2-Amino-3-nitro-pyridinium perchlorate.

The title compound, C(5)H(6)N(3)O(2) (+)·ClO(4) (-), is comprised of discrete perchlorate anions and 2-amino-3-nitro-pyridinium cations. The anion has a typical tetra-hedral geometry while the cation presents a nearly planar [maximum deviation = 0.007 (8) Å] pyridinium ring. Undulating [C(5)H(6)N(3)O(2) (+)](n) chains extending along the c-axis direction are linked via N-H⋯O hydrogen bonds. The cations are further connected to the anions by N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Akriche & Rzaigui (2000 ▶, 2009a ▶,b ▶,c ▶); Nicoud et al. (1997 ▶). For details of hydrogen bonding, see: Steiner & Saenger (1994 ▶). For bond lengths in related structures, see: Aakeröy et al. (1998 ▶); Messai et al. (2009 ▶).

Experimental

Crystal data

C5H6N3O2 +·ClO4 −

M = 239.58

Monoclinic,

a = 5.888 (2) Å

b = 18.342 (6) Å

c = 9.170 (4) Å

β = 116.61 (3)°

V = 885.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 293 K

0.29 × 0.25 × 0.21 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.725, T max = 0.912

3574 measured reflections

2130 independent reflections

1109 reflections with I > 2σ(I)

R int = 0.046

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.189

S = 1.00

2130 reflections

136 parameters

66 restraints

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.30 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: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000425/pv2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000425/pv2249Isup2.hkl

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

C5H6N3O2+·ClO4−	F(000) = 488
Mr = 239.58	Dx = 1.797 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.888 (2) Å	θ = 9–11°
b = 18.342 (6) Å	µ = 0.45 mm−1
c = 9.170 (4) Å	T = 293 K
β = 116.61 (3)°	Prism, colorless
V = 885.3 (6) Å3	0.29 × 0.25 × 0.21 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	1109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
graphite	θmax = 28.0°, θmin = 2.2°
Non–profiled ω scans	h = −7→7
Absorption correction: multi-scan (Blessing, 1995)	k = −24→0
Tmin = 0.725, Tmax = 1.101	l = −11→12
3574 measured reflections	2 standard reflections every 120 min
2130 independent reflections	intensity decay: 1%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.096P)2] where P = (Fo2 + 2Fc2)/3
2130 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.52 e Å−3
66 restraints	Δρmin = −0.30 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
O1	0.6409 (9)	0.45343 (19)	0.9234 (4)	0.0967 (12)
O2	0.9810 (6)	0.4058 (2)	0.8940 (5)	0.1130 (15)
O3	0.6657 (6)	0.46634 (17)	0.6814 (4)	0.0750 (9)
O4	0.5876 (7)	0.35339 (19)	0.7581 (5)	0.0970 (12)
N1	0.3798 (6)	0.58877 (17)	0.7702 (4)	0.0563 (8)
H1	0.4836	0.5686	0.8602	0.068*
N2	0.7098 (6)	0.6608 (2)	0.7939 (4)	0.0663 (10)
H2A	0.8051	0.6381	0.8826	0.080*
H2B	0.7720	0.6953	0.7592	0.080*
N3	0.3603 (7)	0.73452 (18)	0.4915 (4)	0.0562 (9)
C1	0.4694 (7)	0.6428 (2)	0.7117 (4)	0.0453 (9)
C2	0.2906 (7)	0.67427 (18)	0.5653 (4)	0.0419 (8)
C3	0.0457 (7)	0.6493 (2)	0.4903 (5)	0.0498 (9)
H3	−0.0702	0.6705	0.3932	0.060*
C4	−0.0302 (7)	0.5927 (2)	0.5582 (5)	0.0544 (10)
H4	−0.1957	0.5750	0.5077	0.065*
C5	0.1418 (9)	0.5641 (2)	0.6989 (5)	0.0591 (11)
H5	0.0944	0.5265	0.7475	0.071*
O5	0.5840 (6)	0.75060 (17)	0.5457 (4)	0.0767 (9)
O6	0.1928 (6)	0.76632 (17)	0.3776 (4)	0.0757 (9)
Cl1	0.71827 (18)	0.41956 (5)	0.81544 (11)	0.0530 (3)

	U11	U22	U33	U12	U13	U23
O1	0.161 (4)	0.083 (2)	0.076 (2)	0.040 (2)	0.079 (2)	0.0169 (19)
O2	0.057 (2)	0.133 (4)	0.119 (3)	0.022 (2)	0.013 (2)	0.029 (3)
O3	0.090 (2)	0.078 (2)	0.0663 (19)	0.0100 (17)	0.0439 (17)	0.0197 (16)
O4	0.116 (3)	0.066 (2)	0.111 (3)	−0.024 (2)	0.052 (2)	−0.009 (2)
N1	0.068 (2)	0.0509 (19)	0.0523 (19)	0.0097 (18)	0.0286 (17)	0.0124 (16)
N2	0.048 (2)	0.077 (3)	0.065 (2)	0.0020 (18)	0.0174 (17)	0.003 (2)
N3	0.064 (2)	0.0459 (19)	0.070 (2)	0.0006 (18)	0.040 (2)	0.0018 (17)
C1	0.052 (2)	0.044 (2)	0.044 (2)	0.0093 (17)	0.0256 (18)	−0.0033 (16)
C2	0.054 (2)	0.0345 (17)	0.048 (2)	0.0019 (16)	0.0320 (18)	−0.0017 (15)
C3	0.051 (2)	0.052 (2)	0.046 (2)	0.0064 (18)	0.0219 (18)	0.0028 (18)
C4	0.053 (2)	0.055 (2)	0.062 (3)	−0.0066 (19)	0.032 (2)	−0.004 (2)
C5	0.078 (3)	0.049 (2)	0.065 (3)	−0.006 (2)	0.045 (2)	0.000 (2)
O5	0.073 (2)	0.067 (2)	0.103 (2)	−0.0138 (18)	0.0520 (19)	0.0072 (18)
O6	0.085 (2)	0.064 (2)	0.086 (2)	0.0191 (18)	0.0458 (19)	0.0309 (18)
Cl1	0.0554 (6)	0.0519 (6)	0.0498 (6)	0.0047 (5)	0.0219 (4)	0.0041 (5)

O1—Cl1	1.406 (3)	N3—O6	1.216 (4)
O2—Cl1	1.406 (3)	N3—O5	1.218 (4)
O3—Cl1	1.415 (3)	N3—C2	1.448 (5)
O4—Cl1	1.407 (3)	C1—C2	1.406 (5)
N1—C5	1.332 (5)	C2—C3	1.369 (5)
N1—C1	1.343 (5)	C3—C4	1.384 (5)
N1—H1	0.8600	C3—H3	0.9300
N2—C1	1.313 (5)	C4—C5	1.339 (6)
N2—H2A	0.8600	C4—H4	0.9300
N2—H2B	0.8600	C5—H5	0.9300
C5—N1—C1	124.8 (3)	C2—C3—C4	120.3 (4)
C5—N1—H1	117.6	C2—C3—H3	119.8
C1—N1—H1	117.6	C4—C3—H3	119.8
C1—N2—H2A	120.0	C5—C4—C3	118.0 (4)
C1—N2—H2B	120.0	C5—C4—H4	121.0
H2A—N2—H2B	120.0	C3—C4—H4	121.0
O6—N3—O5	123.1 (3)	N1—C5—C4	121.0 (4)
O6—N3—C2	118.5 (3)	N1—C5—H5	119.5
O5—N3—C2	118.4 (3)	C4—C5—H5	119.5
N2—C1—N1	118.1 (4)	O2—Cl1—O1	110.3 (3)
N2—C1—C2	126.8 (4)	O2—Cl1—O4	109.2 (3)
N1—C1—C2	115.1 (3)	O1—Cl1—O4	110.4 (2)
C3—C2—C1	120.8 (3)	O2—Cl1—O3	108.4 (2)
C3—C2—N3	118.4 (3)	O1—Cl1—O3	109.26 (19)
C1—C2—N3	120.8 (4)	O4—Cl1—O3	109.2 (2)
C5—N1—C1—N2	−179.1 (4)	O6—N3—C2—C1	−170.3 (3)
C5—N1—C1—C2	0.9 (5)	O5—N3—C2—C1	10.0 (5)
N2—C1—C2—C3	178.9 (3)	C1—C2—C3—C4	0.3 (5)
N1—C1—C2—C3	−1.1 (5)	N3—C2—C3—C4	−179.0 (3)
N2—C1—C2—N3	−1.8 (6)	C2—C3—C4—C5	0.7 (6)
N1—C1—C2—N3	178.3 (3)	C1—N1—C5—C4	0.1 (6)
O6—N3—C2—C3	9.0 (5)	C3—C4—C5—N1	−0.9 (6)
O5—N3—C2—C3	−170.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.28	2.927 (5)	133
N1—H1···O1i	0.86	2.44	2.969 (5)	121
N2—H2A···O2ii	0.86	2.03	2.886 (5)	173
N2—H2B···O5	0.86	2.04	2.633 (5)	126
N2—H2B···O6iii	0.86	2.32	2.917 (5)	126
C5—H5···O3iv	0.93	2.57	3.270 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.28	2.927 (5)	133
N1—H1⋯O1i	0.86	2.44	2.969 (5)	121
N2—H2A⋯O2ii	0.86	2.03	2.886 (5)	173
N2—H2B⋯O5	0.86	2.04	2.633 (5)	126
N2—H2B⋯O6iii	0.86	2.32	2.917 (5)	126
C5—H5⋯O3iv	0.93	2.57	3.270 (5)	133

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