4-(Dimethyl-amino)pyridinium dibromido(4-bromo-phen-yl)dimethyl-stannate(IV).

The anion in the title compound, (C(7)H(11)N(2))[SnBr(2)(CH(3))(2)(C(6)H(4)Br)], is five-coordinate within a distorted trans-C(3)SnBr(2) 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 = 587.76

Triclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.096

S = 1.13

4346 reflections

194 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −1.24 e Å−3

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 ▶).

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

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

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

(C7H11N2)[SnBr2(CH3)2(C6H4Br)]	Z = 2
Mr = 587.76	F(000) = 560
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0496P)2 + 0.4605P] where P = (Fo2 + 2Fc2)/3
4346 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −1.24 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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