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Acta Cryst. (2007). E63, m2327-m2328    [ doi:10.1107/S1600536807038196 ]

Aqua(N,N-diethylethylenediamine-[kappa]2N,N')(pyridine-2,6-dicarboxylato-[kappa]3N,O,O')nickel(II) 2.5-hydrate

I. Uçar, A. Bulut and C. Kazak

Abstract top

In the title compound, [Ni(C7H3NO4)(C6H16N2)(H2O)]·2.5H2O, the discrete neutral [Ni(dpc)(dien)(H2O)] (dien is diethylethylenediamine and dpc is dipicolinate) complex lies on a mirror plane. The NiII ion is coordinated by the dpc ligand through the pyridine N atom and one O atom of each carboxylate group, an aqua ligand and two N atoms of the bidentate dien ligand, forming a distorted octahedral geometry. One of the C atoms of the ethylenediamine group is disordered across the mirror plane. The symmetry-independent ethyl group is disordered over two orientations with equal occupancy. The complex molecules are connected via O-H...O and N-H...O intermolecular hydrogen-bonding interactions.

Comment top

Pyridine-2,6-dicarboxylic acid, known as dipicolinic acid (H2dpc), is a versatile ligand and it can function as a neutral, mono basic or dibasic tridentate chelating ligand (Nathan & Mai, 2000; Perry et al., 2004). Having potential donor oxygen and nitrogen atoms, dipicolinic acid has attracted the scientist from the coordination chemistry and number of studies have been carried out with dipicolinate (dpc) ligand by both inorganic and bioinorganic chemists during the past few years (Krillova et al., 2007). Dipicolinates commonly coordinate to transition metals by either carboxylate bridges between metal centres, to form polymeric (Ma et al., 2003) or dimeric complexes (Ramezaniopour et al., 2005), or tridentate (O, N, O') chelation to one metal ion (Okabe & Oya, 2000). The dipicolinate ligand with NiII ions commonly has one or two coordination modes. In one coordination mode, a single planar dpc ligand binds in the equatorial plane of a NiII cation and other ligands such as H2O or pyridine based heterocycles occupy the remaining sites, thereby forming square pyramidal or octahedral coordination geometry (Liu et al., 2006; Zhang et al., 2003), or two planar dpc molecules coordinate perpendicularly generating a distorted octahedral coordination geometry (Park et al., 2007). In our ongoing research on determination of further coordination modes of chelates of dipicolinic acid with biologically important transition metal ions, we have recently synthesized mixed-ligand metal(II) complexes of dipicolinic acid and their structures have been reported (Uçar et al., 2005; Uçar et al., 2007). As a continuation of these studies, we have now prepared and characterized a new NiII complex containing dipicolinate anion together with diethylethylenediamine (dien)ligand, namely [Ni(dien)(dpc)(H2O)].2.5H2O.

The asymmetric unit of the title compound consists of one-half of a discrete neutral [Ni(dien)(dpc)(H2O)] unit and 1.25 lattice water molecules. The [Ni(dien)(dpc)(H2O)] unit lies across a mirror plane with atoms Ni1, N1, N2, N3, C4 and C5 on the mirror plane. Atom C6 is disordered over two positions across the mirror plane (Fig. 1). The H2dpc is deprotoned during the reaction and acts as a tridentate ligand. The NiII ion is six-coordinated in a distorted octahedral geometry, with one N (N3) two O atoms of the tridentate dpc dianion and one N atom from the dien (N1) ligand composing the basal plane, and the aqua O atom and the other N atom (N2) of the dien ligand occuping the axial sites.

The fact that the Ni1—Ndpc [1.986 (3) Å] length is significantly shorter than Ni1—Ndien [2.070 (3) and 2.122 (3)] bond lengths indicates that atom N3 is the strongest site, because the two carboxylate groups in ortho positions enhance the basicity of this atom. The Ni1—Ndpc, Ni1—Odpc [2.145 (2) Å] and Ni1—Oaqua [2.070 (2) Å] bond lengths in the title complex are slightly different from those observed in previously reported mixed-ligand nickel(II) dipicolinate complexes (Ramadevi et al., 2005; Liu et al., 2006; Park et al., 2007). The dpc chelate angle is 77.79 (10)°, which is comparable to that found in other dipicolinate-metal complexes (Chaigneau et al., 2004; Altin et al., 2004).

The crystal packing is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds, involving the oxygen atoms of coordinated and free water molecules (see Table 2 and Fig. 2).

Related literature top

For related literature, see: Altin et al. (2004); Chaigneau et al. (2004); Krillova et al. (2007); Liu et al. (2006); Ma et al. (2003); Nathan & Mai (2000); Okabe & Oya (2000); Park et al. (2007); Perry et al. (2004); Ramadevi et al. (2005); Ramezaniopour et al. (2005); Uçar et al. (2005, 2007); Zhang et al. (2003).

Experimental top

To an ethanol/water (30 ml, 1:1) containing NiCl24H2O (1 mmol) and disodium dipicolinate (1 mmol), dien (1 mmol) was added slowly with continuous stirring. The resulting solution was refluxed for 1 h and then filtered. The green filtrate was allowed to stand for about two weeks at room temperature, after which time light-green crystals of the title compound suitable for X-ray diffraction analysis were collected.

Refinement top

Atoms Ni1, N1, N2, N3, C4 and C5 lie on the crystallographic mirror plane. Atom C6 is disordered across the mirror plane and as a result the occupancy factor for the disordered components were fixed at 0.50 each. The independent ethyl group is disordered over two orientations with equal occupancy. The corresponding N—C and C—C distances involving the disorder components were restrained to be equal. In the ethyl group, the components of the displacement parameters in the direction of the bond were restrained to be equal. The displacement parameters of atoms C22A, C23A, C22B, C23B and O4 were restrained to approximate isotropic behaviour. The N1—C6 distance was restrained to 1.45 (1) Å. H atoms of the coordinated water molecule were located in a difference map and refined with O—H and H···H distances restrained to 0.84 (1) and 1.37 (2) Å, respectively. H atoms on O5 and N2 were located in a difference map and refined freely. H atoms on O5 are disordered over two positions. H atoms on one of the free water molecules (O4) could not be located from the difference map. H atoms attached to C atoms were placed at calculated positions (C—H = 0.93–0.97 Å) and were allowed to ride on the parent atom [Uiso(H) = 1.2–1.5Ueq(C)].

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The structure of [Ni(C7H3NO4)(C6H16N2)(H2O)] complex in the title compound. Displacement ellipsoids are drawn at the 30% probability level. Atoms Ni1, N1, N2, N3, C4 and C5 lie on a crystallographic mirror plane. Only one component of the disordered ethyl group is shown. Hydrogen atoms have been omitted for clarity. Symmetry code: (i) −x, y, z.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
Aqua(N,N-diethylethylenediamine-κ2N,N')(pyridine-2,6-\ dicarboxylato-κ3N,O,O')nickel(II) 2.5-hydrate top
Crystal data top
[Ni(C7H3NO4)(C6H16N2)(H2O)]·2.5H2OF000 = 1672.0
Mr = 403.08Dx = 1.457 Mg m−3
Orthorhombic, ImcbMo Kα radiation
λ = 0.71069 Å
Hall symbol: -I 2a 2Cell parameters from 1657 reflections
a = 11.268 (4) Åθ = 1.7–27.2º
b = 14.141 (5) ŵ = 1.11 mm−1
c = 22.831 (12) ÅT = 297 (2) K
V = 3638 (3) Å3Prism, light green
Z = 80.42 × 0.30 × 0.25 mm
Data collection top
Stoe IPDS2
diffractometer		2120 independent reflections
Radiation source: fine-focus sealed tube1926 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
Detector resolution: 6.67 pixels mm-1θmax = 27.2º
T = 297(2) Kθmin = 1.7º
ω scansh = −14→14
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −18→18
Tmin = 0.925, Tmax = 0.974l = −29→29
28305 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0761P)2 + 2.2047P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.001
2120 reflectionsΔρmax = 0.41 e Å−3
157 parametersΔρmin = −1.12 e Å−3
38 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C7H3NO4)(C6H16N2)(H2O)]·2.5H2OV = 3638 (3) Å3
Mr = 403.08Z = 8
Orthorhombic, ImcbMo Kα
a = 11.268 (4) ŵ = 1.11 mm−1
b = 14.141 (5) ÅT = 297 (2) K
c = 22.831 (12) Å0.42 × 0.30 × 0.25 mm
Data collection top
Stoe IPDS2
diffractometer		2120 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1926 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.974Rint = 0.047
28305 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04638 restraints
wR(F2) = 0.123H atoms treated by a mixture of
independent and constrained refinement
S = 1.18Δρmax = 0.41 e Å−3
2120 reflectionsΔρmin = −1.12 e Å−3
157 parameters
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*/UeqOcc. (<1)
C10.2093 (2)0.13012 (16)0.29423 (11)0.0402 (5)
C20.10328 (19)0.14295 (16)0.33506 (10)0.0392 (5)
C30.1064 (2)0.1627 (2)0.39387 (11)0.0523 (6)
H30.17830.16940.41340.063*
C40.00000.1726 (3)0.42341 (17)0.0602 (10)
H40.00000.18590.46330.072*
C50.0000−0.0869 (3)0.17882 (19)0.0589 (10)
H5A0.0386−0.14710.18300.071*0.50
H5B−0.0800−0.09760.16590.071*0.50
C60.0666 (6)−0.0233 (4)0.1345 (2)0.0596 (14)0.50
H6A0.0663−0.05380.09690.072*0.50
H6B0.1476−0.01530.14660.072*0.50
C22A−0.1050 (6)0.0632 (5)0.1032 (3)0.0673 (16)0.50
H22A−0.07300.06700.06380.081*0.50
H22B−0.15220.00590.10450.081*0.50
C23A−0.1689 (8)0.1566 (5)0.0959 (3)0.0741 (18)0.50
H23A−0.19470.17900.13350.111*0.50
H23B−0.23660.14810.07090.111*0.50
H23C−0.11600.20200.07870.111*0.50
C22B−0.0951 (7)0.1371 (5)0.1028 (3)0.0656 (16)0.50
H22C−0.16700.13190.12590.079*0.50
H22D−0.06770.20190.10600.079*0.50
C23B−0.1277 (10)0.1164 (6)0.0386 (3)0.098 (3)0.50
H23D−0.06380.13620.01350.147*0.50
H23E−0.19850.15050.02840.147*0.50
H23F−0.14100.04990.03370.147*0.50
N10.00000.0711 (2)0.13202 (13)0.0537 (8)
N20.0000−0.0374 (2)0.23465 (14)0.0428 (6)
H20.061 (2)−0.051 (2)0.2546 (12)0.043 (7)*
N30.00000.13362 (19)0.30763 (12)0.0354 (5)
O10.00000.25168 (16)0.20606 (13)0.0472 (6)
H1A0.0615 (9)0.2816 (15)0.1993 (13)0.058 (8)*
O20.18606 (15)0.11705 (12)0.24116 (8)0.0433 (4)
O30.31037 (14)0.13235 (15)0.31665 (8)0.0520 (5)
O40.3847 (3)0.1075 (3)0.43248 (15)0.1158 (13)
O50.25000.00000.50000.1026 (19)
H50.294 (4)0.030 (4)0.4753 (19)0.042 (14)*0.50
Ni10.00000.10766 (2)0.222149 (16)0.03365 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0317 (11)0.0375 (10)0.0516 (12)−0.0017 (9)0.0012 (9)0.0059 (10)
C20.0324 (11)0.0397 (11)0.0455 (11)−0.0001 (8)−0.0018 (9)0.0030 (9)
C30.0415 (14)0.0685 (17)0.0470 (12)−0.0032 (12)−0.0069 (10)−0.0014 (11)
C40.053 (2)0.086 (3)0.0423 (18)0.0000.000−0.0039 (18)
C50.081 (3)0.0297 (15)0.066 (2)0.0000.000−0.0072 (15)
C60.081 (4)0.046 (3)0.052 (3)0.015 (3)0.009 (3)−0.010 (2)
C22A0.081 (4)0.058 (3)0.063 (3)0.002 (3)−0.023 (3)−0.014 (3)
C23A0.087 (5)0.065 (4)0.070 (4)0.013 (4)−0.020 (4)−0.003 (3)
C22B0.085 (5)0.060 (4)0.051 (3)0.010 (3)−0.016 (3)0.001 (3)
C23B0.132 (7)0.097 (5)0.066 (4)0.003 (5)−0.035 (5)0.005 (4)
N10.081 (2)0.0355 (15)0.0451 (15)0.0000.000−0.0027 (12)
N20.0412 (15)0.0309 (13)0.0562 (17)0.0000.0000.0047 (12)
N30.0299 (12)0.0356 (12)0.0408 (13)0.0000.0000.0010 (10)
O10.0350 (12)0.0284 (10)0.0783 (16)0.0000.0000.0055 (11)
O20.0358 (9)0.0462 (9)0.0480 (9)0.0015 (7)0.0037 (7)−0.0003 (7)
O30.0303 (8)0.0657 (11)0.0601 (11)−0.0043 (8)−0.0018 (7)0.0083 (9)
O40.086 (2)0.175 (4)0.0863 (19)0.006 (2)−0.0049 (17)0.0427 (19)
O50.129 (6)0.111 (5)0.068 (4)0.0000.0000.000
Ni10.0328 (3)0.0287 (3)0.0394 (3)0.0000.000−0.00016 (13)
Geometric parameters (Å, °) top
C1—O31.249 (3)C23A—H23A0.96
C1—O21.253 (3)C23A—H23B0.96
C1—C21.526 (3)C23A—H23C0.96
C2—N31.328 (3)C22B—C23B1.540 (8)
C2—C31.372 (3)C22B—N11.570 (7)
C3—C41.382 (3)C22B—H22C0.97
C3—H30.93C22B—H22D0.97
C4—C3i1.382 (3)C23B—H23D0.96
C4—H40.93C23B—H23E0.96
C5—N21.455 (5)C23B—H23F0.96
C5—C6i1.548 (7)N1—C22Ai1.358 (6)
C5—C61.548 (7)N1—C6i1.533 (5)
C5—H5A0.96N1—C22Bi1.570 (7)
C5—H5B0.96N1—Ni12.122 (3)
C6—C22Ai1.481 (9)N2—Ni12.070 (3)
C6—C6i1.501 (13)N2—H20.85 (3)
C6—N11.533 (5)N3—C2i1.328 (3)
C6—H6A0.96N3—Ni11.986 (3)
C6—H6B0.96O1—Ni12.070 (2)
C22A—N11.358 (6)O1—H1A0.827 (10)
C22A—C6i1.481 (9)O2—Ni12.145 (2)
C22A—C23A1.514 (9)O5—H50.862 (11)
C22A—H22A0.97Ni1—O2i2.145 (2)
C22A—H22B0.97
O3—C1—O2126.2 (2)N1—C22B—H22D108.2
O3—C1—C2117.4 (2)H22A—C22B—H22D133.1
O2—C1—C2116.4 (2)H22C—C22B—H22D107.3
N3—C2—C3120.2 (2)C22B—C23B—H23D109.5
N3—C2—C1112.7 (2)C22B—C23B—H23E109.5
C3—C2—C1127.0 (2)H23D—C23B—H23E109.5
C2—C3—C4118.4 (2)C22B—C23B—H23F109.5
C2—C3—H3120.8H23D—C23B—H23F109.5
C4—C3—H3120.8H23E—C23B—H23F109.5
C3i—C4—C3120.2 (3)C22A—N1—C6111.9 (4)
C3i—C4—H4119.9C22A—N1—C22Bi116.0 (5)
C3—C4—H4119.9C6—N1—C22Bi101.5 (4)
N2—C5—C6i107.0 (3)C22Ai—N1—C22B116.0 (5)
N2—C5—C6107.0 (3)C6i—N1—C22B101.5 (4)
N2—C5—H5A109.9C22A—N1—Ni1119.3 (3)
C6—C5—H5A111.1C22Ai—N1—Ni1119.3 (3)
N2—C5—H5B110.1C6—N1—Ni1100.2 (2)
C6—C5—H5B110.2C6i—N1—Ni1100.2 (2)
H5A—C5—H5B108.4C22Bi—N1—Ni1105.5 (3)
N1—C6—C5107.0 (4)C22B—N1—Ni1105.5 (3)
N1—C6—H6A110.9C5—N2—Ni1110.9 (2)
C5—C6—H6A108.8C5—N2—H2111.0 (19)
N1—C6—H6B111.9Ni1—N2—H2108 (2)
C5—C6—H6B109.9C2—N3—C2i122.4 (3)
H6A—C6—H6B108.3C2—N3—Ni1118.79 (14)
N1—C22A—C23A113.3 (6)C2i—N3—Ni1118.79 (14)
N1—C22A—H22A96.9Ni1—O1—H1A122.5 (15)
C23A—C22A—H22A91.5C1—O2—Ni1114.12 (15)
N1—C22A—H22B122.2N3—Ni1—O189.57 (11)
C23A—C22A—H22B118.1N3—Ni1—N292.73 (12)
H22A—C22A—H22B106.1O1—Ni1—N2177.70 (12)
C22A—C23A—H23A109.5N3—Ni1—N1176.55 (11)
C22A—C23A—H23B109.5O1—Ni1—N193.88 (12)
H23A—C23A—H23B109.5N2—Ni1—N183.83 (12)
C23A—C23A—H23C109.5N3—Ni1—O2i77.86 (5)
H23B—C23A—H23C109.5O1—Ni1—O2i88.57 (5)
H23B—C23A—H22C119.6N2—Ni1—O2i91.92 (5)
H23C—C23A—H22C130.6N1—Ni1—O2i102.20 (5)
C23B—C22B—N1117.1 (6)N3—Ni1—O277.86 (5)
C23B—C22B—H22C107.7O1—Ni1—O288.57 (5)
N1—C22B—H22C107.0N2—Ni1—O291.92 (5)
H22A—C22B—H22C117.0N1—Ni1—O2102.20 (5)
C23B—C22B—H22D109.2O2i—Ni1—O2155.57 (10)
O3—C1—C2—N3−176.1 (2)C3—C2—N3—C2i0.1 (5)
O2—C1—C2—N33.0 (3)C1—C2—N3—C2i−179.40 (19)
O3—C1—C2—C34.4 (4)C3—C2—N3—Ni1178.7 (2)
O2—C1—C2—C3−176.5 (2)C1—C2—N3—Ni1−0.8 (3)
N3—C2—C3—C40.0 (5)O3—C1—O2—Ni1175.5 (2)
C1—C2—C3—C4179.4 (3)C2—C1—O2—Ni1−3.5 (2)
C2—C3—C4—C3i−0.1 (6)C2—N3—Ni1—O1−89.3 (2)
N2—C5—C6—C22Ai−41.7 (17)C2i—N3—Ni1—O189.3 (2)
C6i—C5—C6—C22Ai58.1 (17)C2—N3—Ni1—N290.7 (2)
N2—C5—C6—C6i−99.78 (19)C2i—N3—Ni1—N2−90.7 (2)
N2—C5—C6—N1−58.8 (4)C2—N3—Ni1—O2i−177.9 (2)
C6i—C5—C6—N141.0 (4)C2i—N3—Ni1—O2i0.7 (2)
C6i—C22A—N1—C22Ai99.5 (7)C2—N3—Ni1—O2−0.7 (2)
C23A—C22A—N1—C22Ai−106.9 (6)C2i—N3—Ni1—O2177.9 (2)
C6i—C22A—N1—C630.7 (4)C5—N2—Ni1—N3180.0
C23A—C22A—N1—C6−175.6 (5)C5—N2—Ni1—N10.0
C23A—C22A—N1—C6i153.6 (7)C5—N2—Ni1—O2i102.07 (5)
C6i—C22A—N1—C22Bi146.5 (5)C5—N2—Ni1—O2−102.07 (5)
C23A—C22A—N1—C22Bi−59.9 (7)C22A—N1—Ni1—O1−87.5 (4)
C6i—C22A—N1—C22B−165.6 (7)C22Ai—N1—Ni1—O187.5 (4)
C23A—C22A—N1—C22B−11.9 (6)C6—N1—Ni1—O1150.2 (3)
C6i—C22A—N1—Ni1−85.6 (4)C6i—N1—Ni1—O1−150.2 (3)
C23A—C22A—N1—Ni168.0 (7)C22Bi—N1—Ni1—O145.1 (3)
C22Ai—C6—N1—C22A114.6 (7)C22B—N1—Ni1—O1−45.1 (3)
C6i—C6—N1—C22A−31.7 (4)C22A—N1—Ni1—N292.5 (4)
C5—C6—N1—C22A−72.8 (5)C22Ai—N1—Ni1—N2−92.5 (4)
C6i—C6—N1—C22Ai−146.3 (4)C6—N1—Ni1—N2−29.8 (3)
C5—C6—N1—C22Ai172.6 (5)C6i—N1—Ni1—N229.8 (3)
C22Ai—C6—N1—C6i146.3 (4)C22Bi—N1—Ni1—N2−134.9 (3)
C5—C6—N1—C6i−41.1 (4)C22B—N1—Ni1—N2134.9 (3)
C22Ai—C6—N1—C22Bi−9.7 (4)C22A—N1—Ni1—O2i1.9 (4)
C6i—C6—N1—C22Bi−155.9 (4)C22Ai—N1—Ni1—O2i176.9 (4)
C5—C6—N1—C22Bi163.0 (4)C6—N1—Ni1—O2i−120.5 (3)
C22Ai—C6—N1—C22B92.7 (9)C6i—N1—Ni1—O2i−60.8 (3)
C6i—C6—N1—C22B−53.5 (7)C22Bi—N1—Ni1—O2i134.5 (3)
C5—C6—N1—C22B−94.6 (8)C22B—N1—Ni1—O2i44.3 (3)
C22Ai—C6—N1—Ni1−118.0 (3)C22A—N1—Ni1—O2−176.9 (4)
C6i—C6—N1—Ni195.78 (15)C22Ai—N1—Ni1—O2−1.9 (4)
C5—C6—N1—Ni154.7 (4)C6—N1—Ni1—O260.8 (3)
C23B—C22B—N1—C22A−54.3 (7)C6i—N1—Ni1—O2120.5 (3)
C23B—C22B—N1—C22Ai54.2 (8)C22Bi—N1—Ni1—O2−44.3 (3)
C23B—C22B—N1—C6−22.8 (12)C22B—N1—Ni1—O2−134.5 (3)
C23B—C22B—N1—C6i−67.2 (7)C1—O2—Ni1—N32.43 (16)
C23B—C22B—N1—C22Bi83.7 (7)C1—O2—Ni1—O192.30 (17)
C23B—C22B—N1—Ni1−171.3 (6)C1—O2—Ni1—N2−89.94 (17)
C6i—C5—N2—Ni1−30.5 (3)C1—O2—Ni1—N1−174.04 (17)
C6—C5—N2—Ni130.5 (3)C1—O2—Ni1—O2i8.9 (3)
Symmetry codes: (i) −x, y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.862 (11)1.789 (14)2.644 (3)171 (6)
N2—H2···O3ii0.85 (3)2.33 (3)3.142 (3)161 (3)
O1—H1A···O3iii0.827 (10)1.922 (12)2.743 (2)171 (2)
Symmetry codes: (ii) −x+1/2, −y, z; (iii) −x+1/2, −y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å, °) top
N1—Ni12.122 (3)O1—Ni12.070 (2)
N2—Ni12.070 (3)O2—Ni12.145 (2)
N3—Ni11.986 (3)Ni1—O2i2.145 (2)
N3—Ni1—O189.57 (11)N3—Ni1—O277.86 (5)
N3—Ni1—N292.73 (12)O1—Ni1—O288.57 (5)
O1—Ni1—N2177.70 (12)N2—Ni1—O291.92 (5)
N3—Ni1—N1176.55 (11)N1—Ni1—O2102.20 (5)
O1—Ni1—N193.88 (12)O2i—Ni1—O2155.57 (10)
N2—Ni1—N183.83 (12)
Symmetry codes: (i) −x, y, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.862 (11)1.789 (14)2.644 (3)171 (6)
N2—H2···O3ii0.85 (3)2.33 (3)3.142 (3)161 (3)
O1—H1A···O3iii0.827 (10)1.922 (12)2.743 (2)171 (2)
Symmetry codes: (ii) −x+1/2, −y, z; (iii) −x+1/2, −y+1/2, −z+1/2.
references
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