2-Amino-3-nitro-pyridinium hydrogen oxalate.

In the non-centrosymetric title compound, C(5)H(6)N(3)O(2) (+)·C(2)HO(4) (-), the hydrogen oxalate anions form corrugated chains parallel to the c axis, linked by O-H⋯O hydrogen bonds. The 2-amino-3-nitro-pyridinium cations are anchored between theses chains by N-H⋯O and C-H⋯O hydrogen bonds and van der Waals and electrostatic inter-actions, creating a three-dimensional network.

Related literature

For related structures, see: Akriche & Rzaigui (2000 ▶, 2009 ▶); Le Fur et al. (1998 ▶); Nicoud et al. (1997 ▶); For a discussion of hydrogen bonding, see: Desiraju (1989 ▶, 1995 ▶).

Experimental

Crystal data

C5H6N3O2 +·C2HO4 −

M = 229.16

Orthorhombic,

a = 15.268 (4) Å

b = 6.921 (3) Å

c = 8.807 (2) Å

V = 930.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.33 × 0.25 × 0.21 mm

Data collection

Enraf–Nonius Turbo CAD-4 diffractometer

Absorption correction: none

2228 measured reflections

1190 independent reflections

1003 reflections with I > 2σ(I)

R int = 0.020

2 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.06

1190 reflections

147 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (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/S1600536809008666/kj2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008666/kj2116Isup2.hkl

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

C5H6N3O2+·C2HO4−	Dx = 1.636 Mg m−3
Mr = 229.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 25 reflections
a = 15.268 (4) Å	θ = 9–11°
b = 6.921 (3) Å	µ = 0.15 mm−1
c = 8.807 (2) Å	T = 293 K
V = 930.6 (5) Å3	Rectangular prism, yellow
Z = 4	0.33 × 0.25 × 0.21 mm
F(000) = 472

Enraf–Nonius Turbo CAD-4 diffractometer	Rint = 0.020
Radiation source: Enraf–Nonius FR590	θmax = 28.0°, θmin = 2.7°
graphite	h = −20→0
Nonprofiled ω scans	k = −7→9
2228 measured reflections	l = −11→0
1190 independent reflections	2 standard reflections every 120 min
1003 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0295P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1190 reflections	Δρmax = 0.33 e Å−3
147 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.053 (6)

Geometry. H atoms were treated as riding, with C—H = 0.93 A °, N—H = 0.86 A ° and O—H = 0.82 A °, and with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O). 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	0.18864 (12)	0.6389 (3)	0.4311 (2)	0.0512 (5)
O2	0.10055 (11)	0.5552 (3)	0.2423 (2)	0.0408 (4)
O3	0.05130 (11)	0.5172 (3)	0.6129 (2)	0.0391 (4)
H3	0.0051	0.5043	0.6593	0.059*
O4	−0.03139 (11)	0.6833 (3)	0.4481 (2)	0.0494 (5)
O5	0.49613 (12)	0.5813 (3)	0.1226 (3)	0.0532 (5)
O6	0.52023 (11)	0.6750 (3)	−0.1071 (3)	0.0545 (5)
N1	0.23161 (12)	0.5903 (3)	0.0374 (3)	0.0375 (5)
H1	0.1920	0.5818	0.1065	0.045*
N2	0.33259 (15)	0.6060 (3)	0.2291 (3)	0.0462 (6)
H2A	0.2900	0.6012	0.2930	0.055*
H2B	0.3857	0.6133	0.2612	0.055*
N3	0.47122 (12)	0.6244 (3)	−0.0050 (3)	0.0367 (5)
C1	0.31649 (14)	0.6020 (3)	0.0827 (3)	0.0321 (5)
C2	0.37793 (14)	0.6148 (3)	−0.0380 (3)	0.0318 (5)
C3	0.35201 (16)	0.6188 (4)	−0.1871 (3)	0.0363 (5)
H3A	0.3936	0.6300	−0.2638	0.044*
C4	0.26384 (17)	0.6061 (4)	−0.2236 (3)	0.0437 (6)
H4	0.2452	0.6078	−0.3241	0.052*
C5	0.20572 (16)	0.5911 (4)	−0.1078 (3)	0.0421 (6)
H5	0.1463	0.5811	−0.1298	0.050*
C6	0.11677 (14)	0.5994 (3)	0.3773 (3)	0.0303 (5)
C7	0.03636 (14)	0.6065 (3)	0.4838 (3)	0.0302 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0315 (8)	0.0930 (14)	0.0292 (9)	−0.0146 (10)	−0.0004 (7)	−0.0040 (10)
O2	0.0286 (7)	0.0684 (11)	0.0254 (8)	−0.0040 (8)	0.0007 (7)	−0.0037 (9)
O3	0.0300 (8)	0.0618 (12)	0.0256 (7)	0.0005 (8)	0.0063 (7)	0.0065 (8)
O4	0.0346 (9)	0.0660 (12)	0.0475 (11)	0.0110 (8)	0.0040 (8)	0.0115 (10)
O5	0.0342 (9)	0.0727 (13)	0.0528 (12)	0.0094 (9)	−0.0082 (9)	0.0076 (11)
O6	0.0330 (9)	0.0779 (13)	0.0526 (12)	−0.0118 (9)	0.0125 (8)	−0.0050 (11)
N1	0.0243 (9)	0.0522 (14)	0.0361 (12)	−0.0015 (8)	0.0039 (8)	−0.0004 (9)
N2	0.0317 (10)	0.0773 (18)	0.0296 (11)	−0.0022 (10)	0.0002 (8)	0.0046 (11)
N3	0.0259 (9)	0.0401 (10)	0.0440 (12)	0.0007 (8)	0.0035 (9)	−0.0039 (9)
C1	0.0271 (10)	0.0372 (12)	0.0319 (12)	−0.0008 (9)	0.0024 (9)	0.0020 (9)
C2	0.0252 (10)	0.0356 (11)	0.0347 (12)	0.0013 (8)	0.0024 (9)	−0.0014 (10)
C3	0.0352 (12)	0.0427 (14)	0.0311 (12)	0.0002 (10)	0.0057 (10)	−0.0004 (10)
C4	0.0407 (13)	0.0592 (17)	0.0311 (13)	0.0026 (11)	−0.0038 (10)	−0.0018 (11)
C5	0.0271 (10)	0.0585 (16)	0.0406 (15)	0.0020 (10)	−0.0049 (10)	−0.0044 (12)
C6	0.0279 (10)	0.0391 (11)	0.0240 (10)	−0.0029 (9)	0.0015 (9)	0.0033 (9)
C7	0.0263 (10)	0.0382 (11)	0.0261 (11)	−0.0040 (8)	−0.0003 (8)	−0.0026 (9)

O1—C6	1.226 (3)	N2—H2A	0.8600
O2—C6	1.252 (3)	N2—H2B	0.8600
O3—C7	1.314 (3)	N3—C2	1.455 (3)
O3—H3	0.8200	C1—C2	1.420 (3)
O4—C7	1.205 (3)	C2—C3	1.372 (3)
O5—N3	1.223 (3)	C3—C4	1.387 (3)
O6—N3	1.221 (3)	C3—H3A	0.9300
N1—C5	1.338 (4)	C4—C5	1.356 (4)
N1—C1	1.358 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N2—C1	1.313 (3)	C6—C7	1.545 (3)
C7—O3—H3	109.5	C2—C3—C4	120.0 (2)
C5—N1—C1	124.2 (2)	C2—C3—H3A	120.0
C5—N1—H1	117.9	C4—C3—H3A	120.0
C1—N1—H1	117.9	C5—C4—C3	117.8 (2)
C1—N2—H2A	120.0	C5—C4—H4	121.1
C1—N2—H2B	120.0	C3—C4—H4	121.1
H2A—N2—H2B	120.0	N1—C5—C4	121.7 (2)
O6—N3—O5	123.8 (2)	N1—C5—H5	119.1
O6—N3—C2	117.8 (2)	C4—C5—H5	119.1
O5—N3—C2	118.5 (2)	O1—C6—O2	126.8 (2)
N2—C1—N1	117.9 (2)	O1—C6—C7	118.0 (2)
N2—C1—C2	127.6 (2)	O2—C6—C7	115.25 (19)
N1—C1—C2	114.5 (2)	O4—C7—O3	125.6 (2)
C3—C2—C1	121.8 (2)	O4—C7—C6	122.5 (2)
C3—C2—N3	118.2 (2)	O3—C7—C6	111.85 (19)
C1—C2—N3	120.0 (2)
C5—N1—C1—N2	177.8 (3)	C1—C2—C3—C4	−1.3 (4)
C5—N1—C1—C2	−0.2 (4)	N3—C2—C3—C4	178.7 (2)
N2—C1—C2—C3	−176.6 (3)	C2—C3—C4—C5	0.4 (4)
N1—C1—C2—C3	1.2 (3)	C1—N1—C5—C4	−0.7 (5)
N2—C1—C2—N3	3.3 (4)	C3—C4—C5—N1	0.6 (4)
N1—C1—C2—N3	−178.8 (2)	O1—C6—C7—O4	134.2 (3)
O6—N3—C2—C3	14.8 (3)	O2—C6—C7—O4	−45.0 (3)
O5—N3—C2—C3	−165.1 (2)	O1—C6—C7—O3	−46.9 (3)
O6—N3—C2—C1	−165.2 (2)	O2—C6—C7—O3	133.9 (2)
O5—N3—C2—C1	15.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	1.82	2.632 (2)	171
N1—H1···O2	0.86	1.85	2.706 (3)	175
N2—H2A···O1	0.86	1.99	2.837 (3)	170
N2—H2B···O5	0.86	2.09	2.673 (3)	124
N2—H2B···O4ii	0.86	2.51	3.188 (3)	136
C3—H3A···O5iii	0.93	2.44	3.178 (3)	136
C4—H4···O1iv	0.93	2.33	3.258 (3)	174
C5—H5···O6v	0.93	2.57	3.262 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.82	2.632 (2)	171
N1—H1⋯O2	0.86	1.85	2.706 (3)	175
N2—H2A⋯O1	0.86	1.99	2.837 (3)	170
N2—H2B⋯O5	0.86	2.09	2.673 (3)	124
N2—H2B⋯O4ii	0.86	2.51	3.188 (3)	136
C3—H3A⋯O5iii	0.93	2.44	3.178 (3)	136
C4—H4⋯O1iv	0.93	2.33	3.258 (3)	174
C5—H5⋯O6v	0.93	2.57	3.262 (3)	132

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