4-(Dimethylamino)pyridinium dibromidotriphenyl-stannate(IV).

The anion in the title salt, (C(7)H(11)N(2))[SnBr(2)(C(6)H(5))(3)], lies on a twofold rotation axis that passes through the metal atom as well as the C(ipso)-C(para) atoms of one of the aromatic rings. The metal center is five-coordinate in a trans-Br(2)SnC(3) trigonal bipyramidal geometry. The cation is disordered about a center of inversion.

Related literature

For the crystal structures of dibromidotriorganostannates, see: Aslanov et al. (1977 ▶); Spek et al. (2004 ▶); Wharf & Simard (1991 ▶).

Experimental

Crystal data

(C7H11N2)[SnBr2(C6H5)3]

M = 632.99

Monoclinic,

a = 15.5955 (2) Å

b = 10.6897 (1) Å

c = 14.8204 (2) Å

β = 93.924 (1)°

V = 2464.93 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.29 mm−1

T = 100 K

0.3 × 0.2 × 0.1 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.368, T max = 0.651

24740 measured reflections

2840 independent reflections

2328 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.069

S = 1.05

2840 reflections

180 parameters

69 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −1.16 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/S1600536808011094/sg2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011094/sg2227Isup2.hkl

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

(C7H11N2)[SnBr2(C6H5)3]	F000 = 1240
Mr = 632.99	Dx = 1.706 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7191 reflections
a = 15.5955 (2) Å	θ = 2.3–24.8º
b = 10.6897 (1) Å	µ = 4.29 mm−1
c = 14.8204 (2) Å	T = 100 K
β = 93.924 (1)º	Block, yellow
V = 2464.93 (5) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Bruker SMART APEXII diffractometer	2840 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 100 K	θmax = 27.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.368, Tmax = 0.651	k = −13→13
24740 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0352P)2 + 2.1489P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2840 reflections	Δρmax = 0.34 e Å−3
180 parameters	Δρmin = −1.16 e Å−3
69 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.5000	0.76516 (2)	0.7500	0.03975 (9)
Br1	0.56766 (2)	0.76825 (3)	0.928473 (19)	0.05538 (10)
C1	0.60873 (15)	0.8708 (2)	0.71394 (16)	0.0377 (5)
C2	0.69169 (17)	0.8273 (3)	0.73324 (19)	0.0504 (6)
H2	0.7004	0.7512	0.7629	0.061*
C3	0.76163 (18)	0.8960 (3)	0.7087 (2)	0.0613 (8)
H3	0.8169	0.8647	0.7206	0.074*
C4	0.7501 (2)	1.0094 (3)	0.6672 (2)	0.0647 (9)
H4	0.7974	1.0557	0.6515	0.078*
C5	0.6686 (2)	1.0548 (3)	0.6489 (2)	0.0648 (8)
H5	0.6603	1.1322	0.6210	0.078*
C6	0.59864 (18)	0.9851 (3)	0.6720 (2)	0.0518 (7)
H6	0.5435	1.0162	0.6588	0.062*
C7	0.5000	0.5641 (3)	0.7500	0.0372 (7)
C8	0.51067 (16)	0.4971 (3)	0.67160 (19)	0.0461 (6)
H8	0.5173	0.5399	0.6179	0.055*
C9	0.51168 (18)	0.3672 (3)	0.6717 (2)	0.0557 (7)
H9	0.5203	0.3239	0.6187	0.067*
C10	0.5000	0.3029 (4)	0.7500	0.0595 (11)
H10	0.5000	0.2159	0.7500	0.071*
N1	0.3033 (4)	0.9766 (5)	1.0723 (4)	0.0750 (16)	0.50
H1	0.3207	1.0468	1.0950	0.090*	0.50
C11	0.3619 (5)	0.8914 (9)	1.0461 (4)	0.065 (4)	0.50
H11	0.4203	0.9101	1.0530	0.078*	0.50
C12	0.3361 (4)	0.7792 (6)	1.0100 (4)	0.0548 (14)	0.50
H12	0.3757	0.7209	0.9920	0.066*	0.50
C13	0.2490 (6)	0.7552 (8)	1.0011 (6)	0.0454 (9)	0.50
C14	0.1886 (3)	0.8397 (5)	1.0268 (4)	0.0547 (14)	0.50
H14	0.1302	0.8215	1.0199	0.066*	0.50
C15	0.2171 (6)	0.9515 (9)	1.0628 (6)	0.091 (9)	0.50
H15	0.1778	1.0104	1.0808	0.109*	0.50
N2	0.2210 (3)	0.6420 (4)	0.9598 (3)	0.0512 (11)	0.50
C16	0.2813 (5)	0.5487 (7)	0.9338 (7)	0.059 (6)	0.50
H16A	0.3126	0.5803	0.8850	0.089*	0.50
H16B	0.2508	0.4744	0.9145	0.089*	0.50
H16C	0.3208	0.5295	0.9844	0.089*	0.50
C17	0.1314 (6)	0.6173 (12)	0.9365 (9)	0.077 (4)	0.50
H17A	0.0998	0.6239	0.9897	0.116*	0.50
H17B	0.1250	0.5345	0.9119	0.116*	0.50
H17C	0.1096	0.6772	0.8924	0.116*	0.50

	U11	U22	U33	U12	U13	U23
Sn1	0.03660 (13)	0.03341 (14)	0.04972 (15)	0.000	0.00641 (10)	0.000
Br1	0.05950 (19)	0.0641 (2)	0.04166 (16)	−0.00651 (13)	−0.00302 (13)	−0.00418 (12)
C1	0.0366 (12)	0.0376 (13)	0.0393 (12)	−0.0018 (10)	0.0044 (10)	−0.0026 (10)
C2	0.0446 (14)	0.0523 (17)	0.0544 (16)	0.0075 (12)	0.0036 (12)	0.0014 (13)
C3	0.0356 (14)	0.085 (2)	0.0640 (19)	−0.0006 (14)	0.0056 (13)	−0.0193 (17)
C4	0.0598 (19)	0.073 (2)	0.0630 (19)	−0.0290 (17)	0.0163 (15)	−0.0189 (17)
C5	0.078 (2)	0.0459 (17)	0.070 (2)	−0.0193 (15)	0.0078 (17)	0.0074 (15)
C6	0.0485 (15)	0.0409 (15)	0.0651 (18)	−0.0002 (12)	−0.0021 (13)	0.0052 (13)
C7	0.0311 (16)	0.0348 (17)	0.0456 (19)	0.000	0.0023 (14)	0.000
C8	0.0429 (14)	0.0454 (14)	0.0503 (15)	−0.0012 (11)	0.0056 (11)	−0.0031 (12)
C9	0.0529 (16)	0.0472 (16)	0.0668 (19)	0.0020 (13)	0.0029 (14)	−0.0157 (14)
C10	0.055 (2)	0.038 (2)	0.085 (3)	0.000	−0.001 (2)	0.000
N1	0.080 (4)	0.075 (4)	0.070 (3)	−0.024 (3)	0.002 (3)	−0.017 (3)
C11	0.057 (5)	0.077 (7)	0.061 (5)	−0.010 (5)	−0.003 (4)	−0.002 (4)
C12	0.050 (3)	0.066 (4)	0.049 (3)	0.000 (3)	0.003 (2)	0.004 (3)
C13	0.051 (2)	0.050 (2)	0.0354 (18)	−0.0006 (18)	0.0071 (16)	0.0045 (17)
C14	0.050 (3)	0.058 (3)	0.057 (3)	−0.004 (3)	0.009 (3)	−0.007 (3)
C15	0.096 (12)	0.091 (12)	0.088 (12)	−0.004 (8)	0.017 (8)	−0.006 (8)
N2	0.061 (3)	0.046 (2)	0.047 (3)	−0.002 (2)	0.003 (2)	−0.001 (2)
C16	0.068 (8)	0.049 (7)	0.061 (8)	0.005 (5)	0.014 (5)	−0.018 (5)
C17	0.073 (7)	0.068 (6)	0.088 (6)	−0.018 (5)	−0.005 (5)	−0.006 (5)

Sn1—C1	2.135 (2)	C10—C9i	1.372 (4)
Sn1—C1i	2.135 (2)	C10—H10	0.9300
Sn1—C7	2.149 (3)	N1—C11	1.366 (9)
Sn1—Br1i	2.7801 (3)	N1—C15	1.369 (9)
Sn1—Br1	2.7801 (3)	N1—H1	0.8600
C1—C6	1.375 (4)	C11—C12	1.363 (9)
C1—C2	1.386 (3)	C11—H11	0.9300
C2—C3	1.384 (4)	C12—C13	1.379 (9)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.365 (5)	C13—C14	1.378 (9)
C3—H3	0.9300	C13—N2	1.412 (8)
C4—C5	1.371 (5)	C14—C15	1.370 (9)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.383 (4)	C15—H15	0.9300
C5—H5	0.9300	N2—C16	1.441 (7)
C6—H6	0.9300	N2—C17	1.441 (8)
C7—C8	1.384 (3)	C16—H16A	0.9600
C7—C8i	1.384 (3)	C16—H16B	0.9600
C8—C9	1.389 (4)	C16—H16C	0.9600
C8—H8	0.9300	C17—H17A	0.9600
C9—C10	1.372 (4)	C17—H17B	0.9600
C9—H9	0.9300	C17—H17C	0.9600
C1—Sn1—C1i	116.17 (13)	C9—C8—C7	121.2 (3)
C1—Sn1—C7	121.92 (6)	C9—C8—H8	119.4
C1i—Sn1—C7	121.92 (6)	C7—C8—H8	119.4
C1—Sn1—Br1	88.61 (6)	C10—C9—C8	120.0 (3)
C1—Sn1—Br1i	90.68 (6)	C10—C9—H9	120.0
C1i—Sn1—Br1i	88.61 (6)	C8—C9—H9	120.0
C7—Sn1—Br1	90.68 (1)	C9—C10—C9i	119.8 (4)
C7—Sn1—Br1i	90.68 (1)	C9—C10—H10	120.1
C1i—Sn1—Br1	90.68 (6)	C9i—C10—H10	120.1
Br1—Sn1—Br1i	178.64 (2)	C11—N1—C15	120.8 (7)
C6—C1—C2	117.9 (2)	C11—N1—H1	119.6
C6—C1—Sn1	120.98 (18)	C15—N1—H1	119.6
C2—C1—Sn1	121.13 (19)	C12—C11—N1	120.8 (7)
C3—C2—C1	120.6 (3)	C12—C11—H11	119.6
C3—C2—H2	119.7	N1—C11—H11	119.6
C1—C2—H2	119.7	C11—C12—C13	117.7 (6)
C4—C3—C2	120.5 (3)	C11—C12—H12	121.2
C4—C3—H3	119.7	C13—C12—H12	121.2
C2—C3—H3	119.7	C14—C13—C12	122.6 (7)
C3—C4—C5	119.7 (3)	C14—C13—N2	119.0 (7)
C3—C4—H4	120.2	C12—C13—N2	118.3 (7)
C5—C4—H4	120.2	C15—C14—C13	118.0 (7)
C4—C5—C6	119.8 (3)	C15—C14—H14	121.0
C4—C5—H5	120.1	C13—C14—H14	121.0
C6—C5—H5	120.1	C14—C15—N1	120.1 (7)
C1—C6—C5	121.5 (3)	C14—C15—H15	120.0
C1—C6—H6	119.2	N1—C15—H15	120.0
C5—C6—H6	119.2	C13—N2—C16	121.4 (6)
C8—C7—C8i	117.7 (3)	C13—N2—C17	121.8 (7)
C8—C7—Sn1	121.13 (17)	C16—N2—C17	116.7 (7)
C8i—C7—Sn1	121.13 (17)
C1i—Sn1—C1—C6	−32.12 (19)	C1—Sn1—C7—C8i	119.08 (14)
C7—Sn1—C1—C6	147.88 (19)	C1i—Sn1—C7—C8i	−60.92 (14)
Br1i—Sn1—C1—C6	56.7 (2)	Br1i—Sn1—C7—C8i	−149.70 (12)
Br1—Sn1—C1—C6	−122.2 (2)	Br1—Sn1—C7—C8i	30.30 (12)
C1i—Sn1—C1—C2	146.9 (2)	C8i—C7—C8—C9	−0.75 (19)
C7—Sn1—C1—C2	−33.1 (2)	Sn1—C7—C8—C9	179.25 (19)
Br1i—Sn1—C1—C2	−124.3 (2)	C7—C8—C9—C10	1.5 (4)
Br1—Sn1—C1—C2	56.9 (2)	C8—C9—C10—C9i	−0.74 (18)
C6—C1—C2—C3	−1.6 (4)	C15—N1—C11—C12	−0.1 (3)
Sn1—C1—C2—C3	179.4 (2)	N1—C11—C12—C13	−0.1 (3)
C1—C2—C3—C4	1.8 (5)	C11—C12—C13—C14	0.2 (7)
C2—C3—C4—C5	−0.7 (5)	C11—C12—C13—N2	177.0 (7)
C3—C4—C5—C6	−0.4 (5)	C12—C13—C14—C15	−0.2 (10)
C2—C1—C6—C5	0.4 (4)	N2—C13—C14—C15	−177.0 (7)
Sn1—C1—C6—C5	179.5 (2)	C13—C14—C15—N1	0.1 (9)
C4—C5—C6—C1	0.6 (5)	C11—N1—C15—C14	0.1 (7)
C1—Sn1—C7—C8	−60.92 (14)	C14—C13—N2—C16	−178.4 (7)
C1i—Sn1—C7—C8	119.08 (14)	C12—C13—N2—C16	4.7 (11)
Br1i—Sn1—C7—C8	30.30 (12)	C14—C13—N2—C17	5.7 (12)
Br1—Sn1—C7—C8	−149.70 (12)	C12—C13—N2—C17	−171.2 (9)

Sn1—C1	2.135 (2)
Sn1—C7	2.149 (3)
Sn1—Br1	2.7801 (3)

C1—Sn1—C1i	116.17 (13)
C1—Sn1—C7	121.92 (6)
C1—Sn1—Br1	88.61 (6)
C1—Sn1—Br1i	90.68 (6)
C7—Sn1—Br1	90.68 (1)
Br1—Sn1—Br1i	178.64 (2)

Symmetry code: (i) .