2-Amino-3-nitro-pyridinium perrhenate.

In the title mol-ecular salt, (C(5)H(6)N(3)O(2))[ReO(4)], the cations and tetrahedral anions are linked by trifurcated N-H⋯(O,O,O) and bifurcated N-H⋯(O,O) hydrogen bonds, as well as weak C-H⋯O inter-actions. This results in alternating corrugated inorganic and organic layers in the crystal.

Related literature

For hydrogen-bond inter­actions see: Katayev et al. (2006 ▶). For related structures containing 2-amino-3-nitro­pyridinium cations, see: Akriche & Rzaigui (2000 ▶, 2009 ▶); Toumi Akriche et al. (2010 ▶). For related structures containing perrhenate anions, see: Rodrigues et al. (2009 ▶); Ray et al. (2002 ▶, 2003 ▶). For distortion indices, see: Baur (1974 ▶).

Experimental

Crystal data

(C5H6N3O2)[ReO4]

M = 390.33

Monoclinic,

a = 6.235 (3) Å

b = 22.030 (2) Å

c = 7.840 (6) Å

β = 117.52 (5)°

V = 955.0 (9) Å3

Z = 4

Ag Kα radiation

λ = 0.56087 Å

μ = 6.86 mm−1

T = 293 K

0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.054, T max = 0.134

7565 measured reflections

4682 independent reflections

3532 reflections with I > 2σ(I)

R int = 0.027

2 standard reflections every 120 min intensity decay: 4%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.07

4682 reflections

137 parameters

24 restraints

H-atom parameters constrained

Δρmax = 2.71 e Å−3

Δρmin = −2.35 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 (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/S160053681001812X/hb5451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001812X/hb5451Isup2.hkl

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

(C5H6N3O2)[ReO4]	F(000) = 720
Mr = 390.33	Dx = 2.715 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56087 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.235 (3) Å	θ = 9–11°
b = 22.030 (2) Å	µ = 6.86 mm−1
c = 7.840 (6) Å	T = 293 K
β = 117.52 (5)°	Prism, yellow
V = 955.0 (9) Å3	0.50 × 0.40 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	3532 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.027
graphite	θmax = 28.0°, θmin = 2.4°
non–profiled ω scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −36→0
Tmin = 0.054, Tmax = 0.134	l = −12→13
7565 measured reflections	2 standard reflections every 120 min
4682 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.052P)2 + 2.5911P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.037
4682 reflections	Δρmax = 2.71 e Å−3
137 parameters	Δρmin = −2.35 e Å−3
24 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: 0.033 (2)

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
Re1	0.71309 (5)	0.940210 (14)	0.25037 (4)	0.03320 (12)
O1	0.5590 (13)	0.9742 (3)	0.3597 (10)	0.0450 (14)
O2	0.9536 (13)	0.9832 (4)	0.2759 (11)	0.0544 (17)
O3	0.8207 (16)	0.8717 (4)	0.3586 (14)	0.062 (2)
O4	0.5164 (14)	0.9265 (4)	0.0220 (10)	0.0568 (19)
O5	0.2048 (17)	0.7952 (4)	0.6686 (16)	0.073 (2)
O6	0.453 (2)	0.7369 (5)	0.8873 (17)	0.088 (3)
N1	0.7550 (13)	0.9105 (4)	0.7469 (10)	0.0400 (14)
H1	0.7366	0.9443	0.6867	0.048*
N2	0.3526 (15)	0.8922 (3)	0.5588 (11)	0.0427 (15)
H2A	0.3378	0.9264	0.5019	0.051*
H2B	0.2288	0.8690	0.5260	0.051*
N3	0.4105 (19)	0.7821 (4)	0.7905 (14)	0.053 (2)
C1	0.5584 (15)	0.8757 (3)	0.6920 (11)	0.0338 (13)
C2	0.6059 (16)	0.8218 (4)	0.8141 (13)	0.0386 (14)
C3	0.8316 (19)	0.8088 (4)	0.9565 (15)	0.050 (2)
H3	0.8578	0.7733	1.0280	0.060*
C4	1.0226 (19)	0.8481 (6)	0.9954 (18)	0.058 (3)
H4	1.1769	0.8402	1.0937	0.070*
C5	0.9753 (18)	0.8982 (5)	0.8848 (15)	0.050 (2)
H5	1.1009	0.9248	0.9059	0.060*

	U11	U22	U33	U12	U13	U23
Re1	0.03010 (15)	0.03753 (17)	0.03126 (16)	−0.00110 (11)	0.01359 (11)	−0.00198 (11)
O1	0.057 (4)	0.041 (3)	0.045 (3)	−0.001 (3)	0.030 (3)	−0.002 (3)
O2	0.040 (3)	0.067 (5)	0.055 (4)	−0.007 (3)	0.022 (3)	0.008 (3)
O3	0.062 (5)	0.046 (4)	0.076 (6)	0.010 (3)	0.030 (4)	0.017 (4)
O4	0.044 (4)	0.078 (5)	0.039 (3)	0.001 (3)	0.012 (3)	−0.019 (3)
O5	0.057 (5)	0.057 (5)	0.090 (7)	−0.021 (4)	0.021 (4)	0.005 (5)
O6	0.090 (7)	0.059 (6)	0.103 (8)	−0.012 (5)	0.034 (6)	0.036 (5)
N1	0.041 (3)	0.037 (3)	0.046 (4)	−0.001 (2)	0.023 (3)	0.006 (3)
N2	0.046 (4)	0.035 (3)	0.037 (3)	−0.001 (3)	0.010 (3)	0.006 (3)
N3	0.064 (5)	0.031 (3)	0.064 (5)	−0.004 (3)	0.029 (4)	0.003 (3)
C1	0.039 (3)	0.028 (3)	0.034 (3)	−0.001 (2)	0.017 (3)	−0.003 (2)
C2	0.044 (4)	0.028 (3)	0.046 (4)	0.003 (3)	0.023 (3)	0.002 (3)
C3	0.054 (5)	0.038 (4)	0.057 (5)	0.014 (3)	0.024 (4)	0.017 (4)
C4	0.041 (4)	0.062 (6)	0.066 (6)	0.009 (4)	0.021 (4)	0.016 (5)
C5	0.040 (4)	0.057 (5)	0.052 (5)	−0.001 (4)	0.020 (4)	0.008 (4)

Re1—O1	1.726 (6)	C2—C3	1.363 (13)
Re1—O2	1.706 (7)	C2—N3	1.441 (12)
Re1—O3	1.708 (8)	C2—C1	1.466 (11)
Re1—O4	1.665 (7)	O5—N3	1.228 (14)
N1—C5	1.325 (12)	N3—O6	1.206 (12)
N1—C1	1.338 (11)	C3—C4	1.387 (16)
N1—H1	0.8600	C3—H3	0.9300
N2—C1	1.277 (11)	C5—C4	1.350 (15)
N2—H2A	0.8600	C5—H5	0.9300
N2—H2B	0.8600	C4—H4	0.9300
O4—Re1—O2	113.4 (4)	N2—C1—N1	121.7 (8)
O4—Re1—O3	107.4 (4)	N2—C1—C2	126.0 (8)
O2—Re1—O3	108.1 (4)	N1—C1—C2	112.1 (7)
O4—Re1—O1	108.1 (4)	C3—C2—N3	118.0 (8)
O2—Re1—O1	111.2 (4)	C3—C2—C1	121.8 (8)
O3—Re1—O1	108.5 (4)	N3—C2—C1	120.3 (8)
C5—N1—C1	126.5 (8)	C2—C3—C4	120.3 (9)
C5—N1—H1	116.8	C2—C3—H3	119.9
C1—N1—H1	116.8	C4—C3—H3	119.9
C1—N2—H2A	120.0	C5—C4—C3	117.3 (10)
C1—N2—H2B	120.0	C5—C4—H4	121.3
H2A—N2—H2B	120.0	C3—C4—H4	121.3
O6—N3—O5	122.0 (10)	N1—C5—C4	121.9 (10)
O6—N3—C2	119.7 (10)	N1—C5—H5	119.1
O5—N3—C2	118.3 (8)	C4—C5—H5	119.1
C3—C2—N3—O6	−4.7 (15)	C2—C3—C4—C5	−1.3 (17)
C1—C2—N3—O6	177.5 (10)	C5—N1—C1—N2	179.0 (9)
C3—C2—N3—O5	176.6 (10)	C5—N1—C1—C2	4.7 (12)
C1—C2—N3—O5	−1.2 (14)	C3—C2—C1—N2	−178.3 (9)
N3—C2—C3—C4	−174.9 (10)	N3—C2—C1—N2	−0.6 (13)
C1—C2—C3—C4	2.9 (15)	C3—C2—C1—N1	−4.3 (12)
C1—N1—C5—C4	−3.5 (17)	N3—C2—C1—N1	173.5 (8)
N1—C5—C4—C3	1.4 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.37	3.041 (10)	135
N1—H1···O2i	0.86	2.42	3.018 (10)	128
N1—H1···O1ii	0.86	2.48	3.077 (11)	128
N2—H2A···O1	0.86	2.38	3.036 (10)	133
N2—H2A···O1ii	0.86	2.40	3.010 (10)	129
N2—H2A···O2iii	0.86	2.55	3.168 (11)	129
N2—H2B···O5	0.86	2.02	2.624 (11)	127
N2—H2B···O3iii	0.86	2.26	2.976 (12)	141
C3—H3···O5iv	0.93	2.44	3.138 (12)	132
C5—H5···O4v	0.93	2.32	3.094 (13)	141
C5—H5···O2i	0.93	2.41	3.020 (13)	123

Table 1

Selected bond lengths (Å)

Re1—O1	1.726 (6)
Re1—O2	1.706 (7)
Re1—O3	1.708 (8)
Re1—O4	1.665 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.37	3.041 (10)	135
N1—H1⋯O2i	0.86	2.42	3.018 (10)	128
N1—H1⋯O1ii	0.86	2.48	3.077 (11)	128
N2—H2A⋯O1	0.86	2.38	3.036 (10)	133
N2—H2A⋯O1ii	0.86	2.40	3.010 (10)	129
N2—H2A⋯O2iii	0.86	2.55	3.168 (11)	129
N2—H2B⋯O5	0.86	2.02	2.624 (11)	127
N2—H2B⋯O3iii	0.86	2.26	2.976 (12)	141
C3—H3⋯O5iv	0.93	2.44	3.138 (12)	132
C5—H5⋯O4v	0.93	2.32	3.094 (13)	141
C5—H5⋯O2i	0.93	2.41	3.020 (13)	123

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