1,1'-Dimethyl-4,4'-bipyridinium bis-(triiodide).

In the title compound, C(12)H(14)N(2) (2+)·2I(3) (-), the 1,1'-dimethyl-4,4'-bipyridinium (DMBP) dication is charge balanced by two triiodide ions. The DMBP dication is planar within 0.010 (5) Å. The asymmetric unit contains only half of the dication, the other half being generated by an inversion center. Weak C-H⋯I inter-actions link the ions into sheets parallel to (121).

Related literature

For a dication with similar geometry, see: Russell & Wallwork (1972 ▶). For anions with comparable geometry, see: Marsh (2004 ▶); Madsen et al. (1999 ▶).

Experimental

Crystal data

C12H14N2 2+·2I3 −

M = 947.65

Triclinic,

a = 7.5457 (4) Å

b = 7.9541 (6) Å

c = 9.3029 (6) Å

α = 90.306 (5)°

β = 94.192 (4)°

γ = 102.332 (5)°

V = 543.88 (6) Å3

Z = 1

Mo Kα radiation

μ = 8.56 mm−1

T = 296 K

0.22 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.211, T max = 0.504

12956 measured reflections

2683 independent reflections

1468 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.073

S = 1.02

2683 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.86 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015207/ez2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015207/ez2167Isup2.hkl

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

C12H14N22+·2I3−	Z = 1
Mr = 947.65	F(000) = 418
Triclinic, P1	Dx = 2.893 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5457 (4) Å	Cell parameters from 4412 reflections
b = 7.9541 (6) Å	θ = 2.6–27.6°
c = 9.3029 (6) Å	µ = 8.56 mm−1
α = 90.306 (5)°	T = 296 K
β = 94.192 (4)°	Prism, black
γ = 102.332 (5)°	0.22 × 0.16 × 0.08 mm
V = 543.88 (6) Å3

Bruker SMART CCD area-detector diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	1468 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 28.3°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.211, Tmax = 0.504	k = −10→10
12956 measured reflections	l = −11→12

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.005P)2 + 2.2853P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2683 reflections	Δρmax = 0.97 e Å−3
93 parameters	Δρmin = −0.86 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
I1	0.11371 (7)	0.64766 (7)	0.84204 (6)	0.0705 (2)
I2	0.19121 (6)	0.80427 (6)	0.56237 (6)	0.05927 (17)
I3	0.25337 (8)	0.96496 (8)	0.28546 (6)	0.0816 (2)
N1	0.3773 (9)	0.2800 (7)	0.8128 (7)	0.0588 (16)
C1	0.3276 (13)	0.1852 (11)	0.9438 (9)	0.085 (3)
H1A	0.4248	0.2166	1.0179	0.128*
H1B	0.3064	0.0638	0.9235	0.128*
H1C	0.2190	0.2131	0.9758	0.128*
C2	0.5358 (12)	0.3875 (11)	0.8116 (9)	0.074 (2)
H2	0.6149	0.4034	0.8944	0.088*
C3	0.2652 (11)	0.2566 (10)	0.6956 (10)	0.072 (2)
H3	0.1526	0.1813	0.6969	0.086*
C4	0.5864 (9)	0.4764 (10)	0.6903 (8)	0.061 (2)
H4	0.6984	0.5532	0.6924	0.074*
C5	0.3120 (10)	0.3414 (10)	0.5722 (8)	0.066 (2)
H5	0.2309	0.3216	0.4906	0.079*
C6	0.4743 (8)	0.4540 (7)	0.5658 (7)	0.0396 (14)

	U11	U22	U33	U12	U13	U23
I1	0.0689 (4)	0.0899 (4)	0.0576 (3)	0.0291 (3)	0.0010 (3)	0.0076 (3)
I2	0.0503 (3)	0.0648 (3)	0.0672 (3)	0.0224 (2)	0.0040 (2)	0.0045 (2)
I3	0.0838 (4)	0.0895 (4)	0.0816 (4)	0.0335 (3)	0.0267 (3)	0.0292 (3)
N1	0.066 (4)	0.051 (4)	0.063 (4)	0.016 (3)	0.016 (4)	0.010 (3)
C1	0.106 (7)	0.076 (6)	0.075 (6)	0.017 (5)	0.017 (5)	0.015 (5)
C2	0.071 (6)	0.088 (6)	0.061 (5)	0.020 (5)	−0.011 (4)	0.015 (5)
C3	0.062 (5)	0.066 (5)	0.078 (6)	−0.010 (4)	0.011 (5)	−0.003 (5)
C4	0.039 (4)	0.077 (5)	0.058 (5)	−0.004 (4)	−0.016 (3)	0.006 (4)
C5	0.052 (5)	0.080 (6)	0.054 (5)	−0.007 (4)	−0.003 (4)	−0.001 (4)
C6	0.031 (3)	0.032 (3)	0.054 (4)	0.005 (3)	−0.002 (3)	−0.003 (3)

I1—I2	2.9341 (8)	C2—H2	0.9300
I2—I3	2.9061 (8)	C3—C5	1.364 (10)
N1—C2	1.314 (9)	C3—H3	0.9300
N1—C3	1.317 (9)	C4—C6	1.371 (8)
N1—C1	1.467 (9)	C4—H4	0.9300
C1—H1A	0.9600	C5—C6	1.359 (9)
C1—H1B	0.9600	C5—H5	0.9300
C1—H1C	0.9600	C6—C6i	1.464 (12)
C2—C4	1.370 (10)
I3—I2—I1	177.49 (2)	N1—C3—C5	120.9 (7)
C2—N1—C3	119.7 (7)	N1—C3—H3	119.5
C2—N1—C1	119.8 (7)	C5—C3—H3	119.5
C3—N1—C1	120.5 (7)	C2—C4—C6	121.0 (6)
N1—C1—H1A	109.5	C2—C4—H4	119.5
N1—C1—H1B	109.5	C6—C4—H4	119.5
H1A—C1—H1B	109.5	C6—C5—C3	121.6 (7)
N1—C1—H1C	109.5	C6—C5—H5	119.2
H1A—C1—H1C	109.5	C3—C5—H5	119.2
H1B—C1—H1C	109.5	C5—C6—C4	115.9 (6)
N1—C2—C4	121.0 (7)	C5—C6—C6i	122.1 (7)
N1—C2—H2	119.5	C4—C6—C6i	122.1 (7)
C4—C2—H2	119.5
C3—N1—C2—C4	0.3 (12)	N1—C3—C5—C6	−0.7 (13)
C1—N1—C2—C4	179.4 (7)	C3—C5—C6—C4	0.0 (11)
C2—N1—C3—C5	0.6 (12)	C3—C5—C6—C6i	−179.8 (8)
C1—N1—C3—C5	−178.5 (7)	C2—C4—C6—C5	0.9 (11)
N1—C2—C4—C6	−1.0 (12)	C2—C4—C6—C6i	−179.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···I3ii	0.93	3.05	3.951 (8)	163
C2—H2···I1iii	0.93	3.16	4.066 (8)	164
C5—H5···I2ii	0.93	3.13	3.839 (7)	135

I1—I2	2.9341 (8)
I2—I3	2.9061 (8)

I3—I2—I1

177.49 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯I3i	0.93	3.05	3.951 (8)	163
C2—H2⋯I1ii	0.93	3.16	4.066 (8)	164
C5—H5⋯I2i	0.93	3.13	3.839 (7)	135

Symmetry codes: (i) ; (ii) .