Bis(di-2-pyridyl-methane-diol-κN,O,N')nickel(II) dibenzoate.

The title compound, [Ni(C(11)H(10)N(2)O(2))(2)](C(7)H(5)O(2))(2), consists of an Ni(II) ion coordinated by two tridentate chelating (2-py)(2)C(OH)(2) ligands (py is pyrid-yl) and two benzoate anions. The Ni(II) ion is located on a twofold rotation axis, and its geometry is distorted octa-hedral. The gem-diol ligand (2-py)(2)C(OH)(2) adopts an η(1):η(1):η(1) coordination mode. There are O-H⋯O hydrogen bonds between the gem-diol ligands and benzoate anions.

Related literature

For examples of inter­actions between transition metal ions and biologically active mol­ecules, see: Efthymiou et al. (2006 ▶); Daniele et al. (2008 ▶); Parkin (2004 ▶); Tshuva & Lippard (2004 ▶). For related structures of Cu(II) and Zn(II) benzoates, see: Lee et al. (2008 ▶); Yu et al. (2008 ▶); Park et al. (2008 ▶); Shin et al. (2009 ▶); Yu et al. (2010 ▶). For the di-2-pyridyl­ketone [(py)2CO] ligand, see: Papaefstathiou & Perlepes (2002 ▶); Stoumpos et al. (2009 ▶). For related structures, see: Wang et al. (1986 ▶); Li et al. (2005 ▶); Yu et al. (2009a ▶,b ▶).

Experimental

Crystal data

[Ni(C11H10N2O2)2](C7H5O2)2

M = 705.35

Monoclinic,

a = 24.065 (8) Å

b = 8.681 (3) Å

c = 17.718 (6) Å

β = 123.526 (5)°

V = 3085.7 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 173 K

0.08 × 0.05 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.959, T max = 0.966

8329 measured reflections

3031 independent reflections

1818 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.109

S = 1.01

3031 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003669X/dn2601sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003669X/dn2601Isup2.hkl

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

[Ni(C11H10N2O2)2](C7H5O2)2	F(000) = 1464
Mr = 705.35	Dx = 1.518 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 526 reflections
a = 24.065 (8) Å	θ = 2.6–18.8°
b = 8.681 (3) Å	µ = 0.69 mm−1
c = 17.718 (6) Å	T = 173 K
β = 123.526 (5)°	Block, colourless
V = 3085.7 (17) Å3	0.08 × 0.05 × 0.05 mm
Z = 4

Bruker SMART CCD diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	1818 reflections with I > 2σ(I)
graphite	Rint = 0.095
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −29→28
Tmin = 0.959, Tmax = 0.966	k = −10→9
8329 measured reflections	l = −20→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
3031 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.33 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
Ni1	0.5000	0.54475 (8)	0.7500	0.0218 (2)
O1	0.42807 (11)	0.6969 (3)	0.74041 (15)	0.0272 (6)
H1O	0.4294	0.7180	0.7877	0.041*
O2	0.31141 (11)	0.6882 (3)	0.65747 (15)	0.0311 (7)
H2O	0.3095	0.6916	0.7034	0.047*
N1	0.43794 (14)	0.3935 (4)	0.75897 (18)	0.0240 (8)
N2	0.43061 (13)	0.5602 (3)	0.61309 (17)	0.0224 (7)
C1	0.45080 (19)	0.2545 (5)	0.7972 (2)	0.0295 (10)
H1	0.4945	0.2135	0.8250	0.035*
C2	0.4030 (2)	0.1682 (5)	0.7979 (2)	0.0340 (10)
H2	0.4136	0.0696	0.8257	0.041*
C3	0.33914 (19)	0.2273 (5)	0.7573 (2)	0.0336 (10)
H3	0.3053	0.1696	0.7564	0.040*
C4	0.32564 (18)	0.3714 (5)	0.7182 (2)	0.0282 (10)
H4	0.2823	0.4147	0.6904	0.034*
C5	0.37576 (16)	0.4519 (5)	0.7200 (2)	0.0231 (9)
C6	0.36850 (16)	0.6119 (4)	0.6785 (2)	0.0244 (9)
C7	0.36976 (17)	0.5939 (4)	0.5939 (2)	0.0215 (9)
C8	0.31530 (18)	0.6127 (4)	0.5068 (2)	0.0278 (9)
H8	0.2725	0.6345	0.4949	0.033*
C9	0.32512 (19)	0.5986 (4)	0.4372 (2)	0.0306 (10)
H9	0.2886	0.6117	0.3763	0.037*
C10	0.38729 (18)	0.5658 (5)	0.4555 (2)	0.0326 (10)
H10	0.3944	0.5566	0.4081	0.039*
C11	0.43897 (17)	0.5467 (5)	0.5446 (2)	0.0286 (9)
H11	0.4821	0.5230	0.5580	0.034*
O21	0.42695 (12)	0.7889 (3)	0.87550 (16)	0.0364 (7)
O22	0.31909 (12)	0.7353 (3)	0.80877 (16)	0.0409 (8)
C21	0.3730 (2)	0.7889 (5)	0.8723 (3)	0.0306 (10)
C22	0.37566 (18)	0.8581 (5)	0.9521 (2)	0.0272 (9)
C23	0.33218 (19)	0.8072 (5)	0.9755 (3)	0.0329 (10)
H23	0.3011	0.7277	0.9411	0.039*
C24	0.3337 (2)	0.8705 (5)	1.0476 (3)	0.0382 (11)
H24	0.3041	0.8339	1.0632	0.046*
C25	0.3776 (2)	0.9862 (5)	1.0971 (3)	0.0396 (11)
H25	0.3776	1.0312	1.1459	0.047*
C26	0.42184 (18)	1.0377 (5)	1.0767 (3)	0.0356 (10)
H26	0.4527	1.1170	1.1119	0.043*
C27	0.42110 (18)	0.9730 (5)	1.0042 (3)	0.0342 (10)
H27	0.4519	1.0077	0.9903	0.041*

	U11	U22	U33	U12	U13	U23
Ni1	0.0214 (4)	0.0260 (4)	0.0186 (4)	0.000	0.0115 (3)	0.000
O1	0.0272 (14)	0.0340 (17)	0.0230 (13)	−0.0008 (13)	0.0155 (12)	−0.0029 (13)
O2	0.0259 (15)	0.0429 (19)	0.0280 (14)	0.0089 (13)	0.0170 (12)	0.0053 (13)
N1	0.0235 (18)	0.029 (2)	0.0212 (16)	0.0028 (15)	0.0131 (14)	0.0027 (15)
N2	0.0260 (17)	0.0239 (19)	0.0186 (15)	0.0032 (15)	0.0131 (13)	0.0025 (15)
C1	0.034 (2)	0.032 (3)	0.021 (2)	0.003 (2)	0.0150 (18)	0.006 (2)
C2	0.045 (3)	0.031 (3)	0.028 (2)	−0.001 (2)	0.021 (2)	0.005 (2)
C3	0.039 (3)	0.038 (3)	0.027 (2)	−0.016 (2)	0.020 (2)	−0.005 (2)
C4	0.027 (2)	0.035 (3)	0.023 (2)	−0.003 (2)	0.0144 (18)	−0.007 (2)
C5	0.024 (2)	0.029 (2)	0.0179 (18)	−0.003 (2)	0.0125 (16)	−0.0023 (19)
C6	0.0156 (19)	0.031 (2)	0.022 (2)	−0.0003 (17)	0.0067 (16)	−0.0016 (19)
C7	0.023 (2)	0.020 (2)	0.023 (2)	−0.0006 (16)	0.0138 (17)	0.0000 (16)
C8	0.026 (2)	0.027 (2)	0.027 (2)	−0.0004 (18)	0.0124 (18)	−0.0006 (19)
C9	0.037 (2)	0.033 (3)	0.0168 (19)	0.0050 (19)	0.0116 (18)	0.0022 (18)
C10	0.040 (2)	0.037 (3)	0.024 (2)	0.007 (2)	0.0197 (19)	0.002 (2)
C11	0.030 (2)	0.031 (2)	0.026 (2)	0.005 (2)	0.0168 (17)	0.001 (2)
O21	0.0333 (16)	0.044 (2)	0.0411 (16)	−0.0030 (14)	0.0264 (13)	−0.0072 (14)
O22	0.0316 (17)	0.062 (2)	0.0295 (15)	−0.0064 (15)	0.0172 (13)	−0.0119 (15)
C21	0.034 (2)	0.032 (3)	0.036 (2)	0.004 (2)	0.025 (2)	0.004 (2)
C22	0.028 (2)	0.031 (3)	0.027 (2)	0.0065 (19)	0.0184 (18)	0.003 (2)
C23	0.037 (2)	0.032 (3)	0.036 (2)	0.002 (2)	0.024 (2)	0.002 (2)
C24	0.046 (3)	0.046 (3)	0.032 (2)	0.002 (2)	0.028 (2)	0.002 (2)
C25	0.053 (3)	0.039 (3)	0.033 (2)	0.014 (2)	0.027 (2)	0.003 (2)
C26	0.039 (2)	0.030 (3)	0.039 (2)	0.002 (2)	0.022 (2)	−0.004 (2)
C27	0.036 (2)	0.034 (3)	0.042 (2)	0.004 (2)	0.028 (2)	0.004 (2)

Ni1—N2i	2.053 (3)	C6—C7	1.525 (5)
Ni1—N2	2.053 (3)	C7—C8	1.374 (5)
Ni1—N1	2.060 (3)	C8—C9	1.383 (5)
Ni1—N1i	2.060 (3)	C8—H8	0.9500
Ni1—O1i	2.109 (3)	C9—C10	1.374 (5)
Ni1—O1	2.109 (2)	C9—H9	0.9500
O1—C6	1.437 (4)	C10—C11	1.377 (5)
O1—H1O	0.8408	C10—H10	0.9500
O2—C6	1.378 (4)	C11—H11	0.9500
O2—H2O	0.8405	O21—C21	1.267 (4)
N1—C1	1.334 (4)	O22—C21	1.247 (4)
N1—C5	1.353 (4)	C21—C22	1.506 (5)
N2—C7	1.340 (4)	C22—C27	1.388 (5)
N2—C11	1.340 (4)	C22—C23	1.393 (5)
C1—C2	1.379 (5)	C23—C24	1.373 (5)
C1—H1	0.9500	C23—H23	0.9500
C2—C3	1.385 (5)	C24—C25	1.368 (5)
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.379 (5)	C25—C26	1.373 (5)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.379 (5)	C26—C27	1.393 (5)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.535 (5)	C27—H27	0.9500
N2i—Ni1—N2	172.49 (18)	O2—C6—C7	110.0 (3)
N2i—Ni1—N1	95.84 (11)	O1—C6—C7	104.5 (3)
N2—Ni1—N1	88.95 (11)	O2—C6—C5	113.4 (3)
N2i—Ni1—N1i	88.95 (11)	O1—C6—C5	107.3 (3)
N2—Ni1—N1i	95.84 (11)	C7—C6—C5	108.6 (3)
N1—Ni1—N1i	100.79 (17)	N2—C7—C8	122.8 (3)
N2i—Ni1—O1i	76.59 (10)	N2—C7—C6	112.6 (3)
N2—Ni1—O1i	98.62 (10)	C8—C7—C6	124.5 (3)
N1—Ni1—O1i	172.42 (10)	C7—C8—C9	117.6 (4)
N1i—Ni1—O1i	78.91 (11)	C7—C8—H8	121.2
N2i—Ni1—O1	98.62 (10)	C9—C8—H8	121.2
N2—Ni1—O1	76.59 (10)	C10—C9—C8	120.5 (3)
N1—Ni1—O1	78.91 (11)	C10—C9—H9	119.7
N1i—Ni1—O1	172.42 (10)	C8—C9—H9	119.7
O1i—Ni1—O1	102.40 (14)	C9—C10—C11	118.1 (3)
C6—O1—Ni1	99.7 (2)	C9—C10—H10	120.9
C6—O1—H1O	110.2	C11—C10—H10	120.9
Ni1—O1—H1O	118.6	N2—C11—C10	122.3 (3)
C6—O2—H2O	109.5	N2—C11—H11	118.8
C1—N1—C5	118.7 (3)	C10—C11—H11	118.8
C1—N1—Ni1	129.9 (2)	O22—C21—O21	124.8 (4)
C5—N1—Ni1	111.5 (3)	O22—C21—C22	118.6 (3)
C7—N2—C11	118.6 (3)	O21—C21—C22	116.6 (3)
C7—N2—Ni1	112.1 (2)	C27—C22—C23	118.4 (4)
C11—N2—Ni1	129.3 (2)	C27—C22—C21	121.3 (3)
N1—C1—C2	122.4 (4)	C23—C22—C21	120.2 (4)
N1—C1—H1	118.8	C24—C23—C22	120.7 (4)
C2—C1—H1	118.8	C24—C23—H23	119.6
C1—C2—C3	119.0 (4)	C22—C23—H23	119.6
C1—C2—H2	120.5	C25—C24—C23	120.2 (4)
C3—C2—H2	120.5	C25—C24—H24	119.9
C4—C3—C2	118.9 (4)	C23—C24—H24	119.9
C4—C3—H3	120.6	C24—C25—C26	120.6 (4)
C2—C3—H3	120.6	C24—C25—H25	119.7
C3—C4—C5	119.2 (4)	C26—C25—H25	119.7
C3—C4—H4	120.4	C25—C26—C27	119.6 (4)
C5—C4—H4	120.4	C25—C26—H26	120.2
N1—C5—C4	121.9 (4)	C27—C26—H26	120.2
N1—C5—C6	112.7 (3)	C22—C27—C26	120.4 (4)
C4—C5—C6	125.5 (3)	C22—C27—H27	119.8
O2—C6—O1	112.6 (3)	C26—C27—H27	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O21	0.84	1.70	2.537 (3)	171
O2—H2O···O22	0.84	1.79	2.615 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O21	0.84	1.70	2.537 (3)	171
O2—H2O⋯O22	0.84	1.79	2.615 (4)	167