Bis(5-methyl-pyrazine-2-carboxyl-ato-κ²N,O)nickel(II).

In the title complex, [Ni(C₆H₅O₂N₂)₂], the Ni(II) atom is situated on an inversion centre and is coordinated in a square-planar geometry by four O atoms and two N atoms of the chelating ligands.

Related literature

For applications of complexes derived from 2-methyl­pyrazine-5-carb­oxy­lic acid, see: Chapman et al. (2002 ▶); Ptasiewicz-Bak & Leciejewicz (2000 ▶); Tanase et al. (2006 ▶); Wang et al. (2008 ▶) For a related structure, see: Liu et al. (2007 ▶).

Experimental

Crystal data

[Ni(C6H5N2O2)2]

M = 332.95

Monoclinic,

a = 11.3098 (19) Å

b = 7.6721 (11) Å

c = 7.5467 (10) Å

β = 105.647 (2)°

V = 630.56 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.56 mm−1

T = 298 K

0.42 × 0.31 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.560, T max = 0.756

2875 measured reflections

1105 independent reflections

827 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.176

S = 1.03

1105 reflections

97 parameters

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −1.37 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024749/ru2036sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024749/ru2036Isup2.hkl

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

[Ni(C6H5N2O2)2]	F(000) = 340
Mr = 332.95	Dx = 1.754 Mg m−3Dm = 1.754 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2220 reflections
a = 11.3098 (19) Å	θ = 1.3–24.1°
b = 7.6721 (11) Å	µ = 1.56 mm−1
c = 7.5467 (10) Å	T = 298 K
β = 105.647 (2)°	Block, green
V = 630.56 (16) Å3	0.42 × 0.31 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	1105 independent reflections
Radiation source: fine-focus sealed tube	827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
Tmin = 0.560, Tmax = 0.756	k = −9→6
2875 measured reflections	l = −8→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.121P)2 + 0.167P] where P = (Fo2 + 2Fc2)/3
1105 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 1.34 e Å−3
0 restraints	Δρmin = −1.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.0317 (4)
N1	0.3510 (4)	0.4618 (5)	0.5844 (6)	0.0312 (10)
N2	0.1370 (5)	0.4682 (6)	0.6946 (7)	0.0475 (13)
O1	0.4846 (3)	0.7385 (4)	0.5791 (5)	0.0412 (9)
O2	0.3624 (4)	0.9088 (5)	0.6943 (5)	0.0485 (10)
C1	0.3918 (5)	0.7680 (7)	0.6395 (7)	0.0355 (12)
C2	0.3114 (5)	0.6106 (6)	0.6398 (6)	0.0342 (12)
C3	0.2062 (5)	0.6111 (7)	0.6967 (8)	0.0463 (14)
H3	0.1814	0.7151	0.7389	0.056*
C4	0.2869 (4)	0.3151 (7)	0.5865 (7)	0.0360 (12)
H4	0.3148	0.2096	0.5523	0.043*
C5	0.1780 (5)	0.3214 (7)	0.6401 (7)	0.0404 (13)
C6	0.1017 (5)	0.1600 (8)	0.6309 (8)	0.0529 (15)
H6A	0.0434	0.1771	0.7011	0.079*
H6B	0.1541	0.0633	0.6806	0.079*
H6C	0.0588	0.1362	0.5051	0.079*

	U11	U22	U33	U12	U13	U23
Ni1	0.0421 (6)	0.0079 (5)	0.0502 (7)	−0.0023 (3)	0.0210 (4)	−0.0035 (3)
N1	0.039 (2)	0.016 (2)	0.040 (2)	−0.0016 (17)	0.0133 (18)	0.0004 (16)
N2	0.052 (3)	0.033 (3)	0.062 (3)	−0.003 (2)	0.023 (2)	−0.005 (2)
O1	0.053 (2)	0.0154 (18)	0.059 (2)	−0.0040 (16)	0.0209 (18)	−0.0051 (17)
O2	0.067 (2)	0.014 (2)	0.068 (3)	0.0046 (18)	0.0242 (19)	−0.0060 (17)
C1	0.048 (3)	0.016 (3)	0.041 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
C2	0.046 (3)	0.019 (3)	0.039 (3)	0.001 (2)	0.013 (2)	−0.004 (2)
C3	0.059 (4)	0.026 (3)	0.061 (3)	0.004 (2)	0.027 (3)	−0.007 (2)
C4	0.044 (3)	0.016 (3)	0.048 (3)	−0.001 (2)	0.012 (2)	−0.002 (2)
C5	0.050 (3)	0.030 (3)	0.044 (3)	−0.007 (2)	0.018 (2)	0.001 (2)
C6	0.058 (3)	0.037 (3)	0.067 (4)	−0.015 (3)	0.022 (3)	−0.003 (3)

Ni1—O1	1.947 (3)	C1—C2	1.512 (7)
Ni1—O1i	1.947 (3)	C2—C3	1.370 (7)
Ni1—N1	1.977 (4)	C3—H3	0.9300
Ni1—N1i	1.977 (4)	C4—C5	1.397 (7)
N1—C2	1.335 (6)	C4—H4	0.9300
N1—C4	1.341 (6)	C5—C6	1.501 (7)
N2—C5	1.325 (7)	C6—H6A	0.9600
N2—C3	1.345 (7)	C6—H6B	0.9600
O1—C1	1.272 (6)	C6—H6C	0.9600
O2—C1	1.233 (6)
O1—Ni1—O1i	180.000 (1)	C3—C2—C1	124.9 (5)
O1—Ni1—N1	83.45 (16)	N2—C3—C2	123.1 (5)
O1i—Ni1—N1	96.55 (16)	N2—C3—H3	118.5
O1—Ni1—N1i	96.55 (16)	C2—C3—H3	118.5
O1i—Ni1—N1i	83.45 (16)	N1—C4—C5	119.7 (5)
N1—Ni1—N1i	180.0	N1—C4—H4	120.1
C2—N1—C4	119.1 (4)	C5—C4—H4	120.1
C2—N1—Ni1	111.2 (3)	N2—C5—C4	122.0 (5)
C4—N1—Ni1	129.7 (4)	N2—C5—C6	118.1 (5)
C5—N2—C3	116.4 (5)	C4—C5—C6	119.9 (5)
C1—O1—Ni1	115.3 (3)	C5—C6—H6A	109.5
O2—C1—O1	126.8 (5)	C5—C6—H6B	109.5
O2—C1—C2	118.9 (4)	H6A—C6—H6B	109.5
O1—C1—C2	114.4 (4)	C5—C6—H6C	109.5
N1—C2—C3	119.6 (5)	H6A—C6—H6C	109.5
N1—C2—C1	115.5 (4)	H6B—C6—H6C	109.5
O1—Ni1—N1—C2	3.6 (3)	Ni1—N1—C2—C1	−4.3 (5)
O1i—Ni1—N1—C2	−176.4 (3)	O2—C1—C2—N1	−177.9 (4)
N1i—Ni1—N1—C2	−75 (100)	O1—C1—C2—N1	2.7 (6)
O1—Ni1—N1—C4	−178.8 (5)	O2—C1—C2—C3	0.1 (8)
O1i—Ni1—N1—C4	1.2 (5)	O1—C1—C2—C3	−179.3 (5)
N1i—Ni1—N1—C4	102 (100)	C5—N2—C3—C2	2.5 (9)
O1i—Ni1—O1—C1	−153 (100)	N1—C2—C3—N2	−2.2 (9)
N1—Ni1—O1—C1	−2.3 (3)	C1—C2—C3—N2	179.9 (5)
N1i—Ni1—O1—C1	177.7 (3)	C2—N1—C4—C5	2.2 (7)
Ni1—O1—C1—O2	−178.9 (4)	Ni1—N1—C4—C5	−175.2 (3)
Ni1—O1—C1—C2	0.5 (5)	C3—N2—C5—C4	−0.4 (8)
C4—N1—C2—C3	−0.3 (7)	C3—N2—C5—C6	−178.4 (5)
Ni1—N1—C2—C3	177.6 (4)	N1—C4—C5—N2	−1.9 (8)
C4—N1—C2—C1	177.8 (4)	N1—C4—C5—C6	176.0 (5)