Bis(3-amino-pyrazine-2-carboxyl-ato-κ(2) N (1),O)di-aqua-nickel(II) dihydrate.

In the title compound, [Ni(C5H4N3O2)2(H2O)2]·2H2O, the Ni(II) ion lies on an inversion center and is coordinated in an slightly distorted octa-hedral environment by two N,O-chelating 3-amino-pyrazine-2-carboxyl-ate (APZC) ligands in the equatorial plane and two trans-axial aqua ligands. In the crystal, O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds involving the solvent water mol-ecules, aqua and APZC ligands form layers parallel to (010). These layers are linked further via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds involving the axial aqua ligands, amino groups and the carboxyl-ate groups of the APZC ligands, forming a three-dimensional network.

Related literature

For background to hybrid compounds, see: Bouchene et al. (2013 ▶); Bouacida et al. (2007 ▶, 2009 ▶). For the structure of the non-hydrated analogue, see: Ptasiewicz-Bak & Leciejewicz (1999 ▶). For 3-amino­pyrazine-2-carboxyl­ate–metal (M) complexes, see: Bouchene et al. (2013 ▶) [M = Co(II)]; Leciejewicz et al. (1997 ▶) [M = Ca(II)]; Leciejewicz et al. (1998 ▶) [M = Sr(II)]; Ptasiewicz-Bak & Leciejewicz (1997 ▶) [M = Mg(II)]; Tayebee et al. (2008 ▶) [M = Na(I)]; Ptasiewicz-Bak & Leciejewicz (1999 ▶). For proprieties and applications of pyrazine-2-carb­oxy­lic acid, see: Zhang & Mitchison (2003 ▶); Manju & Chaudhary, (2010 ▶); Chanda & Sangeetika (2004 ▶).

Experimental

Crystal data

[Ni(C5H4N3O2)2(H2O)2]·2H2O

M = 406.98

Monoclinic,

a = 9.7939 (15) Å

b = 5.1123 (9) Å

c = 16.776 (3) Å

β = 115.838 (11)°

V = 756.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.34 mm−1

T = 150 K

0.18 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

6200 measured reflections

1326 independent reflections

1121 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.04

1326 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012208/lh5610sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012208/lh5610Isup2.hkl

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

[Ni(C5H4N3O2)2(H2O)2]·2H2O	F(000) = 420
Mr = 406.98	Dx = 1.788 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7939 (15) Å	Cell parameters from 2285 reflections
b = 5.1123 (9) Å	θ = 2.7–25°
c = 16.776 (3) Å	µ = 1.34 mm−1
β = 115.838 (11)°	T = 150 K
V = 756.0 (2) Å3	Cube, white
Z = 2	0.18 × 0.16 × 0.15 mm

Bruker APEXII CCD diffractometer	1121 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.051
Graphite monochromator	θmax = 25.1°, θmin = 2.7°
φ and ω scans	h = −11→11
6200 measured reflections	k = −6→6
1326 independent reflections	l = −19→19

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.4886P] where P = (Fo2 + 2Fc2)/3
1326 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.59 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
C1	0.2428 (3)	0.2367 (5)	0.99519 (16)	0.0089 (5)
C2	0.2750 (3)	0.4494 (4)	1.06347 (15)	0.0079 (5)
C3	0.1864 (3)	0.4915 (5)	1.11094 (15)	0.0090 (5)
C4	0.3430 (3)	0.8353 (5)	1.18295 (16)	0.0098 (5)
H4	0.3692	0.9711	1.2239	0.012*
C5	0.4304 (3)	0.7942 (5)	1.13805 (15)	0.0097 (5)
H5	0.5141	0.8999	1.1492	0.012*
N1	0.3937 (2)	0.6010 (4)	1.07831 (13)	0.0074 (4)
N2	0.2227 (2)	0.6890 (4)	1.17019 (13)	0.0102 (4)
N3	0.0696 (2)	0.3396 (4)	1.10092 (14)	0.0125 (5)
H1N	0.0202	0.3689	1.1316	0.015*
H2N	0.0436	0.2122	1.0637	0.015*
O1	0.33555 (17)	0.2240 (3)	0.96010 (11)	0.0090 (4)
O2	0.13487 (18)	0.0885 (3)	0.97784 (12)	0.0137 (4)
O1W	0.6426 (2)	0.2542 (4)	1.10017 (12)	0.0102 (4)
H1A	0.726 (3)	0.312 (6)	1.1356 (19)	0.015*
H1B	0.652 (3)	0.124 (6)	1.083 (2)	0.015*
O2W	0.0735 (2)	0.6137 (4)	0.76616 (12)	0.0133 (4)
H2A	0.046 (4)	0.472 (6)	0.754 (2)	0.02*
H2B	0.104 (3)	0.663 (6)	0.733 (2)	0.02*
Ni1	0.5	0.5	1	0.00664 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0073 (11)	0.0071 (12)	0.0116 (12)	0.0010 (9)	0.0036 (10)	0.0014 (10)
C2	0.0067 (12)	0.0078 (12)	0.0087 (11)	0.0002 (9)	0.0029 (10)	0.0009 (9)
C3	0.0078 (11)	0.0088 (12)	0.0098 (11)	0.0029 (10)	0.0031 (9)	0.0029 (11)
C4	0.0114 (12)	0.0077 (12)	0.0105 (12)	−0.0014 (9)	0.0050 (10)	−0.0024 (10)
C5	0.0068 (12)	0.0089 (12)	0.0137 (13)	−0.0011 (9)	0.0048 (10)	−0.0017 (10)
N1	0.0040 (10)	0.0067 (10)	0.0102 (10)	0.0004 (8)	0.0019 (8)	0.0009 (8)
N2	0.0097 (10)	0.0101 (11)	0.0123 (10)	−0.0008 (8)	0.0061 (9)	0.0001 (8)
N3	0.0094 (10)	0.0139 (11)	0.0195 (11)	−0.0052 (9)	0.0113 (9)	−0.0056 (9)
O1	0.0069 (8)	0.0093 (8)	0.0137 (9)	−0.0018 (7)	0.0073 (7)	−0.0032 (7)
O2	0.0092 (9)	0.0135 (9)	0.0213 (10)	−0.0055 (7)	0.0092 (8)	−0.0059 (8)
O1W	0.0077 (9)	0.0081 (9)	0.0147 (9)	−0.0015 (7)	0.0046 (8)	−0.0030 (8)
O2W	0.0148 (10)	0.0129 (9)	0.0169 (10)	−0.0035 (8)	0.0115 (8)	−0.0018 (8)
Ni1	0.0049 (2)	0.0062 (2)	0.0106 (2)	−0.00089 (17)	0.00506 (18)	−0.00108 (18)

C1—O2	1.228 (3)	N1—Ni1	2.0657 (19)
C1—O1	1.281 (3)	N3—H1N	0.86
C1—C2	1.510 (3)	N3—H2N	0.86
C2—N1	1.327 (3)	O1—Ni1	2.0233 (16)
C2—C3	1.427 (3)	O1W—Ni1	2.0755 (18)
C3—N3	1.331 (3)	O1W—H1A	0.83 (3)
C3—N2	1.351 (3)	O1W—H1B	0.74 (3)
C4—N2	1.332 (3)	O2W—H2A	0.77 (3)
C4—C5	1.381 (3)	O2W—H2B	0.78 (3)
C4—H4	0.93	Ni1—O1i	2.0233 (16)
C5—N1	1.340 (3)	Ni1—N1i	2.066 (2)
C5—H5	0.93	Ni1—O1Wi	2.0755 (18)
O2—C1—O1	124.7 (2)	H1N—N3—H2N	120
O2—C1—C2	119.8 (2)	C1—O1—Ni1	115.72 (15)
O1—C1—C2	115.5 (2)	Ni1—O1W—H1A	118 (2)
N1—C2—C3	120.2 (2)	Ni1—O1W—H1B	113 (2)
N1—C2—C1	116.0 (2)	H1A—O1W—H1B	110 (3)
C3—C2—C1	123.7 (2)	H2A—O2W—H2B	108 (3)
N3—C3—N2	117.7 (2)	O1—Ni1—O1i	180
N3—C3—C2	122.7 (2)	O1—Ni1—N1	80.54 (7)
N2—C3—C2	119.6 (2)	O1i—Ni1—N1	99.46 (7)
N2—C4—C5	122.8 (2)	O1—Ni1—N1i	99.46 (7)
N2—C4—H4	118.6	O1i—Ni1—N1i	80.54 (7)
C5—C4—H4	118.6	N1—Ni1—N1i	180.0000 (10)
N1—C5—C4	119.5 (2)	O1—Ni1—O1Wi	89.81 (7)
N1—C5—H5	120.3	O1i—Ni1—O1Wi	90.19 (7)
C4—C5—H5	120.3	N1—Ni1—O1Wi	90.92 (7)
C2—N1—C5	119.9 (2)	N1i—Ni1—O1Wi	89.08 (7)
C2—N1—Ni1	112.20 (15)	O1—Ni1—O1W	90.19 (7)
C5—N1—Ni1	127.92 (16)	O1i—Ni1—O1W	89.81 (7)
C4—N2—C3	117.9 (2)	N1—Ni1—O1W	89.08 (7)
C3—N3—H1N	120	N1i—Ni1—O1W	90.92 (7)
C3—N3—H2N	120	O1Wi—Ni1—O1W	180.00 (9)
O2—C1—C2—N1	180.0 (2)	N3—C3—N2—C4	177.5 (2)
O1—C1—C2—N1	1.0 (3)	C2—C3—N2—C4	−1.1 (3)
O2—C1—C2—C3	0.2 (4)	O2—C1—O1—Ni1	178.74 (18)
O1—C1—C2—C3	−178.8 (2)	C2—C1—O1—Ni1	−2.3 (3)
N1—C2—C3—N3	−177.5 (2)	C1—O1—Ni1—N1	2.15 (16)
C1—C2—C3—N3	2.3 (4)	C1—O1—Ni1—N1i	−177.85 (16)
N1—C2—C3—N2	1.0 (3)	C1—O1—Ni1—O1Wi	−88.81 (16)
C1—C2—C3—N2	−179.2 (2)	C1—O1—Ni1—O1W	91.19 (16)
N2—C4—C5—N1	0.5 (4)	C2—N1—Ni1—O1	−1.50 (15)
C3—C2—N1—C5	0.0 (3)	C5—N1—Ni1—O1	179.2 (2)
C1—C2—N1—C5	−179.9 (2)	C2—N1—Ni1—O1i	178.50 (15)
C3—C2—N1—Ni1	−179.41 (17)	C5—N1—Ni1—O1i	−0.8 (2)
C1—C2—N1—Ni1	0.8 (2)	C2—N1—Ni1—O1Wi	88.16 (16)
C4—C5—N1—C2	−0.7 (3)	C5—N1—Ni1—O1Wi	−91.1 (2)
C4—C5—N1—Ni1	178.57 (17)	C2—N1—Ni1—O1W	−91.84 (16)
C5—C4—N2—C3	0.4 (3)	C5—N1—Ni1—O1W	88.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2Wi	0.83 (3)	1.97 (3)	2.789 (3)	169 (3)
O1W—H1B···O1ii	0.75 (3)	1.94 (3)	2.690 (3)	176 (4)
N3—H1N···O2Wiii	0.86	2.27	3.117 (3)	168
O2W—H2A···O2Wiv	0.77 (3)	2.12 (3)	2.867 (3)	164 (4)
O2W—H2B···N2v	0.78 (3)	2.03 (3)	2.792 (3)	168 (3)
N3—H2N···O2	0.86	2.10	2.733 (3)	130
N3—H2N···O2vi	0.86	2.20	2.871 (3)	135
C5—H5···O1Wvii	0.93	2.54	3.377 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2W i	0.83 (3)	1.97 (3)	2.789 (3)	169 (3)
O1W—H1B⋯O1ii	0.75 (3)	1.94 (3)	2.690 (3)	176 (4)
N3—H1N⋯O2W iii	0.86	2.27	3.117 (3)	168
O2W—H2A⋯O2W iv	0.77 (3)	2.12 (3)	2.867 (3)	164 (4)
O2W—H2B⋯N2v	0.78 (3)	2.03 (3)	2.792 (3)	168 (3)
N3—H2N⋯O2	0.86	2.10	2.733 (3)	130
N3—H2N⋯O2vi	0.86	2.20	2.871 (3)	135
C5—H5⋯O1W vii	0.93	2.54	3.377 (4)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .