4-Amino-3-ammonio-pyridinium dichloride.

The anions and cations of the title compound, C(5)H(9)N(3) (2+)·2Cl(-), are connected by two chloride-bridged three-centered N-H⋯Cl hydrogen bonds into a three-dimensional network. The aromatic rings are not involved in stacking inter-actions.

Related literature

For bond distances and angles in pyridine, derived from microwave spectra, see: Sørensen et al. (1974 ▶). For details of the N—H⋯Cl hydrogen bond in 4,4′-bipyridine compounds, see: Iyere et al. (2003 ▶). For N—H⋯Cl and secondary inter­actions in pyridinium chlorides, see: Jones et al. (2002 ▶); in 4-acetyl­pyridinium chloride, see: Kochel (2005 ▶). For N—H⋯Cl and O—H⋯Cl contacts in a triphenyl-pyridinium chloride (1/1) adduct, see: Sykora & Cioffi (2007 ▶).

Experimental

Crystal data

C5H9N3 2+·2Cl−

M = 182.05

Monoclinic,

a = 8.362 (2) Å

b = 7.3218 (19) Å

c = 13.239 (3) Å

β = 92.065 (4)°

V = 810.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.73 mm−1

T = 296 (2) K

0.41 × 0.31 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.734, T max = 0.948

3949 measured reflections

1494 independent reflections

1345 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.068

S = 1.14

1494 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536808041962/si2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041962/si2142Isup2.hkl

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

C5H9N32+·2Cl−	F(000) = 376
Mr = 182.05	Dx = 1.493 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2439 reflections
a = 8.362 (2) Å	θ = 3.1–28.2°
b = 7.3218 (19) Å	µ = 0.73 mm−1
c = 13.239 (3) Å	T = 296 K
β = 92.065 (4)°	Block, colorless
V = 810.0 (4) Å3	0.41 × 0.31 × 0.07 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1494 independent reflections
Radiation source: fine-focus sealed tube	1345 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→9
Tmin = 0.734, Tmax = 0.948	k = −6→8
3949 measured reflections	l = −16→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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0285P)2 + 0.2927P] where P = (Fo2 + 2Fc2)/3
1494 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.05806 (5)	0.10977 (6)	0.30663 (3)	0.03884 (15)
Cl2	0.51526 (5)	0.00029 (6)	0.35359 (3)	0.03603 (14)
N1	0.26647 (16)	0.68257 (19)	0.30328 (10)	0.0320 (3)
H1A	0.3291	0.6281	0.2594	0.048*
H1B	0.3026	0.7949	0.3160	0.048*
H1C	0.1670	0.6887	0.2772	0.048*
N2	0.11914 (19)	0.8105 (2)	0.48188 (12)	0.0439 (4)
H2A	0.1182	0.8773	0.4284	0.053*
H2B	0.0737	0.8485	0.5352	0.053*
N3	0.33856 (18)	0.3102 (2)	0.48536 (11)	0.0376 (4)
H3	0.3861	0.2061	0.4869	0.045*
C1	0.3383 (2)	0.4103 (2)	0.40010 (13)	0.0329 (4)
H1	0.3866	0.3649	0.3431	0.039*
C2	0.26762 (18)	0.5778 (2)	0.39701 (12)	0.0271 (3)
C3	0.19067 (19)	0.6488 (2)	0.48205 (12)	0.0296 (4)
C4	0.1921 (2)	0.5357 (2)	0.56891 (13)	0.0366 (4)
H4	0.1422	0.5751	0.6267	0.044*
C5	0.2655 (2)	0.3703 (2)	0.56862 (14)	0.0391 (4)
H5	0.2656	0.2976	0.6262	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0414 (3)	0.0428 (3)	0.0324 (2)	0.00951 (19)	0.00267 (18)	−0.00166 (18)
Cl2	0.0410 (3)	0.0298 (2)	0.0379 (2)	0.00388 (17)	0.01080 (18)	0.00231 (17)
N1	0.0335 (7)	0.0344 (8)	0.0283 (7)	0.0006 (6)	0.0044 (6)	−0.0002 (6)
N2	0.0617 (10)	0.0360 (8)	0.0348 (8)	0.0202 (8)	0.0147 (7)	0.0032 (7)
N3	0.0403 (8)	0.0265 (7)	0.0462 (9)	0.0089 (6)	0.0023 (7)	0.0007 (6)
C1	0.0319 (9)	0.0323 (9)	0.0346 (9)	0.0018 (7)	0.0031 (7)	−0.0054 (7)
C2	0.0260 (8)	0.0283 (8)	0.0270 (8)	−0.0013 (6)	0.0012 (6)	−0.0008 (6)
C3	0.0309 (8)	0.0274 (8)	0.0306 (8)	0.0029 (7)	0.0017 (7)	−0.0016 (7)
C4	0.0434 (10)	0.0377 (10)	0.0291 (9)	0.0069 (8)	0.0069 (7)	0.0021 (7)
C5	0.0459 (10)	0.0366 (10)	0.0349 (10)	0.0038 (8)	0.0013 (8)	0.0077 (8)

N1—C2	1.458 (2)	N3—H3	0.8600
N1—H1A	0.8900	C1—C2	1.361 (2)
N1—H1B	0.8900	C1—H1	0.9300
N1—H1C	0.8900	C2—C3	1.416 (2)
N2—C3	1.326 (2)	C3—C4	1.417 (2)
N2—H2A	0.8600	C4—C5	1.358 (3)
N2—H2B	0.8600	C4—H4	0.9300
N3—C1	1.346 (2)	C5—H5	0.9300
N3—C5	1.353 (2)
C2—N1—H1A	109.5	C2—C1—H1	119.9
C2—N1—H1B	109.5	C1—C2—C3	121.06 (15)
H1A—N1—H1B	109.5	C1—C2—N1	119.26 (14)
C2—N1—H1C	109.5	C3—C2—N1	119.65 (14)
H1A—N1—H1C	109.5	N2—C3—C2	122.95 (15)
H1B—N1—H1C	109.5	N2—C3—C4	120.92 (15)
C3—N2—H2A	120.0	C2—C3—C4	116.12 (15)
C3—N2—H2B	120.0	C5—C4—C3	120.64 (16)
H2A—N2—H2B	120.0	C5—C4—H4	119.7
C1—N3—C5	121.29 (15)	C3—C4—H4	119.7
C1—N3—H3	119.4	N3—C5—C4	120.64 (16)
C5—N3—H3	119.4	N3—C5—H5	119.7
N3—C1—C2	120.23 (16)	C4—C5—H5	119.7
N3—C1—H1	119.9
C5—N3—C1—C2	1.9 (3)	N1—C2—C3—C4	177.72 (15)
N3—C1—C2—C3	−1.2 (2)	N2—C3—C4—C5	179.99 (18)
N3—C1—C2—N1	−178.99 (14)	C2—C3—C4—C5	0.7 (3)
C1—C2—C3—N2	−179.35 (16)	C1—N3—C5—C4	−1.2 (3)
N1—C2—C3—N2	−1.6 (2)	C3—C4—C5—N3	−0.1 (3)
C1—C2—C3—C4	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2i	0.89	2.22	3.1142 (15)	178
N1—H1B···Cl2ii	0.89	2.37	3.1754 (16)	151
N1—H1C···Cl1iii	0.89	2.23	3.0790 (16)	160
N2—H2A···Cl1ii	0.86	2.39	3.2188 (17)	163
N2—H2B···Cl1iv	0.86	2.42	3.2672 (17)	168
N3—H3···Cl2	0.86	2.59	3.2499 (16)	135
N3—H3···Cl2v	0.86	2.70	3.3198 (16)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2i	0.89	2.22	3.1142 (15)	178
N1—H1B⋯Cl2ii	0.89	2.37	3.1754 (16)	151
N1—H1C⋯Cl1iii	0.89	2.23	3.0790 (16)	160
N2—H2A⋯Cl1ii	0.86	2.39	3.2188 (17)	163
N2—H2B⋯Cl1iv	0.86	2.42	3.2672 (17)	168
N3—H3⋯Cl2	0.86	2.59	3.2499 (16)	135
N3—H3⋯Cl2v	0.86	2.70	3.3198 (16)	130

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