Bis(3-hydroxy­phenyl­acetato-κ2O,O′)bis­(1H-imidazole-κN3)nickel(II)

Nie, X.-Y.; Li, Q.-Z.

doi:10.1107/S1600536809005960

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m330

doi:10.1107/S1600536809005960

Open

access

Bis(3-hydroxyphenylacetato-κ²O,O′)bis(1H-imidazole-κN³)nickel(II)

Xiao-Yan Nie ^a and Qian-Zhu Li ^a ^*

^aDepartment of Chemistry, Bijie University, Bijie 551700, People's Republic of China
^*Correspondence e-mail: qianzhuli77@yahoo.com.cn

(Received 19 January 2009; accepted 19 February 2009; online 28 February 2009)

In the title mononuclear complex, [Ni(C₈H₇O₃)₂(C₃H₄N₂)₂], the Ni^II atom, lying on a twofold rotation axis, is coordinated by four carboxylate O atoms from two bidentate 3-hydroxyphenylacetato ligands and two N atoms from two imidazole molecules in a distorted octahedral geometry. A three-dimensional network is formed via intermolecular O—H⋯O and N—H⋯O hydrogen bonds and π–π stacking interactions between the imidazole and benzene rings of neighboring molecules [centroid–centroid distance = 3.856 (2) Å].

Related literature

For the use of coordination polymers and open framework materials in catalysis, separation, gas storage and molecular recognition, see: James (2003 ); Serre et al. (2004 ); Yaghi et al. (1998 , 2003 ).

Experimental

Crystal data

[Ni(C₈H₇O₃)₂(C₃H₄N₂)₂]
M_r = 497.15
Monoclinic, C 2/c
a = 12.8481 (14) Å
b = 10.6829 (12) Å
c = 16.3051 (19) Å
β = 101.410 (1)°
V = 2193.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 296 K
0.32 × 0.27 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.762, T_max = 0.811
5522 measured reflections
1960 independent reflections
1509 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.094
S = 1.01
1960 reflections
151 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.004 (2)
Ni1—O2	2.1128 (19)
Ni1—O1	2.1404 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	1.88	2.734 (3)	171
O3—H3⋯O2ⁱⁱ	0.82	1.96	2.763 (3)	168
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: 10.1107/S1600536809005960/hy2181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005960/hy2181Isup2.hkl

checkCIF report

Comment top

The use of multifunctional organic linker molecules in the preparation of coordination polymers and open-framework materials has led to the development of a rich field of chemistry, owing to the potential applications of these materials in catalysis, separation, gas storage and molecular recognition (James, 2003; Serre et al., 2004; Yaghi et al., 1998, 2003). 3-Hydroxyphenylacetic acid has a versatile binding ability. Structures of the complexes with 3-hydroxyphenylacetate have not been reported to date. We obtained a new Ni^II complex from the reaction of 3-hydroxyphenylacetic acid, imidazole and NiCl₂ in an alkaline aqueous solution.

As illustrated in Fig. 1, the Ni^II atom, lying on a twofold rotation axis, has a distorted octahedral environment, defined by four carboxylate O atoms from two bidentate 3-hydroxyphenylacetate ligands and two N atoms from two imidazole molecules. Intermolecular O—H···O and N—H···O hydrogen bonds form a three-dimensional network, which is further consolidated by π–π stacking interactions between the imidazole and phenyl rings of neighboring complexes, with a centroid–centroid distance of 3.856 (2) Å.

Related literature top

For general background, see: James (2003); Serre et al. (2004); Yaghi et al. (1998, 2003).

Experimental top

A mixture of nickel chloride (0.13 g, 1 mmol), 3-hydroxyphenylacetic acid (0.152 g, 1 mmol), imidazole (0.068 g, 1 mmol), NaOH (0.06 g, 1.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dried in air.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (iii) -x, y, 1/2 - z.]
	Fig. 2. A packing view of the title compound. The intermolecluar hydrogen bonds and π–π stacking interactions are shown as dashed lines.

Bis(3-hydroxyphenylacetato-κ²O,O')bis(1H- imidazole-κN³)nickel(II) top

Crystal data top

[Ni(C₈H₇O₃)₂(C₃H₄N₂)₂]	F(000) = 1032
M_r = 497.15	D_x = 1.505 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5837 reflections
a = 12.8481 (14) Å	θ = 2.8–27.9°
b = 10.6829 (12) Å	µ = 0.93 mm⁻¹
c = 16.3051 (19) Å	T = 296 K
β = 101.410 (1)°	Block, blue
V = 2193.7 (4) Å³	0.32 × 0.27 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1960 independent reflections
Radiation source: fine-focus sealed tube	1509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
T_min = 0.762, T_max = 0.811	k = −10→12
5522 measured reflections	l = −19→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0443P)²] where P = (F_o² + 2F_c²)/3
1960 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ni(C₈H₇O₃)₂(C₃H₄N₂)₂]	V = 2193.7 (4) Å³
M_r = 497.15	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.8481 (14) Å	µ = 0.93 mm⁻¹
b = 10.6829 (12) Å	T = 296 K
c = 16.3051 (19) Å	0.32 × 0.27 × 0.24 mm
β = 101.410 (1)°

Data collection top

Bruker APEXII CCD diffractometer	1960 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1509 reflections with I > 2σ(I)
T_min = 0.762, T_max = 0.811	R_int = 0.045
5522 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
1960 reflections	Δρ_min = −0.25 e Å⁻³
151 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.0902 (2)	0.0767 (3)	0.43721 (17)	0.0387 (7)
N1	0.10445 (18)	0.5333 (2)	0.22611 (15)	0.0392 (6)
Ni1	0.0000	0.40576 (5)	0.2500	0.03283 (19)
O1	−0.06407 (15)	0.25890 (17)	0.31434 (12)	0.0421 (5)
C2	0.1936 (2)	0.0654 (3)	0.48209 (18)	0.0438 (8)
H2	0.2208	0.1263	0.5213	0.053*
N2	0.2479 (2)	0.6473 (3)	0.24415 (17)	0.0543 (8)
H2A	0.3104	0.6747	0.2651	0.065*
O2	0.07730 (15)	0.36060 (19)	0.37318 (12)	0.0423 (5)
C3	0.2567 (2)	−0.0347 (3)	0.46956 (19)	0.0451 (8)
O3	0.35853 (19)	−0.0487 (2)	0.51162 (17)	0.0704 (8)
H3	0.3769	0.0141	0.5397	0.106*
C4	0.2166 (3)	−0.1259 (3)	0.4120 (2)	0.0521 (9)
H4	0.2580	−0.1945	0.4040	0.063*
C5	0.1146 (3)	−0.1143 (3)	0.3666 (2)	0.0566 (9)
H5	0.0877	−0.1751	0.3272	0.068*
C6	0.0517 (3)	−0.0144 (3)	0.37856 (19)	0.0503 (8)
H6	−0.0169	−0.0079	0.3472	0.060*
C7	0.0230 (3)	0.1885 (3)	0.45013 (18)	0.0476 (8)
H7A	−0.0462	0.1602	0.4578	0.057*
H7B	0.0565	0.2332	0.5002	0.057*
C8	0.0100 (2)	0.2748 (3)	0.37584 (17)	0.0369 (7)
C9	0.1992 (2)	0.5532 (3)	0.2722 (2)	0.0534 (9)
H9	0.2283	0.5060	0.3191	0.064*
C10	0.0930 (3)	0.6207 (3)	0.1660 (2)	0.0586 (10)
H10	0.0335	0.6304	0.1236	0.070*
C11	0.1815 (3)	0.6928 (4)	0.1766 (2)	0.0699 (11)
H11	0.1939	0.7602	0.1437	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0439 (19)	0.0382 (18)	0.0339 (16)	0.0014 (14)	0.0076 (14)	0.0093 (14)
N1	0.0313 (14)	0.0370 (14)	0.0487 (16)	−0.0043 (11)	0.0066 (12)	−0.0007 (12)
Ni1	0.0233 (3)	0.0304 (3)	0.0417 (3)	0.000	−0.0010 (2)	0.000
O1	0.0325 (11)	0.0430 (12)	0.0454 (12)	−0.0088 (9)	−0.0050 (10)	0.0045 (10)
C2	0.055 (2)	0.0348 (18)	0.0385 (17)	−0.0029 (14)	0.0013 (16)	−0.0036 (13)
N2	0.0370 (16)	0.0630 (19)	0.0620 (19)	−0.0242 (14)	0.0077 (14)	−0.0082 (15)
O2	0.0316 (11)	0.0438 (12)	0.0458 (12)	−0.0053 (10)	−0.0060 (10)	−0.0007 (10)
C3	0.0437 (19)	0.0416 (18)	0.0447 (18)	0.0013 (15)	−0.0042 (15)	−0.0026 (15)
O3	0.0543 (15)	0.0611 (16)	0.0821 (19)	0.0126 (13)	−0.0195 (14)	−0.0175 (14)
C4	0.054 (2)	0.0443 (19)	0.053 (2)	0.0052 (16)	0.0004 (18)	−0.0078 (16)
C5	0.062 (2)	0.050 (2)	0.054 (2)	−0.0066 (17)	0.0004 (18)	−0.0176 (16)
C6	0.0437 (19)	0.056 (2)	0.047 (2)	−0.0042 (16)	−0.0015 (16)	−0.0030 (17)
C7	0.053 (2)	0.050 (2)	0.0401 (18)	0.0095 (16)	0.0090 (16)	0.0049 (15)
C8	0.0316 (17)	0.0367 (17)	0.0404 (17)	0.0035 (13)	0.0023 (14)	−0.0021 (13)
C9	0.0348 (18)	0.054 (2)	0.066 (2)	−0.0085 (16)	−0.0027 (17)	0.0087 (18)
C10	0.054 (2)	0.069 (3)	0.046 (2)	−0.0209 (18)	−0.0041 (17)	0.0133 (18)
C11	0.080 (3)	0.070 (3)	0.057 (2)	−0.036 (2)	0.006 (2)	0.010 (2)

Geometric parameters (Å, º) top

C1—C6	1.385 (4)	O2—C8	1.267 (3)
C1—C2	1.389 (4)	C3—O3	1.360 (3)
C1—C7	1.513 (4)	C3—C4	1.380 (4)
N1—C9	1.315 (4)	O3—H3	0.8200
N1—C10	1.340 (4)	C4—C5	1.378 (4)
Ni1—N1	2.004 (2)	C4—H4	0.9300
Ni1—N1ⁱ	2.004 (2)	C5—C6	1.376 (4)
Ni1—O2ⁱ	2.1128 (19)	C5—H5	0.9300
Ni1—O2	2.1128 (19)	C6—H6	0.9300
Ni1—O1ⁱ	2.1404 (18)	C7—C8	1.505 (4)
Ni1—O1	2.1404 (18)	C7—H7A	0.9700
O1—C8	1.250 (3)	C7—H7B	0.9700
C2—C3	1.381 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.356 (4)
N2—C9	1.313 (4)	C10—H10	0.9300
N2—C11	1.343 (4)	C11—H11	0.9300
N2—H2A	0.8600

C6—C1—C2	118.5 (3)	C11—N2—H2A	126.5
C6—C1—C7	121.0 (3)	C8—O2—Ni1	90.11 (16)
C2—C1—C7	120.5 (3)	O3—C3—C2	123.0 (3)
C9—N1—C10	105.1 (3)	O3—C3—C4	117.2 (3)
C9—N1—Ni1	125.3 (2)	C2—C3—C4	119.8 (3)
C10—N1—Ni1	129.4 (2)	C3—O3—H3	109.5
N1—Ni1—N1ⁱ	94.31 (13)	C5—C4—C3	119.3 (3)
N1—Ni1—O2ⁱ	100.22 (9)	C5—C4—H4	120.4
N1ⁱ—Ni1—O2ⁱ	97.65 (9)	C3—C4—H4	120.4
N1—Ni1—O2	97.65 (9)	C6—C5—C4	121.1 (3)
N1ⁱ—Ni1—O2	100.22 (9)	C6—C5—H5	119.4
O2ⁱ—Ni1—O2	153.60 (11)	C4—C5—H5	119.4
N1—Ni1—O1ⁱ	93.78 (8)	C5—C6—C1	120.2 (3)
N1ⁱ—Ni1—O1ⁱ	158.58 (9)	C5—C6—H6	119.9
O2ⁱ—Ni1—O1ⁱ	61.36 (7)	C1—C6—H6	119.9
O2—Ni1—O1ⁱ	98.31 (8)	C8—C7—C1	110.3 (2)
N1—Ni1—O1	158.58 (9)	C8—C7—H7A	109.6
N1ⁱ—Ni1—O1	93.78 (8)	C1—C7—H7A	109.6
O2ⁱ—Ni1—O1	98.31 (8)	C8—C7—H7B	109.6
O2—Ni1—O1	61.36 (7)	C1—C7—H7B	109.6
O1ⁱ—Ni1—O1	85.73 (10)	H7A—C7—H7B	108.1
N1—Ni1—C8ⁱ	98.66 (9)	O1—C8—O2	119.2 (3)
N1ⁱ—Ni1—C8ⁱ	128.39 (10)	O1—C8—C7	120.5 (3)
O2ⁱ—Ni1—C8ⁱ	30.92 (8)	O2—C8—C7	120.2 (3)
O2—Ni1—C8ⁱ	126.79 (9)	N2—C9—N1	112.0 (3)
O1ⁱ—Ni1—C8ⁱ	30.45 (8)	N2—C9—H9	124.0
O1—Ni1—C8ⁱ	91.74 (8)	N1—C9—H9	124.0
C8—O1—Ni1	89.31 (17)	N1—C10—C11	109.5 (3)
C3—C2—C1	121.2 (3)	N1—C10—H10	125.2
C3—C2—H2	119.4	C11—C10—H10	125.2
C1—C2—H2	119.4	N2—C11—C10	106.2 (3)
C9—N2—C11	107.1 (3)	N2—C11—H11	126.9
C9—N2—H2A	126.5	C10—C11—H11	126.9

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱⁱ	0.86	1.88	2.734 (3)	171
O3—H3···O2ⁱⁱⁱ	0.82	1.96	2.763 (3)	168

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₇O₃)₂(C₃H₄N₂)₂]
M_r	497.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	12.8481 (14), 10.6829 (12), 16.3051 (19)
β (°)	101.410 (1)
V (Å³)	2193.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.32 × 0.27 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.762, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	5522, 1960, 1509
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.094, 1.01
No. of reflections	1960
No. of parameters	151
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N1	2.004 (2)	Ni1—O1	2.1404 (18)
Ni1—O2	2.1128 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.88	2.734 (3)	171
O3—H3···O2ⁱⁱ	0.82	1.96	2.763 (3)	168

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

Acknowledgements

The authors acknowledge Bijie University for kindly supporting this work (20072016).

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
James, S. L. (2003). Chem. Soc. Rev. 32, 276–288. Web of Science CrossRef PubMed CAS Google Scholar
Serre, C., Millange, F., Thouvenot, C., Gardant, N., Pelle, F. & Ferey, G. (2004). J. Mater. Chem. 14, 1540–1543. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yaghi, O. M., Li, H. L., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484. Web of Science CrossRef CAS Google Scholar
Yaghi, O. M., O'Keeffe, M., Ockwig, N. W., Chae, H. K., Eddaoudi, M. & Kim, J. (2003). Nature (London), 423, 705–714. Web of Science CrossRef PubMed CAS Google Scholar