4-(Ammonio-meth-yl)pyridinium dichloride.

The title compound, C(6)H(10)N(2) (2+)·2Cl(-), contains a network of 4-(ammonio-meth-yl)pyridinium cations and chloride anions which are inter-connected by N-H⋯Cl hydrogen bonds. The crystal packing is also influenced by inter-molecular π-π stacking inter-actions between identical anti-parallel organic cations with a face-to-face distance of ca 3.52 Å.

Related literature

For common applications of this type of complex, see: Schmidtchen & Berger, (1997 ▶); Pajewski et al. (2004 ▶); Sessler et al. (2003 ▶); Ilioudis et al. (2000 ▶). For structure cohesion, see: Bernstein et al., (1995 ▶); Jin et al., 2005 ▶. For discussion of the C—N—C angle, see: Krygowski et al. (2005 ▶). For bond-length data, see: Oueslati et al. (2006 ▶).

Experimental

Crystal data

C6H10N2 2+·2Cl−

M = 181.06

Triclinic,

a = 7.257 (2) Å

b = 7.339 (3) Å

c = 8.752 (1) Å

α = 79.14 (3)°

β = 70.94 (4)°

γ = 70.19 (3)°

V = 412.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.71 mm−1

T = 293 K

0.16 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3311 measured reflections

1995 independent reflections

1670 reflections with I > 2σ(I)

R int = 0.014

2 standard reflections every 400 reflections intensity decay: 4%

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.030

S = 1.06

1609 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Straver, 1992 ▶); cell refinement: CAD-4 EXPRESS; data reduction: RC93 (Watkin et al., 1994 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034405/bg2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034405/bg2217Isup2.hkl

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

C6H10N22+·2Cl−	Z = 2
Mr = 181.06	F(000) = 188
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.257 (2) Å	Cell parameters from 25 reflections
b = 7.339 (3) Å	θ = 9–11°
c = 8.752 (1) Å	µ = 0.71 mm−1
α = 79.14 (3)°	T = 293 K
β = 70.94 (4)°	Block, colorless
γ = 70.19 (3)°	0.16 × 0.15 × 0.12 mm
V = 412.9 (2) Å3

Enraf–Nonius CAD-4 diffractometer	θmax = 28.0°, θmin = 2.5°
graphite	h = −9→9
ω/2θ scans	k = −9→9
3311 measured reflections	l = −5→11
1995 independent reflections	2 standard reflections every 400 reflections
1670 reflections with I > 2σ(I)	intensity decay: 4%
Rint = 0.014

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.030	[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.823 0.257 0.531
S = 1.06	(Δ/σ)max = 0.001
1609 reflections	Δρmax = 0.29 e Å−3
91 parameters	Δρmin = −0.20 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
Cl1	0.36975 (6)	0.70916 (5)	0.85091 (4)	0.0357
Cl2	0.85118 (6)	0.60355 (5)	0.28807 (4)	0.0385
H1	0.6965	1.2683	0.3992	0.0408*
H2	0.7426	0.9613	0.4009	0.0420*
H3	0.7984	0.7600	0.6294	0.0385*
H4	0.7325	1.2354	0.8318	0.0427*
H5	0.6824	1.4162	0.5939	0.0458*
H6	0.7155	0.9365	1.0028	0.0427*
H7	0.9427	0.8393	0.9126	0.0426*
H8	0.6516	0.6757	0.9274	0.0509*
H9	0.8719	0.5860	0.8743	0.0510*
H10	0.7711	0.6183	1.0429	0.0511*
N1	0.71013 (19)	1.20012 (18)	0.48454 (13)	0.0347
N2	0.76974 (19)	0.66782 (17)	0.94222 (14)	0.0340
C1	0.7421 (2)	1.0097 (2)	0.49055 (16)	0.0330
C2	0.7738 (2)	0.8922 (2)	0.62759 (16)	0.0309
C3	0.76881 (19)	0.97525 (19)	0.76000 (15)	0.0263
C4	0.7352 (2)	1.1743 (2)	0.74770 (16)	0.0350
C5	0.7057 (3)	1.2852 (2)	0.60805 (18)	0.0401
C6	0.8048 (2)	0.8595 (2)	0.91467 (16)	0.0334

	U11	U22	U33	U12	U13	U23
Cl1	0.0459 (2)	0.04261 (19)	0.02508 (16)	−0.01833 (15)	−0.01593 (13)	0.00223 (12)
Cl2	0.0537 (2)	0.03529 (18)	0.02893 (17)	−0.01461 (15)	−0.01409 (14)	−0.00186 (13)
N1	0.0390 (6)	0.0379 (6)	0.0203 (5)	−0.0065 (5)	−0.0087 (4)	0.0048 (4)
N2	0.0397 (6)	0.0337 (6)	0.0276 (5)	−0.0107 (5)	−0.0136 (5)	0.0062 (4)
C1	0.0371 (7)	0.0430 (8)	0.0218 (6)	−0.0148 (6)	−0.0090 (5)	−0.0036 (5)
C2	0.0393 (7)	0.0304 (6)	0.0266 (6)	−0.0136 (5)	−0.0116 (5)	−0.0011 (5)
C3	0.0265 (6)	0.0314 (6)	0.0214 (5)	−0.0101 (5)	−0.0071 (4)	0.0003 (5)
C4	0.0487 (8)	0.0343 (7)	0.0220 (6)	−0.0146 (6)	−0.0070 (6)	−0.0037 (5)
C5	0.0564 (9)	0.0271 (7)	0.0287 (7)	−0.0076 (6)	−0.0074 (6)	−0.0010 (5)
C6	0.0420 (7)	0.0359 (7)	0.0262 (6)	−0.0129 (6)	−0.0162 (5)	0.0024 (5)

H3—C2	0.923	H9—N2	0.899
H2—C1	0.919	N1—C1	1.331 (2)
H5—C5	0.909	N1—C5	1.333 (2)
H8—N2	0.890	N2—C6	1.4750 (19)
H7—C6	0.955	C6—C3	1.5065 (18)
H6—C6	0.961	C1—C2	1.3750 (19)
H1—N1	0.831	C3—C2	1.3929 (18)
H4—C4	0.923	C3—C4	1.386 (2)
H10—N2	0.890	C5—C4	1.371 (2)
H1—N1—C1	118.7	H2—C1—N1	117.8
H1—N1—C5	118.6	H2—C1—C2	122.2
C1—N1—C5	122.62 (12)	N1—C1—C2	120.03 (13)
H9—N2—H8	109.1	C6—C3—C2	123.50 (12)
H9—N2—H10	107.4	C6—C3—C4	117.95 (12)
H8—N2—H10	109.7	C2—C3—C4	118.52 (12)
H9—N2—C6	109.8	H5—C5—N1	116.9
H8—N2—C6	111.9	H5—C5—C4	123.6
H10—N2—C6	108.9	N1—C5—C4	119.51 (14)
N2—C6—H6	109.7	C3—C2—C1	119.26 (13)
N2—C6—H7	108.0	C3—C2—H3	121.6
H6—C6—H7	108.4	C1—C2—H3	119.2
N2—C6—C3	114.31 (11)	C3—C4—H4	121.5
H6—C6—C3	107.3	C3—C4—C5	120.05 (13)
H7—C6—C3	108.9	H4—C4—C5	118.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.83	2.36	3.084 (2)	146
N2—H8···Cl1	0.89	2.28	3.160 (3)	171
N2—H9···Cl2ii	0.90	2.23	3.126 (2)	173
N2—H10···Cl2iii	0.89	2.37	3.190 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.83	2.36	3.084 (2)	146
N2—H8⋯Cl1	0.89	2.28	3.160 (3)	171
N2—H9⋯Cl2ii	0.90	2.23	3.126 (2)	173
N2—H10⋯Cl2iii	0.89	2.37	3.190 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) .