2-Amino-5-nitro­pyridinium tetraoxido­rhenate(VII) monohydrate

Rodrigues, V.H.; Costa, M.M.R.R.; Dekola, T.; Matos Gomes, E. de

doi:10.1107/S1600536809029365

metal-organic compounds

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Volume 65| Part 8| August 2009| Page m1000

doi:10.1107/S1600536809029365

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2-Amino-5-nitropyridinium tetraoxidorhenate(VII) monohydrate

V. H. Rodrigues,^a ^* M. M. R. R. Costa,^a T. Dekola ^b and E. de Matos Gomes ^b

^aCEMDRX, Department of Physics, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bDepartamento de Física, Universidade do Minho, P-4710-057 Braga, Portugal
^*Correspondence e-mail: vhugo@fis.uc.pt

(Received 13 July 2009; accepted 23 July 2009; online 29 July 2009)

All the residues of the title compound, (C₅H₆N₃O₂)[ReO₄]·H₂O, are located on general crystallographic positions. The 2-amino-5-nitropyridinium cation has a typical planar conformation with one of the nitro O atoms −0.058 (5) Å out of plane; the amine H atoms are also a little out of the main ring plane towards the opposite side of the aforementioned O atom [by 0.02 (4) and 0.04 (4) Å]. The perrhenate anion is nearly ideally tetrahedral. Three distinct N—H⋯O hydrogen bonds give rise to C(8) zigzag chains running along [100]. R₄⁴(12) rings involving the two hydrogen bonds in which the water molecules interact with the perrhenate anions are also present.

Related literature

For the structural analyses of related 2-amino-5-nitropyridium salts and their potential application as non-linear optical materials, see: Masse & Zyss (1991 ); Puig-Molina et al. (1998 ); Aakeröy et al. (1998 ); Pecaut et al. (1993 ).

Experimental

Crystal data

(C₅H₆N₃O₂)[ReO₄]·H₂O
M_r = 408.34
Monoclinic, P 2₁ /c
a = 9.6914 (3) Å
b = 9.1357 (3) Å
c = 13.4636 (4) Å
β = 120.120 (2)°
V = 1031.08 (6) Å³
Z = 4
Mo Kα radiation
μ = 11.81 mm⁻¹
T = 295 K
0.10 × 0.06 × 0.05 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.33, T_max = 0.55
30757 measured reflections
2374 independent reflections
2175 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.033
S = 1.05
2374 reflections
158 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	1.93	2.738 (3)	157
N1—H1⋯O6ⁱ	0.86	2.63	3.049 (4)	112
N2—H2A⋯O3	0.89 (3)	2.33 (3)	3.030 (4)	135 (3)
N2—H2A⋯O4ⁱⁱ	0.89 (3)	2.65 (3)	3.259 (4)	127 (3)
N2—H2B⋯O5	0.89 (3)	1.98 (3)	2.846 (3)	164 (3)
O3—H3A⋯O7ⁱⁱⁱ	0.89 (3)	1.93 (3)	2.802 (4)	167 (3)
O3—H3B⋯O4ⁱⁱ	0.89 (3)	2.13 (3)	2.862 (4)	139 (3)
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029365/ez2177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029365/ez2177Isup2.hkl

checkCIF report

Related literature top

For the structural analyses of related 2-amino-5-nitropyridium salts and their potential application as non-linear optical materials, see: Masse et al. (1991); Puig-Molina et al. (1998); Aakeröy et al. (1998); Pecaut et al. (1993).

Experimental top

Crystals of the title compound were obtained by slow evaporation from a water solution of analytical grade reagents on a 1:1 molar ratio. The reagents used were 2-amino-5-nitropyridine (99.5%) and a perrhenic acid solution (65–75% water 99.5%), both purchased from Aldrich.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. Zigzag chain running along the a axis. Small ring motifs made of a perrhenate anion and two water molecules are included in the chain. Hydrogen bonds are indicated with dashed lines.

2-Amino-5-nitropyridinium tetraoxidorhenate(VII) monohydrate top

Crystal data top

(C₅H₆N₃O₂)[ReO₄]·H₂O	F(000) = 760
M_r = 408.34	D_x = 2.631 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9920 reflections
a = 9.6914 (3) Å	θ = 2.4–32.3°
b = 9.1357 (3) Å	µ = 11.81 mm⁻¹
c = 13.4636 (4) Å	T = 295 K
β = 120.120 (2)°	Prism, translucent colourless
V = 1031.08 (6) Å³	0.10 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2374 independent reflections
Radiation source: fine-focus sealed tube	2175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.33, T_max = 0.55	k = −11→11
30757 measured reflections	l = −17→17

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)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.033	w = 1/[σ²(F_o²) + (0.0122P)² + 1.4451P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2374 reflections	Δρ_max = 0.88 e Å⁻³
158 parameters	Δρ_min = −0.72 e Å⁻³
5 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: 0.00774 (16)

Crystal data top

(C₅H₆N₃O₂)[ReO₄]·H₂O	V = 1031.08 (6) Å³
M_r = 408.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6914 (3) Å	µ = 11.81 mm⁻¹
b = 9.1357 (3) Å	T = 295 K
c = 13.4636 (4) Å	0.10 × 0.06 × 0.05 mm
β = 120.120 (2)°

Data collection top

Bruker APEXII diffractometer	2374 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2175 reflections with I > 2σ(I)
T_min = 0.33, T_max = 0.55	R_int = 0.030
30757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	5 restraints
wR(F²) = 0.033	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.88 e Å⁻³
2374 reflections	Δρ_min = −0.72 e Å⁻³
158 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
N1	0.2958 (3)	0.4684 (3)	0.0719 (2)	0.0338 (5)
H1	0.2145	0.4119	0.0493	0.041*
C2	0.4404 (3)	0.4063 (3)	0.1067 (2)	0.0315 (6)
N2	0.4512 (3)	0.2632 (3)	0.1047 (3)	0.0434 (6)
H2A	0.367 (3)	0.204 (3)	0.080 (3)	0.052*
H2B	0.543 (2)	0.219 (4)	0.124 (3)	0.052*
C3	0.5736 (3)	0.4998 (3)	0.1440 (3)	0.0352 (6)
H3	0.6741	0.4605	0.1684	0.042*
C4	0.5549 (3)	0.6463 (3)	0.1442 (2)	0.0362 (6)
H4	0.6420	0.7086	0.1688	0.043*
C5	0.4020 (3)	0.7029 (3)	0.1067 (2)	0.0332 (6)
N3	0.3785 (4)	0.8592 (3)	0.1068 (2)	0.0437 (6)
O1	0.4946 (4)	0.9377 (3)	0.1387 (3)	0.0717 (9)
O2	0.2459 (3)	0.9055 (3)	0.0781 (3)	0.0632 (7)
C6	0.2737 (3)	0.6133 (3)	0.0712 (2)	0.0336 (6)
H6	0.1728	0.6517	0.0469	0.040*
O3	0.1012 (3)	0.2314 (2)	0.0301 (2)	0.0538 (6)
H3A	0.083 (5)	0.174 (3)	0.076 (2)	0.081*
H3B	0.079 (5)	0.174 (3)	−0.030 (2)	0.081*
Re	0.905465 (12)	0.037384 (13)	0.215124 (10)	0.03195 (6)
O4	0.8222 (3)	−0.1153 (3)	0.1338 (2)	0.0680 (7)
O5	0.7677 (3)	0.1758 (3)	0.1707 (3)	0.0632 (7)
O6	0.9713 (4)	−0.0024 (3)	0.3551 (2)	0.0674 (8)
O7	1.0618 (3)	0.0893 (3)	0.1987 (3)	0.0664 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0264 (11)	0.0290 (12)	0.0452 (15)	−0.0007 (9)	0.0174 (11)	0.0031 (11)
C2	0.0289 (12)	0.0319 (14)	0.0329 (15)	0.0032 (11)	0.0150 (11)	0.0054 (12)
N2	0.0375 (13)	0.0281 (13)	0.0627 (18)	0.0052 (11)	0.0237 (14)	0.0057 (13)
C3	0.0262 (13)	0.0400 (16)	0.0369 (16)	0.0004 (11)	0.0142 (12)	0.0010 (13)
C4	0.0312 (13)	0.0411 (17)	0.0341 (16)	−0.0090 (12)	0.0147 (12)	−0.0035 (13)
C5	0.0417 (15)	0.0277 (14)	0.0296 (15)	0.0020 (12)	0.0175 (12)	0.0023 (12)
N3	0.0597 (17)	0.0299 (13)	0.0415 (15)	0.0009 (12)	0.0254 (13)	0.0003 (11)
O1	0.080 (2)	0.0345 (13)	0.108 (3)	−0.0181 (13)	0.0530 (19)	−0.0083 (14)
O2	0.0674 (17)	0.0398 (14)	0.0761 (19)	0.0152 (13)	0.0313 (15)	0.0003 (13)
C6	0.0320 (13)	0.0329 (15)	0.0351 (15)	0.0054 (12)	0.0161 (12)	0.0046 (13)
O3	0.0643 (16)	0.0382 (13)	0.0750 (19)	−0.0090 (12)	0.0471 (15)	−0.0043 (13)
Re	0.02646 (7)	0.03566 (8)	0.03418 (8)	0.00296 (4)	0.01554 (5)	0.00215 (5)
O4	0.0773 (19)	0.0537 (16)	0.0667 (18)	−0.0151 (14)	0.0315 (15)	−0.0156 (14)
O5	0.0447 (13)	0.0583 (16)	0.0843 (19)	0.0226 (12)	0.0307 (13)	0.0131 (15)
O6	0.085 (2)	0.0780 (19)	0.0394 (15)	0.0150 (16)	0.0313 (14)	0.0090 (13)
O7	0.0398 (13)	0.083 (2)	0.086 (2)	0.0057 (13)	0.0389 (14)	0.0225 (17)

Geometric parameters (Å, º) top

N1—C6	1.341 (4)	C5—C6	1.360 (4)
N1—C2	1.358 (3)	C5—N3	1.446 (4)
N1—H1	0.8600	N3—O1	1.216 (4)
C2—N2	1.313 (4)	N3—O2	1.217 (4)
C2—C3	1.413 (4)	C6—H6	0.9300
N2—H2A	0.89 (3)	O3—H3A	0.89 (3)
N2—H2B	0.89 (3)	O3—H3B	0.89 (3)
C3—C4	1.351 (4)	Re—O6	1.698 (3)
C3—H3	0.9300	Re—O7	1.704 (2)
C4—C5	1.402 (4)	Re—O4	1.705 (3)
C4—H4	0.9300	Re—O5	1.714 (2)

C6—N1—C2	123.2 (2)	C6—C5—N3	118.6 (3)
C6—N1—H1	118.4	C4—C5—N3	120.1 (3)
C2—N1—H1	118.4	O1—N3—O2	123.3 (3)
N2—C2—N1	119.2 (3)	O1—N3—C5	117.7 (3)
N2—C2—C3	122.8 (3)	O2—N3—C5	119.0 (3)
N1—C2—C3	118.0 (3)	N1—C6—C5	118.5 (2)
C2—N2—H2A	123 (2)	N1—C6—H6	120.7
C2—N2—H2B	122 (2)	C5—C6—H6	120.7
H2A—N2—H2B	115 (3)	H3A—O3—H3B	104 (3)
C4—C3—C2	120.0 (3)	O6—Re—O7	109.89 (15)
C4—C3—H3	120.0	O6—Re—O4	109.31 (15)
C2—C3—H3	120.0	O7—Re—O4	108.01 (15)
C3—C4—C5	118.9 (3)	O6—Re—O5	109.77 (14)
C3—C4—H4	120.6	O7—Re—O5	109.69 (13)
C5—C4—H4	120.6	O4—Re—O5	110.15 (14)
C6—C5—C4	121.3 (3)

C6—N1—C2—N2	179.9 (3)	C4—C5—N3—O1	1.0 (4)
C6—N1—C2—C3	0.1 (4)	C6—C5—N3—O2	1.9 (4)
N2—C2—C3—C4	−179.9 (3)	C4—C5—N3—O2	−177.2 (3)
N1—C2—C3—C4	−0.1 (4)	C2—N1—C6—C5	0.1 (4)
C2—C3—C4—C5	−0.2 (4)	C4—C5—C6—N1	−0.4 (4)
C3—C4—C5—C6	0.4 (4)	N3—C5—C6—N1	−179.5 (3)
C3—C4—C5—N3	179.5 (3)	N1—C2—N2—H2A	1 (3)
C6—C5—N3—O1	−179.9 (3)	C3—C2—N2—H2B	−3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.93	2.738 (3)	157
N1—H1···O6ⁱ	0.86	2.63	3.049 (4)	112
N2—H2A···O3	0.89 (3)	2.33 (3)	3.030 (4)	135 (3)
N2—H2A···O4ⁱⁱ	0.89 (3)	2.65 (3)	3.259 (4)	127 (3)
N2—H2B···O5	0.89 (3)	1.98 (3)	2.846 (3)	164 (3)
O3—H3A···O7ⁱⁱⁱ	0.89 (3)	1.93 (3)	2.802 (4)	167 (3)
O3—H3B···O4ⁱⁱ	0.89 (3)	2.13 (3)	2.862 (4)	139 (3)

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

Experimental details

Crystal data
Chemical formula	(C₅H₆N₃O₂)[ReO₄]·H₂O
M_r	408.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.6914 (3), 9.1357 (3), 13.4636 (4)
β (°)	120.120 (2)
V (Å³)	1031.08 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	11.81
Crystal size (mm)	0.10 × 0.06 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.33, 0.55
No. of measured, independent and observed [I > 2σ(I)] reflections	30757, 2374, 2175
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.033, 1.05
No. of reflections	2374
No. of parameters	158
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.72

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.93	2.738 (3)	157.1
N1—H1···O6ⁱ	0.86	2.63	3.049 (4)	111.7
N2—H2A···O3	0.89 (3)	2.33 (3)	3.030 (4)	135 (3)
N2—H2A···O4ⁱⁱ	0.89 (3)	2.65 (3)	3.259 (4)	127 (3)
N2—H2B···O5	0.89 (3)	1.98 (3)	2.846 (3)	164 (3)
O3—H3A···O7ⁱⁱⁱ	0.89 (3)	1.93 (3)	2.802 (4)	167 (3)
O3—H3B···O4ⁱⁱ	0.89 (3)	2.13 (3)	2.862 (4)	139 (3)

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

Acknowledgements

This work was supported by Fundação para a Ciência e a Tecnologia (FCT).

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