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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.031
• wR factor = 0.098
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    --  Br1     ..      15.28 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    --  Br2     ..      15.87 su

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Related literature

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

S1. Experimental

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.

S2. Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The final difference Fourier map had peak near Sn1 and a hole near Br2.

The refinement program suggested a rather larger second parameter for the weighting scheme. The scheme was arbitrarily selected as (0.05 5.00), which led to a satisfactory, albeit somewhat large, goodness-of-fit.

Computing details

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

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)

Crystal data

(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) Å^3	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	3427 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.24	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 5.0P] where P = (Fo^2 + 2Fc^2)/3
3916 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 1.28 e Å^−3
0 restraints	Δρmin = −1.03 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Sn1—C1^i	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—Br1^i	2.7368 (4)	C8—H8	0.9300
Sn1—Br2^i	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
C1^i—Sn1—C1	180.000 (1)	C1—C6—H6	119.7
C1^i—Sn1—Br1	90.29 (8)	C12—C7—C8	119.8 (4)
C1—Sn1—Br1	89.71 (8)	C12—C7—N1	120.8 (4)
C1^i—Sn1—Br1^i	89.71 (8)	C8—C7—N1	119.4 (4)
C1—Sn1—Br1^i	90.29 (8)	C9—C8—C7	119.4 (5)
Br1—Sn1—Br1^i	180.0	C9—C8—H8	120.3
C1^i—Sn1—Br2^i	90.43 (8)	C7—C8—H8	120.3
C1—Sn1—Br2^i	89.57 (8)	C8—C9—C10	121.7 (5)
Br1—Sn1—Br2^i	90.173 (13)	C8—C9—H9	119.1
Br1^i—Sn1—Br2^i	89.827 (12)	C10—C9—H9	119.1
C1^i—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
Br1^i—Sn1—Br2	90.173 (13)	C10—C11—C12	121.5 (5)
Br2^i—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)
Br1^i—Sn1—C1—C6	46.8 (3)	Sn1—C1—C6—C5	177.9 (3)
Br2^i—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)
Br1^i—Sn1—C1—C2	−134.7 (3)	C14—N1—C7—C8	−40.4 (6)
Br2^i—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)

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