2-Amino-5-chloro-pyridinium nitrate.

The title structure, C(5)H(6)ClN(2) (+)·NO(3) (-), is held together by extensive hydrogen bonding between the NO(3) (-) ions and 2-amino-5-chloro-pyridinium H atoms. The cation-anion N-H⋯O hydrogen bonds link the ions into a zigzag- chain which develops parallel to the b axis. The structure may be compared with that of the related 2-amino-5-cyano-pyridinium nitrate.

Related literature

For metal-organic frameworks involving amine derivatives, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶). For related structures, see: Pourayoubi et al. (2007 ▶); Rademeyer (2005 ▶, 2007 ▶); Dai (2008 ▶).

Experimental

Crystal data

C5H6ClN2 +·NO3 −

M = 191.58

Monoclinic,

a = 4.788 (4) Å

b = 13.029 (3) Å

c = 12.779 (2) Å

β = 101.445 (18)°

V = 781.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 299 K

0.40 × 0.40 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.838, T max = 0.914

2057 measured reflections

1691 independent reflections

1312 reflections with I > 2σ(I)

R int = 0.017

2 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.02

1691 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904149X/dn2495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904149X/dn2495Isup2.hkl

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

C5H6ClN2+·NO3−	F(000) = 392.0
Mr = 191.58	Dx = 1.620 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.788 (4) Å	θ = 10–15°
b = 13.029 (3) Å	µ = 0.46 mm−1
c = 12.779 (2) Å	T = 299 K
β = 101.445 (18)°	Prism, yellow
V = 781.3 (7) Å3	0.40 × 0.40 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1312 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 27.0°, θmin = 2.3°
Nonprofiled ω/2θ scans	h = −1→6
Absorption correction: ψ scan (North et al., 1968)	k = −16→1
Tmin = 0.838, Tmax = 0.914	l = −16→15
2057 measured reflections	2 standard reflections every 120 min
1691 independent reflections	intensity decay: none

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1965P] where P = (Fo2 + 2Fc2)/3
1691 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied (North et al., 1968).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.35469 (12)	0.37026 (4)	0.42068 (4)	0.0558 (2)
N1	−0.4403 (4)	−0.03452 (11)	0.63887 (12)	0.0404 (4)
N2	−0.2955 (4)	0.22776 (13)	0.73365 (13)	0.0484 (4)
H2A	−0.3487	0.1646	0.7301	0.058*
H2B	−0.3440	0.2679	0.7804	0.058*
N3	−0.0639 (3)	0.19881 (11)	0.59367 (12)	0.0373 (3)
H3	−0.1153	0.1356	0.5943	0.045*
C1	−0.1377 (4)	0.26344 (13)	0.66666 (13)	0.0349 (4)
C2	−0.0428 (4)	0.36615 (14)	0.66731 (15)	0.0399 (4)
H2	−0.0854	0.4122	0.7175	0.048*
C3	0.1112 (4)	0.39778 (15)	0.59430 (15)	0.0411 (4)
H3A	0.1751	0.4652	0.5950	0.049*
C4	0.1737 (4)	0.32811 (14)	0.51762 (14)	0.0373 (4)
C5	0.0878 (4)	0.22883 (14)	0.51921 (14)	0.0383 (4)
H5	0.1318	0.1819	0.4701	0.046*
O1	−0.5381 (3)	−0.12309 (10)	0.62043 (12)	0.0545 (4)
O2	−0.2376 (3)	−0.00614 (11)	0.59683 (13)	0.0523 (4)
O3	−0.5384 (4)	0.02366 (12)	0.70018 (14)	0.0635 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0681 (4)	0.0477 (3)	0.0615 (3)	−0.0101 (2)	0.0366 (3)	−0.0017 (2)
N1	0.0517 (9)	0.0326 (8)	0.0380 (8)	−0.0009 (7)	0.0115 (7)	0.0026 (6)
N2	0.0649 (10)	0.0414 (9)	0.0454 (9)	−0.0019 (8)	0.0269 (8)	−0.0030 (7)
N3	0.0455 (8)	0.0264 (7)	0.0427 (8)	−0.0034 (6)	0.0156 (7)	−0.0047 (6)
C1	0.0387 (9)	0.0339 (8)	0.0324 (8)	0.0019 (7)	0.0081 (7)	−0.0013 (7)
C2	0.0495 (10)	0.0318 (9)	0.0389 (9)	0.0003 (7)	0.0098 (8)	−0.0077 (7)
C3	0.0495 (10)	0.0290 (8)	0.0445 (10)	−0.0039 (7)	0.0088 (8)	−0.0051 (7)
C4	0.0384 (9)	0.0362 (9)	0.0396 (9)	−0.0013 (7)	0.0136 (7)	−0.0006 (7)
C5	0.0444 (9)	0.0333 (9)	0.0406 (9)	−0.0005 (7)	0.0171 (8)	−0.0082 (7)
O1	0.0784 (10)	0.0347 (7)	0.0552 (8)	−0.0152 (7)	0.0251 (8)	−0.0006 (6)
O2	0.0590 (9)	0.0369 (7)	0.0685 (9)	−0.0069 (6)	0.0308 (8)	−0.0010 (6)
O3	0.0788 (11)	0.0513 (9)	0.0708 (10)	−0.0089 (8)	0.0403 (9)	−0.0158 (8)

Cl1—C4	1.7358 (19)	N3—H3	0.8600
N1—O3	1.247 (2)	C1—C2	1.413 (3)
N1—O1	1.250 (2)	C2—C3	1.363 (3)
N1—O2	1.255 (2)	C2—H2	0.9300
N2—C1	1.333 (2)	C3—C4	1.411 (3)
N2—H2A	0.8600	C3—H3A	0.9300
N2—H2B	0.8600	C4—C5	1.359 (3)
N3—C1	1.355 (2)	C5—H5	0.9300
N3—C5	1.364 (2)
O3—N1—O1	120.41 (17)	C3—C2—C1	119.96 (16)
O3—N1—O2	120.64 (16)	C3—C2—H2	120.0
O1—N1—O2	118.93 (16)	C1—C2—H2	120.0
C1—N2—H2A	120.0	C2—C3—C4	119.95 (17)
C1—N2—H2B	120.0	C2—C3—H3A	120.0
H2A—N2—H2B	120.0	C4—C3—H3A	120.0
C1—N3—C5	123.36 (15)	C5—C4—C3	119.70 (17)
C1—N3—H3	118.3	C5—C4—Cl1	120.49 (14)
C5—N3—H3	118.3	C3—C4—Cl1	119.80 (14)
N2—C1—N3	118.95 (16)	C4—C5—N3	119.23 (16)
N2—C1—C2	123.31 (16)	C4—C5—H5	120.4
N3—C1—C2	117.74 (15)	N3—C5—H5	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	2.05	2.900 (2)	169
N2—H2B···O1i	0.86	2.06	2.912 (2)	174
N3—H3···O2	0.86	1.94	2.800 (2)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	2.05	2.900 (2)	169
N2—H2B⋯O1i	0.86	2.06	2.912 (2)	174
N3—H3⋯O2	0.86	1.94	2.800 (2)	179

Symmetry code: (i) .