0.0038 (12)	0.0105 (12)	0.0032 (11)
C2	0.040 (2)	0.0401 (18)	0.0415 (19)	−0.0019 (16)	0.0111 (16)	0.0051 (15)
C3	0.055 (2)	0.0371 (18)	0.043 (2)	0.0073 (17)	0.0149 (18)	0.0098 (15)
C4	0.044 (2)	0.053 (2)	0.0394 (19)	0.0212 (18)	0.0114 (16)	0.0108 (17)
C5	0.0280 (18)	0.062 (3)	0.057 (2)	0.0037 (18)	0.0080 (17)	0.010 (2)
C6	0.0301 (17)	0.0438 (19)	0.048 (2)	0.0015 (15)	0.0110 (15)	0.0100 (16)
C7	0.040 (2)	0.0405 (18)	0.0363 (18)	−0.0006 (15)	0.0168 (16)	0.0021 (14)
C8	0.049 (3)	0.081 (3)	0.058 (3)	−0.008 (2)	0.012 (2)	−0.021 (2)
C9	0.039 (3)	0.102 (4)	0.089 (4)	−0.008 (3)	0.010 (3)	−0.007 (3)
C10	0.053 (3)	0.069 (3)	0.099 (4)	0.012 (2)	0.041 (3)	0.016 (3)
C11	0.083 (4)	0.055 (3)	0.098 (4)	0.009 (3)	0.053 (3)	−0.009 (3)
C12	0.051 (2)	0.051 (2)	0.068 (3)	−0.005 (2)	0.024 (2)	−0.014 (2)
C13	0.047 (3)	0.105 (4)	0.047 (2)	0.016 (3)	0.013 (2)	−0.003 (2)
C14	0.082 (4)	0.040 (2)	0.120 (5)	0.001 (2)	0.065 (4)	−0.001 (3)
C15	0.070 (3)	0.064 (3)	0.051 (2)	−0.006 (2)	0.038 (2)	0.004 (2)

Sn1—C1i	2.156 (3)	C7—C12	1.380 (6)
Sn1—C1	2.156 (3)	C7—C8	1.380 (6)
Sn1—Br1	2.7368 (4)	C8—C9	1.365 (8)
Sn1—Br1i	2.7368 (4)	C8—H8	0.9300
Sn1—Br2i	2.7386 (4)	C9—C10	1.349 (8)
Sn1—Br2	2.7386 (4)	C9—H9	0.9300
Cl1—C4	1.743 (4)	C10—C11	1.362 (8)
N1—C14	1.499 (5)	C10—H10	0.9300
N1—C15	1.495 (5)	C11—C12	1.377 (7)
N1—C7	1.499 (5)	C11—H11	0.9300
N1—C13	1.510 (6)	C12—H12	0.9300
C1—C6	1.379 (5)	C13—H13A	0.9600
C1—C2	1.389 (5)	C13—H13B	0.9600
C2—C3	1.371 (5)	C13—H13C	0.9600
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.378 (6)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.364 (6)	C15—H15A	0.9600
C5—C6	1.384 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
C1i—Sn1—C1	180.000 (1)	C1—C6—H6	119.7
C1i—Sn1—Br1	90.29 (8)	C12—C7—C8	119.8 (4)
C1—Sn1—Br1	89.71 (8)	C12—C7—N1	120.8 (4)
C1i—Sn1—Br1i	89.71 (8)	C8—C7—N1	119.4 (4)
C1—Sn1—Br1i	90.29 (8)	C9—C8—C7	119.4 (5)
Br1—Sn1—Br1i	180.0	C9—C8—H8	120.3
C1i—Sn1—Br2i	90.43 (8)	C7—C8—H8	120.3
C1—Sn1—Br2i	89.57 (8)	C8—C9—C10	121.7 (5)
Br1—Sn1—Br2i	90.173 (13)	C8—C9—H9	119.1
Br1i—Sn1—Br2i	89.827 (12)	C10—C9—H9	119.1
C1i—Sn1—Br2	89.57 (8)	C11—C10—C9	118.9 (5)
C1—Sn1—Br2	90.43 (8)	C11—C10—H10	120.5
Br1—Sn1—Br2	89.827 (12)	C9—C10—H10	120.5
Br1i—Sn1—Br2	90.173 (13)	C10—C11—C12	121.5 (5)
Br2i—Sn1—Br2	180.000 (10)	C10—C11—H11	119.2
C14—N1—C15	108.9 (4)	C12—C11—H11	119.2
C14—N1—C7	111.7 (3)	C11—C12—C7	118.6 (5)
C15—N1—C7	109.3 (3)	C11—C12—H12	120.7
C14—N1—C13	107.4 (4)	C7—C12—H12	120.7
C15—N1—C13	107.0 (4)	N1—C13—H13A	109.5
C7—N1—C13	112.5 (3)	N1—C13—H13B	109.5
C6—C1—C2	118.6 (3)	H13A—C13—H13B	109.5
C6—C1—Sn1	120.4 (2)	N1—C13—H13C	109.5
C2—C1—Sn1	121.0 (3)	H13A—C13—H13C	109.5
C3—C2—C1	121.4 (4)	H13B—C13—H13C	109.5
C3—C2—H2	119.3	N1—C14—H14A	109.5
C1—C2—H2	119.3	N1—C14—H14B	109.5
C2—C3—C4	118.6 (4)	H14A—C14—H14B	109.5
C2—C3—H3	120.7	N1—C14—H14C	109.5
C4—C3—H3	120.7	H14A—C14—H14C	109.5
C5—C4—C3	121.6 (3)	H14B—C14—H14C	109.5
C5—C4—Cl1	119.5 (3)	N1—C15—H15A	109.5
C3—C4—Cl1	118.8 (3)	N1—C15—H15B	109.5
C4—C5—C6	119.2 (4)	H15A—C15—H15B	109.5
C4—C5—H5	120.4	N1—C15—H15C	109.5
C6—C5—H5	120.4	H15A—C15—H15C	109.5
C5—C6—C1	120.6 (4)	H15B—C15—H15C	109.5
C5—C6—H6	119.7
Br1—Sn1—C1—C6	−133.2 (3)	C2—C1—C6—C5	−0.7 (6)
Br1i—Sn1—C1—C6	46.8 (3)	Sn1—C1—C6—C5	177.9 (3)
Br2i—Sn1—C1—C6	136.6 (3)	C14—N1—C7—C12	140.8 (5)
Br2—Sn1—C1—C6	−43.4 (3)	C15—N1—C7—C12	−98.7 (5)
Br1—Sn1—C1—C2	45.3 (3)	C13—N1—C7—C12	20.0 (5)
Br1i—Sn1—C1—C2	−134.7 (3)	C14—N1—C7—C8	−40.4 (6)
Br2i—Sn1—C1—C2	−44.8 (3)	C15—N1—C7—C8	80.2 (5)
Br2—Sn1—C1—C2	135.2 (3)	C13—N1—C7—C8	−161.2 (4)
C6—C1—C2—C3	1.2 (6)	C12—C7—C8—C9	0.9 (8)
Sn1—C1—C2—C3	−177.4 (3)	N1—C7—C8—C9	−178.0 (5)
C1—C2—C3—C4	−0.8 (6)	C7—C8—C9—C10	−1.0 (10)
C2—C3—C4—C5	−0.2 (6)	C8—C9—C10—C11	−0.1 (10)
C2—C3—C4—Cl1	177.4 (3)	C9—C10—C11—C12	1.4 (9)
C3—C4—C5—C6	0.7 (7)	C10—C11—C12—C7	−1.5 (8)
Cl1—C4—C5—C6	−176.9 (3)	C8—C7—C12—C11	0.3 (7)
C4—C5—C6—C1	−0.2 (7)	N1—C7—C12—C11	179.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Br1	0.96	2.91	3.839 (5)	163

Table 1

Selected bond lengths (Å)

Sn1—C1	2.156 (3)
Sn1—Br1	2.7368 (4)
Sn1—Br2	2.7386 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯Br1	0.96	2.91	3.839 (5)	163