supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m330    [ doi:10.1107/S1600536809005960 ]

Bis(3-hydroxyphenylacetato-[kappa]2O,O')bis(1H-imidazole-[kappa]N3)nickel(II)

X.-Y. Nie and Q.-Z. Li

Abstract top

In the title mononuclear complex, [Ni(C8H7O3)2(C3H4N2)2], the NiII 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 [pi]-[pi] stacking interactions between the imidazole and benzene rings of neighboring molecules [centroid-centroid distance = 3.856 (2) Å].

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 NiII complex from the reaction of 3-hydroxyphenylacetic acid, imidazole and NiCl2 in an alkaline aqueous solution.

As illustrated in Fig. 1, the NiII 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.

Refinement top

H atoms were positioned geometrically and treated as riding on the parent C atoms, with C—H = 0.93 (CH) and 0.97 (CH2) Å, N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C, N).

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
[Figure 1] 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.]
[Figure 2] 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
Mr = 497.15Dx = 1.505 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5837 reflections
a = 12.8481 (14) Åθ = 2.8–27.9°
b = 10.6829 (12) ŵ = 0.93 mm−1
c = 16.3051 (19) ÅT = 296 K
β = 101.410 (1)°Block, blue
V = 2193.7 (4) Å30.32 × 0.27 × 0.24 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		1960 independent reflections
Radiation source: fine-focus sealed tube1509 reflections with I > 2σ(I)
graphiteRint = 0.045
φ and ω scansθmax = 25.2°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→15
Tmin = 0.762, Tmax = 0.811k = −10→12
5522 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
1960 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
[Ni(C8H7O3)2(C3H4N2)2]V = 2193.7 (4) Å3
Mr = 497.15Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.8481 (14) ŵ = 0.93 mm−1
b = 10.6829 (12) ÅT = 296 K
c = 16.3051 (19) Å0.32 × 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)
Tmin = 0.762, Tmax = 0.811Rint = 0.045
5522 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.29 e Å−3
S = 1.01Δρmin = −0.25 e Å−3
1960 reflectionsAbsolute structure: ?
151 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0902 (2)0.0767 (3)0.43721 (17)0.0387 (7)
N10.10445 (18)0.5333 (2)0.22611 (15)0.0392 (6)
Ni10.00000.40576 (5)0.25000.03283 (19)
O1−0.06407 (15)0.25890 (17)0.31434 (12)0.0421 (5)
C20.1936 (2)0.0654 (3)0.48209 (18)0.0438 (8)
H20.22080.12630.52130.053*
N20.2479 (2)0.6473 (3)0.24415 (17)0.0543 (8)
H2A0.31040.67470.26510.065*
O20.07730 (15)0.36060 (19)0.37318 (12)0.0423 (5)
C30.2567 (2)−0.0347 (3)0.46956 (19)0.0451 (8)
O30.35853 (19)−0.0487 (2)0.51162 (17)0.0704 (8)
H30.37690.01410.53970.106*
C40.2166 (3)−0.1259 (3)0.4120 (2)0.0521 (9)
H40.2580−0.19450.40400.063*
C50.1146 (3)−0.1143 (3)0.3666 (2)0.0566 (9)
H50.0877−0.17510.32720.068*
C60.0517 (3)−0.0144 (3)0.37856 (19)0.0503 (8)
H6−0.0169−0.00790.34720.060*
C70.0230 (3)0.1885 (3)0.45013 (18)0.0476 (8)
H7A−0.04620.16020.45780.057*
H7B0.05650.23320.50020.057*
C80.0100 (2)0.2748 (3)0.37584 (17)0.0369 (7)
C90.1992 (2)0.5532 (3)0.2722 (2)0.0534 (9)
H90.22830.50600.31910.064*
C100.0930 (3)0.6207 (3)0.1660 (2)0.0586 (10)
H100.03350.63040.12360.070*
C110.1815 (3)0.6928 (4)0.1766 (2)0.0699 (11)
H110.19390.76020.14370.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0439 (19)0.0382 (18)0.0339 (16)0.0014 (14)0.0076 (14)0.0093 (14)
N10.0313 (14)0.0370 (14)0.0487 (16)−0.0043 (11)0.0066 (12)−0.0007 (12)
Ni10.0233 (3)0.0304 (3)0.0417 (3)0.000−0.0010 (2)0.000
O10.0325 (11)0.0430 (12)0.0454 (12)−0.0088 (9)−0.0050 (10)0.0045 (10)
C20.055 (2)0.0348 (18)0.0385 (17)−0.0029 (14)0.0013 (16)−0.0036 (13)
N20.0370 (16)0.0630 (19)0.0620 (19)−0.0242 (14)0.0077 (14)−0.0082 (15)
O20.0316 (11)0.0438 (12)0.0458 (12)−0.0053 (10)−0.0060 (10)−0.0007 (10)
C30.0437 (19)0.0416 (18)0.0447 (18)0.0013 (15)−0.0042 (15)−0.0026 (15)
O30.0543 (15)0.0611 (16)0.0821 (19)0.0126 (13)−0.0195 (14)−0.0175 (14)
C40.054 (2)0.0443 (19)0.053 (2)0.0052 (16)0.0004 (18)−0.0078 (16)
C50.062 (2)0.050 (2)0.054 (2)−0.0066 (17)0.0004 (18)−0.0176 (16)
C60.0437 (19)0.056 (2)0.047 (2)−0.0042 (16)−0.0015 (16)−0.0030 (17)
C70.053 (2)0.050 (2)0.0401 (18)0.0095 (16)0.0090 (16)0.0049 (15)
C80.0316 (17)0.0367 (17)0.0404 (17)0.0035 (13)0.0023 (14)−0.0021 (13)
C90.0348 (18)0.054 (2)0.066 (2)−0.0085 (16)−0.0027 (17)0.0087 (18)
C100.054 (2)0.069 (3)0.046 (2)−0.0209 (18)−0.0041 (17)0.0133 (18)
C110.080 (3)0.070 (3)0.057 (2)−0.036 (2)0.006 (2)0.010 (2)
Geometric parameters (Å, °) top
C1—C61.385 (4)O2—C81.267 (3)
C1—C21.389 (4)C3—O31.360 (3)
C1—C71.513 (4)C3—C41.380 (4)
N1—C91.315 (4)O3—H30.8200
N1—C101.340 (4)C4—C51.378 (4)
Ni1—N12.004 (2)C4—H40.9300
Ni1—N1i2.004 (2)C5—C61.376 (4)
Ni1—O2i2.1128 (19)C5—H50.9300
Ni1—O22.1128 (19)C6—H60.9300
Ni1—O1i2.1404 (18)C7—C81.505 (4)
Ni1—O12.1404 (18)C7—H7A0.9700
O1—C81.250 (3)C7—H7B0.9700
C2—C31.381 (4)C9—H90.9300
C2—H20.9300C10—C111.356 (4)
N2—C91.313 (4)C10—H100.9300
N2—C111.343 (4)C11—H110.9300
N2—H2A0.8600
C6—C1—C2118.5 (3)C11—N2—H2A126.5
C6—C1—C7121.0 (3)C8—O2—Ni190.11 (16)
C2—C1—C7120.5 (3)O3—C3—C2123.0 (3)
C9—N1—C10105.1 (3)O3—C3—C4117.2 (3)
C9—N1—Ni1125.3 (2)C2—C3—C4119.8 (3)
C10—N1—Ni1129.4 (2)C3—O3—H3109.5
N1—Ni1—N1i94.31 (13)C5—C4—C3119.3 (3)
N1—Ni1—O2i100.22 (9)C5—C4—H4120.4
N1i—Ni1—O2i97.65 (9)C3—C4—H4120.4
N1—Ni1—O297.65 (9)C6—C5—C4121.1 (3)
N1i—Ni1—O2100.22 (9)C6—C5—H5119.4
O2i—Ni1—O2153.60 (11)C4—C5—H5119.4
N1—Ni1—O1i93.78 (8)C5—C6—C1120.2 (3)
N1i—Ni1—O1i158.58 (9)C5—C6—H6119.9
O2i—Ni1—O1i61.36 (7)C1—C6—H6119.9
O2—Ni1—O1i98.31 (8)C8—C7—C1110.3 (2)
N1—Ni1—O1158.58 (9)C8—C7—H7A109.6
N1i—Ni1—O193.78 (8)C1—C7—H7A109.6
O2i—Ni1—O198.31 (8)C8—C7—H7B109.6
O2—Ni1—O161.36 (7)C1—C7—H7B109.6
O1i—Ni1—O185.73 (10)H7A—C7—H7B108.1
N1—Ni1—C8i98.66 (9)O1—C8—O2119.2 (3)
N1i—Ni1—C8i128.39 (10)O1—C8—C7120.5 (3)
O2i—Ni1—C8i30.92 (8)O2—C8—C7120.2 (3)
O2—Ni1—C8i126.79 (9)N2—C9—N1112.0 (3)
O1i—Ni1—C8i30.45 (8)N2—C9—H9124.0
O1—Ni1—C8i91.74 (8)N1—C9—H9124.0
C8—O1—Ni189.31 (17)N1—C10—C11109.5 (3)
C3—C2—C1121.2 (3)N1—C10—H10125.2
C3—C2—H2119.4C11—C10—H10125.2
C1—C2—H2119.4N2—C11—C10106.2 (3)
C9—N2—C11107.1 (3)N2—C11—H11126.9
C9—N2—H2A126.5C10—C11—H11126.9
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.861.882.734 (3)171
O3—H3···O2iii0.821.962.763 (3)168
Symmetry codes: (ii) x+1/2, y+1/2, z; (iii) −x+1/2, −y+1/2, −z+1.
Table 1
Selected geometric parameters (Å) top
Ni1—N12.004 (2)Ni1—O12.1404 (18)
Ni1—O22.1128 (19)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.861.882.734 (3)171
O3—H3···O2ii0.821.962.763 (3)168
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1/2, −y+1/2, −z+1.
Acknowledgements top

The authors acknowledge Bijie University for supporting this work.

references
References top

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

James, S. L. (2003). Chem. Soc. Rev. 32, 276–288.

Serre, C., Millange, F., Thouvenot, C., Gardant, N., Pelle, F. & Ferey, G. (2004). J. Mater. Chem. 14, 1540–1543.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Yaghi, O. M., Li, H. L., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484.

Yaghi, O. M., O'Keeffe, M., Ockwig, N. W., Chae, H. K., Eddaoudi, M. & Kim, J. (2003). Nature (London), 423, 705–714.