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Acta Cryst. (2009). E65, m352-m353    [ doi:10.1107/S1600536809006515 ]

Bis(6'-carboxy-2,2'-bipyridine-6-carboxylato-[kappa]3N,N',O6)nickel(II) tetrahydrate

H. Wang, H. Su, J. Xu, F. Bai and Y. Gao

Abstract top

In the title compound, [Ni(C12H7N2O4)2]·4H2O, the Ni atom is located at the centre of a distorted octahedron, formed by four N atoms and two O atoms from the same two tridentating chelated 6-carboxy-2,2'-bipyridine-6'-carboxylate (L) ligands. Face-to-face [pi]-stacking interactions between inversion-related pyridine rings with centroid-centroid distances of 3.548 (3) and 3.662 (3) Å (perpendicular distances between the respective rings are 3.314 and 3.438 Å) are found. Intermolecular O-H...O hydrogen bonds between water molecules and L ligands form R53(10), R65(14) and R55(12) rings and also a centrosymmetric cage-like unit of water molecules, which link eight adjacent NiII centers, forming a three-dimensional framework.

Comment top

Pyridylcarboxylic acid is the 'ligand star' in coordination chemistry at all times (Gao et al., 2006). Many multidentate ligands containing N– or O–donors, such as pyridine-2,6-dicarboxylic acid (Liu et al., 2008), 2,2'-dipyridine-4,4'-dicarboxylic acid (Law et al., 2007), 2,2'-dipyridine-5,5'-dicarboxylic acid (Szeto et al., 2006) have been widely used because of their diverse coordination modes, which make the final architecture turn more stable and fascinating. Furthermore, they also offer more supramolecule contacts, such as hydrogen bonding or π···π stacking interactions, which further make the whole framework more stable (Robin & Fromm, 2006). However, a complex with the title ligand is still rare (Bünzli et al., 2000; Knight et al., 2006).

The molecule of the title complex (Fig. 1), shows that the Ni atom is located at the centre of a distorted octahedron of six coordinating atoms, four N atoms and two O atoms from the same two tridentating chelated 6-carboxy-2,2'-bipyridine-6'-carboxylate ligands L. The coordinated bipyridine fragments are nearly coplanar [torsion angles = 0.1 (7) and 3.5 (6)°, Table 1].

Three different hydrogen-bond ring patterns (see Table 2) are found in the structure: R53(10) (formed by O9-H9A..O10-H10A..O2..H12A-O12-H12B.. O6..H9B-); R65(14) (formed by O11-H11B..O12-H12A..O2..H10A-O10-H10B. .O5-C13-O6..H9B-O9..H11A-); and R55(12) (formed by O11-H11B..O12- H12B..O6-C13-O5..H10B-O10..H9A-O9..H11A-) (Bernstein et al., 1995). The intermolecular O—H···O hydrogen bonded cage-like units (assisted by the ligands L (Fig.2) and consisted of three different hydrogen-bond ring patterns), with four intermolecular hydrogen bonds, two O3—H3···O9 and two O7—H7···O11v (with H-bond patterns D, Bernstein et al., 1995), link eight adjacent NiII centers to form a three-dimensional framework (Fig.3). Face-to-face π-stacking interactions between inversion related pyridine rings with Cg5···Cg6vi and Cg7···Cg8iv distances of 3.548 (3) and 3.662 (3) Å (perpendicular distances between the respective rings are 3.314 and 3.438 Å) make the title compound more stable. Cg5, Cg6, Cg7, and Cg8 are the centroids of the pyridine rings (N1, C2 - C6), (N2, C7 - C11), (N3, C14 - C18) and (N4, C19 - C23), respectively. Symmetry codes: (vi) = -x, -y, -z, and (iv) = 1 - x, 1 - y, 1 - z, see Fig. 1.

Related literature top

For hydrogen-bonding motifs, see: Bernstein et al. (1995). For the structural and photophysical properties of LnIII complexes with the title ligand, see: Bünzli et al., (2000). For a catena-poly diaqua CdII complex with the title ligand, see: Knight et al. (2006). For an explanation of `ligand star', see: Gao et al. (2006). For the structural characterization and fluorescent properties of LnIII complexes with pyridine-2,6-dicarboxylic acid, see: Liu et al. (2008). For the structural and photophysical properties of EuIII complexes with 2,2'-dipyridine-4, 4'-dicarboxylic acid, see: Law et al. (2007). For the structural properties of a metal-organic framework (MOF) based on Pt, Y and 2,2'-bipyridine-5,5'-dicarboxylate, see: Szeto et al. (2006). For a review of the properties of coordination polymer networks via O– and N-atoms, see: Robin & Fromm (2006).

Experimental top

The title compound was obtained by the reaction of the mixture of Ni(NO3)2.6H2O, and 2,2'-dipyridine-6,6'-dicarboxylic acid in a molar ratio of 1:0.8 and 10 ml of water under hydrothermal conditions (at 413 K for 6 days and cooled to room temperature with a 5°C h-1 rate). The green block crystals were washed by water, ethanol. (Yield: 68%)

Refinement top

The H atoms were placed in geometrically idealized positions (C—H = 0.95 Å and O—H = 0.82–0.84 Å), with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku/MSC , 2005); cell refinement: CrystalClear (Rigaku/MSC , 2005); data reduction: CrystalClear (Rigaku/MSC , 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. The molecule structure of the title compound, with atom labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The ligand assisted hydrogen-bond cage like unit in the compound. The two complex units linked with O11 atoms and all the H atoms, have been omitted for clarity.
[Figure 3] Fig. 3. The packing of the title compound showing hydrogen bonds (dashed lines) holding the molecules together in the crystal structure. The two complex units linked with O11 atoms and all the H atoms, have been omitted for clarity.
Bis(6'-carboxy-2,2'-bipyridine-6-carboxylato- κ3N,N',O6)nickel(II) tetrahydrate top
Crystal data top
[Ni(C12H7N2O4)2]·4H2OZ = 2
Mr = 617.17F(000) = 636
Triclinic, P1Dx = 1.659 Mg m−3
a = 9.990 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.896 (2) ÅCell parameters from 3636 reflections
c = 12.565 (3) Åθ = 1.8–27.9°
α = 112.97 (3)°µ = 0.86 mm−1
β = 100.09 (3)°T = 113 K
γ = 90.30 (3)°Block, green
V = 1235.7 (4) Å30.20 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4305 independent reflections
Radiation source: rotating anode2745 reflections with I > 2σ(I)
confocalRint = 0.126
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω and φ scansh = −10→11
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −12→11
Tmin = 0.846, Tmax = 0.934l = −14→14
7165 measured reflections
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1025P)2]
where P = (Fo2 + 2Fc2)/3
4305 reflections(Δ/σ)max < 0.001
372 parametersΔρmax = 0.96 e Å−3
0 restraintsΔρmin = −0.75 e Å−3
Crystal data top
[Ni(C12H7N2O4)2]·4H2Oγ = 90.30 (3)°
Mr = 617.17V = 1235.7 (4) Å3
Triclinic, P1Z = 2
a = 9.990 (2) ÅMo Kα radiation
b = 10.896 (2) ŵ = 0.86 mm−1
c = 12.565 (3) ÅT = 113 K
α = 112.97 (3)°0.20 × 0.10 × 0.08 mm
β = 100.09 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4305 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		2745 reflections with I > 2σ(I)
Tmin = 0.846, Tmax = 0.934Rint = 0.126
7165 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.211Δρmax = 0.96 e Å−3
S = 1.05Δρmin = −0.75 e Å−3
4305 reflectionsAbsolute structure: ?
372 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.26176 (6)0.23748 (6)0.25373 (5)0.0128 (3)
O10.1825 (4)0.4096 (3)0.3635 (3)0.0170 (9)
O20.0298 (4)0.5584 (4)0.3582 (3)0.0206 (9)
O30.5431 (4)0.0527 (4)0.2154 (4)0.0236 (10)
H30.60060.04450.26920.035*
O40.4382 (5)−0.1285 (5)0.2149 (4)0.0463 (15)
O50.1553 (4)0.1112 (3)0.3108 (3)0.0168 (8)
O60.1883 (4)0.0088 (4)0.4363 (4)0.0259 (10)
O70.3576 (4)0.2726 (4)−0.0101 (4)0.0279 (10)
H70.31610.2681−0.07590.042*
O80.2810 (5)0.4775 (5)0.0577 (5)0.0513 (15)
N10.1132 (4)0.2644 (4)0.1406 (4)0.0130 (10)
N20.2678 (4)0.0647 (4)0.0940 (4)0.0113 (9)
N30.3979 (4)0.2352 (4)0.3886 (4)0.0130 (10)
N40.4370 (4)0.3585 (4)0.2514 (4)0.0142 (10)
C10.0871 (5)0.4564 (5)0.3123 (5)0.0161 (12)
C20.0440 (5)0.3747 (5)0.1788 (5)0.0149 (12)
C3−0.0525 (5)0.4060 (5)0.1044 (5)0.0194 (13)
H3A−0.09800.48550.13200.023*
C4−0.0825 (5)0.3167 (5)−0.0151 (5)0.0192 (13)
H4−0.14820.3361−0.06960.023*
C5−0.0156 (5)0.2000 (5)−0.0527 (5)0.0179 (13)
H5−0.03850.1370−0.13210.021*
C60.0848 (5)0.1768 (5)0.0271 (4)0.0110 (11)
C70.1705 (5)0.0604 (5)0.0014 (5)0.0108 (11)
C80.1510 (5)−0.0456 (5)−0.1094 (5)0.0134 (12)
H80.0834−0.0443−0.17230.016*
C90.2307 (5)−0.1519 (5)−0.1265 (5)0.0217 (13)
H90.2192−0.2246−0.20120.026*
C100.3280 (5)−0.1511 (5)−0.0330 (5)0.0188 (13)
H100.3835−0.2237−0.04220.023*
C110.3433 (5)−0.0420 (5)0.0749 (5)0.0141 (12)
C120.4464 (5)−0.0429 (5)0.1771 (5)0.0185 (13)
C130.2244 (6)0.0881 (5)0.3940 (5)0.0188 (13)
C140.3639 (5)0.1643 (5)0.4469 (5)0.0154 (12)
C150.4503 (5)0.1663 (5)0.5468 (5)0.0177 (12)
H150.42580.11600.58850.021*
C160.5741 (5)0.2441 (5)0.5845 (5)0.0172 (12)
H160.63540.24740.65270.021*
C170.6077 (5)0.3174 (5)0.5216 (5)0.0162 (12)
H170.69190.37050.54610.019*
C180.5161 (5)0.3109 (5)0.4234 (5)0.0139 (12)
C190.5397 (5)0.3818 (5)0.3460 (5)0.0142 (12)
C200.6567 (5)0.4637 (5)0.3709 (5)0.0175 (12)
H200.72620.47510.43690.021*
C210.6713 (6)0.5292 (5)0.2978 (5)0.0211 (13)
H210.75100.58600.31300.025*
C220.5682 (6)0.5107 (5)0.2029 (5)0.0215 (13)
H220.57410.55660.15310.026*
C230.4553 (5)0.4231 (5)0.1817 (5)0.0166 (12)
C240.3523 (5)0.3942 (5)0.0712 (5)0.0189 (12)
O90.7524 (3)0.0424 (4)0.3682 (3)0.0213 (9)
H9A0.80780.10920.39090.026*
H9B0.78260.01580.42060.026*
O100.0754 (4)0.7452 (4)0.5945 (3)0.0225 (9)
H10A0.05970.67380.53530.027*
H10B−0.00390.75360.60570.027*
O110.2191 (4)0.2207 (4)0.7879 (4)0.0285 (10)
H11A0.23090.14390.74350.034*
H11B0.13650.23020.77140.034*
O120.0448 (4)0.7657 (4)0.2859 (4)0.0331 (11)
H12A0.05110.71130.31790.040*
H12B0.06700.83840.34290.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0129 (4)0.0140 (4)0.0094 (4)0.0003 (3)−0.0015 (3)0.0039 (3)
O10.0182 (19)0.019 (2)0.011 (2)0.0034 (16)0.0013 (16)0.0030 (16)
O20.026 (2)0.017 (2)0.016 (2)0.0074 (17)0.0057 (18)0.0026 (17)
O30.022 (2)0.031 (2)0.021 (2)−0.0004 (18)−0.0032 (18)0.0160 (19)
O40.049 (3)0.057 (3)0.041 (3)−0.021 (2)−0.018 (3)0.039 (3)
O50.0155 (18)0.0175 (19)0.017 (2)−0.0024 (15)−0.0002 (16)0.0075 (16)
O60.026 (2)0.028 (2)0.025 (2)−0.0090 (18)−0.0022 (19)0.016 (2)
O70.030 (2)0.024 (2)0.023 (2)0.0009 (18)−0.0092 (19)0.0076 (19)
O80.056 (3)0.030 (3)0.047 (3)0.015 (2)−0.022 (3)0.005 (2)
N10.012 (2)0.016 (2)0.012 (2)−0.0013 (18)0.0019 (18)0.006 (2)
N20.011 (2)0.015 (2)0.008 (2)0.0007 (17)0.0021 (18)0.0052 (18)
N30.016 (2)0.014 (2)0.009 (2)0.0040 (18)0.0026 (19)0.0040 (18)
N40.013 (2)0.010 (2)0.016 (2)0.0051 (17)0.0036 (19)0.0015 (19)
C10.019 (3)0.013 (3)0.013 (3)0.000 (2)0.001 (2)0.003 (2)
C20.018 (3)0.013 (3)0.013 (3)0.002 (2)0.003 (2)0.004 (2)
C30.015 (3)0.021 (3)0.021 (3)0.004 (2)0.003 (2)0.008 (3)
C40.017 (3)0.023 (3)0.017 (3)0.005 (2)−0.001 (2)0.010 (2)
C50.017 (3)0.017 (3)0.017 (3)−0.004 (2)−0.002 (2)0.007 (2)
C60.015 (3)0.011 (3)0.007 (3)−0.001 (2)0.005 (2)0.004 (2)
C70.010 (2)0.011 (2)0.012 (3)0.001 (2)0.004 (2)0.004 (2)
C80.013 (3)0.014 (3)0.012 (3)−0.001 (2)0.002 (2)0.004 (2)
C90.022 (3)0.023 (3)0.014 (3)0.001 (2)0.002 (3)0.001 (2)
C100.021 (3)0.018 (3)0.016 (3)0.006 (2)0.002 (2)0.005 (2)
C110.014 (3)0.018 (3)0.011 (3)0.000 (2)0.001 (2)0.006 (2)
C120.018 (3)0.017 (3)0.018 (3)0.002 (2)0.001 (2)0.006 (2)
C130.022 (3)0.022 (3)0.012 (3)0.002 (2)−0.002 (2)0.008 (2)
C140.018 (3)0.014 (3)0.014 (3)0.000 (2)0.000 (2)0.007 (2)
C150.020 (3)0.018 (3)0.015 (3)0.003 (2)0.003 (2)0.007 (2)
C160.019 (3)0.023 (3)0.009 (3)0.002 (2)−0.002 (2)0.007 (2)
C170.017 (3)0.017 (3)0.010 (3)−0.001 (2)−0.001 (2)0.002 (2)
C180.013 (3)0.011 (2)0.015 (3)0.002 (2)0.000 (2)0.004 (2)
C190.016 (3)0.011 (3)0.011 (3)0.003 (2)0.003 (2)−0.001 (2)
C200.017 (3)0.017 (3)0.017 (3)0.001 (2)0.002 (2)0.005 (2)
C210.021 (3)0.026 (3)0.016 (3)0.000 (2)0.004 (2)0.008 (3)
C220.024 (3)0.019 (3)0.020 (3)−0.001 (2)0.007 (3)0.006 (2)
C230.018 (3)0.015 (3)0.016 (3)0.008 (2)0.006 (2)0.005 (2)
C240.018 (3)0.022 (3)0.020 (3)0.004 (2)0.005 (2)0.011 (3)
O90.019 (2)0.022 (2)0.021 (2)0.0013 (16)−0.0014 (18)0.0083 (18)
O100.0187 (19)0.025 (2)0.019 (2)0.0007 (17)0.0052 (18)0.0025 (18)
O110.030 (2)0.029 (2)0.021 (2)0.0026 (19)−0.0017 (19)0.0071 (19)
O120.042 (3)0.027 (2)0.028 (3)−0.008 (2)−0.003 (2)0.013 (2)
Geometric parameters (Å, °) top
Ni1—N11.975 (4)C7—C81.399 (7)
Ni1—N31.987 (4)C8—C91.377 (7)
Ni1—O12.104 (4)C8—H80.9500
Ni1—O52.136 (4)C9—C101.385 (7)
Ni1—N22.161 (5)C9—H90.9500
Ni1—N42.197 (4)C10—C111.394 (7)
O1—C11.276 (6)C10—H100.9500
O2—C11.231 (6)C11—C121.503 (6)
O3—C121.299 (6)C13—C141.519 (7)
O3—H30.8400C14—C151.385 (7)
O4—C121.207 (6)C15—C161.394 (7)
O5—C131.260 (6)C15—H150.9500
O6—C131.258 (6)C16—C171.399 (7)
O7—C241.329 (7)C16—H160.9500
O7—H70.8400C17—C181.379 (7)
O8—C241.202 (6)C17—H170.9500
N1—C61.348 (7)C18—C191.505 (7)
N1—C21.352 (6)C19—C201.379 (8)
N2—C111.354 (6)C20—C211.390 (7)
N2—C71.364 (6)C20—H200.9500
N3—C141.332 (7)C21—C221.380 (7)
N3—C181.339 (6)C21—H210.9500
N4—C231.354 (7)C22—C231.392 (7)
N4—C191.365 (6)C22—H220.9500
C1—C21.539 (7)C23—C241.496 (7)
C2—C31.363 (6)O9—H9A0.8341
C3—C41.410 (8)O9—H9B0.8302
C3—H3A0.9500O10—H10A0.8296
C4—C51.392 (7)O10—H10B0.8283
C4—H40.9500O11—H11A0.8278
C5—C61.387 (6)O11—H11B0.8319
C5—H50.9500O12—H12A0.8320
C6—C71.495 (7)O12—H12B0.8299
N1—Ni1—N3170.11 (18)C7—C8—H8120.3
N1—Ni1—O178.57 (16)C8—C9—C10118.9 (5)
N3—Ni1—O191.64 (15)C8—C9—H9120.5
N1—Ni1—O5100.61 (15)C10—C9—H9120.5
N3—Ni1—O578.13 (15)C9—C10—C11118.9 (5)
O1—Ni1—O592.18 (14)C9—C10—H10120.5
N1—Ni1—N278.15 (17)C11—C10—H10120.5
N3—Ni1—N2111.50 (16)N2—C11—C10123.5 (4)
O1—Ni1—N2156.37 (14)N2—C11—C12117.6 (5)
O5—Ni1—N288.21 (15)C10—C11—C12118.8 (4)
N1—Ni1—N4103.32 (16)O4—C12—O3125.4 (5)
N3—Ni1—N478.03 (17)O4—C12—C11121.3 (5)
O1—Ni1—N491.03 (15)O3—C12—C11113.3 (4)
O5—Ni1—N4156.02 (15)O6—C13—O5126.1 (5)
N2—Ni1—N498.14 (17)O6—C13—C14117.9 (4)
C1—O1—Ni1115.9 (3)O5—C13—C14116.0 (5)
C12—O3—H3109.5N3—C14—C15120.9 (5)
C13—O5—Ni1114.2 (3)N3—C14—C13113.2 (4)
C24—O7—H7109.5C15—C14—C13125.8 (5)
C6—N1—C2121.0 (4)C14—C15—C16118.3 (5)
C6—N1—Ni1120.6 (3)C14—C15—H15120.9
C2—N1—Ni1118.4 (3)C16—C15—H15120.9
C11—N2—C7116.5 (5)C15—C16—C17119.7 (5)
C11—N2—Ni1130.6 (3)C15—C16—H16120.1
C7—N2—Ni1112.6 (3)C17—C16—H16120.1
C14—N3—C18121.8 (4)C18—C17—C16118.6 (5)
C14—N3—Ni1118.1 (3)C18—C17—H17120.7
C18—N3—Ni1119.9 (3)C16—C17—H17120.7
C23—N4—C19115.6 (4)N3—C18—C17120.6 (5)
C23—N4—Ni1132.1 (3)N3—C18—C19114.9 (4)
C19—N4—Ni1111.9 (3)C17—C18—C19124.5 (5)
O2—C1—O1127.0 (5)N4—C19—C20123.8 (5)
O2—C1—C2118.6 (4)N4—C19—C18114.7 (4)
O1—C1—C2114.4 (5)C20—C19—C18121.5 (4)
N1—C2—C3122.0 (5)C19—C20—C21118.9 (5)
N1—C2—C1112.4 (4)C19—C20—H20120.6
C3—C2—C1125.6 (5)C21—C20—H20120.6
C2—C3—C4117.9 (5)C22—C21—C20119.0 (5)
C2—C3—H3A121.1C22—C21—H21120.5
C4—C3—H3A121.1C20—C21—H21120.5
C5—C4—C3119.8 (5)C21—C22—C23118.5 (5)
C5—C4—H4120.1C21—C22—H22120.7
C3—C4—H4120.1C23—C22—H22120.7
C6—C5—C4119.2 (5)N4—C23—C22124.1 (5)
C6—C5—H5120.4N4—C23—C24118.6 (5)
C4—C5—H5120.4C22—C23—C24117.2 (5)
N1—C6—C5120.0 (5)O8—C24—O7125.3 (5)
N1—C6—C7113.5 (4)O8—C24—C23122.1 (5)
C5—C6—C7126.5 (5)O7—C24—C23112.4 (4)
N2—C7—C8122.7 (4)H9A—O9—H9B97.5
N2—C7—C6115.1 (4)H10A—O10—H10B97.1
C8—C7—C6122.2 (4)H11A—O11—H11B106.3
C9—C8—C7119.4 (5)H12A—O12—H12B102.5
C9—C8—H8120.3
N1—Ni1—O1—C1−3.7 (4)Ni1—N1—C6—C72.8 (6)
N3—Ni1—O1—C1177.7 (4)C4—C5—C6—N12.4 (8)
O5—Ni1—O1—C1−104.1 (4)C4—C5—C6—C7−177.5 (5)
N2—Ni1—O1—C1−13.6 (6)C11—N2—C7—C8−2.2 (7)
N4—Ni1—O1—C199.7 (4)Ni1—N2—C7—C8−176.9 (4)
N1—Ni1—O5—C13−173.4 (4)C11—N2—C7—C6177.3 (4)
N3—Ni1—O5—C13−3.4 (4)Ni1—N2—C7—C62.6 (5)
O1—Ni1—O5—C13−94.6 (4)N1—C6—C7—N2−3.5 (6)
N2—Ni1—O5—C13109.0 (4)C5—C6—C7—N2176.4 (5)
N4—Ni1—O5—C132.8 (6)N1—C6—C7—C8176.0 (4)
N3—Ni1—N1—C6−168.7 (8)C5—C6—C7—C8−4.1 (8)
O1—Ni1—N1—C6−177.2 (4)N2—C7—C8—C91.3 (8)
O5—Ni1—N1—C6−87.1 (4)C6—C7—C8—C9−178.1 (5)
N2—Ni1—N1—C6−1.2 (4)C7—C8—C9—C100.2 (8)
N4—Ni1—N1—C694.5 (4)C8—C9—C10—C11−0.8 (8)
N3—Ni1—N1—C213.4 (12)C7—N2—C11—C101.5 (7)
O1—Ni1—N1—C25.0 (4)Ni1—N2—C11—C10175.2 (4)
O5—Ni1—N1—C295.1 (4)C7—N2—C11—C12−177.0 (4)
N2—Ni1—N1—C2−179.0 (4)Ni1—N2—C11—C12−3.3 (7)
N4—Ni1—N1—C2−83.3 (4)C9—C10—C11—N2−0.1 (8)
N1—Ni1—N2—C11−174.7 (5)C9—C10—C11—C12178.4 (5)
N3—Ni1—N2—C113.0 (5)N2—C11—C12—O4117.9 (6)
O1—Ni1—N2—C11−164.9 (4)C10—C11—C12—O4−60.7 (8)
O5—Ni1—N2—C11−73.5 (4)N2—C11—C12—O3−64.1 (7)
N4—Ni1—N2—C1183.3 (4)C10—C11—C12—O3117.3 (6)
N1—Ni1—N2—C7−0.9 (3)Ni1—O5—C13—O6−174.0 (5)
N3—Ni1—N2—C7176.8 (3)Ni1—O5—C13—C146.1 (6)
O1—Ni1—N2—C79.0 (6)C18—N3—C14—C150.1 (8)
O5—Ni1—N2—C7100.3 (3)Ni1—N3—C14—C15−175.3 (4)
N4—Ni1—N2—C7−102.9 (3)C18—N3—C14—C13178.8 (5)
N1—Ni1—N3—C1483.3 (10)Ni1—N3—C14—C133.3 (6)
O1—Ni1—N3—C1491.6 (4)O6—C13—C14—N3173.7 (5)
O5—Ni1—N3—C14−0.3 (4)O5—C13—C14—N3−6.4 (7)
N2—Ni1—N3—C14−83.6 (4)O6—C13—C14—C15−7.7 (9)
N4—Ni1—N3—C14−177.7 (4)O5—C13—C14—C15172.2 (5)
N1—Ni1—N3—C18−92.2 (10)N3—C14—C15—C16−0.3 (8)
O1—Ni1—N3—C18−84.0 (4)C13—C14—C15—C16−178.8 (5)
O5—Ni1—N3—C18−175.9 (4)C14—C15—C16—C170.1 (8)
N2—Ni1—N3—C18100.9 (4)C15—C16—C17—C180.3 (8)
N4—Ni1—N3—C186.7 (4)C14—N3—C18—C170.3 (8)
N1—Ni1—N4—C23−8.8 (5)Ni1—N3—C18—C17175.6 (4)
N3—Ni1—N4—C23−178.8 (5)C14—N3—C18—C19178.7 (5)
O1—Ni1—N4—C23−87.3 (5)Ni1—N3—C18—C19−6.0 (6)
O5—Ni1—N4—C23175.0 (4)C16—C17—C18—N3−0.4 (8)
N2—Ni1—N4—C2370.9 (5)C16—C17—C18—C19−178.7 (5)
N1—Ni1—N4—C19163.7 (3)C23—N4—C19—C20−0.9 (8)
N3—Ni1—N4—C19−6.3 (3)Ni1—N4—C19—C20−174.7 (4)
O1—Ni1—N4—C1985.2 (3)C23—N4—C19—C18179.0 (4)
O5—Ni1—N4—C19−12.5 (6)Ni1—N4—C19—C185.2 (5)
N2—Ni1—N4—C19−116.7 (3)N3—C18—C19—N4−0.1 (7)
Ni1—O1—C1—O2−177.0 (5)C17—C18—C19—N4178.2 (5)
Ni1—O1—C1—C21.9 (6)N3—C18—C19—C20179.8 (5)
C6—N1—C2—C3−3.1 (8)C17—C18—C19—C20−1.9 (8)
Ni1—N1—C2—C3174.7 (4)N4—C19—C20—C211.5 (8)
C6—N1—C2—C1176.8 (4)C18—C19—C20—C21−178.4 (5)
Ni1—N1—C2—C1−5.4 (6)C19—C20—C21—C220.2 (8)
O2—C1—C2—N1−178.9 (5)C20—C21—C22—C23−2.2 (8)
O1—C1—C2—N12.1 (7)C19—N4—C23—C22−1.3 (8)
O2—C1—C2—C31.0 (8)Ni1—N4—C23—C22170.9 (4)
O1—C1—C2—C3−178.1 (5)C19—N4—C23—C24175.3 (4)
N1—C2—C3—C42.2 (8)Ni1—N4—C23—C24−12.4 (7)
C1—C2—C3—C4−177.7 (5)C21—C22—C23—N42.9 (9)
C2—C3—C4—C51.0 (8)C21—C22—C23—C24−173.8 (5)
C3—C4—C5—C6−3.2 (8)N4—C23—C24—O8114.4 (7)
C2—N1—C6—C50.7 (7)C22—C23—C24—O8−68.8 (8)
Ni1—N1—C6—C5−177.1 (4)N4—C23—C24—O7−70.5 (7)
C2—N1—C6—C7−179.4 (4)C22—C23—C24—O7106.4 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12B···O6i0.832.022.783 (6)153
O12—H12A···O20.831.942.755 (5)165
O11—H11B···O12ii0.831.842.662 (5)172
O11—H11A···O9iii0.831.992.821 (6)177
O10—H10B···O5ii0.832.222.953 (5)148
O10—H10A···O20.832.052.822 (6)155
O9—H9B···O6iii0.831.892.694 (5)162
O9—H9A···O10iv0.831.902.714 (5)167
O7—H7···O11v0.841.692.513 (5)166
O3—H3···O90.841.792.614 (5)166
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1.
Table 1
Selected geometric parameters (Å, °) top
Ni1—N11.975 (4)Ni1—O52.136 (4)
Ni1—N31.987 (4)Ni1—N22.161 (5)
Ni1—O12.104 (4)Ni1—N42.197 (4)
N3—Ni1—N2111.50 (16)N3—Ni1—N478.03 (17)
N1—Ni1—N4103.32 (16)O5—Ni1—N4156.02 (15)
N1—C6—C7—N2−3.5 (6)N3—C18—C19—N4−0.1 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12B···O6i0.832.022.783 (6)153
O12—H12A···O20.831.942.755 (5)165
O11—H11B···O12ii0.831.842.662 (5)172
O11—H11A···O9iii0.831.992.821 (6)177
O10—H10B···O5ii0.832.222.953 (5)148
O10—H10A···O20.832.052.822 (6)155
O9—H9B···O6iii0.831.892.694 (5)162
O9—H9A···O10iv0.831.902.714 (5)167
O7—H7···O11v0.841.692.513 (5)166
O3—H3···O90.841.792.614 (5)166
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1.
Acknowledgements top

This work was supported by the Program for New Century Excellent Talents in Universities (NCET-04–0261) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry.

references
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