Bis(benzyl­triethyl­ammonium) hexa­chloridostannate(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810038122

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1334

doi:10.1107/S1600536810038122

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Bis(benzyltriethylammonium) hexachloridostannate(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 September 2010; accepted 24 September 2010; online 30 September 2010)

The reaction between benzyltriethylammonium chloride and dimethyltin dichloride yields the title salt, [(C₆H₅CH₂)(C₂H₅)₃N]₂[SnCl₆]. The Sn^IV atom, located on a center of inversion, exists in an octahedral coordination environment. The cation links with the anion via weak C—H⋯Cl hydrogen bonding.

Related literature

For bis(tetramethylammonium) hexachloridostannate(IV), see: Furukawa et al. (1982 ). For bis(tetra-n-propylammonium) hexachloridostannate(IV), see: James et al. (1992 ). For bis(tetraethylammonium) hexachloridostannate(IV), see: Sowa et al. (1981 ).

Experimental

Crystal data

(C₁₃H₂₂N)₂[SnCl₆]
M_r = 716.02
Monoclinic, P 2₁ /n
a = 11.2096 (6) Å
b = 11.2306 (6) Å
c = 12.9796 (7) Å
β = 90.872 (1)°
V = 1633.82 (15) Å³
Z = 2
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.698, T_max = 0.882
15028 measured reflections
3756 independent reflections
3276 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.059
S = 1.01
3756 reflections
160 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cl1ⁱ	0.96	2.74	3.685 (3)	169
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038122/xu5035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038122/xu5035Isup2.hkl

checkCIF report

Comment top

The reaction of dimethyltin dichloride with ammonium halides sometimes leads to tin-carbon cleave to result in the formation of a hexahalogenostannate. Tin-methyl cleavage was noted in the reaction of dimethyltin dichloride with and benzyltriethylammonium chloride; the resulting the title salt (Scheme I, Fig. 1) consists of ammonium cations and hexachloridostannate anions. The reported ammonium hexachloridostannates all have symmetrically substituted ammonium cations.

Related literature top

For bis(tetramethylammonium) hexachloridostannate, see: Furukawa et al. (1982). For bis(tetra-n-propylammonium) hexachloridostannate, see: James et al. (1992). For bis(tetra-ethylammonium) hexachloridostannate, see: Sowa et al. (1981).

Experimental top

Dimethyltin(IV) dichloride (0.219 g, 1 mmol) and benzyltriethylammonium chloride (0.455 g, 2 mmol) were dissolved in methanol and the solution kept at 333 K. Crystals were isolated after several days; m.p. 452–454 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the 2(C₆H₅CH₂)(C₂H₅)₃N⁺ SnCl₆^2- salt at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(benzyltriethylammonium) hexachloridostannate(IV) top

Crystal data top

(C₁₃H₂₂N)₂[SnCl₆]	F(000) = 732
M_r = 716.02	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8245 reflections
a = 11.2096 (6) Å	θ = 2.4–28.2°
b = 11.2306 (6) Å	µ = 1.29 mm⁻¹
c = 12.9796 (7) Å	T = 295 K
β = 90.872 (1)°	Prism, colorless
V = 1633.82 (15) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	3276 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.698, T_max = 0.882	k = −14→14
15028 measured reflections	l = −16→16

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.032P)² + 0.4848P] where P = (F_o² + 2F_c²)/3
3756 reflections	(Δ/σ)_max = 0.001
160 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

(C₁₃H₂₂N)₂[SnCl₆]	V = 1633.82 (15) Å³
M_r = 716.02	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.2096 (6) Å	µ = 1.29 mm⁻¹
b = 11.2306 (6) Å	T = 295 K
c = 12.9796 (7) Å	0.30 × 0.20 × 0.10 mm
β = 90.872 (1)°

Data collection top

Bruker SMART APEX diffractometer	3756 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3276 reflections with I > 2σ(I)
T_min = 0.698, T_max = 0.882	R_int = 0.022
15028 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
3756 reflections	Δρ_min = −0.39 e Å⁻³
160 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.5000	0.5000	0.03041 (6)
Cl1	0.53546 (4)	0.67877 (4)	0.60050 (3)	0.04330 (11)
Cl2	0.45054 (4)	0.39111 (4)	0.65796 (3)	0.04483 (12)
Cl3	0.70731 (4)	0.44472 (5)	0.52383 (4)	0.04963 (13)
N1	0.10908 (13)	0.22025 (14)	0.56788 (12)	0.0390 (3)
C1	0.1030 (2)	0.3475 (2)	0.60638 (18)	0.0534 (5)
H1A	0.1762	0.3649	0.6443	0.064*
H1B	0.0997	0.4002	0.5472	0.064*
C2	−0.0015 (2)	0.3758 (2)	0.6748 (2)	0.0659 (7)
H2A	0.0027	0.4576	0.6958	0.099*
H2B	0.0013	0.3254	0.7345	0.099*
H2C	−0.0748	0.3622	0.6373	0.099*
C3	−0.00149 (17)	0.1864 (2)	0.50650 (16)	0.0519 (5)
H3A	−0.0680	0.1816	0.5533	0.062*
H3B	0.0103	0.1075	0.4779	0.062*
C4	−0.0354 (2)	0.2704 (3)	0.41919 (19)	0.0744 (8)
H4A	−0.1066	0.2421	0.3853	0.112*
H4B	0.0283	0.2736	0.3707	0.112*
H4C	−0.0492	0.3486	0.4464	0.112*
C5	0.11816 (18)	0.13332 (19)	0.65726 (15)	0.0460 (5)
H5A	0.1295	0.0539	0.6296	0.055*
H5B	0.0429	0.1336	0.6932	0.055*
C6	0.2178 (2)	0.1584 (3)	0.73500 (17)	0.0627 (6)
H6A	0.2181	0.0979	0.7873	0.094*
H6B	0.2051	0.2348	0.7662	0.094*
H6C	0.2930	0.1583	0.7007	0.094*
C7	0.22048 (17)	0.21310 (18)	0.50080 (15)	0.0436 (4)
H7A	0.2122	0.2710	0.4457	0.052*
H7B	0.2891	0.2363	0.5426	0.052*
C8	0.24596 (17)	0.09404 (19)	0.45360 (15)	0.0429 (4)
C9	0.3185 (3)	0.0112 (2)	0.5036 (2)	0.0660 (7)
H9	0.3492	0.0284	0.5689	0.079*
C10	0.3458 (3)	−0.0965 (3)	0.4577 (2)	0.0798 (8)
H10	0.3933	−0.1515	0.4927	0.096*
C11	0.3032 (3)	−0.1225 (2)	0.3612 (2)	0.0713 (7)
H11	0.3217	−0.1949	0.3306	0.086*
C12	0.2334 (2)	−0.0415 (3)	0.3098 (2)	0.0632 (6)
H12	0.2049	−0.0587	0.2438	0.076*
C13	0.2049 (2)	0.0659 (2)	0.35541 (16)	0.0524 (5)
H13	0.1574	0.1202	0.3195	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02733 (9)	0.03422 (10)	0.02977 (9)	−0.00209 (6)	0.00331 (6)	0.00222 (6)
Cl1	0.0462 (3)	0.0419 (2)	0.0420 (2)	−0.0050 (2)	0.00723 (19)	−0.00544 (19)
Cl2	0.0483 (3)	0.0508 (3)	0.0354 (2)	−0.0082 (2)	0.00231 (18)	0.00960 (19)
Cl3	0.0344 (2)	0.0550 (3)	0.0595 (3)	0.0041 (2)	0.0010 (2)	0.0053 (2)
N1	0.0344 (8)	0.0408 (8)	0.0418 (8)	−0.0066 (6)	0.0041 (6)	0.0081 (7)
C1	0.0606 (14)	0.0438 (11)	0.0561 (12)	−0.0041 (10)	0.0122 (10)	0.0042 (9)
C2	0.0721 (16)	0.0610 (15)	0.0650 (15)	0.0120 (13)	0.0182 (12)	0.0052 (12)
C3	0.0346 (10)	0.0675 (15)	0.0536 (12)	−0.0047 (9)	−0.0041 (9)	0.0039 (10)
C4	0.0640 (16)	0.101 (2)	0.0578 (14)	0.0305 (15)	−0.0091 (12)	0.0077 (14)
C5	0.0429 (11)	0.0497 (11)	0.0454 (10)	−0.0070 (9)	0.0037 (8)	0.0154 (9)
C6	0.0511 (13)	0.0902 (19)	0.0467 (12)	−0.0049 (12)	−0.0053 (10)	0.0124 (12)
C7	0.0375 (10)	0.0483 (11)	0.0453 (10)	−0.0073 (8)	0.0074 (8)	0.0075 (8)
C8	0.0348 (10)	0.0498 (11)	0.0443 (10)	−0.0025 (8)	0.0033 (8)	0.0071 (8)
C9	0.0628 (16)	0.0793 (19)	0.0554 (14)	0.0197 (13)	−0.0120 (12)	0.0016 (12)
C10	0.081 (2)	0.0746 (19)	0.084 (2)	0.0352 (16)	−0.0011 (15)	0.0087 (15)
C11	0.0777 (18)	0.0575 (15)	0.0793 (18)	0.0054 (13)	0.0182 (14)	−0.0086 (13)
C12	0.0640 (15)	0.0723 (16)	0.0535 (13)	−0.0050 (13)	0.0044 (11)	−0.0103 (12)
C13	0.0502 (12)	0.0615 (14)	0.0453 (11)	0.0037 (10)	−0.0008 (9)	0.0070 (10)

Geometric parameters (Å, º) top

Sn1—Cl3ⁱ	2.4207 (5)	C4—H4C	0.9600
Sn1—Cl3	2.4207 (5)	C5—C6	1.520 (3)
Sn1—Cl1	2.4237 (5)	C5—H5A	0.9700
Sn1—Cl1ⁱ	2.4237 (5)	C5—H5B	0.9700
Sn1—Cl2ⁱ	2.4579 (4)	C6—H6A	0.9600
Sn1—Cl2	2.4579 (4)	C6—H6B	0.9600
N1—C3	1.512 (2)	C6—H6C	0.9600
N1—C1	1.515 (3)	C7—C8	1.500 (3)
N1—C5	1.518 (2)	C7—H7A	0.9700
N1—C7	1.535 (2)	C7—H7B	0.9700
C1—C2	1.515 (3)	C8—C13	1.385 (3)
C1—H1A	0.9700	C8—C9	1.390 (3)
C1—H1B	0.9700	C9—C10	1.386 (4)
C2—H2A	0.9600	C9—H9	0.9300
C2—H2B	0.9600	C10—C11	1.364 (4)
C2—H2C	0.9600	C10—H10	0.9300
C3—C4	1.519 (3)	C11—C12	1.367 (4)
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—C13	1.384 (4)
C4—H4A	0.9600	C12—H12	0.9300
C4—H4B	0.9600	C13—H13	0.9300

Cl3ⁱ—Sn1—Cl3	180.0	H4A—C4—H4B	109.5
Cl3ⁱ—Sn1—Cl1	90.320 (18)	C3—C4—H4C	109.5
Cl3—Sn1—Cl1	89.680 (18)	H4A—C4—H4C	109.5
Cl3ⁱ—Sn1—Cl1ⁱ	89.680 (18)	H4B—C4—H4C	109.5
Cl3—Sn1—Cl1ⁱ	90.320 (18)	N1—C5—C6	115.36 (17)
Cl1—Sn1—Cl1ⁱ	180.0	N1—C5—H5A	108.4
Cl3ⁱ—Sn1—Cl2ⁱ	89.662 (17)	C6—C5—H5A	108.4
Cl3—Sn1—Cl2ⁱ	90.338 (17)	N1—C5—H5B	108.4
Cl1—Sn1—Cl2ⁱ	89.974 (17)	C6—C5—H5B	108.4
Cl1ⁱ—Sn1—Cl2ⁱ	90.026 (17)	H5A—C5—H5B	107.5
Cl3ⁱ—Sn1—Cl2	90.338 (17)	C5—C6—H6A	109.5
Cl3—Sn1—Cl2	89.662 (17)	C5—C6—H6B	109.5
Cl1—Sn1—Cl2	90.026 (17)	H6A—C6—H6B	109.5
Cl1ⁱ—Sn1—Cl2	89.974 (17)	C5—C6—H6C	109.5
Cl2ⁱ—Sn1—Cl2	180.00 (2)	H6A—C6—H6C	109.5
C3—N1—C1	111.75 (17)	H6B—C6—H6C	109.5
C3—N1—C5	106.60 (15)	C8—C7—N1	116.09 (15)
C1—N1—C5	110.92 (16)	C8—C7—H7A	108.3
C3—N1—C7	110.82 (15)	N1—C7—H7A	108.3
C1—N1—C7	106.10 (14)	C8—C7—H7B	108.3
C5—N1—C7	110.73 (15)	N1—C7—H7B	108.3
C2—C1—N1	115.49 (18)	H7A—C7—H7B	107.4
C2—C1—H1A	108.4	C13—C8—C9	117.5 (2)
N1—C1—H1A	108.4	C13—C8—C7	121.09 (19)
C2—C1—H1B	108.4	C9—C8—C7	121.3 (2)
N1—C1—H1B	108.4	C10—C9—C8	121.0 (2)
H1A—C1—H1B	107.5	C10—C9—H9	119.5
C1—C2—H2A	109.5	C8—C9—H9	119.5
C1—C2—H2B	109.5	C11—C10—C9	120.3 (3)
H2A—C2—H2B	109.5	C11—C10—H10	119.8
C1—C2—H2C	109.5	C9—C10—H10	119.8
H2A—C2—H2C	109.5	C10—C11—C12	119.7 (3)
H2B—C2—H2C	109.5	C10—C11—H11	120.1
N1—C3—C4	115.5 (2)	C12—C11—H11	120.1
N1—C3—H3A	108.4	C11—C12—C13	120.4 (2)
C4—C3—H3A	108.4	C11—C12—H12	119.8
N1—C3—H3B	108.4	C13—C12—H12	119.8
C4—C3—H3B	108.4	C8—C13—C12	121.1 (2)
H3A—C3—H3B	107.5	C8—C13—H13	119.4
C3—C4—H4A	109.5	C12—C13—H13	119.4
C3—C4—H4B	109.5

C3—N1—C1—C2	58.9 (2)	C5—N1—C7—C8	59.4 (2)
C5—N1—C1—C2	−59.9 (2)	N1—C7—C8—C13	93.4 (2)
C7—N1—C1—C2	179.8 (2)	N1—C7—C8—C9	−91.3 (3)
C1—N1—C3—C4	52.4 (2)	C13—C8—C9—C10	−1.7 (4)
C5—N1—C3—C4	173.76 (19)	C7—C8—C9—C10	−177.2 (3)
C7—N1—C3—C4	−65.7 (2)	C8—C9—C10—C11	1.1 (5)
C3—N1—C5—C6	−174.68 (19)	C9—C10—C11—C12	0.0 (5)
C1—N1—C5—C6	−52.8 (2)	C10—C11—C12—C13	−0.5 (4)
C7—N1—C5—C6	64.7 (2)	C9—C8—C13—C12	1.2 (3)
C3—N1—C7—C8	−58.7 (2)	C7—C8—C13—C12	176.7 (2)
C1—N1—C7—C8	179.82 (17)	C11—C12—C13—C8	−0.1 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl1ⁱⁱ	0.96	2.74	3.685 (3)	169

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

Experimental details

Crystal data
Chemical formula	(C₁₃H₂₂N)₂[SnCl₆]
M_r	716.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.2096 (6), 11.2306 (6), 12.9796 (7)
β (°)	90.872 (1)
V (Å³)	1633.82 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.698, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	15028, 3756, 3276
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.059, 1.01
No. of reflections	3756
No. of parameters	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.39

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl1ⁱ	0.96	2.74	3.685 (3)	169

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

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

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