metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Pages m925-m926

Tris(ethyl­enedi­amine)­nickel(II) 1H-pyrazole-3,5-di­carboxyl­ate 1.67-hydrate

aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts and Sciences, Osmangazi University, 26480 Eskişehir, Turkey
*Correspondence e-mail: gunesd@omu.edu.tr

(Received 3 July 2010; accepted 8 July 2010; online 14 July 2010)

The asymmetric unit of the title compound, [Ni(C2H8N2)3](C5H2N2O4)·1.67H2O, consists of three [Ni(en)3]2+ dications (en is ethyl­enediamine), three [(pzdc)3]2− dianions (pzdc is pyrazole-3,5-dicarboxyl­ate) and five water mol­ecules. In each complex dication, the NiII atom is coordinated by six N atoms from three en ligands forming a distorted octa­hedral coordination geometry. In the crystal, the ions and water mol­ecules are linked into a three-dimensional framework by a large number of N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological activity of pyrazole compounds, see: Chambers et al. (1985[Chambers, D., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1985). J. Org. Chem. 50, 4736-4738.]); Lee et al. (1989[Lee, H. H., Cain, B. F., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1989). J. Org. Chem. 54, 428-431.]). For the crystal structures of pyrazole derivatives, see: Foces-Foces et al. (2006[Foces-Foces, C., Rodríguez, M. L. & Elguero, J. (2006). Acta Cryst. E62, o3351-o3353.]); Qu (2009[Qu, Z.-R. (2009). Acta Cryst. E65, o1646.]); Xiao et al. (2007[Xiao, J.-P., Zhou, Q.-X. & Tu, J.-H. (2007). Acta Cryst. E63, o2785.], 2009[Xiao, J., Yao, J.-Y. & Zhao, H. (2009). Acta Cryst. E65, o1132.]); Xiao & Zhao (2009[Xiao, J. & Zhao, H. (2009). Acta Cryst. E65, o1175.]); Yao et al. (2009[Yao, J.-Y., Xiao, J. & Zhao, H. (2009). Acta Cryst. E65, o1158.]). For Ni—N bond lengths, see: Emam et al. (2008[Emam, S. M., McArdle, P., McManus, J. & Mahon, M. (2008). Polyhedron, 27, 2379-2385.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C2H8N2)3](C5H2N2O4)·1.67H2O

  • Mr = 423.13

  • Triclinic, [P \overline 1]

  • a = 12.8145 (7) Å

  • b = 12.9218 (7) Å

  • c = 18.6311 (13) Å

  • α = 72.008 (5)°

  • β = 75.446 (5)°

  • γ = 73.480 (4)°

  • V = 2767.5 (3) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 1.10 mm−1

  • T = 296 K

  • 0.52 × 0.35 × 0.07 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.582, Tmax = 0.949

  • 42996 measured reflections

  • 11465 independent reflections

  • 6232 reflections with I > 2σ(I)

  • Rint = 0.091

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.146

  • S = 0.91

  • 11465 reflections

  • 706 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.25 e Å−3

  • Δρmin = −1.59 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1W1⋯O4 0.82 (5) 1.93 (3) 2.725 (6) 162 (8)
O1W—H2W1⋯O9 0.83 (8) 1.94 (8) 2.739 (8) 163 (8)
O2W—H1W2⋯O6 0.82 (7) 1.90 (3) 2.674 (5) 159 (6)
O2W—H2W2⋯O1 0.83 (6) 2.04 (3) 2.856 (6) 167 (8)
O3W—H1W3⋯O7 0.84 (6) 1.95 (6) 2.787 (6) 175 (2)
O3W—H2W3⋯O11i 0.84 (6) 2.36 (4) 3.074 (6) 144 (6)
O3W—H2W3⋯N24i 0.84 (6) 2.55 (5) 3.236 (6) 141 (7)
O4W—H1W4⋯O1Wii 0.83 (8) 2.37 (5) 3.094 (8) 146 (8)
O4W—H1W4⋯O9ii 0.83 (8) 2.57 (5) 3.293 (6) 146 (8)
O4W—H2W4⋯O5W 0.84 (7) 2.03 (7) 2.839 (6) 163 (7)
O5W—H1W5⋯O12iii 0.83 (2) 2.01 (3) 2.819 (5) 165 (6)
O5W—H2W5⋯O12ii 0.84 (4) 2.06 (2) 2.888 (5) 176 (7)
N1—H1C⋯O1ii 0.90 2.34 3.215 (6) 164
N1—H1D⋯O3Wii 0.90 2.27 3.159 (7) 170
N2—H2C⋯O9iv 0.90 2.25 3.118 (6) 162
N2—H2D⋯O1iv 0.90 2.55 3.358 (6) 150
N3—H3D⋯N21v 0.90 2.24 3.066 (5) 153
N4—H4C⋯O2ii 0.90 2.24 3.091 (5) 158
N4—H4D⋯O1iv 0.90 2.15 3.039 (5) 168
N5—H5C⋯O2ii 0.90 2.28 3.091 (6) 150
N5—H5D⋯O5v 0.90 2.02 2.913 (5) 174
N6—H6C⋯O10iv 0.90 2.38 3.154 (6) 144
N6—H6C⋯O9iv 0.90 2.54 3.357 (6) 152
N7—H7C⋯N19vi 0.90 2.07 2.950 (5) 165
N7—H7D⋯O3W 0.90 2.45 3.314 (6) 162
N8—H8C⋯O2W 0.90 2.22 3.029 (6) 149
N8—H8D⋯O5vii 0.90 2.57 3.388 (6) 152
N8—H8D⋯O6vii 0.90 2.59 3.345 (5) 142
N9—H9C⋯O2vi 0.90 2.19 3.071 (5) 166
N9—H9D⋯O5vii 0.90 2.18 3.049 (6) 162
N10—H10D⋯O11i 0.90 2.21 3.066 (6) 159
N11—H11C⋯O1Wvii 0.90 2.33 3.173 (7) 156
N11—H11D⋯O6vii 0.90 2.09 2.959 (6) 162
N12—H12C⋯O2W 0.90 2.22 3.100 (7) 166
N12—H12D⋯O3W 0.90 2.46 3.213 (6) 142
N13—H13C⋯O8viii 0.90 2.08 2.929 (6) 157
N13—H13D⋯O7 0.90 2.57 3.307 (7) 139
N14—H14C⋯O4vii 0.90 2.08 2.976 (6) 173
N14—H14D⋯O12vii 0.90 2.41 3.284 (7) 163
N15—H15C⋯O3vii 0.90 2.13 2.940 (6) 149
N16—H16C⋯O8viii 0.90 2.20 3.017 (6) 151
N16—H16D⋯O12vii 0.90 2.27 3.147 (5) 164
N17—H17C⋯O7viii 0.90 2.42 3.290 (6) 162
N17—H17C⋯O8viii 0.90 2.59 3.351 (6) 142
N17—H17D⋯O10ix 0.90 2.31 3.151 (6) 155
N18—H18C⋯O3vii 0.90 2.25 3.100 (6) 157
N20—H20⋯O11x 0.86 2.35 3.058 (6) 140
N22—H22⋯O4W 0.86 2.00 2.819 (5) 160
N23—H23⋯O10xi 0.86 2.03 2.856 (6) 160
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z-1; (iv) x, y+1, z; (v) -x+1, -y+2, -z+1; (vi) -x, -y, -z+1; (vii) -x, -y+1, -z+1; (viii) -x+1, -y+1, -z; (ix) x, y+1, z-1; (x) -x, -y, -z+2; (xi) -x+1, -y, -z+2.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Pyrazole derivatives exhibit biological activities (Lee et al., 1989; Chambers et al.,1985). As a result, crystal structures of many pyrazole derivatives have been reported (Xiao et al., 2007, 2009; Xiao & Zhao, 2009; Foces-Foces et al., 2006; Qu et al., 2009; Yao et al., 2009). We report here the crystal structure of the title compound, {[Ni(en)3](pzdc)}3.5H2O.

The asymmetric unit of the title compound consists of three [Ni(en)3]2+ cations, three [(pzdc)3]2- dianions and five water molecules (Fig. 1). In each complex cation, the NiII ion is six-coordinated by six N atoms from three pzdc ligands in a distorted octahedral coordination geometry. The Ni—N bond distances range from 2.108 (5) Å to 2.130 (4) Å for Ni1, from 2.106 (4) Å to 2.130 (4) Å for Ni2, and from 2.121 (5) Å to 2.147 (5) Å for Ni3 atom. These values are consistent with those reported in the literature (Emam et al., 2008). The N—Ni—N bond angles range from 81.46 (18)° to 172.19 (18)° for Ni1, from 81.63 (16)° to 175.39 (16)° for Ni2, and from 81.65 (19)° to 172.13 (18)° for Ni3 atom.

In the crystal structure, the ions and water molecules are linked through a large number of N—H···O and O—H···O hydrogen bonds (Table 1) into a three-dimensional framework.

Related literature top

For the biological activity of pyrazole compounds, see: Chambers et al. (1985); Lee et al. (1989). For the crystal structures of pyrazole derivatives, see: Foces-Foces et al. (2006); Qu et al. (2009); Xiao et al. (2007, 2009); Xiao & Zhao (2009); Yao et al. (2009). For Ni—N bond lengths, see: Emam et al. (2008).

Experimental top

A solution of 3,5-pyrazoledicarboxylic acid monohydrate (0.5 g, 2.87 mmol) in water (20 ml) was added dropwise with stirring at 323 K to a solution of nickel(II) acetatetetrahydrate (0.71 g, 2.87 mmol) in distilled water (15 ml). The solution immediately became a suspension and was stirred for 2 h at 323 K. Then ethylenediamine (0.51 g, 8.61 mmol) in water (10 ml) was added dropwise to this suspension. The clear solution obtained was stirred for 2 h at 323 K and then cooled to room temperature. Single crystals formed were filtered and washed with 10 ml of water and were dried in air.

Refinement top

H atoms of the water molecules were located in a difference map and were refined with O–H and H···H distance restraints of 0.83 (1) and 1.35 (1) Å, respectively. H atoms attached to C and N atoms were positioned geometrically [N–H = 0.86 or 0.90 Å and C–H = 0.93 or 0.97 Å] and treated as riding with Uiso(H) = 1.1Ueq (C,N).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Tris(ethylenediamine)nickel(II) 1H-pyrazole-3,5-dicarboxylate 1.67-hydrate top
Crystal data top
[Ni(C2H8N2)3](C5H2N2O4)·1.67H2OZ = 6
Mr = 423.13F(000) = 1348
Triclinic, P1Dx = 1.523 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.8145 (7) ÅCell parameters from 64545 reflections
b = 12.9218 (7) Åθ = 1.7–27.2°
c = 18.6311 (13) ŵ = 1.10 mm1
α = 72.008 (5)°T = 296 K
β = 75.446 (5)°Prism, violet
γ = 73.480 (4)°0.52 × 0.35 × 0.07 mm
V = 2767.5 (3) Å3
Data collection top
Stoe IPDS 2
diffractometer
11465 independent reflections
Radiation source: fine-focus sealed tube6232 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
w–scan rotationθmax = 26.5°, θmin = 1.7°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 1616
Tmin = 0.582, Tmax = 0.949k = 1616
42996 measured reflectionsl = 2323
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0702P)2]
where P = (Fo2 + 2Fc2)/3
11465 reflections(Δ/σ)max = 0.001
706 parametersΔρmax = 1.25 e Å3
15 restraintsΔρmin = 1.59 e Å3
Crystal data top
[Ni(C2H8N2)3](C5H2N2O4)·1.67H2Oγ = 73.480 (4)°
Mr = 423.13V = 2767.5 (3) Å3
Triclinic, P1Z = 6
a = 12.8145 (7) ÅMo Kα radiation
b = 12.9218 (7) ŵ = 1.10 mm1
c = 18.6311 (13) ÅT = 296 K
α = 72.008 (5)°0.52 × 0.35 × 0.07 mm
β = 75.446 (5)°
Data collection top
Stoe IPDS 2
diffractometer
11465 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
6232 reflections with I > 2σ(I)
Tmin = 0.582, Tmax = 0.949Rint = 0.091
42996 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05815 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 1.25 e Å3
11465 reflectionsΔρmin = 1.59 e Å3
706 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*/Ueq
C10.5179 (5)0.8673 (4)0.6477 (3)0.0582 (15)
H1A0.54330.78700.65610.070*
H1B0.48120.89580.60360.070*
C20.4380 (5)0.8948 (4)0.7174 (4)0.0583 (15)
H2A0.37310.86520.72600.070*
H2B0.47270.86170.76240.070*
C30.4048 (5)1.2976 (5)0.5923 (4)0.0623 (16)
H3A0.38731.37820.58370.075*
H3B0.33601.27390.60210.075*
C40.4784 (5)1.2657 (5)0.5223 (4)0.0604 (15)
H4A0.43931.29470.47930.073*
H4B0.54371.29630.50870.073*
C50.7686 (4)1.0853 (5)0.6721 (3)0.0574 (15)
H5A0.82421.12820.66140.069*
H5B0.80591.00770.67560.069*
C60.6919 (4)1.0963 (5)0.7464 (3)0.0573 (14)
H6A0.73231.06350.78860.069*
H6B0.66041.17450.74490.069*
N10.6134 (3)0.9188 (3)0.6332 (3)0.0513 (11)
H1C0.64990.92310.58470.062*
H1D0.66060.87750.66540.062*
N20.4062 (3)1.0173 (3)0.7039 (3)0.0523 (11)
H2C0.37671.03590.74870.063*
H2D0.35531.04610.67320.063*
N30.4596 (3)1.2453 (3)0.6588 (3)0.0543 (12)
H3C0.40911.24200.70230.065*
H3D0.50621.28570.65910.065*
N40.5103 (3)1.1424 (3)0.5405 (3)0.0499 (11)
H4C0.56941.12040.50620.060*
H4D0.45421.11520.53830.060*
N50.7031 (3)1.1269 (3)0.6100 (3)0.0474 (10)
H5C0.73991.09750.57030.057*
H5D0.69251.20170.59340.057*
N60.6034 (3)1.0385 (4)0.7576 (3)0.0546 (12)
H6C0.54701.05950.79390.065*
H6D0.62900.96410.77290.065*
Ni10.54902 (5)1.08143 (5)0.65171 (4)0.04029 (17)
C70.0582 (4)0.1370 (4)0.4329 (3)0.0499 (13)
H7A0.12900.15290.42990.060*
H7B0.06900.05720.44070.060*
C80.0235 (4)0.1734 (4)0.4997 (3)0.0521 (13)
H8A0.09180.15030.50650.063*
H8B0.00680.13930.54650.063*
C90.2880 (4)0.3775 (5)0.3375 (3)0.0557 (14)
H9A0.31280.45690.33360.067*
H9B0.35240.34730.34560.067*
C100.2115 (5)0.3580 (5)0.2650 (4)0.0601 (15)
H10A0.19200.27900.26700.072*
H10B0.24790.39800.22130.072*
C110.0287 (4)0.5638 (4)0.3781 (3)0.0556 (14)
H11A0.00320.53070.42670.067*
H11B0.04720.64430.36960.067*
C120.0612 (4)0.5309 (4)0.3144 (3)0.0540 (14)
H12A0.03770.56720.26530.065*
H12B0.12760.55340.31360.065*
N70.0171 (3)0.1960 (3)0.3615 (3)0.0473 (11)
H7C0.02820.15950.35430.057*
H7D0.07410.19860.32180.057*
N80.0452 (3)0.2964 (3)0.4829 (3)0.0485 (11)
H8C0.01270.31740.48890.058*
H8D0.10590.32250.51460.058*
N90.2290 (3)0.3226 (3)0.4019 (2)0.0465 (10)
H9C0.22300.24840.41430.056*
H9D0.26580.34830.44310.056*
N100.1108 (3)0.3976 (4)0.2566 (3)0.0548 (11)
H10C0.12290.47190.23570.066*
H10D0.05470.36400.22550.066*
N110.1269 (3)0.5248 (3)0.3801 (3)0.0494 (11)
H11C0.16270.56920.34180.059*
H11D0.17360.52570.42510.059*
N120.0836 (3)0.4093 (3)0.3281 (3)0.0491 (11)
H12C0.12720.37590.36370.059*
H12D0.11880.38920.28450.059*
Ni20.06954 (5)0.35919 (5)0.36689 (4)0.03914 (17)
C130.2460 (5)0.4831 (4)0.0518 (3)0.0571 (15)
H13A0.27340.40370.07200.069*
H13B0.21230.49370.00820.069*
C140.1618 (4)0.5309 (4)0.1126 (3)0.0565 (15)
H14A0.09910.49610.12790.068*
H14B0.19430.51700.15740.068*
C150.1245 (5)0.9129 (5)0.0625 (4)0.0708 (17)
H15A0.10610.99340.08270.085*
H15B0.05640.88660.04510.085*
C160.1991 (6)0.8584 (5)0.1240 (4)0.0714 (17)
H16A0.16150.87430.16660.086*
H16B0.26580.88720.14300.086*
C170.4890 (4)0.7190 (5)0.0333 (4)0.0573 (15)
H17A0.55390.75050.01670.069*
H17B0.51280.63850.05060.069*
C180.4118 (4)0.7649 (5)0.0977 (4)0.0575 (15)
H18A0.44900.74500.14100.069*
H18B0.39110.84570.08080.069*
N130.3379 (4)0.5407 (3)0.0279 (3)0.0564 (12)
H13C0.37770.53030.01760.068*
H13D0.38280.51350.06280.068*
N140.1256 (4)0.6523 (4)0.0802 (3)0.0574 (12)
H14C0.09170.68640.11810.069*
H14D0.07770.66560.04870.069*
N150.1838 (4)0.8835 (4)0.0012 (3)0.0621 (13)
H15C0.13570.89440.04400.075*
H15D0.23240.92700.00970.075*
N160.2278 (4)0.7364 (4)0.0897 (3)0.0586 (12)
H16C0.28570.70350.12010.070*
H16D0.16990.70630.08390.070*
N170.4282 (4)0.7491 (4)0.0312 (3)0.0592 (13)
H17C0.46430.70860.06520.071*
H17D0.42170.82200.05550.071*
N180.3118 (4)0.7189 (4)0.1212 (3)0.0594 (12)
H18C0.25600.76270.14610.071*
H18D0.32540.64990.15280.071*
Ni30.26857 (5)0.71329 (5)0.01860 (4)0.04165 (18)
C190.2427 (4)0.0035 (4)0.5734 (3)0.0423 (12)
C200.1570 (4)0.0170 (4)0.6440 (3)0.0383 (11)
C210.1256 (4)0.1049 (4)0.6794 (3)0.0438 (12)
H210.15590.16730.66520.053*
C220.0413 (4)0.0806 (4)0.7392 (3)0.0410 (11)
C230.0293 (4)0.1371 (4)0.7996 (3)0.0498 (13)
N190.0961 (3)0.0585 (3)0.6795 (2)0.0448 (10)
N200.0263 (3)0.0180 (3)0.7365 (2)0.0463 (10)
H200.02300.05110.76820.056*
O10.2991 (3)0.0760 (3)0.5451 (2)0.0532 (9)
O20.2527 (3)0.0794 (3)0.5490 (2)0.0597 (10)
O30.1076 (3)0.0967 (3)0.8401 (2)0.0678 (12)
O40.0034 (3)0.2208 (3)0.8036 (2)0.0678 (12)
C240.3028 (4)0.5553 (4)0.4199 (3)0.0475 (13)
C250.3711 (4)0.5281 (4)0.3483 (3)0.0405 (11)
C260.3625 (4)0.4521 (4)0.3106 (3)0.0424 (12)
H260.31200.40660.32620.051*
C270.4437 (4)0.4588 (4)0.2468 (3)0.0410 (11)
C280.4774 (4)0.4047 (4)0.1820 (3)0.0508 (13)
N210.4528 (3)0.5795 (3)0.3084 (3)0.0476 (11)
N220.4953 (3)0.5362 (3)0.2476 (2)0.0479 (11)
H220.54960.55570.21280.057*
O50.3164 (4)0.6324 (3)0.4400 (2)0.0716 (12)
O60.2352 (3)0.4949 (3)0.4575 (2)0.0657 (12)
O70.4196 (4)0.3450 (4)0.1783 (3)0.0773 (13)
O80.5616 (4)0.4255 (4)0.1348 (3)0.0832 (14)
C290.3700 (5)0.0707 (6)0.9111 (4)0.0794 (8)
C300.2975 (5)0.1155 (6)0.9743 (4)0.0794 (8)
C310.1929 (4)0.1807 (4)0.9841 (3)0.0474 (13)
H310.14640.21160.94810.057*
C320.1700 (4)0.1916 (4)1.0591 (3)0.0450 (12)
C330.0673 (4)0.2544 (4)1.1000 (3)0.0496 (13)
N230.3316 (3)0.0913 (3)1.0412 (3)0.0537 (12)
H230.39560.05061.04930.064*
N240.2560 (4)0.1369 (4)1.0951 (3)0.0526 (11)
O90.3421 (3)0.1163 (4)0.8460 (3)0.0794 (8)
O100.4521 (3)0.0015 (4)0.9213 (3)0.0794 (8)
O110.0524 (4)0.2313 (3)1.1713 (2)0.0737 (12)
O120.0028 (3)0.3259 (3)1.0575 (2)0.0560 (10)
O1W0.1964 (5)0.2779 (5)0.7625 (3)0.0983 (16)
H1W10.132 (3)0.273 (7)0.768 (5)0.147*
H2W10.229 (6)0.225 (6)0.793 (5)0.147*
O2W0.1946 (4)0.2970 (3)0.4715 (3)0.0768 (13)
H1W20.221 (6)0.347 (4)0.473 (4)0.115*
H2W20.223 (6)0.237 (3)0.499 (4)0.115*
O3W0.2482 (4)0.2325 (4)0.2382 (3)0.0741 (12)
H1W30.301 (4)0.264 (6)0.218 (3)0.111*
H2W30.219 (5)0.231 (6)0.203 (3)0.111*
O4W0.6821 (4)0.6201 (4)0.1617 (3)0.0881 (16)
H1W40.698 (6)0.672 (5)0.171 (5)0.132*
H2W40.737 (4)0.590 (6)0.134 (4)0.132*
O5W0.8951 (3)0.5382 (3)0.0821 (2)0.0658 (11)
H1W50.918 (5)0.4715 (19)0.081 (4)0.099*
H2W50.924 (5)0.576 (4)0.040 (2)0.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (4)0.048 (3)0.061 (4)0.016 (3)0.004 (3)0.021 (3)
C20.061 (3)0.051 (3)0.063 (4)0.021 (3)0.000 (3)0.015 (3)
C30.051 (3)0.050 (3)0.084 (5)0.003 (3)0.011 (3)0.022 (3)
C40.055 (3)0.058 (3)0.063 (4)0.010 (3)0.017 (3)0.006 (3)
C50.042 (3)0.072 (4)0.056 (4)0.016 (3)0.006 (3)0.013 (3)
C60.059 (3)0.066 (4)0.051 (4)0.016 (3)0.012 (3)0.018 (3)
N10.051 (2)0.052 (3)0.051 (3)0.011 (2)0.003 (2)0.019 (2)
N20.048 (2)0.057 (3)0.057 (3)0.015 (2)0.003 (2)0.022 (2)
N30.047 (2)0.053 (3)0.069 (3)0.017 (2)0.000 (2)0.026 (2)
N40.047 (2)0.051 (3)0.051 (3)0.013 (2)0.005 (2)0.014 (2)
N50.042 (2)0.050 (2)0.049 (3)0.011 (2)0.003 (2)0.014 (2)
N60.045 (2)0.065 (3)0.054 (3)0.015 (2)0.002 (2)0.020 (2)
Ni10.0378 (3)0.0423 (3)0.0431 (4)0.0097 (3)0.0033 (3)0.0166 (3)
C70.048 (3)0.037 (3)0.064 (4)0.008 (2)0.012 (3)0.012 (3)
C80.050 (3)0.046 (3)0.053 (4)0.012 (3)0.009 (3)0.002 (3)
C90.043 (3)0.059 (3)0.063 (4)0.006 (3)0.013 (3)0.015 (3)
C100.064 (4)0.058 (3)0.062 (4)0.003 (3)0.021 (3)0.023 (3)
C110.062 (3)0.044 (3)0.061 (4)0.012 (3)0.006 (3)0.017 (3)
C120.055 (3)0.042 (3)0.059 (4)0.018 (3)0.003 (3)0.008 (3)
N70.045 (2)0.043 (2)0.057 (3)0.0115 (19)0.005 (2)0.019 (2)
N80.044 (2)0.046 (2)0.056 (3)0.011 (2)0.006 (2)0.017 (2)
N90.043 (2)0.047 (2)0.046 (3)0.0086 (19)0.005 (2)0.012 (2)
N100.048 (2)0.054 (3)0.054 (3)0.003 (2)0.007 (2)0.011 (2)
N110.045 (2)0.042 (2)0.054 (3)0.0074 (19)0.004 (2)0.014 (2)
N120.040 (2)0.042 (2)0.059 (3)0.0080 (19)0.002 (2)0.011 (2)
Ni20.0380 (3)0.0353 (3)0.0421 (4)0.0070 (3)0.0037 (3)0.0110 (3)
C130.071 (4)0.044 (3)0.057 (4)0.017 (3)0.010 (3)0.013 (3)
C140.058 (3)0.054 (3)0.055 (4)0.021 (3)0.003 (3)0.013 (3)
C150.079 (4)0.055 (4)0.070 (5)0.009 (3)0.026 (4)0.017 (3)
C160.088 (5)0.070 (4)0.043 (4)0.003 (4)0.014 (3)0.008 (3)
C170.050 (3)0.053 (3)0.074 (4)0.010 (3)0.011 (3)0.025 (3)
C180.062 (3)0.054 (3)0.066 (4)0.010 (3)0.016 (3)0.027 (3)
N130.057 (3)0.054 (3)0.059 (3)0.009 (2)0.002 (2)0.024 (2)
N140.059 (3)0.056 (3)0.057 (3)0.011 (2)0.005 (2)0.020 (2)
N150.065 (3)0.054 (3)0.060 (3)0.004 (2)0.006 (3)0.018 (2)
N160.055 (3)0.063 (3)0.058 (3)0.011 (2)0.004 (2)0.024 (3)
N170.057 (3)0.053 (3)0.065 (3)0.010 (2)0.002 (2)0.025 (2)
N180.061 (3)0.057 (3)0.057 (3)0.008 (2)0.000 (2)0.022 (2)
Ni30.0409 (3)0.0397 (3)0.0433 (4)0.0069 (3)0.0033 (3)0.0145 (3)
C190.039 (3)0.043 (3)0.047 (3)0.006 (2)0.007 (2)0.016 (2)
C200.036 (2)0.037 (2)0.042 (3)0.009 (2)0.006 (2)0.010 (2)
C210.041 (3)0.038 (3)0.052 (3)0.007 (2)0.005 (2)0.016 (2)
C220.042 (3)0.037 (3)0.045 (3)0.004 (2)0.010 (2)0.015 (2)
C230.049 (3)0.055 (3)0.047 (3)0.000 (3)0.012 (3)0.023 (3)
N190.044 (2)0.043 (2)0.049 (3)0.0107 (19)0.000 (2)0.019 (2)
N200.042 (2)0.051 (2)0.048 (3)0.014 (2)0.001 (2)0.020 (2)
O10.0483 (19)0.054 (2)0.059 (3)0.0201 (17)0.0051 (17)0.0202 (18)
O20.073 (2)0.053 (2)0.057 (3)0.0213 (19)0.010 (2)0.0291 (19)
O30.054 (2)0.086 (3)0.069 (3)0.025 (2)0.016 (2)0.043 (2)
O40.075 (3)0.054 (2)0.078 (3)0.016 (2)0.010 (2)0.038 (2)
C240.055 (3)0.040 (3)0.046 (3)0.007 (2)0.003 (3)0.016 (2)
C250.042 (3)0.031 (2)0.049 (3)0.008 (2)0.006 (2)0.012 (2)
C260.040 (2)0.042 (3)0.047 (3)0.013 (2)0.002 (2)0.015 (2)
C270.043 (3)0.036 (2)0.045 (3)0.005 (2)0.008 (2)0.015 (2)
C280.057 (3)0.044 (3)0.048 (3)0.001 (3)0.011 (3)0.015 (3)
N210.049 (2)0.045 (2)0.050 (3)0.016 (2)0.001 (2)0.017 (2)
N220.046 (2)0.051 (2)0.046 (3)0.016 (2)0.005 (2)0.017 (2)
O50.107 (3)0.054 (2)0.062 (3)0.032 (2)0.010 (2)0.034 (2)
O60.074 (3)0.060 (2)0.064 (3)0.031 (2)0.021 (2)0.029 (2)
O70.088 (3)0.084 (3)0.078 (3)0.021 (3)0.014 (3)0.046 (3)
O80.095 (3)0.084 (3)0.062 (3)0.022 (3)0.023 (3)0.035 (2)
C290.0634 (15)0.099 (2)0.0613 (18)0.0140 (14)0.0077 (14)0.0332 (16)
C300.0634 (15)0.099 (2)0.0613 (18)0.0140 (14)0.0077 (14)0.0332 (16)
C310.041 (3)0.053 (3)0.049 (3)0.011 (2)0.005 (2)0.016 (3)
C320.043 (3)0.040 (3)0.046 (3)0.010 (2)0.005 (2)0.013 (2)
C330.053 (3)0.043 (3)0.053 (4)0.012 (3)0.002 (3)0.021 (3)
N230.044 (2)0.041 (2)0.063 (3)0.0027 (19)0.003 (2)0.015 (2)
N240.051 (3)0.052 (3)0.050 (3)0.003 (2)0.003 (2)0.019 (2)
O90.0634 (15)0.099 (2)0.0613 (18)0.0140 (14)0.0077 (14)0.0332 (16)
O100.0634 (15)0.099 (2)0.0613 (18)0.0140 (14)0.0077 (14)0.0332 (16)
O110.084 (3)0.071 (3)0.050 (3)0.004 (2)0.004 (2)0.024 (2)
O120.047 (2)0.052 (2)0.066 (3)0.0041 (18)0.0037 (19)0.021 (2)
O1W0.107 (4)0.107 (4)0.093 (4)0.056 (4)0.006 (3)0.022 (3)
O2W0.079 (3)0.056 (2)0.110 (4)0.024 (2)0.042 (3)0.014 (3)
O3W0.074 (3)0.085 (3)0.065 (3)0.021 (2)0.016 (2)0.015 (3)
O4W0.072 (3)0.065 (3)0.115 (4)0.030 (2)0.029 (3)0.029 (3)
O5W0.071 (3)0.056 (2)0.057 (3)0.008 (2)0.004 (2)0.014 (2)
Geometric parameters (Å, º) top
C1—N11.483 (6)C14—H14A0.97
C1—C21.507 (7)C14—H14B0.97
C1—H1A0.97C15—N151.462 (8)
C1—H1B0.97C15—C161.512 (8)
C2—N21.474 (6)C15—H15A0.97
C2—H2A0.97C15—H15B0.97
C2—H2B0.97C16—N161.482 (7)
C3—N31.461 (7)C16—H16A0.97
C3—C41.502 (8)C16—H16B0.97
C3—H3A0.97C17—N171.486 (7)
C3—H3B0.97C17—C181.510 (8)
C4—N41.478 (7)C17—H17A0.97
C4—H4A0.97C17—H17B0.97
C4—H4B0.97C18—N181.476 (6)
C5—N51.475 (7)C18—H18A0.97
C5—C61.505 (7)C18—H18B0.97
C5—H5A0.97N13—Ni32.122 (4)
C5—H5B0.97N13—H13C0.90
C6—N61.467 (6)N13—H13D0.90
C6—H6A0.97N14—Ni32.122 (4)
C6—H6B0.97N14—H14C0.90
N1—Ni12.130 (4)N14—H14D0.90
N1—H1C0.90N15—Ni32.121 (5)
N1—H1D0.90N15—H15C0.90
N2—Ni12.110 (4)N15—H15D0.90
N2—H2C0.90N16—Ni32.122 (5)
N2—H2D0.90N16—H16C0.90
N3—Ni12.128 (4)N16—H16D0.90
N3—H3C0.90N17—Ni32.140 (4)
N3—H3D0.90N17—H17C0.90
N4—Ni12.108 (5)N17—H17D0.90
N4—H4C0.90N18—Ni32.147 (5)
N4—H4D0.90N18—H18C0.90
N5—Ni12.111 (3)N18—H18D0.90
N5—H5C0.90C19—O11.251 (5)
N5—H5D0.90C19—O21.252 (5)
N6—Ni12.118 (5)C19—C201.507 (6)
N6—H6C0.90C20—N191.331 (5)
N6—H6D0.90C20—C211.399 (6)
C7—N71.457 (7)C21—C221.371 (6)
C7—C81.514 (7)C21—H210.93
C7—H7A0.97C22—N201.358 (5)
C7—H7B0.97C22—C231.496 (7)
C8—N81.479 (6)C23—O31.234 (6)
C8—H8A0.97C23—O41.247 (6)
C8—H8B0.97N19—N201.343 (5)
C9—N91.462 (7)N20—H200.86
C9—C101.501 (8)C24—O51.235 (6)
C9—H9A0.97C24—O61.262 (5)
C9—H9B0.97C24—C251.483 (7)
C10—N101.475 (6)C25—N211.337 (5)
C10—H10A0.97C25—C261.413 (6)
C10—H10B0.97C26—C271.367 (6)
C11—N111.471 (6)C26—H260.93
C11—C121.504 (7)C27—N221.353 (5)
C11—H11A0.97C27—C281.490 (7)
C11—H11B0.97C28—O71.236 (6)
C12—N121.466 (6)C28—O81.246 (6)
C12—H12A0.97N21—N221.342 (5)
C12—H12B0.97N22—H220.86
N7—Ni22.106 (4)C29—O101.202 (8)
N7—H7C0.90C29—O91.266 (8)
N7—H7D0.90C29—C301.465 (9)
N8—Ni22.130 (4)C30—N231.342 (8)
N8—H8C0.90C30—C311.368 (8)
N8—H8D0.90C31—C321.397 (7)
N9—Ni22.124 (4)C31—H310.93
N9—H9C0.90C32—N241.341 (7)
N9—H9D0.90C32—C331.497 (7)
N10—Ni22.125 (5)C33—O111.246 (7)
N10—H10C0.90C33—O121.266 (7)
N10—H10D0.90N23—N241.358 (6)
N11—Ni22.126 (4)N23—H230.8600
N11—H11C0.90O1W—H1W10.82 (5)
N11—H11D0.90O1W—H2W10.83 (8)
N12—Ni22.125 (4)O2W—H1W20.82 (7)
N12—H12C0.90O2W—H2W20.83 (6)
N12—H12D0.90O3W—H1W30.84 (6)
C13—N131.472 (6)O3W—H2W30.84 (6)
C13—C141.505 (7)O4W—H1W40.83 (8)
C13—H13A0.97O4W—H2W40.84 (7)
C13—H13B0.97O5W—H1W50.830 (19)
C14—N141.477 (7)O5W—H2W50.84 (4)
N1—C1—C2109.1 (4)N7—Ni2—N1092.46 (18)
N1—C1—H1A109.9N9—Ni2—N1081.63 (16)
C2—C1—H1A109.9N12—Ni2—N1096.23 (17)
N1—C1—H1B109.9N7—Ni2—N11167.90 (16)
C2—C1—H1B109.9N9—Ni2—N1194.38 (15)
H1A—C1—H1B108.3N12—Ni2—N1181.74 (14)
N2—C2—C1108.1 (4)N10—Ni2—N1195.75 (18)
N2—C2—H2A110.1N7—Ni2—N882.19 (17)
C1—C2—H2A110.1N9—Ni2—N889.41 (16)
N2—C2—H2B110.1N12—Ni2—N893.14 (16)
C1—C2—H2B110.1N10—Ni2—N8169.09 (15)
H2A—C2—H2B108.4N11—Ni2—N891.10 (17)
N3—C3—C4110.2 (5)N13—C13—C14108.6 (4)
N3—C3—H3A109.6N13—C13—H13A110.0
C4—C3—H3A109.6C14—C13—H13A110.0
N3—C3—H3B109.6N13—C13—H13B110.0
C4—C3—H3B109.6C14—C13—H13B110.0
H3A—C3—H3B108.1H13A—C13—H13B108.4
N4—C4—C3107.6 (5)N14—C14—C13108.0 (4)
N4—C4—H4A110.2N14—C14—H14A110.1
C3—C4—H4A110.2C13—C14—H14A110.1
N4—C4—H4B110.2N14—C14—H14B110.1
C3—C4—H4B110.2C13—C14—H14B110.1
H4A—C4—H4B108.5H14A—C14—H14B108.4
N5—C5—C6108.7 (4)N15—C15—C16107.8 (5)
N5—C5—H5A109.9N15—C15—H15A110.1
C6—C5—H5A109.9C16—C15—H15A110.1
N5—C5—H5B109.9N15—C15—H15B110.1
C6—C5—H5B109.9C16—C15—H15B110.1
H5A—C5—H5B108.3H15A—C15—H15B108.5
N6—C6—C5108.6 (4)N16—C16—C15108.1 (5)
N6—C6—H6A110.0N16—C16—H16A110.1
C5—C6—H6A110.0C15—C16—H16A110.1
N6—C6—H6B110.0N16—C16—H16B110.1
C5—C6—H6B110.0C15—C16—H16B110.1
H6A—C6—H6B108.4H16A—C16—H16B108.4
C1—N1—Ni1107.1 (3)N17—C17—C18108.0 (4)
C1—N1—H1C110.3N17—C17—H17A110.1
Ni1—N1—H1C110.3C18—C17—H17A110.1
C1—N1—H1D110.3N17—C17—H17B110.1
Ni1—N1—H1D110.3C18—C17—H17B110.1
H1C—N1—H1D108.6H17A—C17—H17B108.4
C2—N2—Ni1108.4 (3)N18—C18—C17109.8 (4)
C2—N2—H2C110.0N18—C18—H18A109.7
Ni1—N2—H2C110.0C17—C18—H18A109.7
C2—N2—H2D110.0N18—C18—H18B109.7
Ni1—N2—H2D110.0C17—C18—H18B109.7
H2C—N2—H2D108.4H18A—C18—H18B108.2
C3—N3—Ni1108.4 (3)C13—N13—Ni3107.7 (3)
C3—N3—H3C110.0C13—N13—H13C110.2
Ni1—N3—H3C110.0Ni3—N13—H13C110.2
C3—N3—H3D110.0C13—N13—H13D110.2
Ni1—N3—H3D110.0Ni3—N13—H13D110.2
H3C—N3—H3D108.4H13C—N13—H13D108.5
C4—N4—Ni1108.7 (3)C14—N14—Ni3107.5 (3)
C4—N4—H4C110.0C14—N14—H14C110.2
Ni1—N4—H4C110.0Ni3—N14—H14C110.2
C4—N4—H4D110.0C14—N14—H14D110.2
Ni1—N4—H4D110.0Ni3—N14—H14D110.2
H4C—N4—H4D108.3H14C—N14—H14D108.5
C5—N5—Ni1109.3 (3)C15—N15—Ni3108.7 (4)
C5—N5—H5C109.8C15—N15—H15C109.9
Ni1—N5—H5C109.8Ni3—N15—H15C109.9
C5—N5—H5D109.8C15—N15—H15D109.9
Ni1—N5—H5D109.8Ni3—N15—H15D109.9
H5C—N5—H5D108.3H15C—N15—H15D108.3
C6—N6—Ni1107.8 (3)C16—N16—Ni3106.9 (3)
C6—N6—H6C110.1C16—N16—H16C110.3
Ni1—N6—H6C110.1Ni3—N16—H16C110.3
C6—N6—H6D110.1C16—N16—H16D110.3
Ni1—N6—H6D110.1Ni3—N16—H16D110.3
H6C—N6—H6D108.5H16C—N16—H16D108.6
N4—Ni1—N295.88 (17)C17—N17—Ni3106.3 (3)
N4—Ni1—N590.55 (16)C17—N17—H17C110.5
N2—Ni1—N5172.19 (18)Ni3—N17—H17C110.5
N4—Ni1—N6171.11 (14)C17—N17—H17D110.5
N2—Ni1—N692.32 (17)Ni3—N17—H17D110.5
N5—Ni1—N681.55 (16)H17C—N17—H17D108.7
N4—Ni1—N381.46 (18)C18—N18—Ni3107.1 (3)
N2—Ni1—N391.30 (16)C18—N18—H18C110.3
N5—Ni1—N394.04 (15)Ni3—N18—H18C110.3
N6—Ni1—N394.97 (19)C18—N18—H18D110.3
N4—Ni1—N189.94 (17)Ni3—N18—H18D110.3
N2—Ni1—N182.15 (15)H18C—N18—H18D108.6
N5—Ni1—N193.46 (15)N15—Ni3—N1681.65 (19)
N6—Ni1—N194.56 (18)N15—Ni3—N1494.13 (17)
N3—Ni1—N1168.64 (17)N16—Ni3—N1493.26 (18)
N7—C7—C8110.1 (4)N15—Ni3—N13172.13 (18)
N7—C7—H7A109.6N16—Ni3—N1391.78 (18)
C8—C7—H7A109.6N14—Ni3—N1381.87 (16)
N7—C7—H7B109.6N15—Ni3—N1794.52 (17)
C8—C7—H7B109.6N16—Ni3—N1793.09 (18)
H7A—C7—H7B108.2N14—Ni3—N17169.93 (19)
N8—C8—C7108.2 (4)N13—Ni3—N1790.13 (16)
N8—C8—H8A110.1N15—Ni3—N1890.18 (19)
C7—C8—H8A110.1N16—Ni3—N18170.30 (17)
N8—C8—H8B110.1N14—Ni3—N1892.52 (18)
C7—C8—H8B110.1N13—Ni3—N1896.74 (19)
H8A—C8—H8B108.4N17—Ni3—N1882.31 (18)
N9—C9—C10108.9 (4)O1—C19—O2125.7 (5)
N9—C9—H9A109.9O1—C19—C20116.6 (4)
C10—C9—H9A109.9O2—C19—C20117.7 (4)
N9—C9—H9B109.9N19—C20—C21110.8 (4)
C10—C9—H9B109.9N19—C20—C19120.6 (4)
H9A—C9—H9B108.3C21—C20—C19128.5 (4)
N10—C10—C9109.0 (4)C22—C21—C20106.2 (4)
N10—C10—H10A109.9C22—C21—H21126.9
C9—C10—H10A109.9C20—C21—H21126.9
N10—C10—H10B109.9N20—C22—C21105.2 (4)
C9—C10—H10B109.9N20—C22—C23120.1 (4)
H10A—C10—H10B108.3C21—C22—C23134.7 (4)
N11—C11—C12109.2 (4)O3—C23—O4126.5 (5)
N11—C11—H11A109.8O3—C23—C22116.9 (4)
C12—C11—H11A109.8O4—C23—C22116.6 (5)
N11—C11—H11B109.8C20—N19—N20104.6 (4)
C12—C11—H11B109.8N19—N20—C22113.1 (4)
H11A—C11—H11B108.3N19—N20—H20123.4
N12—C12—C11107.9 (4)C22—N20—H20123.4
N12—C12—H12A110.1O5—C24—O6124.2 (5)
C11—C12—H12A110.1O5—C24—C25119.2 (4)
N12—C12—H12B110.1O6—C24—C25116.5 (4)
C11—C12—H12B110.1N21—C25—C26109.9 (4)
H12A—C12—H12B108.4N21—C25—C24121.2 (4)
C7—N7—Ni2109.3 (3)C26—C25—C24128.9 (4)
C7—N7—H7C109.8C27—C26—C25106.0 (4)
Ni2—N7—H7C109.8C27—C26—H26127.0
C7—N7—H7D109.8C25—C26—H26127.0
Ni2—N7—H7D109.8N22—C27—C26105.9 (4)
H7C—N7—H7D108.3N22—C27—C28120.3 (4)
C8—N8—Ni2106.3 (3)C26—C27—C28133.8 (4)
C8—N8—H8C110.5O7—C28—O8125.3 (5)
Ni2—N8—H8C110.5O7—C28—C27118.3 (5)
C8—N8—H8D110.5O8—C28—C27116.4 (5)
Ni2—N8—H8D110.5C25—N21—N22105.3 (4)
H8C—N8—H8D108.7N21—N22—C27112.8 (4)
C9—N9—Ni2107.4 (3)N21—N22—H22123.6
C9—N9—H9C110.2C27—N22—H22123.6
Ni2—N9—H9C110.2O10—C29—O9123.3 (6)
C9—N9—H9D110.2O10—C29—C30121.2 (7)
Ni2—N9—H9D110.2O9—C29—C30115.4 (6)
H9C—N9—H9D108.5N23—C30—C31105.5 (5)
C10—N10—Ni2108.5 (3)N23—C30—C29120.0 (6)
C10—N10—H10C110.0C31—C30—C29134.5 (7)
Ni2—N10—H10C110.0C30—C31—C32106.1 (5)
C10—N10—H10D110.0C30—C31—H31126.9
Ni2—N10—H10D110.0C32—C31—H31126.9
H10C—N10—H10D108.4N24—C32—C31111.2 (4)
C11—N11—Ni2106.8 (3)N24—C32—C33120.1 (5)
C11—N11—H11C110.4C31—C32—C33128.7 (5)
Ni2—N11—H11C110.4O11—C33—O12126.3 (5)
C11—N11—H11D110.4O11—C33—C32118.0 (6)
Ni2—N11—H11D110.4O12—C33—C32115.7 (5)
H11C—N11—H11D108.6C30—N23—N24113.9 (5)
C12—N12—Ni2108.4 (3)C30—N23—H23123.0
C12—N12—H12C110.0N24—N23—H23123.0
Ni2—N12—H12C110.0C32—N24—N23103.2 (4)
C12—N12—H12D110.0H1W1—O1W—H2W1110 (8)
Ni2—N12—H12D110.0H1W2—O2W—H2W2110 (7)
H12C—N12—H12D108.4H1W3—O3W—H2W3108 (3)
N7—Ni2—N995.60 (15)H1W4—O4W—H2W4108 (7)
N7—Ni2—N1288.56 (15)H1W5—O5W—H2W5107 (3)
N9—Ni2—N12175.39 (16)
N1—C1—C2—N256.5 (6)C18—C17—N17—Ni345.2 (4)
N3—C3—C4—N454.5 (5)C17—C18—N18—Ni339.3 (5)
N5—C5—C6—N654.8 (6)C15—N15—Ni3—N1613.0 (4)
C2—C1—N1—Ni141.4 (5)C15—N15—Ni3—N1479.7 (4)
C1—C2—N2—Ni141.9 (5)C15—N15—Ni3—N17105.5 (4)
C4—C3—N3—Ni138.2 (5)C15—N15—Ni3—N18172.2 (4)
C3—C4—N4—Ni142.6 (5)C16—N16—Ni3—N1517.6 (4)
C6—C5—N5—Ni137.3 (5)C16—N16—Ni3—N14111.3 (4)
C5—C6—N6—Ni144.0 (5)C16—N16—Ni3—N13166.8 (4)
C4—N4—Ni1—N2108.0 (3)C16—N16—Ni3—N1776.6 (4)
C4—N4—Ni1—N576.4 (3)C14—N14—Ni3—N15170.9 (4)
C4—N4—Ni1—N317.6 (3)C14—N14—Ni3—N16107.2 (4)
C4—N4—Ni1—N1169.9 (3)C14—N14—Ni3—N1315.9 (4)
C2—N2—Ni1—N4104.3 (4)C14—N14—Ni3—N1721.8 (12)
C2—N2—Ni1—N679.1 (4)C14—N14—Ni3—N1880.6 (4)
C2—N2—Ni1—N3174.1 (4)C13—N13—Ni3—N1678.8 (4)
C2—N2—Ni1—N115.2 (4)C13—N13—Ni3—N1414.2 (4)
C5—N5—Ni1—N4173.5 (3)C13—N13—Ni3—N17171.9 (4)
C5—N5—Ni1—N610.6 (3)C13—N13—Ni3—N18105.8 (4)
C5—N5—Ni1—N3105.0 (4)C17—N17—Ni3—N15108.4 (3)
C5—N5—Ni1—N183.5 (4)C17—N17—Ni3—N16169.8 (3)
C6—N6—Ni1—N2166.5 (3)C17—N17—Ni3—N1440.7 (12)
C6—N6—Ni1—N518.4 (3)C17—N17—Ni3—N1378.0 (3)
C6—N6—Ni1—N375.0 (3)C17—N17—Ni3—N1818.8 (3)
C6—N6—Ni1—N1111.2 (3)C18—N18—Ni3—N1583.6 (3)
C3—N3—Ni1—N411.2 (3)C18—N18—Ni3—N14177.7 (3)
C3—N3—Ni1—N284.6 (3)C18—N18—Ni3—N13100.2 (3)
C3—N3—Ni1—N5101.1 (3)C18—N18—Ni3—N1711.0 (3)
C3—N3—Ni1—N6177.0 (3)O1—C19—C20—N19177.5 (4)
C3—N3—Ni1—N130.1 (10)O2—C19—C20—N191.3 (7)
C1—N1—Ni1—N481.6 (4)O1—C19—C20—C215.4 (8)
C1—N1—Ni1—N214.3 (4)O2—C19—C20—C21175.8 (5)
C1—N1—Ni1—N5172.2 (4)N19—C20—C21—C220.1 (6)
C1—N1—Ni1—N6106.1 (4)C19—C20—C21—C22177.2 (5)
C1—N1—Ni1—N340.9 (10)C20—C21—C22—N200.3 (6)
N7—C7—C8—N854.6 (5)C20—C21—C22—C23180.0 (6)
N9—C9—C10—N1055.8 (6)N20—C22—C23—O37.8 (8)
N11—C11—C12—N1257.5 (6)C21—C22—C23—O3171.9 (6)
C8—C7—N7—Ni234.9 (4)N20—C22—C23—O4172.7 (5)
C7—C8—N8—Ni245.1 (4)C21—C22—C23—O47.6 (9)
C10—C9—N9—Ni244.4 (5)C21—C20—N19—N200.4 (5)
C9—C10—N10—Ni237.7 (5)C19—C20—N19—N20177.1 (4)
C12—C11—N11—Ni243.8 (5)C20—N19—N20—C220.6 (6)
C11—C12—N12—Ni240.6 (5)C21—C22—N20—N190.6 (6)
C7—N7—Ni2—N996.4 (3)C23—C22—N20—N19179.7 (4)
C7—N7—Ni2—N1285.6 (3)O5—C24—C25—N215.4 (8)
C7—N7—Ni2—N10178.2 (3)O6—C24—C25—N21173.2 (5)
C7—N7—Ni2—N1149.1 (9)O5—C24—C25—C26173.1 (5)
C7—N7—Ni2—N87.7 (3)O6—C24—C25—C268.3 (8)
C9—N9—Ni2—N7110.1 (3)N21—C25—C26—C270.7 (6)
C9—N9—Ni2—N1018.4 (3)C24—C25—C26—C27179.4 (5)
C9—N9—Ni2—N1176.8 (3)C25—C26—C27—N220.6 (6)
C9—N9—Ni2—N8167.9 (3)C25—C26—C27—C28177.7 (6)
C12—N12—Ni2—N7173.8 (4)N22—C27—C28—O7171.1 (5)
C12—N12—Ni2—N1081.5 (4)C26—C27—C28—O75.6 (9)
C12—N12—Ni2—N1113.4 (4)N22—C27—C28—O87.7 (8)
C12—N12—Ni2—N8104.1 (4)C26—C27—C28—O8175.6 (6)
C10—N10—Ni2—N784.6 (3)C26—C25—N21—N220.5 (6)
C10—N10—Ni2—N910.7 (3)C24—C25—N21—N22179.3 (5)
C10—N10—Ni2—N12173.4 (3)C25—N21—N22—C270.1 (6)
C10—N10—Ni2—N11104.3 (3)C26—C27—N22—N210.3 (6)
C10—N10—Ni2—N824.3 (11)C28—C27—N22—N21177.9 (5)
C11—N11—Ni2—N720.5 (10)O10—C29—C30—N2312.0 (11)
C11—N11—Ni2—N9166.0 (3)O9—C29—C30—N23165.3 (6)
C11—N11—Ni2—N1216.5 (3)O10—C29—C30—C31166.6 (7)
C11—N11—Ni2—N10112.0 (3)O9—C29—C30—C3116.1 (12)
C11—N11—Ni2—N876.5 (3)N23—C30—C31—C320.2 (7)
C8—N8—Ni2—N720.8 (3)C29—C30—C31—C32178.6 (8)
C8—N8—Ni2—N974.9 (3)C30—C31—C32—N240.5 (6)
C8—N8—Ni2—N12108.9 (3)C30—C31—C32—C33179.9 (5)
C8—N8—Ni2—N1040.3 (10)N24—C32—C33—O1118.3 (7)
C8—N8—Ni2—N11169.3 (3)C31—C32—C33—O11162.3 (5)
N13—C13—C14—N1457.6 (6)N24—C32—C33—O12162.4 (4)
N15—C15—C16—N1658.0 (6)C31—C32—C33—O1217.0 (7)
N17—C17—C18—N1858.2 (6)C31—C30—N23—N240.2 (7)
C14—C13—N13—Ni341.8 (5)C29—C30—N23—N24179.2 (6)
C13—C14—N14—Ni343.0 (5)C31—C32—N24—N230.6 (5)
C16—C15—N15—Ni340.8 (6)C33—C32—N24—N23179.9 (4)
C15—C16—N16—Ni344.7 (6)C30—N23—N24—C320.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O40.82 (5)1.93 (3)2.725 (6)162 (8)
O1W—H2W1···O90.83 (8)1.94 (8)2.739 (8)163 (8)
O2W—H1W2···O60.82 (7)1.90 (3)2.674 (5)159 (6)
O2W—H2W2···O10.83 (6)2.04 (3)2.856 (6)167 (8)
O3W—H1W3···O70.84 (6)1.95 (6)2.787 (6)175 (2)
O3W—H2W3···O11i0.84 (6)2.36 (4)3.074 (6)144 (6)
O3W—H2W3···N24i0.84 (6)2.55 (5)3.236 (6)141 (7)
O4W—H1W4···O1Wii0.83 (8)2.37 (5)3.094 (8)146 (8)
O4W—H1W4···O9ii0.83 (8)2.57 (5)3.293 (6)146 (8)
O4W—H2W4···O5W0.84 (7)2.03 (7)2.839 (6)163 (7)
O5W—H1W5···O12iii0.83 (2)2.01 (3)2.819 (5)165 (6)
O5W—H2W5···O12ii0.84 (4)2.06 (2)2.888 (5)176 (7)
N1—H1C···O1ii0.902.343.215 (6)164
N1—H1D···O3Wii0.902.273.159 (7)170
N2—H2C···O9iv0.902.253.118 (6)162
N2—H2D···O1iv0.902.553.358 (6)150
N3—H3D···N21v0.902.243.066 (5)153
N4—H4C···O2ii0.902.243.091 (5)158
N4—H4D···O1iv0.902.153.039 (5)168
N5—H5C···O2ii0.902.283.091 (6)150
N5—H5D···O5v0.902.022.913 (5)174
N6—H6C···O10iv0.902.383.154 (6)144
N6—H6C···O9iv0.902.543.357 (6)152
N7—H7C···N19vi0.902.072.950 (5)165
N7—H7D···O3W0.902.453.314 (6)162
N8—H8C···O2W0.902.223.029 (6)149
N8—H8D···O5vii0.902.573.388 (6)152
N8—H8D···O6vii0.902.593.345 (5)142
N9—H9C···O2vi0.902.193.071 (5)166
N9—H9D···O5vii0.902.183.049 (6)162
N10—H10D···O11i0.902.213.066 (6)159
N11—H11C···O1Wvii0.902.333.173 (7)156
N11—H11D···O6vii0.902.092.959 (6)162
N12—H12C···O2W0.902.223.100 (7)166
N12—H12D···O3W0.902.463.213 (6)142
N13—H13C···O8viii0.902.082.929 (6)157
N13—H13D···O70.902.573.307 (7)139
N14—H14C···O4vii0.902.082.976 (6)173
N14—H14D···O12vii0.902.413.284 (7)163
N15—H15C···O3vii0.902.132.940 (6)149
N16—H16C···O8viii0.902.203.017 (6)151
N16—H16D···O12vii0.902.273.147 (5)164
N17—H17C···O7viii0.902.423.290 (6)162
N17—H17C···O8viii0.902.593.351 (6)142
N17—H17D···O10ix0.902.313.151 (6)155
N18—H18C···O3vii0.902.253.100 (6)157
N20—H20···O11x0.862.353.058 (6)140
N22—H22···O4W0.862.002.819 (5)160
N23—H23···O10xi0.862.032.856 (6)160
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z+1; (iii) x+1, y, z1; (iv) x, y+1, z; (v) x+1, y+2, z+1; (vi) x, y, z+1; (vii) x, y+1, z+1; (viii) x+1, y+1, z; (ix) x, y+1, z1; (x) x, y, z+2; (xi) x+1, y, z+2.

Experimental details

Crystal data
Chemical formula[Ni(C2H8N2)3](C5H2N2O4)·1.67H2O
Mr423.13
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)12.8145 (7), 12.9218 (7), 18.6311 (13)
α, β, γ (°)72.008 (5), 75.446 (5), 73.480 (4)
V3)2767.5 (3)
Z6
Radiation typeMo Kα
µ (mm1)1.10
Crystal size (mm)0.52 × 0.35 × 0.07
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.582, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
42996, 11465, 6232
Rint0.091
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.146, 0.91
No. of reflections11465
No. of parameters706
No. of restraints15
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.25, 1.59

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O40.82 (5)1.93 (3)2.725 (6)162 (8)
O1W—H2W1···O90.83 (8)1.94 (8)2.739 (8)163 (8)
O2W—H1W2···O60.82 (7)1.90 (3)2.674 (5)159 (6)
O2W—H2W2···O10.83 (6)2.04 (3)2.856 (6)167 (8)
O3W—H1W3···O70.84 (6)1.95 (6)2.787 (6)175 (2)
O3W—H2W3···O11i0.84 (6)2.36 (4)3.074 (6)144 (6)
O3W—H2W3···N24i0.84 (6)2.55 (5)3.236 (6)141 (7)
O4W—H1W4···O1Wii0.83 (8)2.37 (5)3.094 (8)146 (8)
O4W—H1W4···O9ii0.83 (8)2.57 (5)3.293 (6)146 (8)
O4W—H2W4···O5W0.84 (7)2.03 (7)2.839 (6)163 (7)
O5W—H1W5···O12iii0.83 (2)2.01 (3)2.819 (5)165 (6)
O5W—H2W5···O12ii0.84 (4)2.06 (2)2.888 (5)176 (7)
N1—H1C···O1ii0.902.343.215 (6)164
N1—H1D···O3Wii0.902.273.159 (7)170
N2—H2C···O9iv0.902.253.118 (6)162
N2—H2D···O1iv0.902.553.358 (6)150
N3—H3D···N21v0.902.243.066 (5)153
N4—H4C···O2ii0.902.243.091 (5)158
N4—H4D···O1iv0.902.153.039 (5)168
N5—H5C···O2ii0.902.283.091 (6)150
N5—H5D···O5v0.902.022.913 (5)174
N6—H6C···O10iv0.902.383.154 (6)144
N6—H6C···O9iv0.902.543.357 (6)152
N7—H7C···N19vi0.902.072.950 (5)165
N7—H7D···O3W0.902.453.314 (6)162
N8—H8C···O2W0.902.223.029 (6)149
N8—H8D···O5vii0.902.573.388 (6)152
N8—H8D···O6vii0.902.593.345 (5)142
N9—H9C···O2vi0.902.193.071 (5)166
N9—H9D···O5vii0.902.183.049 (6)162
N10—H10D···O11i0.902.213.066 (6)159
N11—H11C···O1Wvii0.902.333.173 (7)156
N11—H11D···O6vii0.902.092.959 (6)162
N12—H12C···O2W0.902.223.100 (7)166
N12—H12D···O3W0.902.463.213 (6)142
N13—H13C···O8viii0.902.082.929 (6)157
N13—H13D···O70.902.573.307 (7)139
N14—H14C···O4vii0.902.082.976 (6)173
N14—H14D···O12vii0.902.413.284 (7)163
N15—H15C···O3vii0.902.132.940 (6)149
N16—H16C···O8viii0.902.203.017 (6)151
N16—H16D···O12vii0.902.273.147 (5)164
N17—H17C···O7viii0.902.423.290 (6)162
N17—H17C···O8viii0.902.593.351 (6)142
N17—H17D···O10ix0.902.313.151 (6)155
N18—H18C···O3vii0.902.253.100 (6)157
N20—H20···O11x0.862.353.058 (6)140
N22—H22···O4W0.862.002.819 (5)160
N23—H23···O10xi0.862.032.856 (6)160
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z+1; (iii) x+1, y, z1; (iv) x, y+1, z; (v) x+1, y+2, z+1; (vi) x, y, z+1; (vii) x, y+1, z+1; (viii) x+1, y+1, z; (ix) x, y+1, z1; (x) x, y, z+2; (xi) x+1, y, z+2.
 

Acknowledgements

The authors thank the Ondokuz Mayis University Research Fund for financial support.

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Volume 66| Part 8| August 2010| Pages m925-m926
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