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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 68| Part 7| July 2012| Page m970
https://doi.org/10.1107/S1600536812027985

Bis(cyanato-κN)tetra­kis­(2,6-di­methyl­pyrazine-κN4)nickel(II)

Susanne Wöhlert,a* Inke Jessa and Christian Näthera

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
*Correspondence e-mail: swoehlert@ac.uni-kiel.de

(Received 15 June 2012; accepted 20 June 2012; online 23 June 2012)

Reaction of nickel(II) chloride with sodium cyanate and 2,6-di­methyl­pyrazine leads to single crystals of the title com­pound, [Ni(NCO)2(C6H8N2)4]. The nickel(II) cation is located about a centre of inversion and is octa­hedrally coordinated by two cyanate anions and four 2,6-dimethyl­pyrazine ligands, forming discrete complexes.

Related literature

For the background to this work relating to complexes with thio­cyanato and seleno­cyanato and N-donor ligands, see: Boeckmann & Näther (2010[Boeckmann, J. & Näther, C. (2010). Dalton Trans. 39, 11019-11026.]); Wriedt et al. (2009[Wriedt, M., Jess, I. & Näther, C. (2009). Eur. J. Inorg. Chem. pp. 1406-1413.]); Boeckmann et al. (2010[Boeckmann, J., Wriedt, M. & Näther, C. (2010). Eur. J. Inorg. Chem. pp. 1820-1828.]).

[Scheme 1]

Experimental

Crystal data

  • [Ni(NCO)2(C6H8N2)4]

  • Mr = 575.33

  • Monoclinic, C 2/c

  • a = 24.932 (2) Å

  • b = 8.4963 (3) Å

  • c = 18.1748 (13) Å

  • β = 133.148 (7)°

  • V = 2808.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.73 mm−1

  • T = 293 K

  • 0.07 × 0.04 × 0.03 mm
Data collection

  • Stoe IPDS-2 diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.888, Tmax = 0.969

  • 8293 measured reflections

  • 3341 independent reflections

  • 2516 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.102

  • S = 1.01

  • 3341 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—N1 2.0396 (19)
Ni1—N10 2.1475 (17)
Ni1—N20 2.1983 (15)

Data collection: X-AREA (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2011[Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: XCIF in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812027985/zl2488sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027985/zl2488Isup2.hkl

checkCIF report


Comment top

Recently we have reported on the synthesis, structures and properties of new coordination polymers based on paramagnetic transition metals, small-sized anionic ligands such as thiocyanato and selenocyanato, and N-donor ligands. In the course of these investigations we found that new coordination compounds with bridging anionic ligands can be prepared by thermal decomposition of suitable precursor compounds, in which the anionic ligands are only terminally coordinated (Wriedt et al., 2009 and Boeckmann & Näther, 2010). In further investigations we also have shown that even metal formate coordination compounds can be prepared by this method (Boeckmann, Wriedt & Näther, 2010). In our current investigations we tried to prepare similar compounds based on transition metal cyanates with 2,6-dimethylpyrazine as a neutral co-ligand. Therefore, we have reacted nickel(II) chloride with sodium cyanate and 2,6-dimethylpyrazine which resulted in the formation of crystals of the title compound that were identified by single crystal X-ray diffraction.

The asymmetric unit of the title compound consists of one nickel(II) cation, which is located on a centre of inversion, one cyanato anion and two 2,6-dimethylpyrazine ligands in general positions (Fig. 1). In the crystal structure each nickel(II) cation is coordinated by two terminal N-bonded cyanato anions and four 2,6-dimethylpyrazine ligands into discrete complexes, and the coordination polyhedra around the Ni cations corresponds to a slightly distorted octahedra. The anionic ligands are trans to each other and because of sterical crowding the 2,6-dimethylpyrazine ligand is coordinated via the nitrogen atom that is not neighbouring the methyl groups. The Ni—N distances range from 2.0396 (19) Å to 2.1983 (15) Å with angles between 88.72 (6) ° and 180 ° (Table 1). The shortest intermolecular distances between the nickel(II) cations is 8.4963 (3) Å.

Related literature top

For the background to this work relating to complexes with thiocyanato and selenocyanato and N-donor ligands, see: Boeckmann & Näther (2010); Wriedt et al. (2009); Boeckmann et al. (2010).

Experimental top

Nickel(II) chloride hexahydrate (NiCl2×6H2O), sodium cyanate (NaNCO) and 2,6-dimethylpyrazine were obtained from Alfa Aesar. All chemicals were used without further purification. 0.15 mmol (35.5 mg) NiCl2×6H2O and 0.3 mmol (19.5 mg) NaNCO were reacted in 0.6 mmol (65 µL) 2,6-dimethylpyrazine. Green shaped single-crystals suitable for structure determination were obtained after one week at room temperature.

Refinement top

C—H H atoms were positioned with idealized geometry (methyl H atoms were allowed to rotate but not to tip) and were refined isotropically with Uiso(H) = 1.2Ueq(C) (1.5 for methyl H atoms) and C—H distances of 0.93 Å for aromatic and 0.96 Å for methyl H atoms using a riding model.

Structure description top

Recently we have reported on the synthesis, structures and properties of new coordination polymers based on paramagnetic transition metals, small-sized anionic ligands such as thiocyanato and selenocyanato, and N-donor ligands. In the course of these investigations we found that new coordination compounds with bridging anionic ligands can be prepared by thermal decomposition of suitable precursor compounds, in which the anionic ligands are only terminally coordinated (Wriedt et al., 2009 and Boeckmann & Näther, 2010). In further investigations we also have shown that even metal formate coordination compounds can be prepared by this method (Boeckmann, Wriedt & Näther, 2010). In our current investigations we tried to prepare similar compounds based on transition metal cyanates with 2,6-dimethylpyrazine as a neutral co-ligand. Therefore, we have reacted nickel(II) chloride with sodium cyanate and 2,6-dimethylpyrazine which resulted in the formation of crystals of the title compound that were identified by single crystal X-ray diffraction.

The asymmetric unit of the title compound consists of one nickel(II) cation, which is located on a centre of inversion, one cyanato anion and two 2,6-dimethylpyrazine ligands in general positions (Fig. 1). In the crystal structure each nickel(II) cation is coordinated by two terminal N-bonded cyanato anions and four 2,6-dimethylpyrazine ligands into discrete complexes, and the coordination polyhedra around the Ni cations corresponds to a slightly distorted octahedra. The anionic ligands are trans to each other and because of sterical crowding the 2,6-dimethylpyrazine ligand is coordinated via the nitrogen atom that is not neighbouring the methyl groups. The Ni—N distances range from 2.0396 (19) Å to 2.1983 (15) Å with angles between 88.72 (6) ° and 180 ° (Table 1). The shortest intermolecular distances between the nickel(II) cations is 8.4963 (3) Å.

For the background to this work relating to complexes with thiocyanato and selenocyanato and N-donor ligands, see: Boeckmann & Näther (2010); Wriedt et al. (2009); Boeckmann et al. (2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50 % probability level. Symmetry code: i = -x + 3/2, -y + 3/2, -z + 1.
Bis(cyanato-κN)tetrakis(2,6-dimethylpyrazine-κN4)nickel(II) top
Crystal data top
[Ni(NCO)2(C6H8N2)4]F(000) = 1208
Mr = 575.33Dx = 1.360 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8293 reflections
a = 24.932 (2) Åθ = 2.7–28.0°
b = 8.4963 (3) ŵ = 0.73 mm−1
c = 18.1748 (13) ÅT = 293 K
β = 133.148 (7)°Block, green
V = 2808.9 (3) Å30.07 × 0.04 × 0.03 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer		3341 independent reflections
Radiation source: fine-focus sealed tube2516 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scanθmax = 28.0°, θmin = 2.7°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie 2008)		h = −25→32
Tmin = 0.888, Tmax = 0.969k = −11→10
8293 measured reflectionsl = −23→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0632P)2]
where P = (Fo2 + 2Fc2)/3
3341 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
[Ni(NCO)2(C6H8N2)4]V = 2808.9 (3) Å3
Mr = 575.33Z = 4
Monoclinic, C2/cMo Kα radiation
a = 24.932 (2) ŵ = 0.73 mm−1
b = 8.4963 (3) ÅT = 293 K
c = 18.1748 (13) Å0.07 × 0.04 × 0.03 mm
β = 133.148 (7)°
Data collection top
Stoe IPDS-2
diffractometer		3341 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie 2008)		2516 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.969Rint = 0.047
8293 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å−3
3341 reflectionsΔρmin = −0.40 e Å−3
182 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 > 2sigma(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
Ni10.75000.75000.50000.01887 (11)
N200.64456 (8)0.8103 (2)0.34913 (11)0.0212 (3)
N100.79329 (8)0.6983 (2)0.43337 (11)0.0231 (4)
C10.68822 (10)0.4093 (3)0.46580 (14)0.0255 (4)
N10.71677 (9)0.5219 (2)0.47971 (13)0.0275 (4)
N210.50923 (9)0.8818 (2)0.15700 (13)0.0270 (4)
C100.82299 (10)0.5593 (3)0.44444 (15)0.0261 (4)
H100.82390.48040.48070.031*
C230.62225 (10)0.9586 (2)0.31901 (15)0.0237 (4)
H230.65261.04010.36310.028*
N110.85370 (10)0.6399 (3)0.35157 (14)0.0364 (5)
C220.55452 (10)0.9952 (3)0.22309 (15)0.0251 (4)
C200.59907 (10)0.6966 (3)0.28228 (14)0.0239 (4)
H200.61300.59180.30020.029*
O10.65623 (11)0.2844 (2)0.45025 (18)0.0568 (6)
C110.85283 (11)0.5294 (3)0.40292 (15)0.0312 (5)
C130.79369 (10)0.8085 (3)0.38110 (14)0.0267 (4)
H130.77250.90600.37080.032*
C120.82493 (11)0.7812 (3)0.34183 (16)0.0330 (5)
C140.88376 (15)0.3709 (3)0.4124 (2)0.0454 (6)
H14A0.85800.32950.34640.068*
H14B0.87800.30060.44790.068*
H14C0.93500.38120.44900.068*
C150.82941 (15)0.9083 (4)0.2884 (2)0.0526 (8)
H15A0.87990.93570.32760.079*
H15B0.80290.99940.28000.079*
H15C0.80820.87070.22340.079*
C210.53149 (10)0.7326 (3)0.18668 (14)0.0272 (4)
C250.53126 (11)1.1627 (3)0.19022 (17)0.0341 (5)
H25A0.53821.19150.14610.051*
H25B0.56041.23020.24830.051*
H25C0.48031.17380.15520.051*
C240.48127 (12)0.6054 (3)0.11260 (18)0.0405 (6)
H24A0.43420.61600.09170.061*
H24B0.50190.50450.14370.061*
H24C0.47560.61430.05490.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01411 (16)0.02221 (18)0.01902 (17)−0.00050 (14)0.01083 (13)0.00029 (14)
N200.0161 (7)0.0272 (8)0.0213 (7)0.0021 (6)0.0131 (6)0.0022 (6)
N100.0158 (7)0.0312 (9)0.0196 (7)−0.0012 (6)0.0111 (6)−0.0006 (6)
C10.0202 (9)0.0288 (11)0.0239 (9)0.0043 (8)0.0137 (8)−0.0008 (8)
N10.0210 (8)0.0326 (10)0.0254 (8)0.0028 (7)0.0145 (7)0.0032 (7)
N210.0194 (7)0.0364 (10)0.0244 (8)0.0039 (7)0.0147 (7)0.0044 (7)
C100.0234 (9)0.0324 (11)0.0243 (9)0.0031 (8)0.0171 (8)0.0017 (8)
C230.0181 (8)0.0290 (10)0.0244 (9)0.0022 (7)0.0146 (8)0.0021 (8)
N110.0289 (9)0.0556 (13)0.0335 (9)0.0103 (8)0.0248 (8)0.0102 (9)
C220.0179 (8)0.0344 (11)0.0270 (9)0.0061 (8)0.0169 (8)0.0062 (8)
C200.0180 (8)0.0299 (10)0.0200 (9)0.0013 (7)0.0116 (8)0.0001 (7)
O10.0535 (11)0.0307 (10)0.0848 (15)−0.0174 (8)0.0467 (12)−0.0082 (9)
C110.0245 (10)0.0445 (13)0.0267 (10)0.0061 (9)0.0183 (9)0.0020 (9)
C130.0204 (9)0.0361 (11)0.0240 (9)0.0012 (8)0.0153 (8)0.0037 (8)
C120.0230 (9)0.0498 (15)0.0281 (10)0.0058 (8)0.0183 (8)0.0114 (9)
C140.0521 (14)0.0546 (16)0.0491 (14)0.0189 (12)0.0422 (13)0.0102 (12)
C150.0500 (14)0.0681 (19)0.0591 (17)0.0181 (14)0.0449 (14)0.0293 (15)
C210.0192 (8)0.0378 (13)0.0218 (9)0.0020 (8)0.0129 (8)0.0004 (8)
C250.0263 (10)0.0380 (13)0.0365 (11)0.0115 (9)0.0210 (9)0.0139 (9)
C240.0270 (10)0.0422 (14)0.0292 (10)−0.0009 (10)0.0102 (9)−0.0066 (10)
Geometric parameters (Å, º) top
Ni1—N1i2.0396 (19)C22—C251.498 (3)
Ni1—N12.0396 (19)C20—C211.395 (3)
Ni1—N102.1475 (17)C20—H200.9300
Ni1—N10i2.1475 (17)C11—C141.502 (3)
Ni1—N202.1983 (15)C13—C121.389 (3)
Ni1—N20i2.1983 (15)C13—H130.9300
N20—C231.335 (3)C12—C151.507 (3)
N20—C201.345 (3)C14—H14A0.9600
N10—C101.334 (3)C14—H14B0.9600
N10—C131.339 (3)C14—H14C0.9600
C1—N11.113 (3)C15—H15A0.9600
C1—O11.238 (3)C15—H15B0.9600
N21—C221.339 (3)C15—H15C0.9600
N21—C211.341 (3)C21—C241.497 (3)
C10—C111.398 (3)C25—H25A0.9600
C10—H100.9300C25—H25B0.9600
C23—C221.400 (3)C25—H25C0.9600
C23—H230.9300C24—H24A0.9600
N11—C111.334 (3)C24—H24B0.9600
N11—C121.347 (3)C24—H24C0.9600
N1i—Ni1—N1180.00 (13)N11—C11—C10121.2 (2)
N1i—Ni1—N1089.86 (7)N11—C11—C14117.3 (2)
N1—Ni1—N1090.14 (7)C10—C11—C14121.5 (2)
N1i—Ni1—N10i90.14 (7)N10—C13—C12121.8 (2)
N1—Ni1—N10i89.86 (7)N10—C13—H13119.1
N10—Ni1—N10i180.000C12—C13—H13119.1
N1i—Ni1—N2089.74 (7)N11—C12—C13121.1 (2)
N1—Ni1—N2090.26 (7)N11—C12—C15117.1 (2)
N10—Ni1—N2088.72 (6)C13—C12—C15121.7 (2)
N10i—Ni1—N2091.28 (6)C11—C14—H14A109.5
N1i—Ni1—N20i90.26 (7)C11—C14—H14B109.5
N1—Ni1—N20i89.74 (7)H14A—C14—H14B109.5
N10—Ni1—N20i91.28 (6)C11—C14—H14C109.5
N10i—Ni1—N20i88.72 (6)H14A—C14—H14C109.5
N20—Ni1—N20i180.000H14B—C14—H14C109.5
C23—N20—C20116.73 (16)C12—C15—H15A109.5
C23—N20—Ni1122.62 (13)C12—C15—H15B109.5
C20—N20—Ni1120.64 (14)H15A—C15—H15B109.5
C10—N10—C13116.95 (19)C12—C15—H15C109.5
C10—N10—Ni1122.49 (14)H15A—C15—H15C109.5
C13—N10—Ni1120.51 (15)H15B—C15—H15C109.5
N1—C1—O1179.7 (2)N21—C21—C20121.5 (2)
C1—N1—Ni1167.16 (17)N21—C21—C24117.32 (18)
C22—N21—C21117.19 (17)C20—C21—C24121.1 (2)
N10—C10—C11121.7 (2)C22—C25—H25A109.5
N10—C10—H10119.2C22—C25—H25B109.5
C11—C10—H10119.2H25A—C25—H25B109.5
N20—C23—C22122.01 (19)C22—C25—H25C109.5
N20—C23—H23119.0H25A—C25—H25C109.5
C22—C23—H23119.0H25B—C25—H25C109.5
C11—N11—C12117.2 (2)C21—C24—H24A109.5
N21—C22—C23121.1 (2)C21—C24—H24B109.5
N21—C22—C25117.86 (17)H24A—C24—H24B109.5
C23—C22—C25121.1 (2)C21—C24—H24C109.5
N20—C20—C21121.5 (2)H24A—C24—H24C109.5
N20—C20—H20119.3H24B—C24—H24C109.5
C21—C20—H20119.3
Symmetry code: (i) −x+3/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula[Ni(NCO)2(C6H8N2)4]
Mr575.33
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)24.932 (2), 8.4963 (3), 18.1748 (13)
β (°) 133.148 (7)
V (Å3)2808.9 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.73
Crystal size (mm)0.07 × 0.04 × 0.03
Data collection
DiffractometerStoe IPDS2
Absorption correctionNumerical
(X-SHAPE and X-RED32; Stoe & Cie 2008)
Tmin, Tmax0.888, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections		8293, 3341, 2516
Rint0.047
(sin θ/λ)max (Å−1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 1.01
No. of reflections3341
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.40

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011), XCIF in SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—N12.0396 (19)Ni1—N202.1983 (15)
Ni1—N102.1475 (17)
 

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/3-1) and the State of Schleswig-Holstein. We thank Professor Dr. Bensch for access to his experimental facilities.

References

First citationBoeckmann, J. & Näther, C. (2010). Dalton Trans. 39, 11019–11026.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationBoeckmann, J., Wriedt, M. & Näther, C. (2010). Eur. J. Inorg. Chem. pp. 1820–1828.  Web of Science CSD CrossRef Google Scholar
 First citationBrandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page m970
https://doi.org/10.1107/S1600536812027985
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