Bis(trimethyl­phenyl­ammonium) tetra­bromidobis(4-chloro­phen­yl)stannate(IV)

Lo, K.M.; Ng, S.W.

doi:10.1107/S160053680904940X

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1677

doi:10.1107/S160053680904940X

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Bis(trimethylphenylammonium) tetrabromidobis(4-chlorophenyl)stannate(IV)

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

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

(Received 18 November 2009; accepted 19 November 2009; online 25 November 2009)

The Sn^IV atom in the title salt, [N(CH₃)₃(C₆H₅)]₂[SnBr₄(C₆H₄Cl)₂], exists in a distorted all-trans SnC₂Br₄ octahedral geometry. The Sn^IV atom lies on a center of inversion. Weak intermolecular C—H⋯Br hydrogen bonding is observed between trimethylphenylammonium 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_r = 933.84
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.098
S = 1.24
3916 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −1.03 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

Related literature top

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

Experimental top

In an attempt to cleave a tin-carbon bond in a tetraorganotin compound, tetrakis(4-chlorophenyl)tin (0.57 g, 1 mmol) and trimethylphenylammonium tribromide (0.38 g, 1 mmol) were heated in ethanol for six hours. Colorless crystals of the stannate separated from the solution after a few days.

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

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent formula units of 2[N(CH₃)₃(C₆H₅)] [SnBr₄(C₆H₄Cl)₂] at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(trimethylphenylammonium) tetrabromidobis(4-chlorophenyl)stannate(IV) top

Crystal data top

(C₉H₁₄N)₂[SnBr₄(C₆H₄Cl)₂]	F(000) = 1816
M_r = 933.84	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	3427 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→33
T_min = 0.482, T_max = 0.756	k = −11→11
15816 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.24	w = 1/[σ²(F_o²) + (0.05P)² + 5.0P] where P = (F_o² + 2F_c²)/3
3916 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 1.28 e Å⁻³
0 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

(C₉H₁₄N)₂[SnBr₄(C₆H₄Cl)₂]	V = 3407.30 (7) Å³
M_r = 933.84	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.7930 (3) Å	µ = 5.62 mm⁻¹
b = 9.0937 (1) Å	T = 293 K
c = 15.8303 (2) Å	0.30 × 0.25 × 0.20 mm
β = 113.4146 (6)°

Data collection top

Bruker SMART APEX diffractometer	3916 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3427 reflections with I > 2σ(I)
T_min = 0.482, T_max = 0.756	R_int = 0.025
15816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.24	Δρ_max = 1.28 e Å⁻³
3916 reflections	Δρ_min = −1.03 e Å⁻³
181 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	(C₉H₁₄N)₂[SnBr₄(C₆H₄Cl)₂]
M_r	933.84
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	25.7930 (3), 9.0937 (1), 15.8303 (2)
β (°)	113.4146 (6)
V (Å³)	3407.30 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.62
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.482, 0.756
No. of measured, independent and observed [I > 2σ(I)] reflections	15816, 3916, 3427
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.098, 1.24
No. of reflections	3916
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.28, −1.03

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

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Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Yap, Q. L., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m696. Web of Science CSD CrossRef IUCr Journals Google Scholar