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In the title compound, [Ni(C5H3N2O2)2], the NiII cation is four-coordinated by two N and two O atoms belonging to two pyrazine-2-carboxyl­ate ligands. The NiII cation lies on a centre of symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026268/br2043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026268/br2043Isup2.hkl
Contains datablock I

CCDC reference: 654700

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.056
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity. PLAT761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? PLAT762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 7.18 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N1 .. 7.82 su PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C5 .. 2.99 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. C5 .. 3.18 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 1.90
4 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Hybrid organic–inorganic materials occupy a prominent position by virtue of their applications to catalysis, optical materials, membranes, and sorption (Ngo et al., 2004; Evans et al., 2001; Vioux et al., 2004; Sanchez et al., 2003; Evans & Lin, 2001; Jannasch, 2003; Javaid et al., 2001; Honma et al., 2001; Sudik et al., 2005; Rowsell et al., 2004; Kitaura et al., 2002). The design of organic-inorganic hybrid materials is conceived of the metal, metal cluster, or metal oxide substructure as a node from which rigid or flexible multitopic organic ligands radiate to act as tethers to adjacent nodes in the bottom-up construction of complex extended architectures. While a variety of organic molecules have been investigated as potential tethers, materials incorporating multitopic carboxylates and pyridine ligands have witnessed the most significant development. However, ligands offering alternative tether lengths, different charge-balance requirements, and orientations of donor groups may afford advantages in the design of materials. One such ligand is 2-pyrazine caboxylate, a member of the polyazaheteroaromatic family of compounds, which exhibit an extensively documented ability to bridge metal ions to afford polynuclear compounds. 2-pyrazine caboxylate is an attractive ligand for the design of novel hybrid materials because of the unusual structural diversity associated with the di- and trinucleating properties of the neutral and anionic ligand forms, respectively. Herein, one new complex,[di(2-pyrazine caboxylato) nickel(II)], obtained from 2-pyrazine caboxylate and nickel acetate under hydrothermal reaction is reported.

The coordination of the nickel atom is shown in Fig. 1 which can be described as a co-planar. The nickel cation is four-coordinated by two nitrogen atoms and two oxygen atoms belonging to two 2-pyrazine caboxylate ligands. The Ni—N and Ni—O bond lengths are 1.9763 (18) and 1.9297 (15) Å, respectively. The angle of O(N)—Ni—O(N) are in the range of 83.71 (7)–96.29 (7) Å.

Related literature top

For related literature, see: Ngo et al., 2004; Evans et al., 2001; Vioux et al., 2004; Sanchez et al., 2003; Evans & Lin, 2001; Jannasch, 2003; Javaid et al., 2001; Honma et al., 2001; Sudik et al., 2005; Rowsell et al., 2004; Kitaura et al., 2004.

Experimental top

All chemicals were used as purchased from Shanghai Chemical Co. Ltd. A mixture of Nickel(II) acetate (0.5 mmol), potassium hydroxide (0.5 mmol), 2-pyrazine caboxylic acid(0.5 mmol) and EtOH (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 413 K for 2 d, and then cooled to room temperature. Green, block-shaped crystals of (I) were obtained in a yield of 12%. Anal. Calc. for C10H6N4NiO4: C 39.34, H 1.97, N 18.36, Ni 19.25%; Found: C 39.39, H 2.01, N 18.33, Ni 19.18%.

Refinement top

All H atoms on C atoms were generated geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2 times Ueq(C).

Structure description top

Hybrid organic–inorganic materials occupy a prominent position by virtue of their applications to catalysis, optical materials, membranes, and sorption (Ngo et al., 2004; Evans et al., 2001; Vioux et al., 2004; Sanchez et al., 2003; Evans & Lin, 2001; Jannasch, 2003; Javaid et al., 2001; Honma et al., 2001; Sudik et al., 2005; Rowsell et al., 2004; Kitaura et al., 2002). The design of organic-inorganic hybrid materials is conceived of the metal, metal cluster, or metal oxide substructure as a node from which rigid or flexible multitopic organic ligands radiate to act as tethers to adjacent nodes in the bottom-up construction of complex extended architectures. While a variety of organic molecules have been investigated as potential tethers, materials incorporating multitopic carboxylates and pyridine ligands have witnessed the most significant development. However, ligands offering alternative tether lengths, different charge-balance requirements, and orientations of donor groups may afford advantages in the design of materials. One such ligand is 2-pyrazine caboxylate, a member of the polyazaheteroaromatic family of compounds, which exhibit an extensively documented ability to bridge metal ions to afford polynuclear compounds. 2-pyrazine caboxylate is an attractive ligand for the design of novel hybrid materials because of the unusual structural diversity associated with the di- and trinucleating properties of the neutral and anionic ligand forms, respectively. Herein, one new complex,[di(2-pyrazine caboxylato) nickel(II)], obtained from 2-pyrazine caboxylate and nickel acetate under hydrothermal reaction is reported.

The coordination of the nickel atom is shown in Fig. 1 which can be described as a co-planar. The nickel cation is four-coordinated by two nitrogen atoms and two oxygen atoms belonging to two 2-pyrazine caboxylate ligands. The Ni—N and Ni—O bond lengths are 1.9763 (18) and 1.9297 (15) Å, respectively. The angle of O(N)—Ni—O(N) are in the range of 83.71 (7)–96.29 (7) Å.

For related literature, see: Ngo et al., 2004; Evans et al., 2001; Vioux et al., 2004; Sanchez et al., 2003; Evans & Lin, 2001; Jannasch, 2003; Javaid et al., 2001; Honma et al., 2001; Sudik et al., 2005; Rowsell et al., 2004; Kitaura et al., 2004.

Computing details top

Data collection: XSCANS (Bruker, 2001); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1999); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the structure for the title compound,showing 30% probability displacement ellipsoids. Atoms labeled with I at the symmetry positions (-x + 1,-y + 1,-z + 2).
Bis(pyrazine-2-caboxylato-κ2N1,O)nickel(II) top
Crystal data top
[Ni(C5H3N2O2)2]F(000) = 308
Mr = 304.90Dx = 1.925 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4678 reflections
a = 5.0501 (9) Åθ = 2.0–26.0°
b = 15.370 (3) ŵ = 1.86 mm1
c = 7.0704 (13) ÅT = 293 K
β = 106.60 (2)°Block, green
V = 525.9 (3) Å30.10 × 0.10 × 0.10 mm
Z = 2
Data collection top
Bruker P4
diffractometer
776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 26.0°, θmin = 2.7°
ω scansh = 66
4336 measured reflectionsk = 1819
1014 independent reflectionsl = 88
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)] = 0.028H-atom parameters constrained
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0234P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.011
1014 reflectionsΔρmax = 0.43 e Å3
88 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (3)
Crystal data top
[Ni(C5H3N2O2)2]V = 525.9 (3) Å3
Mr = 304.90Z = 2
Monoclinic, P21/cMo Kα radiation
a = 5.0501 (9) ŵ = 1.86 mm1
b = 15.370 (3) ÅT = 293 K
c = 7.0704 (13) Å0.10 × 0.10 × 0.10 mm
β = 106.60 (2)°
Data collection top
Bruker P4
diffractometer
776 reflections with I > 2σ(I)
4336 measured reflectionsRint = 0.039
1014 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.00Δρmax = 0.43 e Å3
1014 reflectionsΔρmin = 0.24 e Å3
88 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
xyzUiso*/Ueq
Ni10.50000.50001.00000.03121 (15)
O20.1700 (3)0.43181 (10)0.8941 (2)0.0391 (4)
N10.2849 (4)0.59243 (12)0.8293 (3)0.0319 (5)
C50.0329 (5)0.47318 (15)0.7773 (4)0.0352 (6)
O30.2701 (3)0.44533 (12)0.7132 (3)0.0500 (5)
C40.0334 (5)0.56447 (14)0.7293 (3)0.0312 (5)
N20.0889 (4)0.70172 (14)0.5766 (3)0.0466 (6)
C30.1486 (5)0.61873 (16)0.6001 (3)0.0393 (6)
H30.31870.59680.52700.047*
C20.1568 (5)0.72928 (16)0.6837 (4)0.0435 (6)
H20.20120.78760.67550.052*
C10.3507 (5)0.67537 (15)0.8072 (4)0.0374 (6)
H10.52470.69660.87410.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0198 (2)0.0274 (2)0.0392 (3)0.00080 (18)0.00327 (17)0.0042 (2)
O20.0307 (9)0.0315 (9)0.0469 (11)0.0020 (7)0.0024 (8)0.0036 (8)
N10.0272 (11)0.0318 (11)0.0342 (11)0.0005 (8)0.0045 (8)0.0011 (9)
C50.0309 (14)0.0379 (14)0.0338 (14)0.0008 (11)0.0042 (11)0.0033 (11)
O30.0283 (10)0.0493 (11)0.0597 (12)0.0116 (8)0.0077 (8)0.0042 (9)
C40.0267 (12)0.0324 (13)0.0319 (13)0.0024 (10)0.0041 (10)0.0028 (11)
N20.0473 (14)0.0392 (13)0.0464 (13)0.0084 (10)0.0026 (11)0.0058 (10)
C30.0341 (15)0.0429 (15)0.0375 (15)0.0028 (11)0.0046 (12)0.0007 (12)
C20.0494 (17)0.0321 (14)0.0487 (16)0.0001 (12)0.0137 (14)0.0023 (13)
C10.0338 (14)0.0355 (15)0.0413 (15)0.0033 (10)0.0081 (12)0.0024 (12)
Geometric parameters (Å, º) top
Ni1—O2i1.9297 (15)C5—O31.230 (3)
Ni1—O21.9297 (15)C5—C41.504 (3)
Ni1—N1i1.9763 (18)C4—C31.377 (3)
Ni1—N11.9763 (18)N2—C21.325 (3)
O2—C51.286 (3)N2—C31.332 (3)
N1—C41.336 (3)C2—C11.386 (3)
N1—C11.338 (3)
O2i—Ni1—N1i83.71 (7)O3—C5—C4119.9 (2)
O2—Ni1—N1i96.29 (7)O2—C5—C4114.74 (19)
O2i—Ni1—N196.29 (7)N1—C4—C3120.7 (2)
O2—Ni1—N183.71 (7)N1—C4—C5114.85 (19)
C5—O2—Ni1114.96 (14)C3—C4—C5124.4 (2)
C4—N1—C1118.4 (2)C2—N2—C3116.3 (2)
C4—N1—Ni1111.44 (15)N2—C3—C4122.1 (2)
C1—N1—Ni1130.15 (16)N2—C2—C1123.2 (2)
O3—C5—O2125.3 (2)N1—C1—C2119.3 (2)
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula[Ni(C5H3N2O2)2]
Mr304.90
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)5.0501 (9), 15.370 (3), 7.0704 (13)
β (°) 106.60 (2)
V3)525.9 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.86
Crystal size (mm)0.10 × 0.10 × 0.10
Data collection
DiffractometerBruker P4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4336, 1014, 776
Rint0.039
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.056, 1.00
No. of reflections1014
No. of parameters88
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.24

Computer programs: XSCANS (Bruker, 2001), XSCANS, SHELXTL (Bruker, 1999), SHELXL97 (Sheldrick, 1997), SHELXTL.

 

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