4-(Dimethyl­amino)pyridinium dibromido(4-bromo­phen­yl)dimethyl­stannate(IV)

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

doi:10.1107/S1600536808032248

metal-organic compounds

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Volume 64| Part 11| November 2008| Page m1391

doi:10.1107/S1600536808032248

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4-(Dimethylamino)pyridinium dibromido(4-bromophenyl)dimethylstannate(IV)

Chin Koon Yau,^a 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 6 October 2008; accepted 7 October 2008; online 11 October 2008)

The anion in the title compound, (C₇H₁₁N₂)[SnBr₂(CH₃)₂(C₆H₄Br)], is five-coordinate within a distorted trans-C₃SnBr₂ trigonal–bipyramidal geometry. The cation and anion are linked by an N—H⋯Br hydrogen bond.

Related literature

For the crystal structure of 4-(dimethylamino)pyridinium dibromidotriphenylstannate(IV), see: Norhafiza et al. (2008 ).

Experimental

Crystal data

(C₇H₁₁N₂)[SnBr₂(CH₃)₂(C₆H₄Br)]
M_r = 587.76
Triclinic, $[P \overline 1]$
a = 7.3397 (1) Å
b = 11.1034 (2) Å
c = 12.2270 (2) Å
α = 100.038 (1)°
β = 102.472 (1)°
γ = 94.679 (1)°
V = 950.65 (3) Å³
Z = 2
Mo Kα radiation
μ = 7.64 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.208, T_max = 0.862
8826 measured reflections
4346 independent reflections
3718 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.096
S = 1.13
4346 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 1.07 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1	0.88	2.56	3.319 (3)	146

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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032248/tk2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032248/tk2315Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 4-dimethylaminopyridinium dibromidotriphenylstannate, see: Norhafiza et al. (2008).

Experimental top

Bis(4-bromophenyl)dimethyltin (0.10 g, 0.2 mmol) [which was prepared by the reaction between dimethyltin dichloride and 4-bromophenylmagnesium bromide] and 4-dimethylaminopyridine hydrobromide perbromide (0.08 g, 0.2 mmol) were heated in chloroform (100 ml) for 3 h. The solution was filtered and the solvent allow to evaporate to give colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C₇H₁₁N₂][SnBr₂(CH₃)₂(C₆H₄Br)] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

4-(Dimethylamino)pyridinium dibromido(4-bromophenyl)dimethylstannate(IV) top

Crystal data top

(C₇H₁₁N₂)[SnBr₂(CH₃)₂(C₆H₄Br)]	Z = 2
M_r = 587.76	F(000) = 560
Triclinic, P1	D_x = 2.053 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3397 (1) Å	Cell parameters from 5297 reflections
b = 11.1034 (2) Å	θ = 2.3–28.3°
c = 12.2270 (2) Å	µ = 7.64 mm⁻¹
α = 100.038 (1)°	T = 100 K
β = 102.472 (1)°	Plate, colourless
γ = 94.679 (1)°	0.30 × 0.20 × 0.02 mm
V = 950.65 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	4346 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.208, T_max = 0.862	k = −14→14
8826 measured reflections	l = −15→15

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) = 0.096	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0496P)² + 0.4605P] where P = (F_o² + 2F_c²)/3
4346 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

(C₇H₁₁N₂)[SnBr₂(CH₃)₂(C₆H₄Br)]	γ = 94.679 (1)°
M_r = 587.76	V = 950.65 (3) Å³
Triclinic, P1	Z = 2
a = 7.3397 (1) Å	Mo Kα radiation
b = 11.1034 (2) Å	µ = 7.64 mm⁻¹
c = 12.2270 (2) Å	T = 100 K
α = 100.038 (1)°	0.30 × 0.20 × 0.02 mm
β = 102.472 (1)°

Data collection top

Bruker SMART APEX diffractometer	4346 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3718 reflections with I > 2σ(I)
T_min = 0.208, T_max = 0.862	R_int = 0.029
8826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.13	Δρ_max = 1.07 e Å⁻³
4346 reflections	Δρ_min = −1.24 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.38417 (3)	0.25338 (2)	0.773249 (19)	0.01548 (9)
Br1	0.74942 (5)	0.26874 (4)	0.91216 (3)	0.01853 (11)
Br2	0.02956 (5)	0.24575 (4)	0.63868 (3)	0.01814 (11)
Br3	0.36372 (6)	−0.36881 (4)	0.72001 (4)	0.03322 (13)
N1	0.8504 (5)	0.0064 (3)	0.7756 (3)	0.0221 (7)
H1	0.8438	0.0862	0.7872	0.027*
N2	0.8761 (5)	−0.3667 (3)	0.7213 (2)	0.0199 (7)
C1	0.3068 (6)	0.3599 (4)	0.9145 (3)	0.0251 (9)
H1A	0.1740	0.3357	0.9112	0.038*
H1B	0.3263	0.4475	0.9115	0.038*
H1C	0.3845	0.3456	0.9859	0.038*
C2	0.5034 (5)	0.3149 (4)	0.6446 (3)	0.0198 (8)
H2A	0.4313	0.2714	0.5690	0.030*
H2B	0.6343	0.2976	0.6553	0.030*
H2C	0.4994	0.4037	0.6507	0.030*
C3	0.3607 (5)	0.0584 (4)	0.7558 (3)	0.0164 (7)
C4	0.3542 (5)	0.0007 (4)	0.8482 (3)	0.0208 (8)
H4	0.3511	0.0496	0.9196	0.025*
C5	0.3520 (5)	−0.1260 (4)	0.8384 (3)	0.0227 (8)
H5	0.3462	−0.1637	0.9018	0.027*
C6	0.3585 (5)	−0.1962 (4)	0.7338 (3)	0.0201 (8)
C7	0.3613 (5)	−0.1437 (4)	0.6397 (3)	0.0238 (8)
H7	0.3632	−0.1933	0.5685	0.029*
C8	0.3611 (6)	−0.0170 (4)	0.6514 (3)	0.0217 (8)
H8	0.3611	0.0195	0.5866	0.026*
C9	0.8666 (6)	−0.0529 (4)	0.6733 (3)	0.0237 (8)
H9	0.8744	−0.0076	0.6150	0.028*
C10	0.8721 (5)	−0.1769 (4)	0.6517 (3)	0.0191 (8)
H10	0.8787	−0.2176	0.5778	0.023*
C11	0.8680 (5)	−0.2459 (4)	0.7390 (3)	0.0179 (8)
C12	0.8551 (5)	−0.1788 (4)	0.8470 (3)	0.0205 (8)
H12	0.8542	−0.2199	0.9089	0.025*
C13	0.8440 (5)	−0.0552 (4)	0.8610 (3)	0.0232 (8)
H13	0.8315	−0.0115	0.9325	0.028*
C14	0.8600 (6)	−0.4359 (4)	0.6050 (3)	0.0236 (9)
H14A	0.9550	−0.3986	0.5715	0.035*
H14B	0.7343	−0.4337	0.5581	0.035*
H14C	0.8799	−0.5217	0.6078	0.035*
C15	0.8821 (6)	−0.4367 (4)	0.8132 (3)	0.0244 (9)
H15A	0.9843	−0.3978	0.8788	0.037*
H15B	0.9039	−0.5215	0.7858	0.037*
H15C	0.7622	−0.4377	0.8362	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01676 (15)	0.01707 (15)	0.01403 (14)	0.00355 (11)	0.00520 (10)	0.00423 (10)
Br1	0.0172 (2)	0.0208 (2)	0.01645 (19)	0.00236 (15)	0.00153 (14)	0.00369 (15)
Br2	0.0158 (2)	0.0221 (2)	0.01817 (19)	0.00498 (15)	0.00386 (14)	0.00728 (15)
Br3	0.0257 (2)	0.0189 (2)	0.0537 (3)	0.00577 (17)	0.0064 (2)	0.0061 (2)
N1	0.0209 (17)	0.0167 (16)	0.0251 (16)	0.0044 (14)	−0.0002 (14)	0.0005 (13)
N2	0.0215 (17)	0.0251 (18)	0.0133 (14)	0.0041 (14)	0.0044 (13)	0.0033 (13)
C1	0.021 (2)	0.035 (2)	0.0181 (18)	0.0055 (18)	0.0048 (16)	0.0007 (17)
C2	0.0186 (19)	0.025 (2)	0.0178 (17)	0.0023 (16)	0.0069 (15)	0.0064 (15)
C3	0.0104 (17)	0.0211 (19)	0.0173 (17)	0.0010 (14)	0.0017 (14)	0.0047 (15)
C4	0.0190 (19)	0.027 (2)	0.0184 (18)	0.0039 (16)	0.0047 (15)	0.0083 (16)
C5	0.0160 (19)	0.031 (2)	0.0216 (19)	0.0047 (17)	0.0023 (15)	0.0092 (17)
C6	0.0133 (18)	0.0131 (18)	0.033 (2)	0.0031 (14)	0.0044 (16)	0.0037 (16)
C7	0.018 (2)	0.028 (2)	0.0228 (19)	0.0056 (17)	0.0033 (16)	−0.0019 (17)
C8	0.024 (2)	0.024 (2)	0.0183 (17)	0.0051 (16)	0.0055 (15)	0.0061 (16)
C9	0.020 (2)	0.028 (2)	0.0218 (19)	0.0023 (17)	0.0000 (16)	0.0076 (17)
C10	0.0155 (18)	0.024 (2)	0.0183 (17)	0.0041 (15)	0.0034 (15)	0.0038 (15)
C11	0.0113 (17)	0.025 (2)	0.0187 (17)	0.0056 (15)	0.0047 (14)	0.0048 (15)
C12	0.020 (2)	0.024 (2)	0.0188 (18)	0.0052 (16)	0.0057 (15)	0.0048 (16)
C13	0.0167 (19)	0.029 (2)	0.0241 (19)	0.0082 (17)	0.0055 (16)	0.0022 (17)
C14	0.033 (2)	0.022 (2)	0.0182 (18)	0.0088 (18)	0.0084 (17)	0.0027 (16)
C15	0.030 (2)	0.024 (2)	0.0202 (18)	0.0065 (18)	0.0052 (17)	0.0087 (16)

Geometric parameters (Å, º) top

Sn1—C1	2.127 (4)	C4—H4	0.9500
Sn1—C2	2.139 (3)	C5—C6	1.390 (6)
Sn1—C3	2.127 (4)	C5—H5	0.9500
Sn1—Br1	2.8211 (4)	C6—C7	1.380 (6)
Sn1—Br2	2.7486 (4)	C7—C8	1.390 (6)
Br3—C6	1.899 (4)	C7—H7	0.9500
N1—C9	1.343 (5)	C8—H8	0.9500
N1—C13	1.351 (5)	C9—C10	1.361 (6)
N1—H1	0.8800	C9—H9	0.9500
N2—C11	1.329 (5)	C10—C11	1.422 (5)
N2—C15	1.469 (5)	C10—H10	0.9500
N2—C14	1.469 (5)	C11—C12	1.426 (5)
C1—H1A	0.9800	C12—C13	1.364 (6)
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—H13	0.9500
C2—H2A	0.9800	C14—H14A	0.9800
C2—H2B	0.9800	C14—H14B	0.9800
C2—H2C	0.9800	C14—H14C	0.9800
C3—C4	1.400 (5)	C15—H15A	0.9800
C3—C8	1.400 (5)	C15—H15B	0.9800
C4—C5	1.390 (6)	C15—H15C	0.9800

C1—Sn1—C2	128.9 (2)	C7—C6—C5	121.7 (4)
C1—Sn1—C3	118.8 (2)	C7—C6—Br3	119.2 (3)
C2—Sn1—C3	112.1 (1)	C5—C6—Br3	119.1 (3)
C1—Sn1—Br2	90.82 (11)	C6—C7—C8	118.7 (3)
C3—Sn1—Br2	92.78 (10)	C6—C7—H7	120.7
C2—Sn1—Br2	89.98 (10)	C8—C7—H7	120.7
C1—Sn1—Br1	88.38 (11)	C7—C8—C3	121.8 (4)
C3—Sn1—Br1	88.88 (10)	C7—C8—H8	119.1
C2—Sn1—Br1	89.39 (10)	C3—C8—H8	119.1
Br1—Sn1—Br2	178.33 (1)	N1—C9—C10	121.1 (4)
C9—N1—C13	120.7 (3)	N1—C9—H9	119.4
C9—N1—H1	119.7	C10—C9—H9	119.4
C13—N1—H1	119.7	C9—C10—C11	120.4 (3)
C11—N2—C15	121.9 (3)	C9—C10—H10	119.8
C11—N2—C14	119.9 (3)	C11—C10—H10	119.8
C15—N2—C14	117.9 (3)	N2—C11—C10	122.0 (3)
Sn1—C1—H1A	109.5	N2—C11—C12	121.5 (3)
Sn1—C1—H1B	109.5	C10—C11—C12	116.5 (4)
H1A—C1—H1B	109.5	C13—C12—C11	119.6 (3)
Sn1—C1—H1C	109.5	C13—C12—H12	120.2
H1A—C1—H1C	109.5	C11—C12—H12	120.2
H1B—C1—H1C	109.5	N1—C13—C12	121.6 (3)
Sn1—C2—H2A	109.5	N1—C13—H13	119.2
Sn1—C2—H2B	109.5	C12—C13—H13	119.2
H2A—C2—H2B	109.5	N2—C14—H14A	109.5
Sn1—C2—H2C	109.5	N2—C14—H14B	109.5
H2A—C2—H2C	109.5	H14A—C14—H14B	109.5
H2B—C2—H2C	109.5	N2—C14—H14C	109.5
C4—C3—C8	117.4 (4)	H14A—C14—H14C	109.5
C4—C3—Sn1	122.0 (3)	H14B—C14—H14C	109.5
C8—C3—Sn1	120.5 (3)	N2—C15—H15A	109.5
C5—C4—C3	121.9 (4)	N2—C15—H15B	109.5
C5—C4—H4	119.1	H15A—C15—H15B	109.5
C3—C4—H4	119.1	N2—C15—H15C	109.5
C4—C5—C6	118.4 (4)	H15A—C15—H15C	109.5
C4—C5—H5	120.8	H15B—C15—H15C	109.5
C6—C5—H5	120.8

C1—Sn1—C3—C4	−20.4 (4)	C6—C7—C8—C3	0.9 (6)
C2—Sn1—C3—C4	156.0 (3)	C4—C3—C8—C7	−2.1 (6)
Br2—Sn1—C3—C4	−112.9 (3)	Sn1—C3—C8—C7	174.7 (3)
Br1—Sn1—C3—C4	67.2 (3)	C13—N1—C9—C10	1.7 (6)
C1—Sn1—C3—C8	162.9 (3)	N1—C9—C10—C11	−2.4 (6)
C2—Sn1—C3—C8	−20.6 (3)	C15—N2—C11—C10	176.6 (4)
Br2—Sn1—C3—C8	70.5 (3)	C14—N2—C11—C10	−9.5 (6)
Br1—Sn1—C3—C8	−109.5 (3)	C15—N2—C11—C12	−3.3 (6)
C8—C3—C4—C5	1.3 (6)	C14—N2—C11—C12	170.6 (3)
Sn1—C3—C4—C5	−175.5 (3)	C9—C10—C11—N2	−179.0 (4)
C3—C4—C5—C6	0.7 (6)	C9—C10—C11—C12	0.9 (5)
C4—C5—C6—C7	−2.0 (6)	N2—C11—C12—C13	−178.9 (4)
C4—C5—C6—Br3	178.0 (3)	C10—C11—C12—C13	1.2 (5)
C5—C6—C7—C8	1.2 (6)	C9—N1—C13—C12	0.5 (6)
Br3—C6—C7—C8	−178.8 (3)	C11—C12—C13—N1	−1.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.88	2.56	3.319 (3)	146

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[SnBr₂(CH₃)₂(C₆H₄Br)]
M_r	587.76
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3397 (1), 11.1034 (2), 12.2270 (2)
α, β, γ (°)	100.038 (1), 102.472 (1), 94.679 (1)
V (Å³)	950.65 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.64
Crystal size (mm)	0.30 × 0.20 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.208, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	8826, 4346, 3718
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.096, 1.13
No. of reflections	4346
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −1.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.88	2.56	3.319 (3)	146

Acknowledgements

The authors thank the University of Malaya for funding this study (grant No. FS339/2008A).

References

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