Bis(di-2-pyridylmethane-diol-κN,O,N')nickel(II) dinitrate.

The title compound, [Ni(C(11)H(10)N(2)O(2))(2)](NO(3))(2), consists of an Ni(II) atom coordinated by two tridentate chelating di-2-pyridylmethane-diol [(2-py)(2)C(OH)(2)] ligands. The Ni(II) atom is located on an inversion center. The geometry around the Ni(II) atom is distorted octa-hedral. The gem-diol (2-py)(2)C(OH)(2) ligand adopts the coordination mode η(1):η(1):η(1). The Ni-N and Ni-O bond lengths are typical for high-spin Ni(II) in an octa-hedral environment [Ni-N = 2.094 (2) and 2.124 (3) Å, and Ni-O = 2.108 (3) Å]. One of the hydr-oxy H atoms is split over two positions which both inter-act with the nitrate anion. The occurence of different O-H⋯O hydrogen bonds leads to the formation of a layer parallel to the (101) plane.

Related literature

For background information, see: Efthymiou et al. (2006 ▶); Moragues-Cánovas et al. (2004 ▶); Papaefstathiou & Perlepes (2002 ▶); Papatriantafyllopoulou et al. (2007 ▶); Stoumpos et al. (2008 ▶, 2009 ▶). For related structures, see: Li et al. (2005 ▶); Wang et al. (1986 ▶).

Experimental

Crystal data

[Ni(C11H10N2O2)2](NO3)2

M = 587.15

Monoclinic,

a = 8.4077 (9) Å

b = 15.5098 (16) Å

c = 9.5556 (10) Å

β = 94.644 (2)°

V = 1242.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.85 mm−1

T = 293 K

0.20 × 0.10 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

7646 measured reflections

2442 independent reflections

1826 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.135

S = 1.06

2442 reflections

179 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536809018728/dn2454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018728/dn2454Isup2.hkl

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

[Ni(C11H10N2O2)2](NO3)2	F(000) = 604
Mr = 587.15	Dx = 1.570 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2352 reflections
a = 8.4077 (9) Å	θ = 2.5–25.6°
b = 15.5098 (16) Å	µ = 0.85 mm−1
c = 9.5556 (10) Å	T = 293 K
β = 94.644 (2)°	Plate, pale brown
V = 1242.0 (2) Å3	0.20 × 0.10 × 0.03 mm
Z = 2

Bruker SMART CCD diffractometer	1826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 26.0°, θmin = 2.5°
φ and ω scans	h = −11→11
7646 measured reflections	k = −20→12
2442 independent reflections	l = −12→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.0426P] where P = (Fo2 + 2Fc2)/3
2442 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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 > 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	Occ. (<1)
Ni1	0.5000	0.5000	0.5000	0.0334 (2)
N1	0.3937 (3)	0.52480 (18)	0.2948 (3)	0.0389 (6)
N2	0.2830 (3)	0.54084 (17)	0.5703 (3)	0.0347 (6)
O1	0.5183 (3)	0.63487 (17)	0.4873 (2)	0.0574 (7)
H1A	0.5905	0.6553	0.4370	0.086*	0.50
H1B	0.5305	0.6590	0.5688	0.086*	0.50
O2	0.3337 (3)	0.74355 (14)	0.3938 (3)	0.0539 (6)
H2	0.3866	0.7720	0.4530	0.081*
C1	0.3774 (4)	0.4731 (2)	0.1816 (4)	0.0478 (9)
H1	0.4155	0.4169	0.1884	0.057*
C2	0.3053 (5)	0.5019 (3)	0.0558 (4)	0.0639 (11)
H2A	0.2927	0.4653	−0.0214	0.077*
C3	0.2515 (5)	0.5865 (3)	0.0458 (4)	0.0685 (12)
H3	0.2048	0.6076	−0.0389	0.082*
C4	0.2677 (4)	0.6386 (3)	0.1615 (4)	0.0562 (10)
H4	0.2310	0.6951	0.1573	0.067*
C5	0.3394 (4)	0.6055 (2)	0.2841 (3)	0.0394 (7)
C6	0.3583 (4)	0.6549 (2)	0.4213 (3)	0.0386 (7)
C7	0.2392 (3)	0.61766 (19)	0.5177 (3)	0.0353 (7)
C8	0.0989 (4)	0.6581 (2)	0.5451 (4)	0.0459 (8)
H8	0.0700	0.7112	0.5054	0.055*
C9	0.0030 (4)	0.6160 (3)	0.6345 (4)	0.0594 (10)
H9	−0.0919	0.6414	0.6569	0.071*
C10	0.0462 (4)	0.5378 (3)	0.6898 (4)	0.0521 (9)
H10	−0.0182	0.5097	0.7500	0.063*
C11	0.1873 (4)	0.5008 (2)	0.6552 (3)	0.0434 (8)
H11	0.2164	0.4470	0.6916	0.052*
N3	0.3476 (4)	0.7718 (2)	0.7595 (4)	0.0585 (8)
O3	0.4512 (4)	0.71600 (19)	0.7535 (3)	0.0755 (9)
O4	0.3188 (5)	0.8218 (2)	0.6577 (3)	0.1014 (12)
O5	0.2759 (4)	0.7785 (2)	0.8634 (4)	0.0834 (9)

	U11	U22	U33	U12	U13	U23
Ni1	0.0362 (3)	0.0326 (3)	0.0319 (3)	0.0023 (2)	0.0050 (2)	−0.0004 (2)
N1	0.0396 (15)	0.0451 (16)	0.0326 (15)	0.0016 (11)	0.0079 (11)	−0.0016 (11)
N2	0.0340 (13)	0.0360 (15)	0.0343 (14)	0.0020 (11)	0.0047 (11)	−0.0012 (11)
O1	0.0609 (16)	0.0526 (16)	0.0587 (16)	−0.0010 (12)	0.0049 (13)	−0.0001 (12)
O2	0.0675 (17)	0.0363 (13)	0.0578 (16)	0.0069 (12)	0.0054 (12)	0.0050 (11)
C1	0.054 (2)	0.050 (2)	0.040 (2)	0.0031 (16)	0.0081 (16)	−0.0051 (16)
C2	0.084 (3)	0.072 (3)	0.036 (2)	−0.001 (2)	0.0032 (19)	−0.0137 (19)
C3	0.087 (3)	0.079 (3)	0.038 (2)	0.011 (2)	−0.004 (2)	0.006 (2)
C4	0.072 (3)	0.054 (2)	0.043 (2)	0.0102 (19)	0.0005 (18)	0.0078 (17)
C5	0.0418 (18)	0.0411 (19)	0.0363 (17)	0.0017 (14)	0.0095 (14)	0.0007 (14)
C6	0.0390 (18)	0.0349 (18)	0.0422 (18)	0.0031 (14)	0.0059 (14)	0.0046 (14)
C7	0.0365 (16)	0.0357 (17)	0.0336 (16)	0.0002 (13)	0.0026 (13)	−0.0053 (13)
C8	0.0391 (18)	0.048 (2)	0.050 (2)	0.0069 (15)	−0.0001 (15)	−0.0015 (15)
C9	0.040 (2)	0.075 (3)	0.065 (2)	0.0062 (19)	0.0128 (18)	−0.010 (2)
C10	0.047 (2)	0.064 (2)	0.047 (2)	−0.0077 (18)	0.0155 (16)	−0.0005 (18)
C11	0.0485 (18)	0.0451 (19)	0.0370 (17)	−0.0049 (16)	0.0053 (14)	0.0002 (15)
N3	0.067 (2)	0.047 (2)	0.061 (2)	−0.0010 (16)	0.0000 (17)	−0.0192 (17)
O3	0.077 (2)	0.077 (2)	0.0714 (19)	0.0337 (16)	0.0032 (15)	−0.0251 (15)
O4	0.173 (4)	0.056 (2)	0.071 (2)	0.016 (2)	−0.014 (2)	−0.0052 (16)
O5	0.071 (2)	0.092 (2)	0.092 (2)	0.0066 (16)	0.0358 (18)	−0.0195 (18)

Ni1—N2	2.093 (2)	C2—H2A	0.9300
Ni1—N2i	2.093 (2)	C3—C4	1.367 (5)
Ni1—O1	2.102 (3)	C3—H3	0.9300
Ni1—O1i	2.102 (3)	C4—C5	1.372 (4)
Ni1—N1	2.123 (3)	C4—H4	0.9300
Ni1—N1i	2.123 (3)	C5—C6	1.515 (4)
N1—C5	1.334 (4)	C6—C7	1.528 (4)
N1—C1	1.345 (4)	C7—C8	1.380 (4)
N2—C7	1.333 (4)	C8—C9	1.385 (5)
N2—C11	1.340 (4)	C8—H8	0.9300
O1—C6	1.472 (4)	C9—C10	1.360 (5)
O1—H1A	0.8650	C9—H9	0.9300
O1—H1B	0.8625	C10—C11	1.382 (5)
O2—C6	1.412 (4)	C10—H10	0.9300
O2—H2	0.8200	C11—H11	0.9300
C1—C2	1.377 (5)	N3—O5	1.206 (4)
C1—H1	0.9300	N3—O3	1.233 (4)
C2—C3	1.388 (5)	N3—O4	1.253 (4)
N2—Ni1—N2i	180.0	C4—C3—C2	119.5 (4)
N2—Ni1—O1	77.70 (10)	C4—C3—H3	120.3
N2i—Ni1—O1	102.30 (10)	C2—C3—H3	120.3
N2—Ni1—O1i	102.30 (10)	C3—C4—C5	118.5 (4)
N2i—Ni1—O1i	77.70 (10)	C3—C4—H4	120.7
O1—Ni1—O1i	180.0	C5—C4—H4	120.7
N2—Ni1—N1	85.93 (9)	N1—C5—C4	122.7 (3)
N2i—Ni1—N1	94.07 (9)	N1—C5—C6	113.4 (3)
O1—Ni1—N1	78.10 (10)	C4—C5—C6	123.9 (3)
O1i—Ni1—N1	101.90 (10)	O2—C6—O1	113.6 (2)
N2—Ni1—N1i	94.07 (9)	O2—C6—C5	109.1 (3)
N2i—Ni1—N1i	85.93 (9)	O1—C6—C5	107.0 (2)
O1—Ni1—N1i	101.90 (10)	O2—C6—C7	112.8 (2)
O1i—Ni1—N1i	78.10 (10)	O1—C6—C7	106.4 (2)
N1—Ni1—N1i	180.000 (1)	C5—C6—C7	107.6 (2)
C5—N1—C1	119.1 (3)	N2—C7—C8	123.3 (3)
C5—N1—Ni1	110.9 (2)	N2—C7—C6	113.0 (2)
C1—N1—Ni1	130.0 (2)	C8—C7—C6	123.7 (3)
C7—N2—C11	118.7 (3)	C7—C8—C9	116.8 (3)
C7—N2—Ni1	111.76 (19)	C7—C8—H8	121.6
C11—N2—Ni1	129.5 (2)	C9—C8—H8	121.6
C6—O1—Ni1	99.56 (17)	C10—C9—C8	120.7 (3)
C6—O1—H1A	110.0	C10—C9—H9	119.7
Ni1—O1—H1A	117.0	C8—C9—H9	119.7
C6—O1—H1B	109.5	C9—C10—C11	119.0 (3)
Ni1—O1—H1B	112.6	C9—C10—H10	120.5
H1A—O1—H1B	107.8	C11—C10—H10	120.5
C6—O2—H2	109.5	N2—C11—C10	121.5 (3)
N1—C1—C2	121.2 (4)	N2—C11—H11	119.3
N1—C1—H1	119.4	C10—C11—H11	119.3
C2—C1—H1	119.4	O5—N3—O3	120.1 (4)
C1—C2—C3	119.0 (4)	O5—N3—O4	120.5 (4)
C1—C2—H2A	120.5	O3—N3—O4	119.4 (4)
C3—C2—H2A	120.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	2.22	2.810 (4)	129
O1—H1B···O3	0.86	2.13	2.933 (4)	155
O1—H1A···O5ii	0.87	2.04	2.884 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.82	2.22	2.810 (4)	129
O1—H1B⋯O3	0.86	2.13	2.933 (4)	155
O1—H1A⋯O5i	0.87	2.04	2.884 (4)	165

Symmetry code: (i) .