Diaqua-(2,2'-bipyridine-6,6'-dicarboxyl-ato)nickel(II).

In the title compound, [Ni(C(12)H(6)N(2)O(4))(H(2)O)(2)], the Ni(II) atom (site symmetry 2) displays a distorted cis-NiN(2)O(4) octa-hedral coordination geometry with two N atoms and two O atoms of the tetra-dentate 2,2'-bipyridine-6,6'-dicarboxyl-ate ligand in the equatorial plane and two water mol-ecules in axial positions. The complete dianionic ligand is generated by crystallographic twofold symmetry. In the crystal, a two-dimensional supra-molecular structure parallel to (001) is formed through O-H⋯O hydrogen-bond inter-actions between the coordinated water mol-ecules and the O atoms of nearby carboxyl-ate groups.

Related literature

For transition metal complexes with the title ligand, see: Knight et al. (2006 ▶); Duan et al. (2009 ▶); Wang et al. (2009 ▶). For lanthanide metal complexes with the title ligand, see: Bunzli et al. (2000 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

[Ni(C12H6N2O4)(H2O)2]

M = 336.93

Orthorhombic,

a = 7.1056 (9) Å

b = 11.3608 (15) Å

c = 15.3334 (19) Å

V = 1237.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.60 mm−1

T = 296 K

0.24 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.766, T max = 0.857

6269 measured reflections

1274 independent reflections

1098 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.06

1274 reflections

102 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536811016400/hb5864sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016400/hb5864Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016400/hb5864Isup3.cdx

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

[Ni(C12H6N2O4)(H2O)2]	F(000) = 688
Mr = 336.93	Dx = 1.808 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1650 reflections
a = 7.1056 (9) Å	θ = 3.2–25.2°
b = 11.3608 (15) Å	µ = 1.60 mm−1
c = 15.3334 (19) Å	T = 296 K
V = 1237.8 (3) Å3	Block, green
Z = 4	0.24 × 0.16 × 0.10 mm

Bruker APEXII CCD diffractometer	1274 independent reflections
Radiation source: fine-focus sealed tube	1098 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.766, Tmax = 0.857	k = −13→14
6269 measured reflections	l = −10→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.5888P] where P = (Fo2 + 2Fc2)/3
1274 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.48 e Å−3
2 restraints	Δρmin = −0.23 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	0.2500	0.7500	0.16327 (3)	0.02540 (16)
N1	0.0931 (3)	0.80137 (16)	0.06211 (12)	0.0285 (4)
O1	0.0167 (2)	0.83346 (15)	0.22531 (11)	0.0360 (4)
O2	−0.2446 (2)	0.93408 (18)	0.19595 (16)	0.0517 (6)
C1	−0.1035 (3)	0.8756 (2)	0.17424 (18)	0.0348 (6)
C2	−0.0683 (4)	0.8569 (2)	0.07707 (17)	0.0332 (6)
C3	−0.1808 (4)	0.8936 (2)	0.0083 (2)	0.0464 (7)
H3	−0.2934	0.9332	0.0182	0.056*
C4	−0.1204 (5)	0.8695 (3)	−0.0750 (2)	0.0563 (9)
H4	−0.1951	0.8915	−0.1221	0.068*
C5	0.0486 (5)	0.8132 (2)	−0.09017 (18)	0.0506 (8)
H5	0.0894	0.7982	−0.1467	0.061*
C6	0.1564 (4)	0.7796 (2)	−0.01856 (16)	0.0348 (6)
O3	0.1216 (2)	0.58888 (16)	0.17647 (13)	0.0380 (5)
H3A	0.009 (3)	0.584 (3)	0.1803 (18)	0.046*
H3B	0.169 (4)	0.545 (2)	0.2135 (15)	0.046*

	U11	U22	U33	U12	U13	U23
Ni1	0.0254 (3)	0.0293 (3)	0.0215 (2)	0.00250 (16)	0.000	0.000
N1	0.0341 (11)	0.0256 (10)	0.0260 (11)	−0.0004 (9)	−0.0053 (9)	−0.0005 (8)
O1	0.0336 (9)	0.0402 (10)	0.0343 (10)	0.0040 (8)	0.0046 (8)	−0.0040 (8)
O2	0.0263 (10)	0.0466 (12)	0.0821 (15)	0.0055 (8)	−0.0004 (9)	−0.0232 (11)
C1	0.0248 (12)	0.0269 (12)	0.0526 (17)	−0.0047 (10)	0.0005 (12)	−0.0078 (11)
C2	0.0316 (13)	0.0217 (12)	0.0464 (16)	−0.0021 (10)	−0.0109 (11)	−0.0021 (10)
C3	0.0437 (15)	0.0291 (14)	0.067 (2)	−0.0016 (11)	−0.0276 (15)	0.0050 (13)
C4	0.073 (2)	0.0378 (16)	0.059 (2)	−0.0073 (15)	−0.0407 (18)	0.0134 (14)
C5	0.085 (2)	0.0380 (16)	0.0289 (15)	−0.0094 (16)	−0.0177 (15)	0.0061 (11)
C6	0.0530 (17)	0.0261 (12)	0.0252 (12)	−0.0045 (11)	−0.0073 (12)	0.0018 (9)
O3	0.0259 (9)	0.0364 (10)	0.0519 (12)	0.0001 (8)	0.0044 (9)	0.0117 (8)

Ni1—N1i	1.9975 (19)	C2—C3	1.387 (4)
Ni1—N1	1.9975 (19)	C3—C4	1.375 (5)
Ni1—O3i	2.0553 (18)	C3—H3	0.9300
Ni1—O3	2.0553 (18)	C4—C5	1.381 (5)
Ni1—O1i	2.1335 (16)	C4—H4	0.9300
Ni1—O1	2.1335 (16)	C5—C6	1.392 (4)
N1—C2	1.329 (3)	C5—H5	0.9300
N1—C6	1.339 (3)	C6—C6i	1.491 (5)
O1—C1	1.254 (3)	O3—H3A	0.806 (18)
O2—C1	1.247 (3)	O3—H3B	0.827 (17)
C1—C2	1.526 (4)
N1i—Ni1—N1	78.11 (11)	O2—C1—C2	117.8 (2)
N1i—Ni1—O3i	95.10 (8)	O1—C1—C2	116.4 (2)
N1—Ni1—O3i	93.67 (8)	N1—C2—C3	120.6 (3)
N1i—Ni1—O3	93.67 (8)	N1—C2—C1	112.1 (2)
N1—Ni1—O3	95.10 (8)	C3—C2—C1	127.3 (3)
O3i—Ni1—O3	168.70 (11)	C4—C3—C2	117.8 (3)
N1i—Ni1—O1i	77.45 (7)	C4—C3—H3	121.1
N1—Ni1—O1i	155.48 (8)	C2—C3—H3	121.1
O3i—Ni1—O1i	90.40 (7)	C3—C4—C5	121.4 (3)
O3—Ni1—O1i	84.56 (7)	C3—C4—H4	119.3
N1i—Ni1—O1	155.48 (8)	C5—C4—H4	119.3
N1—Ni1—O1	77.45 (7)	C4—C5—C6	118.2 (3)
O3i—Ni1—O1	84.56 (7)	C4—C5—H5	120.9
O3—Ni1—O1	90.40 (7)	C6—C5—H5	120.9
O1i—Ni1—O1	127.04 (9)	N1—C6—C5	119.5 (3)
C2—N1—C6	122.5 (2)	N1—C6—C6i	112.53 (14)
C2—N1—Ni1	119.11 (17)	C5—C6—C6i	127.93 (19)
C6—N1—Ni1	118.41 (17)	Ni1—O3—H3A	121 (2)
C1—O1—Ni1	114.88 (15)	Ni1—O3—H3B	115 (2)
O2—C1—O1	125.7 (3)	H3A—O3—H3B	108 (3)
N1i—Ni1—N1—C2	−178.6 (2)	Ni1—N1—C2—C3	−179.86 (17)
O3i—Ni1—N1—C2	−84.19 (18)	C6—N1—C2—C1	−177.4 (2)
O3—Ni1—N1—C2	88.68 (18)	Ni1—N1—C2—C1	1.8 (3)
O1i—Ni1—N1—C2	176.75 (16)	O2—C1—C2—N1	175.2 (2)
O1—Ni1—N1—C2	−0.59 (17)	O1—C1—C2—N1	−2.6 (3)
N1i—Ni1—N1—C6	0.53 (13)	O2—C1—C2—C3	−3.1 (4)
O3i—Ni1—N1—C6	94.98 (18)	O1—C1—C2—C3	179.2 (2)
O3—Ni1—N1—C6	−92.15 (18)	N1—C2—C3—C4	0.6 (4)
O1i—Ni1—N1—C6	−4.1 (3)	C1—C2—C3—C4	178.7 (2)
O1—Ni1—N1—C6	178.57 (19)	C2—C3—C4—C5	−1.5 (4)
N1i—Ni1—O1—C1	3.7 (3)	C3—C4—C5—C6	1.0 (4)
N1—Ni1—O1—C1	−0.96 (16)	C2—N1—C6—C5	−1.6 (4)
O3i—Ni1—O1—C1	94.04 (17)	Ni1—N1—C6—C5	179.24 (19)
O3—Ni1—O1—C1	−96.09 (17)	C2—N1—C6—C6i	177.8 (2)
O1i—Ni1—O1—C1	−179.58 (17)	Ni1—N1—C6—C6i	−1.4 (3)
Ni1—O1—C1—O2	−175.4 (2)	C4—C5—C6—N1	0.6 (4)
Ni1—O1—C1—C2	2.1 (3)	C4—C5—C6—C6i	−178.7 (3)
C6—N1—C2—C3	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ii	0.81 (2)	1.90 (2)	2.708 (2)	176 (3)
O3—H3B···O2iii	0.83 (2)	1.95 (2)	2.772 (3)	172 (3)

Table 1

Selected bond lengths (Å)

Ni1—N1	1.9975 (19)
Ni1—O3	2.0553 (18)
Ni1—O1	2.1335 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.81 (2)	1.90 (2)	2.708 (2)	176 (3)
O3—H3B⋯O2ii	0.83 (2)	1.95 (2)	2.772 (3)	172 (3)

Symmetry codes: (i) ; (ii) .