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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page m689
https://doi.org/10.1107/S160053681001812X

2-Amino-3-nitro­pyridinium perrhenate

Zeid Abdellah Al Othman,a Samah Toumi Akriche,b* Mohamed Rzaiguib and Refaat Mohamed Mahfouza

aChemistry Department, Faculty of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and bLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
*Correspondence e-mail: toumiakriche@yahoo.fr

(Received 13 May 2010; accepted 16 May 2010; online 22 May 2010)

In the title mol­ecular salt, (C5H6N3O2)[ReO4], 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 inter­actions. This results in alternating corrugated inorganic and organic layers in the crystal.

Related literature

For hydrogen-bond inter­actions see: Katayev et al. (2006[Katayev, E. A., Ustynyuk, Y. A. & Sessler, J. L. (2006). Coord. Chem. Rev. 250, 3004-3037.]). For related structures containing 2-amino-3-nitro­pyridinium cations, see: Akriche & Rzaigui (2000[Akriche, S. & Rzaigui, M. (2000). Z. Kristallogr. New Cryst. Struct. 215, 617-618.], 2009[Akriche, S. & Rzaigui, M. (2009). Acta Cryst. E65, o1648.]); Toumi Akriche et al. (2010[Toumi Akriche, S., Rzaigui, M., Al-Hokbany, N. & Mahfouz, R. M. (2010). Acta Cryst. E66, o300.]). For related structures containing perrhenate anions, see: Rodrigues et al. (2009[Rodrigues, V. H., Costa, M. M. R. R., Dekola, T. & de Matos Gomes, E. (2009). Acta Cryst. E65, m19.]); Ray et al. (2002[Ray, U. S., Mostafa, G., Lu, T. H. & Sinha, C. (2002). Cryst. Eng. 5, 95-104.], 2003[Ray, U., Chand, B., Dasmahapatra, A. K., Mostafa, G., Lu, T. H. & Sinha, C. (2003). Inorg. Chem. Commun. 6, 634-638.]). For distortion indices, see: Baur (1974[Baur, W. H. (1974). Acta Cryst. B30, 1195-1215.]).

[Scheme 1]

Experimental

Crystal data

  • (C5H6N3O2)[ReO4]

  • Mr = 390.33

  • Monoclinic, P 21 /c

  • 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[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.054, Tmax = 0.134

  • 7565 measured reflections

  • 4682 independent reflections

  • 3532 reflections with I > 2σ(I)

  • Rint = 0.027

  • 2 standard reflections every 120 min intensity decay: 4%
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 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

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) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x-1, y, z; (iv) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) x+1, y, z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681001812X/hb5451sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001812X/hb5451Isup2.hkl

checkCIF report


Comment top

A new engineering strategy aimed at building very cohesive frameworks based on oxyanion subnetworks in which the organic molecules are strongly anchored thanks to different interactions (electrostatic, H-bonds, Van der Waals). These interactions are all important in the construction of atomic arrangement but short and multiple hydrogen-bonds observed in these frameworks appear to be the most exciting since they have been recognized as the steering force responsible for the formation of special networks (Katayev et al., 2006). The oxoanions are good hydrogen bond acceptors, that's why they have been employed in the purification, extraction and detection techniques of dangerous pollutants (Ray et al., 2003; Ray et al., 2002; Rodrigues et al., 2009). The 2-amino-3-nitropyridine molecule has a dual nature because of its donor and acceptor groups. It can be protonated and thus serve as a hydrogen bond donor and electrostatic attractive element and also serve as a hydrogen bond acceptor which is especially useful for the binding of oxoanions. In this paper, we will account on the crystal engineering of 2-amino-3-nitropyridininium perrhenate, (C5H6N3O2)+, ReO4- (I).

The asymmetric unit of (I) consists of one perrhenate anion (ReO4- ) and one organic cation (C5H6N3O2)+ (Fig. 1).

The atomic arrangement of this salt is an organized dispersion of oganic cations and inorganic anions which form alternate corrugated layers (Fig. 2). This projection shows too the extensive network of H-bonds, N—H···O and C—H···O between cation and anion and C—H···O between cations (Table 1). These interactions constitute a key factor as well as electrostatic interaction in the stabilization of this structure. The nitropyridinium cations form chains running parallel to the [101/2] direction. The C—H···O interactions have the same H-bonds geometric parameters as the N—H···O ones which may also consolidate the cohesion of this structure. The neighbour nitropyridinium cations, are linked to form one-dimensional chains via C3—H3···O5 H-bonds (see Table 1 for symmetry codes) with C···O distance of 2.44 Å. Such chains of 2-amino-3-nitropyridinium are also observed in the related structure of 2 A3NPClO4 (Toumi Akriche et al., 2010). In this structure, the (C5H6N3O2)+n chains connect the discrete ReO4- anions through N—H···O and C—H···O hydrogen bonds in all directions to develop a three-dimensional network. It's worth noticing that the particular behaviour of hydrogen of nitrogen atoms which establish bi- and trifurcated H-bonds, that well explains the weak values of the corresponding angles spreading between 123 and 141°.

The ReO4- anion have an expected but slightly distorted tetrahedral geometry around Re atom with the Re—O bond lengths ranging from 1.665 (7) to 1.726 (6) Å and the O—Re—O bond angles ranging from 107.4 (4) to 113.4 (4)°. The average Re—O bond distances and O—Re—O bond angles are 1.701 Å and 109.45°, respectively, confirming a tetrahedral configuration, similar to other studied perrhenates (Ray et al., 2003; Ray et al., 2002). Nevertheless, the calculated average values of the distortion indices (Baur et al., 1974) corresponding to the different angles and distances in the independent ReO4 tetrahedron (DI(Re—O) = 0.011, DI(O—Re—O) = 0.017, and DI( O—O ) = 0.013) show an above distortion of the O—O distances compared to Re—O distances. The same feature is observed in ClO4 tetrahedron of the related structure of 2-amino-3-nitropyridinium perchlorate (Toumi Akriche et al., 2010). However, the distortion indices observed in 2-amino-3-nitropyridinium phosphate and selenate structures show an above distortion of the X—O (X = P and Se) distances compared to O—O distances (Akriche et al., 2000; Akriche et al., 2009), that well explain the distortion of XO4 tetrahedra (X = P and Se) in which the P and Se atoms are displaced of 0.114 to 0.065 Å from gravity center of XO4. The ReO4 tetrahedron is thus described by a regular oxygen atoms arrangement with the rhenium atom slightly shifted from gravity center of ReO4 (0.042 Å).

As expected, the pyridinium ring of 2-amino-3-nitropyridinium cation is nearly planar, with maximum deviation from planarity equal to 0.021 (5) Å. The diedral angle between the planes of the NO2 group and the pyridinium ring is close to 4.25 (9)° indicating a deformation of the NO2 group since the oxygen atoms of this later are the seat of various types of inter-and intramolecular hydrogen bonds. The geometrical charcteristics of the (I) organic cation are normal and comparable to that observed for the same species in other structure (Akriche et al., 2000; Toumi Akriche et al., 2010; Akriche et al., 2009 ).

Related literature top

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 top

An aqueous solution (10 ml) of NH4ReO4 (0.27 g; 1 mmol) is added drop by drop under stirring to an ethanolic solution (5 ml) of 2-amino-3-nitropyridine (0,139 g; 1 mmol) in the presence of HCL (1 M, 1 ml). Yellow solution was left in air for a week until yellow prisms of (I) were deposited on the wall of the beaker.

Refinement top

All H atoms attached to C and N atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C or N).

Structure description top

A new engineering strategy aimed at building very cohesive frameworks based on oxyanion subnetworks in which the organic molecules are strongly anchored thanks to different interactions (electrostatic, H-bonds, Van der Waals). These interactions are all important in the construction of atomic arrangement but short and multiple hydrogen-bonds observed in these frameworks appear to be the most exciting since they have been recognized as the steering force responsible for the formation of special networks (Katayev et al., 2006). The oxoanions are good hydrogen bond acceptors, that's why they have been employed in the purification, extraction and detection techniques of dangerous pollutants (Ray et al., 2003; Ray et al., 2002; Rodrigues et al., 2009). The 2-amino-3-nitropyridine molecule has a dual nature because of its donor and acceptor groups. It can be protonated and thus serve as a hydrogen bond donor and electrostatic attractive element and also serve as a hydrogen bond acceptor which is especially useful for the binding of oxoanions. In this paper, we will account on the crystal engineering of 2-amino-3-nitropyridininium perrhenate, (C5H6N3O2)+, ReO4- (I).

The asymmetric unit of (I) consists of one perrhenate anion (ReO4- ) and one organic cation (C5H6N3O2)+ (Fig. 1).

The atomic arrangement of this salt is an organized dispersion of oganic cations and inorganic anions which form alternate corrugated layers (Fig. 2). This projection shows too the extensive network of H-bonds, N—H···O and C—H···O between cation and anion and C—H···O between cations (Table 1). These interactions constitute a key factor as well as electrostatic interaction in the stabilization of this structure. The nitropyridinium cations form chains running parallel to the [101/2] direction. The C—H···O interactions have the same H-bonds geometric parameters as the N—H···O ones which may also consolidate the cohesion of this structure. The neighbour nitropyridinium cations, are linked to form one-dimensional chains via C3—H3···O5 H-bonds (see Table 1 for symmetry codes) with C···O distance of 2.44 Å. Such chains of 2-amino-3-nitropyridinium are also observed in the related structure of 2 A3NPClO4 (Toumi Akriche et al., 2010). In this structure, the (C5H6N3O2)+n chains connect the discrete ReO4- anions through N—H···O and C—H···O hydrogen bonds in all directions to develop a three-dimensional network. It's worth noticing that the particular behaviour of hydrogen of nitrogen atoms which establish bi- and trifurcated H-bonds, that well explains the weak values of the corresponding angles spreading between 123 and 141°.

The ReO4- anion have an expected but slightly distorted tetrahedral geometry around Re atom with the Re—O bond lengths ranging from 1.665 (7) to 1.726 (6) Å and the O—Re—O bond angles ranging from 107.4 (4) to 113.4 (4)°. The average Re—O bond distances and O—Re—O bond angles are 1.701 Å and 109.45°, respectively, confirming a tetrahedral configuration, similar to other studied perrhenates (Ray et al., 2003; Ray et al., 2002). Nevertheless, the calculated average values of the distortion indices (Baur et al., 1974) corresponding to the different angles and distances in the independent ReO4 tetrahedron (DI(Re—O) = 0.011, DI(O—Re—O) = 0.017, and DI( O—O ) = 0.013) show an above distortion of the O—O distances compared to Re—O distances. The same feature is observed in ClO4 tetrahedron of the related structure of 2-amino-3-nitropyridinium perchlorate (Toumi Akriche et al., 2010). However, the distortion indices observed in 2-amino-3-nitropyridinium phosphate and selenate structures show an above distortion of the X—O (X = P and Se) distances compared to O—O distances (Akriche et al., 2000; Akriche et al., 2009), that well explain the distortion of XO4 tetrahedra (X = P and Se) in which the P and Se atoms are displaced of 0.114 to 0.065 Å from gravity center of XO4. The ReO4 tetrahedron is thus described by a regular oxygen atoms arrangement with the rhenium atom slightly shifted from gravity center of ReO4 (0.042 Å).

As expected, the pyridinium ring of 2-amino-3-nitropyridinium cation is nearly planar, with maximum deviation from planarity equal to 0.021 (5) Å. The diedral angle between the planes of the NO2 group and the pyridinium ring is close to 4.25 (9)° indicating a deformation of the NO2 group since the oxygen atoms of this later are the seat of various types of inter-and intramolecular hydrogen bonds. The geometrical charcteristics of the (I) organic cation are normal and comparable to that observed for the same species in other structure (Akriche et al., 2000; Toumi Akriche et al., 2010; Akriche et al., 2009 ).

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).

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 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) with displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are represented as dashed lines.
[Figure 2] Fig. 2. Projection of (I) along the a axis. The H-atoms not involved in H-bonding are omitted.
2-Amino-3-nitropyridinium perrhenate top
Crystal data top
(C5H6N3O2)[ReO4]F(000) = 720
Mr = 390.33Dx = 2.715 Mg m−3
Monoclinic, P21/cAg Kα radiation, λ = 0.56087 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 6.235 (3) Åθ = 9–11°
b = 22.030 (2) ŵ = 6.86 mm−1
c = 7.840 (6) ÅT = 293 K
β = 117.52 (5)°Prism, yellow
V = 955.0 (9) Å30.50 × 0.40 × 0.30 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		3532 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590Rint = 0.027
Graphite monochromatorθmax = 28.0°, θmin = 2.4°
non–profiled ω scansh = −10→10
Absorption correction: multi-scan
(Blessing, 1995)		k = −36→0
Tmin = 0.054, Tmax = 0.134l = −12→13
7565 measured reflections2 standard reflections every 120 min
4682 independent reflections intensity decay: 4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 2.71 e Å−3
137 parametersΔρmin = −2.35 e Å−3
24 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (2)
Crystal data top
(C5H6N3O2)[ReO4]V = 955.0 (9) Å3
Mr = 390.33Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56087 Å
a = 6.235 (3) ŵ = 6.86 mm−1
b = 22.030 (2) ÅT = 293 K
c = 7.840 (6) Å0.50 × 0.40 × 0.30 mm
β = 117.52 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		3532 reflections with I > 2σ(I)
Absorption correction: multi-scan
(Blessing, 1995)		Rint = 0.027
Tmin = 0.054, Tmax = 0.1342 standard reflections every 120 min
7565 measured reflections intensity decay: 4%
4682 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04024 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.07Δρmax = 2.71 e Å−3
4682 reflectionsΔρmin = −2.35 e Å−3
137 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Re10.71309 (5)0.940210 (14)0.25037 (4)0.03320 (12)
O10.5590 (13)0.9742 (3)0.3597 (10)0.0450 (14)
O20.9536 (13)0.9832 (4)0.2759 (11)0.0544 (17)
O30.8207 (16)0.8717 (4)0.3586 (14)0.062 (2)
O40.5164 (14)0.9265 (4)0.0220 (10)0.0568 (19)
O50.2048 (17)0.7952 (4)0.6686 (16)0.073 (2)
O60.453 (2)0.7369 (5)0.8873 (17)0.088 (3)
N10.7550 (13)0.9105 (4)0.7469 (10)0.0400 (14)
H10.73660.94430.68670.048*
N20.3526 (15)0.8922 (3)0.5588 (11)0.0427 (15)
H2A0.33780.92640.50190.051*
H2B0.22880.86900.52600.051*
N30.4105 (19)0.7821 (4)0.7905 (14)0.053 (2)
C10.5584 (15)0.8757 (3)0.6920 (11)0.0338 (13)
C20.6059 (16)0.8218 (4)0.8141 (13)0.0386 (14)
C30.8316 (19)0.8088 (4)0.9565 (15)0.050 (2)
H30.85780.77331.02800.060*
C41.0226 (19)0.8481 (6)0.9954 (18)0.058 (3)
H41.17690.84021.09370.070*
C50.9753 (18)0.8982 (5)0.8848 (15)0.050 (2)
H51.10090.92480.90590.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.03010 (15)0.03753 (17)0.03126 (16)−0.00110 (11)0.01359 (11)−0.00198 (11)
O10.057 (4)0.041 (3)0.045 (3)−0.001 (3)0.030 (3)−0.002 (3)
O20.040 (3)0.067 (5)0.055 (4)−0.007 (3)0.022 (3)0.008 (3)
O30.062 (5)0.046 (4)0.076 (6)0.010 (3)0.030 (4)0.017 (4)
O40.044 (4)0.078 (5)0.039 (3)0.001 (3)0.012 (3)−0.019 (3)
O50.057 (5)0.057 (5)0.090 (7)−0.021 (4)0.021 (4)0.005 (5)
O60.090 (7)0.059 (6)0.103 (8)−0.012 (5)0.034 (6)0.036 (5)
N10.041 (3)0.037 (3)0.046 (4)−0.001 (2)0.023 (3)0.006 (3)
N20.046 (4)0.035 (3)0.037 (3)−0.001 (3)0.010 (3)0.006 (3)
N30.064 (5)0.031 (3)0.064 (5)−0.004 (3)0.029 (4)0.003 (3)
C10.039 (3)0.028 (3)0.034 (3)−0.001 (2)0.017 (3)−0.003 (2)
C20.044 (4)0.028 (3)0.046 (4)0.003 (3)0.023 (3)0.002 (3)
C30.054 (5)0.038 (4)0.057 (5)0.014 (3)0.024 (4)0.017 (4)
C40.041 (4)0.062 (6)0.066 (6)0.009 (4)0.021 (4)0.016 (5)
C50.040 (4)0.057 (5)0.052 (5)−0.001 (4)0.020 (4)0.008 (4)
Geometric parameters (Å, º) top
Re1—O11.726 (6)C2—C31.363 (13)
Re1—O21.706 (7)C2—N31.441 (12)
Re1—O31.708 (8)C2—C11.466 (11)
Re1—O41.665 (7)O5—N31.228 (14)
N1—C51.325 (12)N3—O61.206 (12)
N1—C11.338 (11)C3—C41.387 (16)
N1—H10.8600C3—H30.9300
N2—C11.277 (11)C5—C41.350 (15)
N2—H2A0.8600C5—H50.9300
N2—H2B0.8600C4—H40.9300
O4—Re1—O2113.4 (4)N2—C1—N1121.7 (8)
O4—Re1—O3107.4 (4)N2—C1—C2126.0 (8)
O2—Re1—O3108.1 (4)N1—C1—C2112.1 (7)
O4—Re1—O1108.1 (4)C3—C2—N3118.0 (8)
O2—Re1—O1111.2 (4)C3—C2—C1121.8 (8)
O3—Re1—O1108.5 (4)N3—C2—C1120.3 (8)
C5—N1—C1126.5 (8)C2—C3—C4120.3 (9)
C5—N1—H1116.8C2—C3—H3119.9
C1—N1—H1116.8C4—C3—H3119.9
C1—N2—H2A120.0C5—C4—C3117.3 (10)
C1—N2—H2B120.0C5—C4—H4121.3
H2A—N2—H2B120.0C3—C4—H4121.3
O6—N3—O5122.0 (10)N1—C5—C4121.9 (10)
O6—N3—C2119.7 (10)N1—C5—H5119.1
O5—N3—C2118.3 (8)C4—C5—H5119.1
C3—C2—N3—O6−4.7 (15)C2—C3—C4—C5−1.3 (17)
C1—C2—N3—O6177.5 (10)C5—N1—C1—N2179.0 (9)
C3—C2—N3—O5176.6 (10)C5—N1—C1—C24.7 (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—C42.9 (15)C3—C2—C1—N1−4.3 (12)
C1—N1—C5—C4−3.5 (17)N3—C2—C1—N1173.5 (8)
N1—C5—C4—C31.4 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.373.041 (10)135
N1—H1···O2i0.862.423.018 (10)128
N1—H1···O1ii0.862.483.077 (11)128
N2—H2A···O10.862.383.036 (10)133
N2—H2A···O1ii0.862.403.010 (10)129
N2—H2A···O2iii0.862.553.168 (11)129
N2—H2B···O50.862.022.624 (11)127
N2—H2B···O3iii0.862.262.976 (12)141
C3—H3···O5iv0.932.443.138 (12)132
C5—H5···O4v0.932.323.094 (13)141
C5—H5···O2i0.932.413.020 (13)123
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x−1, y, z; (iv) x+1, −y+3/2, z+1/2; (v) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula(C5H6N3O2)[ReO4]
Mr390.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)6.235 (3), 22.030 (2), 7.840 (6)
β (°) 117.52 (5)
V (Å3)955.0 (9)
Z4
Radiation typeAg Kα, λ = 0.56087 Å
µ (mm−1)6.86
Crystal size (mm)0.50 × 0.40 × 0.30
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.054, 0.134
No. of measured, independent and
observed [I > 2σ(I)] reflections		7565, 4682, 3532
Rint0.027
(sin θ/λ)max (Å−1)0.836
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.111, 1.07
No. of reflections4682
No. of parameters137
No. of restraints24
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)2.71, −2.35

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

Selected bond lengths (Å) top
Re1—O11.726 (6)Re1—O31.708 (8)
Re1—O21.706 (7)Re1—O41.665 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.373.041 (10)135
N1—H1···O2i0.862.423.018 (10)128
N1—H1···O1ii0.862.483.077 (11)128
N2—H2A···O10.862.383.036 (10)133
N2—H2A···O1ii0.862.403.010 (10)129
N2—H2A···O2iii0.862.553.168 (11)129
N2—H2B···O50.862.022.624 (11)127
N2—H2B···O3iii0.862.262.976 (12)141
C3—H3···O5iv0.932.443.138 (12)132
C5—H5···O4v0.932.323.094 (13)141
C5—H5···O2i0.932.413.020 (13)123
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x−1, y, z; (iv) x+1, −y+3/2, z+1/2; (v) x+1, y, z+1.
 

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page m689
https://doi.org/10.1107/S160053681001812X
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