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

The asymmetric unit of the title compound, C(5)H(6)N(3)O(2) (+)·HSeO(4) (-), contains two monoprotonated 2-amino-3-nitro-pyridinium cations and two hydrogen selenate anions which are connected through N-H⋯O and O-H⋯O hydrogen bonds, building chains parallel to the a direction. These chains are further connected to each other by weaker C-H⋯O hydrogen-bonding inter-actions, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Akriche et al. (2009 ▶); Fleck (2006 ▶); Le Fur, Masse & Nicoud (1998 ▶); Nicoud et al. (1997 ▶); Maalej et al. (2008 ▶).

Experimental

Crystal data

C5H6N3O2 +·HSeO4 −

M = 284.10

Monoclinic,

a = 9.090 (3) Å

b = 20.130 (2) Å

c = 10.434 (4) Å

β = 104.84 (2)°

V = 1845.6 (10) Å3

Z = 8

Mo Kα radiation

μ = 4.09 mm−1

T = 298 K

0.37 × 0.29 × 0.19 mm

Data collection

Enraf–Nonius Turbo-CAD-4 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.145, T max = 0.298 (expected range = 0.224–0.460)

7325 measured reflections

4433 independent reflections

2980 reflections with I > 2σ(I)

R int = 0.040

2 standard reflections frequency: 120 min intensity decay: 4%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.112

S = 1.01

4433 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.75 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 n class="Disease">DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022879/dn2458sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022879/dn2458Isup2.hkl

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

C5H6N3O2+·HO4Se−	F(000) = 1120
Mr = 284.10	Dx = 2.045 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.090 (3) Å	θ = 9–11°
b = 20.130 (2) Å	µ = 4.09 mm−1
c = 10.434 (4) Å	T = 298 K
β = 104.84 (2)°	Prism, yellow
V = 1845.6 (10) Å3	0.37 × 0.29 × 0.19 mm
Z = 8

Enraf–Nonius Turbo-CAD-4 diffractometer	2980 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 28.0°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (Blessing, 1995)	k = 0→26
Tmin = 0.145, Tmax = 0.298	l = −6→13
7325 measured reflections	2 standard reflections every 120 min
4433 independent reflections	intensity decay: 4%

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0549P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4433 reflections	Δρmax = 0.80 e Å−3
274 parameters	Δρmin = −0.75 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (7)

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
Se1	0.39573 (5)	0.57437 (2)	0.26743 (5)	0.03205 (15)
Se2	0.88010 (5)	0.61095 (2)	0.28019 (5)	0.02924 (14)
O1	0.4598 (4)	0.65134 (18)	0.2463 (5)	0.0680 (13)
H1	0.5519	0.6530	0.2786	0.102*
O3	0.3344 (5)	0.5426 (2)	0.1228 (4)	0.0756 (14)
O2	0.2627 (4)	0.58545 (19)	0.3409 (4)	0.0576 (11)
O4	0.5374 (4)	0.53198 (15)	0.3555 (3)	0.0411 (8)
O5	1.0304 (3)	0.66505 (15)	0.3064 (4)	0.0401 (8)
H5	1.1091	0.6443	0.3109	0.060*
O6	0.7514 (3)	0.65653 (16)	0.3186 (4)	0.0433 (8)
O7	0.9371 (4)	0.54843 (15)	0.3783 (3)	0.0405 (8)
O8	0.8397 (4)	0.58792 (17)	0.1281 (3)	0.0478 (9)
O9	0.4200 (5)	0.2899 (2)	−0.0205 (4)	0.0656 (12)
O10	0.6241 (5)	0.23103 (19)	0.0156 (4)	0.0672 (12)
O11	0.8828 (4)	0.33319 (18)	−0.0323 (4)	0.0498 (9)
O12	1.0837 (4)	0.27232 (16)	−0.0052 (4)	0.0503 (9)
N1	0.6363 (4)	0.41805 (19)	0.2743 (4)	0.0361 (9)
H1A	0.6010	0.4565	0.2869	0.043*
N2	0.4378 (4)	0.4105 (2)	0.0899 (4)	0.0442 (10)
H2A	0.4098	0.4494	0.1082	0.053*
H2B	0.3862	0.3897	0.0211	0.053*
N3	0.5509 (5)	0.2774 (2)	0.0413 (5)	0.0454 (10)
N4	1.1029 (4)	0.44386 (17)	0.2922 (4)	0.0333 (9)
H4	1.0723	0.4821	0.3116	0.040*
N5	0.9152 (4)	0.4497 (2)	0.0988 (4)	0.0413 (10)
H5A	0.8914	0.4881	0.1236	0.050*
H5B	0.8653	0.4335	0.0241	0.050*
N6	1.0111 (5)	0.31667 (18)	0.0290 (4)	0.0348 (9)
C1	0.5601 (5)	0.3828 (2)	0.1677 (5)	0.0337 (10)
C2	0.6231 (5)	0.3199 (2)	0.1535 (5)	0.0339 (10)
C3	0.7524 (5)	0.2982 (2)	0.2424 (5)	0.0400 (12)
H3	0.7922	0.2568	0.2303	0.048*
C4	0.8245 (5)	0.3366 (3)	0.3493 (5)	0.0427 (12)
H4A	0.9114	0.3214	0.4103	0.051*
C5	0.7647 (5)	0.3970 (2)	0.3629 (5)	0.0381 (11)
H5C	0.8120	0.4243	0.4333	0.046*
C6	1.0279 (5)	0.4158 (2)	0.1752 (4)	0.0288 (9)
C7	1.0836 (5)	0.3528 (2)	0.1496 (4)	0.0286 (9)
C8	1.2031 (5)	0.3237 (2)	0.2393 (5)	0.0387 (11)
H8	1.2366	0.2819	0.2216	0.046*
C9	1.2739 (6)	0.3557 (3)	0.3550 (5)	0.0443 (12)
H9	1.3562	0.3363	0.4150	0.053*
C10	1.2217 (5)	0.4159 (2)	0.3799 (5)	0.0402 (11)
H10	1.2680	0.4382	0.4580	0.048*

	U11	U22	U33	U12	U13	U23
Se1	0.0214 (2)	0.0312 (2)	0.0401 (3)	0.00508 (17)	0.00162 (18)	−0.0022 (2)
Se2	0.0249 (2)	0.0232 (2)	0.0358 (3)	−0.00061 (17)	0.00088 (18)	−0.00011 (18)
O1	0.0320 (19)	0.040 (2)	0.129 (4)	0.0059 (17)	0.015 (2)	0.030 (2)
O3	0.079 (3)	0.075 (3)	0.049 (3)	0.045 (2)	−0.026 (2)	−0.021 (2)
O2	0.040 (2)	0.055 (2)	0.088 (3)	0.0112 (18)	0.034 (2)	0.009 (2)
O4	0.0365 (17)	0.0333 (17)	0.045 (2)	0.0110 (14)	−0.0050 (15)	−0.0029 (15)
O5	0.0281 (16)	0.0327 (17)	0.057 (2)	−0.0049 (13)	0.0061 (16)	−0.0020 (16)
O6	0.0299 (17)	0.0338 (17)	0.066 (2)	0.0023 (14)	0.0125 (16)	−0.0058 (17)
O7	0.0416 (18)	0.0311 (16)	0.048 (2)	0.0056 (14)	0.0099 (16)	0.0142 (15)
O8	0.055 (2)	0.0375 (18)	0.041 (2)	0.0050 (17)	−0.0043 (17)	−0.0050 (16)
O9	0.054 (2)	0.061 (3)	0.071 (3)	−0.007 (2)	−0.004 (2)	−0.023 (2)
O10	0.084 (3)	0.046 (2)	0.074 (3)	0.004 (2)	0.026 (2)	−0.023 (2)
O11	0.0348 (18)	0.057 (2)	0.050 (2)	−0.0048 (17)	−0.0036 (17)	−0.0155 (18)
O12	0.066 (2)	0.0294 (18)	0.057 (2)	0.0063 (17)	0.018 (2)	−0.0091 (16)
N1	0.037 (2)	0.031 (2)	0.038 (2)	0.0060 (17)	0.0050 (18)	−0.0043 (18)
N2	0.039 (2)	0.041 (2)	0.046 (3)	0.0080 (19)	0.000 (2)	−0.004 (2)
N3	0.055 (3)	0.029 (2)	0.055 (3)	−0.006 (2)	0.019 (2)	−0.0050 (19)
N4	0.039 (2)	0.0234 (17)	0.032 (2)	0.0039 (16)	−0.0007 (17)	−0.0015 (15)
N5	0.046 (2)	0.036 (2)	0.033 (2)	0.0113 (18)	−0.0072 (19)	−0.0061 (17)
N6	0.043 (2)	0.0291 (19)	0.034 (2)	−0.0076 (17)	0.0117 (19)	−0.0040 (16)
C1	0.033 (2)	0.032 (2)	0.037 (3)	0.0022 (19)	0.010 (2)	0.003 (2)
C2	0.034 (2)	0.031 (2)	0.038 (3)	−0.0001 (19)	0.012 (2)	0.000 (2)
C3	0.042 (3)	0.027 (2)	0.055 (3)	0.008 (2)	0.020 (2)	0.007 (2)
C4	0.037 (3)	0.047 (3)	0.042 (3)	0.009 (2)	0.005 (2)	0.014 (2)
C5	0.035 (2)	0.041 (3)	0.035 (3)	0.002 (2)	0.003 (2)	−0.001 (2)
C6	0.032 (2)	0.029 (2)	0.023 (2)	−0.0036 (18)	0.0041 (19)	0.0005 (18)
C7	0.035 (2)	0.023 (2)	0.029 (2)	−0.0039 (17)	0.0094 (19)	−0.0007 (18)
C8	0.043 (3)	0.027 (2)	0.047 (3)	0.006 (2)	0.012 (2)	0.005 (2)
C9	0.041 (3)	0.045 (3)	0.038 (3)	0.013 (2)	−0.005 (2)	0.005 (2)
C10	0.044 (3)	0.038 (3)	0.031 (3)	−0.003 (2)	−0.005 (2)	0.000 (2)

Se1—O3	1.602 (4)	N4—C10	1.347 (5)
Se1—O2	1.604 (3)	N4—C6	1.359 (5)
Se1—O4	1.620 (3)	N4—H4	0.8600
Se1—O1	1.689 (4)	N5—C6	1.316 (5)
Se2—O8	1.603 (3)	N5—H5A	0.8600
Se2—O6	1.616 (3)	N5—H5B	0.8600
Se2—O7	1.621 (3)	N6—C7	1.456 (5)
Se2—O5	1.713 (3)	C1—C2	1.412 (6)
O1—H1	0.8200	C2—C3	1.369 (7)
O5—H5	0.8200	C3—C4	1.377 (7)
O9—N3	1.225 (5)	C3—H3	0.9300
O10—N3	1.216 (5)	C4—C5	1.355 (7)
O11—N6	1.224 (5)	C4—H4A	0.9300
O12—N6	1.217 (5)	C5—H5C	0.9300
N1—C1	1.352 (6)	C6—C7	1.417 (6)
N1—C5	1.357 (6)	C7—C8	1.370 (6)
N1—H1A	0.8600	C8—C9	1.374 (7)
N2—C1	1.321 (6)	C8—H8	0.9300
N2—H2A	0.8600	C9—C10	1.351 (7)
N2—H2B	0.8600	C9—H9	0.9300
N3—C2	1.463 (6)	C10—H10	0.9300
O3—Se1—O2	112.5 (2)	O11—N6—C7	118.4 (4)
O3—Se1—O4	111.03 (18)	N2—C1—N1	117.2 (4)
O2—Se1—O4	112.89 (19)	N2—C1—C2	127.9 (5)
O3—Se1—O1	106.9 (3)	N1—C1—C2	114.9 (4)
O2—Se1—O1	105.2 (2)	C3—C2—C1	121.1 (4)
O4—Se1—O1	107.86 (17)	C3—C2—N3	119.1 (4)
O8—Se2—O6	114.36 (18)	C1—C2—N3	119.8 (4)
O8—Se2—O7	110.84 (17)	C2—C3—C4	121.1 (4)
O6—Se2—O7	114.76 (17)	C2—C3—H3	119.4
O8—Se2—O5	108.25 (19)	C4—C3—H3	119.4
O6—Se2—O5	101.41 (16)	C5—C4—C3	117.9 (4)
O7—Se2—O5	106.24 (17)	C5—C4—H4A	121.0
Se1—O1—H1	109.5	C3—C4—H4A	121.0
Se2—O5—H5	109.5	C4—C5—N1	120.4 (5)
C1—N1—C5	124.5 (4)	C4—C5—H5C	119.8
C1—N1—H1A	117.7	N1—C5—H5C	119.8
C5—N1—H1A	117.7	N5—C6—N4	117.6 (4)
C1—N2—H2A	120.0	N5—C6—C7	127.6 (4)
C1—N2—H2B	120.0	N4—C6—C7	114.8 (4)
H2A—N2—H2B	120.0	C8—C7—C6	120.8 (4)
O10—N3—O9	123.6 (5)	C8—C7—N6	118.7 (4)
O10—N3—C2	117.8 (4)	C6—C7—N6	120.4 (4)
O9—N3—C2	118.6 (4)	C7—C8—C9	120.8 (4)
C10—N4—C6	124.6 (4)	C7—C8—H8	119.6
C10—N4—H4	117.7	C9—C8—H8	119.6
C6—N4—H4	117.7	C10—C9—C8	118.7 (4)
C6—N5—H5A	120.0	C10—C9—H9	120.6
C6—N5—H5B	120.0	C8—C9—H9	120.6
H5A—N5—H5B	120.0	N4—C10—C9	120.3 (4)
O12—N6—O11	124.2 (4)	N4—C10—H10	119.9
O12—N6—C7	117.5 (4)	C9—C10—H10	119.9

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82	1.75	2.565 (5)	170
O5—H5···O2i	0.82	1.80	2.601 (5)	167
N1—H1A···O4	0.86	1.84	2.679 (5)	166
N2—H2A···O3	0.86	2.02	2.870 (6)	172
N2—H2B···O9	0.86	2.09	2.675 (6)	124
N2—H2B···O8ii	0.86	2.28	2.933 (5)	133
N4—H4···O7	0.86	2.05	2.864 (5)	157
N5—H5A···O8	0.86	2.07	2.900 (5)	163
N5—H5B···O3ii	0.86	2.11	2.798 (5)	137
N5—H5B···O11	0.86	2.12	2.693 (5)	124
C3—H3···O5iii	0.93	2.54	3.443 (5)	163
C4—H4A···O12iv	0.93	2.47	3.290 (6)	148
C8—H8···O6iii	0.93	2.57	3.463 (6)	162
C10—H10···O4v	0.93	2.35	3.228 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6	0.82	1.75	2.565 (5)	170
O5—H5⋯O2i	0.82	1.80	2.601 (5)	167
N1—H1A⋯O4	0.86	1.84	2.679 (5)	166
N2—H2A⋯O3	0.86	2.02	2.870 (6)	172
N2—H2B⋯O9	0.86	2.09	2.675 (6)	124
N2—H2B⋯O8ii	0.86	2.28	2.933 (5)	133
N4—H4⋯O7	0.86	2.05	2.864 (5)	157
N5—H5A⋯O8	0.86	2.07	2.900 (5)	163
N5—H5B⋯O3ii	0.86	2.11	2.798 (5)	137
N5—H5B⋯O11	0.86	2.12	2.693 (5)	124
C3—H3⋯O5iii	0.93	2.54	3.443 (5)	163
C4—H4A⋯O12iv	0.93	2.47	3.290 (6)	148
C8—H8⋯O6iii	0.93	2.57	3.463 (6)	162
C10—H10⋯O4v	0.93	2.35	3.228 (6)	158

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