2-Amino-3-nitro­pyridinium hydrogen selenate

Akriche, S.; Rzaigui, M.

doi:10.1107/S1600536809022879

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1648

doi:10.1107/S1600536809022879

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2-Amino-3-nitropyridinium hydrogen selenate

Samah Akriche ^a ^* and Mohamed Rzaigui ^a

^aLaboratoire de chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: samah.akriche@fsb.rnu.tn

(Received 14 May 2009; accepted 14 June 2009; online 20 June 2009)

The asymmetric unit of the title compound, C₅H₆N₃O₂⁺·HSeO₄⁻, contains two monoprotonated 2-amino-3-nitropyridinium 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 interactions, 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_r = 284.10
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.112
S = 1.01
4433 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.75 e Å⁻³

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⋯O12^iv	0.93	2.47	3.290 (6)	148
C8—H8⋯O6ⁱⁱⁱ	0.93	2.57	3.463 (6)	162
C10—H10⋯O4^v	0.93	2.35	3.228 (6)	158
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+2, -y+1, -z+1.

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 DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

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

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

checkCIF report

Comment top

The important advantage of hybrid organic inorganic salts is the opportunity offered by the chromophores that when anchored onto inorganic host matrices, lead to non-centrosymmetric frameworks suitable for NLO devices. The approach of this new engineering has been applied to 2-amino-3-nitropyridinium cation (2 A3NP⁺) encapsulated in various anionic subnetworks (Akriche et al., 2009, Nicoud et al.,1997, Le Fur et al., 1998). The attempt using (HSO₄^-) _n polymeric anions has been successful with the cristallization of the non-centrosymmetric 2-Amino-3-nitropyridinium sulfate (Le Fur et al., 1998). The encapsulation of this cation in (HSeO₄^-)_n polymeric anions leads to the title compound (I).

The asymmetric unit of (I) contains two monoprotonated 2-amino-3-nitropyridinium cations and two hydrogen selenate anions (Fig.1) which are connected through N—H···O, C—H···O and O—H···O hydrogen bonds. The hydrogen selenate anions are interconnected between themselves by H-bonds involving the proton of selenate groups leading to (HSeO₄^-) _n chains parallel to the a axis (Fig. 2).

In this atomic arrangement the HSeO₄^- tetraedra are slightly distorted with Se—O distances from 1.594 (6) to 1.713 (4) Å. The Se—O bonds in selenate tetrahedra depends greatly on the nature of the O atoms acting as an acceptor or a donor atoms: the longer bonds (1.713 (4) and 1.692 (5) Å) involve oxygen atoms acting as a H-donor whereas shorter bonds ranging from 1.594 (6) to 1.623 (4) relate to oxygen atoms acting as H-acceptor participating in hydrogen bonds of type N—H···O and C—H···O. As expected, the geometrical features of anion agree with those previously observed for this group in other analogues (Fleck, 2006, Maalej et al., 2008).

The 2-amino-3-nitropyridinium cations are onchored onto anionic chains through short hydrogen bonds originating from the NH₂ and NH⁺ groups. The unique inter-cation contact C4—H4A···O11(H4A···O11 = 2.45 Å) induces the aggregation of cations in pairs (2 A3NP⁺)₂ elongated in -(a+c) direction. Two hydrogen bonds, N2—H2B···O10 (2.10 Å) and N5—H5B···O12 (2.11 Å) (see Table 1) ensure the intra-cation links. This situation is well observed in nitroaniline derivatives in which nitro and amino groups are ortho to one another which precludes the rotation of the nitro group with respect to the pyridinium rings. The diedral angles between the planes of the NO₂ groups and the two pyridinium planes are 19.0 (3) and 15.9 (4) % indicating a distortion of the NO₂ groups under the influence of C—H···O hydrogn bonds of neighbouring cations. This situation is alawys observed in other 2-amino-3-nitropyridinium salts (Nicoud et al.,1997, Le Fur et al., 1998). The bond lengths and angles in (I) are normal and comparable with the corresponding values observed in the related structure (Akriche et al., 2009, Nicoud et al.,1997, Le Fur et al., 1998).

Related literature top

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

Experimental top

The title compound (I) was cristallized by slow evaporation at room temperature of an aqueous solution (20 ml) of 2-amino-3-nitropyridine (4 mmol) and selenic acid (4 mmol) in a 1:1 stochiometric ratio.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEP view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are represented as dashed lines.
	Fig. 2. A perspective view of (I) showing the (HSeO₄^-) _n polymeric anions running along the a axis. The C—H···O bonds are omitted for clarity of figure.

2-Amino-3-nitropyridinium hydrogen selenate top

Crystal data top

C₅H₆N₃O₂⁺·HO₄Se⁻	F(000) = 1120
M_r = 284.10	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0549P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4433 reflections	Δρ_max = 0.80 e Å⁻³
274 parameters	Δρ_min = −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)

Crystal data top

C₅H₆N₃O₂⁺·HO₄Se⁻	V = 1845.6 (10) Å³
M_r = 284.10	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.090 (3) Å	µ = 4.09 mm⁻¹
b = 20.130 (2) Å	T = 298 K
c = 10.434 (4) Å	0.37 × 0.29 × 0.19 mm
β = 104.84 (2)°

Data collection top

Enraf–Nonius Turbo-CAD-4 diffractometer	2980 reflections with I > 2σ(I)
Absorption correction: multi-scan (Blessing, 1995)	R_int = 0.040
T_min = 0.145, T_max = 0.298	2 standard reflections every 120 min
7325 measured reflections	intensity decay: 4%
4433 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	Δρ_max = 0.80 e Å⁻³
4433 reflections	Δρ_min = −0.75 e Å⁻³
274 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O12^iv	0.93	2.47	3.290 (6)	148
C8—H8···O6ⁱⁱⁱ	0.93	2.57	3.463 (6)	162
C10—H10···O4^v	0.93	2.35	3.228 (6)	158

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) x, −y+1/2, z+1/2; (v) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₅H₆N₃O₂⁺·HO₄Se⁻
M_r	284.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.090 (3), 20.130 (2), 10.434 (4)
β (°)	104.84 (2)
V (Å³)	1845.6 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.09
Crystal size (mm)	0.37 × 0.29 × 0.19

Data collection
Diffractometer	Enraf–Nonius Turbo-CAD-4 diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.145, 0.298
No. of measured, independent and observed [I > 2σ(I)] reflections	7325, 4433, 2980
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.112, 1.01
No. of reflections	4433
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.75

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82	1.75	2.565 (5)	169.8
O5—H5···O2ⁱ	0.82	1.80	2.601 (5)	167.0
N1—H1A···O4	0.86	1.84	2.679 (5)	166.2
N2—H2A···O3	0.86	2.02	2.870 (6)	171.9
N2—H2B···O9	0.86	2.09	2.675 (6)	124.3
N2—H2B···O8ⁱⁱ	0.86	2.28	2.933 (5)	132.6
N4—H4···O7	0.86	2.05	2.864 (5)	156.9
N5—H5A···O8	0.86	2.07	2.900 (5)	163.0
N5—H5B···O3ⁱⁱ	0.86	2.11	2.798 (5)	136.7
N5—H5B···O11	0.86	2.12	2.693 (5)	123.7
C3—H3···O5ⁱⁱⁱ	0.93	2.54	3.443 (5)	162.7
C4—H4A···O12^iv	0.93	2.47	3.290 (6)	147.7
C8—H8···O6ⁱⁱⁱ	0.93	2.57	3.463 (6)	162.4
C10—H10···O4^v	0.93	2.35	3.228 (6)	157.6

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) x, −y+1/2, z+1/2; (v) −x+2, −y+1, −z+1.

References

Akriche, S. & Rzaigui, M. (2009). Acta Cryst. E65, o793. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Volume 65| Part 7| July 2009| Page o1648

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