4,4'-Dimethyl-2,2'-bipyridinium dichloride.

In the title compound, C(12)H(14)N(2) (2+)·2Cl(-), the 4,4'-dimethyl-2,2'-bipyridinium cation is essentially planar (r.m.s. deviation for all non-H atoms = 0.004 Å) and is located on a crystallographic inversion centre. The cations and chloride anions lie in planes parallel to (111) and are connected by N-H⋯Cl and C-H⋯Cl hydrogen bonds.

Related literature

For related literature, see: Eckensberger (2006 ▶); Scheibitz et al. (2005 ▶). For structures containing the 4,4′-dimethyl-2,2′-bipyridinium cation, see: Linden et al. (1999 ▶); Willett et al. (2001 ▶).

Experimental

Crystal data

C12H14N2 2+·2Cl−

M = 257.15

Triclinic,

a = 5.1999 (10) Å

b = 7.2705 (13) Å

c = 8.4785 (15) Å

α = 93.877 (15)°

β = 102.349 (15)°

γ = 97.759 (15)°

V = 308.71 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.50 mm−1

T = 173 (2) K

0.21 × 0.21 × 0.14 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.902, T max = 0.933

3382 measured reflections

1147 independent reflections

926 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.079

S = 0.97

1147 reflections

78 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026615/bi2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026615/bi2297Isup2.hkl

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

C12H14N22+·2(Cl−)	Z = 1
Mr = 257.15	F(000) = 134
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1999 (10) Å	Cell parameters from 3157 reflections
b = 7.2705 (13) Å	θ = 3.6–25.8°
c = 8.4785 (15) Å	µ = 0.50 mm−1
α = 93.877 (15)°	T = 173 K
β = 102.349 (15)°	Block, colourless
γ = 97.759 (15)°	0.21 × 0.21 × 0.14 mm
V = 308.71 (10) Å3

Stoe IPDSII two-circle diffractometer	1147 independent reflections
Radiation source: fine-focus sealed tube	926 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −6→6
Tmin = 0.902, Tmax = 0.933	k = −8→8
3382 measured reflections	l = −10→9

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
1147 reflections	(Δ/σ)max < 0.001
78 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−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
Cl1	0.97517 (12)	0.22553 (7)	0.26756 (7)	0.02679 (18)
N1	0.6763 (4)	0.3002 (2)	0.5264 (2)	0.0219 (4)
H1	0.749 (6)	0.296 (4)	0.444 (4)	0.047 (8)*
C1	0.5194 (4)	0.4274 (2)	0.5570 (2)	0.0195 (4)
C2	0.7255 (5)	0.1636 (3)	0.6223 (3)	0.0254 (5)
H2	0.8362	0.0774	0.5967	0.031*
C3	0.6195 (5)	0.1455 (3)	0.7564 (3)	0.0273 (5)
H3	0.6568	0.0483	0.8232	0.033*
C4	0.4553 (4)	0.2725 (3)	0.7936 (3)	0.0223 (5)
C5	0.4078 (4)	0.4121 (3)	0.6904 (2)	0.0210 (5)
H5	0.2957	0.4988	0.7125	0.025*
C6	0.3345 (5)	0.2555 (3)	0.9383 (3)	0.0287 (5)
H6A	0.2337	0.3585	0.9488	0.043*
H6B	0.4761	0.2605	1.0362	0.043*
H6C	0.2147	0.1365	0.9244	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0285 (3)	0.0269 (3)	0.0288 (3)	0.00927 (19)	0.0113 (2)	0.00399 (18)
N1	0.0236 (10)	0.0228 (8)	0.0223 (10)	0.0070 (7)	0.0082 (8)	0.0064 (7)
C1	0.0204 (11)	0.0195 (9)	0.0181 (10)	0.0029 (8)	0.0031 (8)	0.0028 (8)
C2	0.0262 (12)	0.0238 (9)	0.0293 (12)	0.0086 (8)	0.0081 (10)	0.0084 (8)
C3	0.0284 (13)	0.0244 (10)	0.0295 (12)	0.0066 (9)	0.0032 (10)	0.0110 (9)
C4	0.0231 (11)	0.0217 (9)	0.0204 (10)	−0.0012 (8)	0.0035 (9)	0.0039 (8)
C5	0.0243 (12)	0.0196 (9)	0.0200 (10)	0.0061 (8)	0.0043 (9)	0.0049 (8)
C6	0.0350 (14)	0.0301 (11)	0.0218 (11)	0.0040 (10)	0.0076 (10)	0.0075 (9)

N1—C2	1.342 (3)	C3—H3	0.950
N1—C1	1.360 (2)	C4—C5	1.397 (3)
N1—H1	0.86 (3)	C4—C6	1.498 (3)
C1—C5	1.382 (3)	C5—H5	0.950
C1—C1i	1.484 (4)	C6—H6A	0.980
C2—C3	1.372 (3)	C6—H6B	0.980
C2—H2	0.950	C6—H6C	0.980
C3—C4	1.404 (3)
C2—N1—C1	121.9 (2)	C5—C4—C3	117.6 (2)
C2—N1—H1	113.5 (19)	C5—C4—C6	121.92 (17)
C1—N1—H1	124.6 (19)	C3—C4—C6	120.46 (19)
N1—C1—C5	118.08 (18)	C1—C5—C4	121.78 (17)
N1—C1—C1i	117.0 (2)	C1—C5—H5	119.1
C5—C1—C1i	124.9 (2)	C4—C5—H5	119.1
N1—C2—C3	121.46 (17)	C4—C6—H6A	109.5
N1—C2—H2	119.3	C4—C6—H6B	109.5
C3—C2—H2	119.3	H6A—C6—H6B	109.5
C2—C3—C4	119.17 (19)	C4—C6—H6C	109.5
C2—C3—H3	120.4	H6A—C6—H6C	109.5
C4—C3—H3	120.4	H6B—C6—H6C	109.5
C2—N1—C1—C5	−0.5 (3)	C2—C3—C4—C6	179.4 (2)
C2—N1—C1—C1i	179.7 (2)	N1—C1—C5—C4	0.9 (3)
C1—N1—C2—C3	0.0 (3)	C1i—C1—C5—C4	−179.3 (2)
N1—C2—C3—C4	0.2 (3)	C3—C4—C5—C1	−0.7 (3)
C2—C3—C4—C5	0.1 (3)	C6—C4—C5—C1	−180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.86 (3)	2.17 (3)	3.009 (2)	165 (3)
C2—H2···Cl1ii	0.95	2.75	3.496 (2)	136
C5—H5···Cl1i	0.95	2.62	3.554 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.86 (3)	2.17 (3)	3.009 (2)	165 (3)
C2—H2⋯Cl1i	0.95	2.75	3.496 (2)	136
C5—H5⋯Cl1ii	0.95	2.62	3.554 (2)	169

Symmetry codes: (i) ; (ii) .