trans-Diaqua­bis­[2-(2-pyrid­yl)acetato-κ2N,O]nickel(II)

Zhou, H.; Zhao, L.; Huang, R.; Li, H.-L.

doi:10.1107/S1600536810030904

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1068

https://doi.org/10.1107/S1600536810030904

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trans-Diaquabis[2-(2-pyridyl)acetato-κ²N,O]nickel(II)

Hong Zhou,^a ^* Lei Zhao,^a Rong Huang ^a and Hao-Liang Li ^a

^aCollege of Basic Science and Information Engineering, Yunnan Agricultural University, Kunming 650201, People's Republic of China
^*Correspondence e-mail: zhouhong928@gmail.com

(Received 13 July 2010; accepted 3 August 2010; online 11 August 2010)

In the centrosymmetric title complex, [Ni(C₇H₆NO₂)₂(H₂O)₂], the Ni^IIatom, located on an inversion center, is six-coordinated in a distorted octahedral geometry defined by two N and four O atoms from the two chelating 2-(2-pyridyl)acetate ligands and two aqua ligands. The molecules form a three-dimensional framework by O—H⋯O hydrogen bonds and aromatic π–π stacking interactions, with a centroid–centroid distance of 3.506 (3) Å.

Related literature

For similar structures, see: Faure & Loiseleur (1972 , 1975 ).

Experimental

Crystal data

[Ni(C₇H₆NO₂)₂(H₂O)₂]
M_r = 367.00
Monoclinic, P 2₁ /n
a = 8.3346 (12) Å
b = 7.100 (1) Å
c = 12.1023 (18) Å
β = 102.977 (2)°
V = 697.87 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.11 mm

Data collection

Bruker APEXII 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.774, T_max = 0.855
4515 measured reflections
1627 independent reflections
1471 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.067
S = 1.00
1627 reflections
114 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O2	2.0397 (10)
Ni1—N1	2.0789 (13)
Ni1—O1W	2.1228 (11)

O2ⁱ—Ni1—N1ⁱ	88.90 (4)
O2ⁱ—Ni1—N1	91.10 (4)
N1ⁱ—Ni1—N1	180
O2ⁱ—Ni1—O1W	94.53 (4)
N1—Ni1—O1W	91.70 (5)
O2ⁱ—Ni1—O1Wⁱ	85.47 (5)
N1—Ni1—O1Wⁱ	88.30 (5)
O1W—Ni1—O1Wⁱ	180
Symmetry code: (i) -x+2, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1ⁱⁱ	0.84 (2)	1.97 (2)	2.8035 (17)	169.7 (19)
O1W—H1WB⋯O1ⁱⁱⁱ	0.87 (3)	1.93 (3)	2.7936 (17)	169 (2)
Symmetry codes: (ii) x, y+1, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810030904/gk2294sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030904/gk2294Isup2.hkl

checkCIF report

Comment top

(2-Pyridinyl)acetic acid is a common ligand. Here we report the synthesis of [Ni(C₅H₄NCH₂CO₂)₂(H₂O)₂], in which the Ni(II) ion coordination environment is the same as in [Zn(C₅H₄NCH₂CO₂)₂(H₂O)₂] reported earlier (Faure & Loiseleur,1972). The Zn and Ni complexes show a high degree of isostructurality.

As shown in Fig. 1, the Ni(II) coordination geometry can be considered as a distorted octahedral with N₂O₄donor set. Due to a special position of Ni(II), the complex molecule is centrosymmetric. The atoms N1, O2, N1ⁱ, O2ⁱ (symmetry code i: -x + 2, -y + 2, -z) from the (2-pyridinyl)acetate ligand are located in the equatorial plane, while O1W and O1Wⁱ are in the axial positions. In the title complex the (2-pyridinyl)acetate anion acts as a chelating bidentate ligand.

Two kinds of intermolecular O—H···O hydrogen bonds (Table 1) were found which link the neighboring molecules into two dimensional layers parallel to the ab plane. The two-dimensional layers are assembled via weak aromatic π-π stacking interactions into three-dimensional network with a centroid-to-centroid distance of 3.506 (3) Å.

Related literature top

For similar structures, see: Faure & Loiseleur (1972, 1975).

Experimental top

All the chemicals and solvents used for the syntheses were of reagent grade and used without further purification. Ni(CH₃COO)₂.4H₂O (24.88 mg, 0.1 mmol) was dissolved in 5 ml of H₂O, while (2-pyridinyl)acetic acid (27.4 mg, 0.2 mmol) was dissolved in 5 ml of methanol at room temperature. The mixture was stirred for one hour. Pale-green single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation at room temperature for two weeks.

Structure description top

For similar structures, see: Faure & Loiseleur (1972, 1975).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms have been omitted. Symmetry code for the atoms with the A label: 2-x, 2-y, -z.
	Fig. 2. Crystal packing diagram with hydrogen bonds shown by dashed lines.

trans-Diaquabis[2-(2-pyridyl)acetato-κ²N,O]nickel(II) top

Crystal data top

[Ni(C₇H₆NO₂)₂(H₂O)₂]	F(000) = 380
M_r = 367.00	D_x = 1.746 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 804 reflections
a = 8.3346 (12) Å	θ = 3.1–27.8°
b = 7.100 (1) Å	µ = 1.43 mm⁻¹
c = 12.1023 (18) Å	T = 293 K
β = 102.977 (2)°	Block, pale-green
V = 697.87 (17) Å³	0.22 × 0.15 × 0.11 mm
Z = 2

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	1627 independent reflections
Radiation source: fine-focus sealed tube	1471 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 28.2°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→11
T_min = 0.774, T_max = 0.855	k = −8→9
4515 measured reflections	l = −16→15

Refinement top

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0413P)² + 0.1727P] where P = (F_o² + 2F_c²)/3
1627 reflections	(Δ/σ)_max < 0.001
114 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

[Ni(C₇H₆NO₂)₂(H₂O)₂]	V = 697.87 (17) Å³
M_r = 367.00	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3346 (12) Å	µ = 1.43 mm⁻¹
b = 7.100 (1) Å	T = 293 K
c = 12.1023 (18) Å	0.22 × 0.15 × 0.11 mm
β = 102.977 (2)°

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	1627 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1471 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.855	R_int = 0.017
4515 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.34 e Å⁻³
1627 reflections	Δρ_min = −0.20 e Å⁻³
114 parameters

Special details top

Experimental. 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 > 2sigma(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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	1.0000	1.0000	0.0000	0.01966 (10)
O1	0.73292 (15)	0.53276 (15)	−0.14497 (10)	0.0320 (3)
O1W	0.87262 (14)	1.17222 (17)	−0.13481 (9)	0.0315 (2)
H1WA	0.820 (2)	1.274 (3)	−0.1354 (18)	0.046 (6)*
H1WB	0.838 (3)	1.115 (4)	−0.199 (2)	0.072 (7)*
O2	0.89799 (12)	0.77910 (14)	−0.09898 (9)	0.0275 (2)
N1	0.79922 (16)	0.99744 (14)	0.07548 (10)	0.0221 (3)
C1	0.70767 (17)	0.8430 (2)	0.08078 (11)	0.0238 (3)
C2	0.56827 (18)	0.8517 (2)	0.12662 (12)	0.0302 (3)
H2A	0.5061	0.7438	0.1297	0.036*
C3	0.5230 (2)	1.0201 (2)	0.16721 (14)	0.0331 (4)
H3A	0.4307	1.0270	0.1983	0.040*
C4	0.61676 (17)	1.1788 (2)	0.16100 (13)	0.0313 (3)
H4A	0.5885	1.2946	0.1871	0.038*
C5	0.75331 (17)	1.1610 (2)	0.11506 (12)	0.0272 (3)
H5A	0.8168	1.2676	0.1113	0.033*
C6	0.76151 (18)	0.6580 (2)	0.04071 (12)	0.0277 (3)
H6A	0.6757	0.5660	0.0412	0.033*
H6B	0.8592	0.6165	0.0950	0.033*
C7	0.79960 (16)	0.65785 (18)	−0.07716 (11)	0.0229 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02185 (15)	0.01823 (15)	0.01945 (15)	−0.00105 (8)	0.00579 (10)	−0.00173 (8)
O1	0.0420 (7)	0.0236 (5)	0.0281 (6)	−0.0050 (4)	0.0029 (5)	−0.0058 (4)
O1W	0.0397 (6)	0.0257 (6)	0.0263 (6)	0.0069 (5)	0.0012 (5)	0.0001 (4)
O2	0.0320 (5)	0.0251 (5)	0.0268 (5)	−0.0052 (4)	0.0099 (4)	−0.0056 (4)
N1	0.0236 (6)	0.0223 (6)	0.0203 (6)	0.0003 (4)	0.0049 (5)	−0.0012 (4)
C1	0.0261 (7)	0.0270 (8)	0.0173 (6)	−0.0018 (5)	0.0030 (5)	0.0007 (5)
C2	0.0271 (7)	0.0385 (9)	0.0247 (7)	−0.0067 (6)	0.0055 (6)	0.0014 (6)
C3	0.0244 (7)	0.0487 (10)	0.0276 (8)	0.0015 (6)	0.0087 (6)	−0.0019 (6)
C4	0.0297 (7)	0.0367 (8)	0.0274 (7)	0.0063 (6)	0.0064 (6)	−0.0068 (6)
C5	0.0284 (7)	0.0251 (7)	0.0279 (7)	0.0006 (6)	0.0060 (6)	−0.0037 (6)
C6	0.0360 (8)	0.0212 (7)	0.0265 (7)	−0.0050 (6)	0.0082 (6)	0.0008 (5)
C7	0.0255 (6)	0.0179 (7)	0.0240 (6)	0.0035 (5)	0.0028 (5)	−0.0009 (5)

Geometric parameters (Å, º) top

Ni1—O2	2.0397 (10)	C2—C3	1.378 (2)
Ni1—N1	2.0789 (13)	C2—H2A	0.9300
Ni1—O1W	2.1228 (11)	C3—C4	1.383 (2)
O1—C7	1.2515 (17)	C3—H3A	0.9300
O1W—H1WA	0.84 (2)	C4—C5	1.380 (2)
O1W—H1WB	0.87 (3)	C4—H4A	0.9300
O2—C7	1.2572 (17)	C5—H5A	0.9300
N1—C5	1.3444 (17)	C6—C7	1.5294 (19)
N1—C1	1.3454 (17)	C6—H6A	0.9700
C1—C2	1.397 (2)	C6—H6B	0.9700
C1—C6	1.503 (2)

O2ⁱ—Ni1—N1ⁱ	88.90 (4)	C1—C2—H2A	120.0
O2ⁱ—Ni1—N1	91.10 (4)	C2—C3—C4	118.97 (15)
N1ⁱ—Ni1—N1	180	C2—C3—H3A	120.5
O2ⁱ—Ni1—O1W	94.53 (4)	C4—C3—H3A	120.5
N1—Ni1—O1W	91.70 (5)	C5—C4—C3	118.35 (14)
O2ⁱ—Ni1—O1Wⁱ	85.47 (5)	C5—C4—H4A	120.8
N1—Ni1—O1Wⁱ	88.30 (5)	C3—C4—H4A	120.8
O1W—Ni1—O1Wⁱ	180	N1—C5—C4	123.29 (14)
Ni1—O1W—H1WA	132.0 (14)	N1—C5—H5A	118.4
Ni1—O1W—H1WB	115.2 (17)	C4—C5—H5A	118.4
H1WA—O1W—H1WB	109 (2)	C1—C6—C7	116.18 (11)
C5—N1—C1	118.50 (13)	C1—C6—H6A	108.2
C5—N1—Ni1	118.07 (9)	C7—C6—H6A	108.2
C1—N1—Ni1	123.31 (9)	C1—C6—H6B	108.2
N1—C1—C2	120.96 (13)	C7—C6—H6B	108.2
N1—C1—C6	118.88 (12)	H6A—C6—H6B	107.4
C2—C1—C6	120.11 (13)	O1—C7—O2	124.25 (13)
C3—C2—C1	119.92 (14)	O1—C7—C6	117.23 (12)
C3—C2—H2A	120.0	O2—C7—C6	118.50 (12)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱⁱ	0.84 (2)	1.97 (2)	2.8035 (17)	169.7 (19)
O1W—H1WB···O1ⁱⁱⁱ	0.87 (3)	1.93 (3)	2.7936 (17)	169 (2)

Symmetry codes: (ii) x, y+1, z; (iii) −x+3/2, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₆NO₂)₂(H₂O)₂]
M_r	367.00
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.3346 (12), 7.100 (1), 12.1023 (18)
β (°)	102.977 (2)
V (Å³)	697.87 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.22 × 0.15 × 0.11

Data collection
Diffractometer	Bruker APEXII 1K CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.774, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	4515, 1627, 1471
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.067, 1.00
No. of reflections	1627
No. of parameters	114
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O2	2.0397 (10)	Ni1—O1W	2.1228 (11)
Ni1—N1	2.0789 (13)

O2ⁱ—Ni1—N1ⁱ	88.90 (4)	N1—Ni1—O1W	91.70 (5)
O2ⁱ—Ni1—N1	91.10 (4)	O2ⁱ—Ni1—O1Wⁱ	85.47 (5)
N1ⁱ—Ni1—N1	180	N1—Ni1—O1Wⁱ	88.30 (5)
O2ⁱ—Ni1—O1W	94.53 (4)	O1W—Ni1—O1Wⁱ	180

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱⁱ	0.84 (2)	1.97 (2)	2.8035 (17)	169.7 (19)
O1W—H1WB···O1ⁱⁱⁱ	0.87 (3)	1.93 (3)	2.7936 (17)	169 (2)

Symmetry codes: (ii) x, y+1, z; (iii) −x+3/2, y+1/2, −z−1/2.

Acknowledgements

This work was supported financially by the Key Project of the Chinese Ministry of Education (project No. 205147).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Faure, R. & Loiseleur, H. (1972). Acta Cryst. B28, 811–815. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Faure, R. & Loiseleur, H. (1975). Acta Cryst. B31, 1472–1475. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar