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Acta Cryst. (2007). E63, m2537    [ doi:10.1107/S160053680704384X ]

Bis{2-[tris(hydroxymethyl)methyliminomethyl]phenolato-[kappa]3N,O,O'}nickel(II) methanol solvate

Q. Wang, X. Li, X. Wang and Y. Zhang

Abstract top

In the crystal structure of [Ni(C11H14NO4)2]·CH4O, the 2-[tris(hydroxymethyl)methyliminomethyl]phenolate monoanions bind in a tridentate mode through the phenolate, alcohol and imine donor atoms to confer an octahedral geometry on nickel. Adjacent molecules are linked by O-H...O hydrogen bonds into a three-dimensional supramolecular network structure.

Comment top

Single-crystal X-ray diffraction analyses revealed that (I) is neutral, mononuclear molecule with the Ni(II) ion being octahedral coordination supplied by monoanionic and tridentate binding through the Ophen, Oalk and Nimi groups from two 2-[tris(hydroxymethyl)methyliminomethyl]phenolate ligands (Fig. 1). And The structure is isostructural with the zinc analog (Dey et al., 2002). Selected bond lengths and bond angels are listed in Table 1. Of the three –CH2OH groups, only one is bound to the nickel center, while the other two remain free. At the same time one methanol molecule is cocrystallized in this complex which makes abundant O—H···O hydrogen bonds (Table 2) between the molecules.

Mononuclear Cu(II) complex coordinatd by one chelate 2-[tris(hydroxymethyl)methyliminomethyl]phenolate was reported in crystal structure (Ni et al., 2005). And the isostructural zinc complex was reported by Dey et al. (2002).

Related literature top

See Dey et al. (2002) for the isostructural zinc analog. For a related CuII complex, see Ni (2005).

Experimental top

2-[tris(hydroxymethyl)methyliminomethyl]phenolate was synthesized using the salicylaldehyde and the 2-amino-2-(hydroxymethyl)propane-1,3-diol. A mixture of Nickel acetate dihydrate (0.11 g, 0.5 mmol), 2-[tris(hydroxymethyl)methyliminomethyl]phenolate (0.13 g, 0.5 mmol), and methanol (15 ml) was heated and stirring for 20 min. Suitable crystals were obtained by evaporation of the filtrate in air at room temperature.

Refinement top

All H atoms besides H atoms bonded to O—H were placed at calculated positions in the riding-model approximation (C—Haromatic = 0.93Å and C—Hmethyl = 0.96 Å), with their displacement parameters tied to those of the parent atoms by Uiso(H) = 1.2–1.5 times Ueq(C). H atoms bonded to O—H were located from different Fourier maps and were refined with restrained O—H distances with O—Hmethyl = 0.82 (1) Å.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of the local coordination of Ni(II) with the coordinated atoms numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Bis{2-[tris(hydroxymethyl)methyliminomethyl]phenolato-κ3 N,O,O'}nickel(II) methanol solvate top
Crystal data top
[Ni(C11H14NO4)2]·CH4ODx = 1.516 Mg m−3
Mr = 539.22Mo Kα radiation
λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 15150 reflections
a = 11.1900 (3) Åθ = 3.4–27.5º
b = 18.8378 (5) ŵ = 0.88 mm−1
c = 22.4202 (8) ÅT = 293 (2) K
V = 4726.1 (2) Å3Block, green
Z = 80.1 × 0.08 × 0.08 mm
F000 = 2272
Data collection top
Nonius KappaCCD
diffractometer		4329 independent reflections
Radiation source: fine-focus sealed tube1833 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.093
Detector resolution: 0.76 pixels mm-1θmax = 25.4º
T = 293(2) Kθmin = 3.5º
CCD scansh = −13→13
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		k = −22→22
Tmin = 0.837, Tmax = 0.962l = −26→27
8161 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)] = 0.040H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.063  w = 1/[σ2(Fo2) + (0.0165P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.001
4329 reflectionsΔρmax = 0.38 e Å−3
340 parametersΔρmin = −0.26 e Å−3
7 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C11H14NO4)2]·CH4OV = 4726.1 (2) Å3
Mr = 539.22Z = 8
Orthorhombic, PbcaMo Kα
a = 11.1900 (3) ŵ = 0.88 mm−1
b = 18.8378 (5) ÅT = 293 (2) K
c = 22.4202 (8) Å0.1 × 0.08 × 0.08 mm
Data collection top
Nonius KappaCCD
diffractometer		4329 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		1833 reflections with I > 2σ(I)
Tmin = 0.837, Tmax = 0.962Rint = 0.093
8161 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0407 restraints
wR(F2) = 0.063H atoms treated by a mixture of
independent and constrained refinement
S = 0.82Δρmax = 0.38 e Å−3
4329 reflectionsΔρmin = −0.26 e Å−3
340 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
Ni10.49786 (4)0.214735 (17)0.619437 (17)0.02801 (13)
N10.5029 (3)0.22644 (12)0.53015 (10)0.0246 (6)
N20.5308 (2)0.20154 (12)0.70767 (11)0.0274 (8)
O70.6646 (2)0.15588 (12)0.61811 (12)0.0351 (6)
O40.5970 (2)0.31185 (12)0.61416 (12)0.0361 (6)
O10.39482 (19)0.12901 (9)0.61149 (10)0.0325 (6)
O50.35296 (18)0.27329 (10)0.63661 (10)0.0338 (6)
O30.6982 (2)0.23657 (13)0.44870 (11)0.0442 (7)
H3A0.744 (3)0.2362 (17)0.4198 (11)0.066*
O80.7673 (3)0.10518 (13)0.79279 (10)0.0448 (7)
H8A0.804 (3)0.1107 (17)0.8242 (9)0.067*
O20.3458 (2)0.31959 (12)0.46821 (11)0.0396 (7)
H2A0.301 (3)0.2989 (16)0.4912 (13)0.059*
O60.4756 (2)0.06072 (12)0.76045 (12)0.0472 (7)
H6A0.4104 (17)0.0748 (18)0.7484 (17)0.071*
O90.5291 (3)0.45139 (14)0.64657 (12)0.0842 (10)
H90.518 (5)0.468 (2)0.6799 (9)0.126*
C230.5141 (4)0.50424 (18)0.60590 (17)0.0995 (18)
H23A0.53930.54850.62290.149*
H23B0.43140.50720.59490.149*
H23C0.56120.49420.57110.149*
C10.3786 (3)0.09038 (17)0.56388 (16)0.0277 (9)
C170.4001 (3)0.30043 (17)0.73773 (17)0.0341 (10)
C110.6375 (3)0.32327 (15)0.55423 (16)0.0355 (10)
H11A0.71380.29970.54880.043*
H11B0.64950.37370.54790.043*
C190.6216 (3)0.14735 (16)0.72315 (15)0.0258 (9)
C160.3750 (4)0.34180 (18)0.78839 (17)0.0491 (12)
H16A0.41810.33350.82320.059*
C100.6118 (3)0.29154 (16)0.44774 (15)0.0378 (10)
H10A0.55400.28250.41640.045*
H10B0.65040.33660.43950.045*
C220.6750 (3)0.15574 (16)0.78512 (14)0.0343 (10)
H22A0.70690.20330.78980.041*
H22B0.61360.14860.81510.041*
C80.5485 (3)0.29521 (17)0.50759 (15)0.0278 (9)
C180.4887 (3)0.24383 (16)0.74729 (15)0.0367 (9)
H18A0.51700.23810.78600.044*
C60.4161 (3)0.11161 (17)0.50603 (16)0.0265 (9)
C50.3961 (3)0.06634 (18)0.45729 (15)0.0384 (10)
H5A0.42060.08090.41960.046*
C70.4713 (3)0.17885 (17)0.49257 (15)0.0288 (10)
H7A0.48530.18870.45250.035*
C210.7194 (3)0.15597 (16)0.67598 (15)0.0347 (10)
H21A0.76190.20020.68230.042*
H21B0.77620.11720.67900.042*
C90.4411 (3)0.34640 (16)0.50372 (15)0.0356 (10)
H9A0.41160.35560.54370.043*
H9B0.46790.39120.48710.043*
C20.3211 (3)0.02409 (17)0.56840 (17)0.0428 (11)
H2B0.29430.00880.60550.051*
C120.3370 (3)0.31122 (17)0.68496 (18)0.0314 (10)
C200.5663 (3)0.07282 (15)0.71672 (15)0.0342 (10)
H20A0.53200.06790.67720.041*
H20B0.62840.03730.72100.041*
C150.2898 (4)0.39380 (18)0.78853 (19)0.0588 (14)
H15A0.27420.42090.82230.071*
C40.3417 (3)0.00142 (19)0.4632 (2)0.0502 (12)
H4A0.3307−0.02820.43050.060*
C130.2489 (3)0.36394 (17)0.68445 (16)0.0445 (11)
H13A0.20490.37200.64990.053*
C140.2268 (4)0.40409 (19)0.73480 (19)0.0565 (14)
H14A0.16840.43910.73320.068*
C30.3036 (4)−0.01862 (18)0.5195 (2)0.0521 (13)
H3B0.2652−0.06200.52430.063*
H4B0.569 (3)0.3489 (10)0.6263 (14)0.071 (16)*
H7B0.716 (2)0.1614 (16)0.5924 (11)0.045 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0288 (3)0.0313 (2)0.0239 (2)−0.0010 (2)−0.0014 (3)−0.0011 (2)
N10.0221 (17)0.0259 (15)0.0259 (17)0.0003 (16)0.0001 (18)−0.0009 (13)
N20.031 (2)0.0269 (16)0.0246 (18)0.0002 (14)−0.0028 (15)−0.0053 (13)
O70.0325 (18)0.0504 (15)0.0224 (17)0.0055 (13)0.0036 (18)−0.0002 (15)
O40.0416 (18)0.0339 (15)0.0328 (18)−0.0023 (13)0.0017 (16)−0.0025 (15)
O10.0404 (17)0.0362 (13)0.0208 (15)−0.0126 (12)0.0043 (14)−0.0043 (12)
O50.0295 (16)0.0443 (14)0.0276 (16)0.0064 (12)−0.0036 (13)−0.0039 (13)
O30.036 (2)0.0597 (16)0.0369 (19)0.0100 (15)0.0150 (14)0.0038 (15)
O80.043 (2)0.0577 (15)0.0336 (18)0.0132 (14)−0.0168 (15)−0.0025 (15)
O20.033 (2)0.0495 (17)0.036 (2)−0.0014 (14)−0.0043 (15)0.0075 (13)
O60.046 (2)0.0514 (15)0.0442 (18)−0.0093 (15)−0.0015 (18)0.0109 (13)
O90.131 (3)0.0654 (19)0.056 (2)0.0266 (19)0.016 (3)−0.0011 (16)
C230.156 (5)0.073 (3)0.069 (4)0.020 (4)−0.012 (4)−0.004 (2)
C10.017 (2)0.031 (2)0.035 (3)0.0017 (19)0.001 (2)0.002 (2)
C170.034 (3)0.035 (2)0.033 (3)0.005 (2)0.000 (2)−0.011 (2)
C110.035 (3)0.033 (2)0.039 (3)−0.0045 (19)0.005 (2)0.0059 (19)
C190.025 (3)0.031 (2)0.021 (2)−0.0009 (19)−0.002 (2)−0.0037 (18)
C160.057 (3)0.043 (2)0.047 (3)−0.001 (2)−0.005 (2)−0.006 (2)
C100.036 (3)0.044 (2)0.033 (3)−0.006 (2)0.003 (2)0.008 (2)
C220.035 (3)0.039 (2)0.029 (3)−0.001 (2)−0.006 (2)0.0011 (19)
C80.024 (2)0.033 (2)0.026 (2)0.0019 (19)−0.0035 (19)0.0041 (19)
C180.044 (3)0.039 (2)0.026 (2)−0.004 (2)−0.007 (3)0.0013 (18)
C60.026 (3)0.029 (2)0.025 (2)0.0015 (18)−0.005 (2)−0.0056 (19)
C50.039 (3)0.043 (2)0.034 (3)0.000 (2)0.000 (2)−0.001 (2)
C70.025 (3)0.040 (2)0.022 (2)0.0035 (18)0.0014 (19)0.0043 (18)
C210.033 (3)0.045 (2)0.026 (3)0.000 (2)−0.007 (2)0.001 (2)
C90.037 (3)0.036 (2)0.034 (3)−0.007 (2)−0.002 (2)0.004 (2)
C20.050 (3)0.036 (2)0.042 (3)−0.008 (2)0.011 (2)−0.003 (2)
C120.028 (3)0.030 (2)0.036 (3)−0.0008 (19)−0.001 (2)0.002 (2)
C200.031 (3)0.040 (2)0.032 (3)0.0047 (19)0.001 (2)0.0019 (19)
C150.071 (4)0.049 (3)0.057 (4)0.010 (3)0.001 (3)−0.021 (3)
C40.052 (3)0.047 (3)0.052 (4)0.003 (2)−0.007 (3)−0.020 (2)
C130.048 (3)0.041 (2)0.044 (3)0.008 (2)−0.001 (2)−0.006 (2)
C140.054 (4)0.041 (2)0.074 (4)0.012 (2)0.008 (3)0.001 (3)
C30.051 (3)0.035 (2)0.070 (4)−0.013 (2)0.002 (3)−0.011 (2)
Geometric parameters (Å, °) top
Ni1—O11.9922 (19)C11—H11B0.9700
Ni1—O51.998 (2)C19—C221.521 (4)
Ni1—N12.015 (2)C19—C211.531 (4)
Ni1—N22.028 (3)C19—C201.541 (4)
Ni1—O42.143 (2)C16—C151.367 (4)
Ni1—O72.170 (2)C16—H16A0.9300
N1—C71.280 (3)C10—C81.519 (4)
N1—C81.481 (3)C10—H10A0.9700
N2—C181.283 (3)C10—H10B0.9700
N2—C191.481 (3)C22—H22A0.9700
O7—C211.435 (3)C22—H22B0.9700
O7—H7B0.823 (10)C8—C91.543 (4)
O4—C111.434 (4)C18—H18A0.9300
O4—H4B0.813 (10)C6—C51.404 (4)
O1—C11.305 (3)C6—C71.441 (4)
O5—C121.311 (4)C5—C41.373 (4)
O3—C101.417 (4)C5—H5A0.9300
O3—H3A0.829 (10)C7—H7A0.9300
O8—C221.416 (4)C21—H21A0.9700
O8—H8A0.824 (10)C21—H21B0.9700
O2—C91.424 (4)C9—H9A0.9700
O2—H2A0.816 (10)C9—H9B0.9700
O6—C201.429 (4)C2—C31.374 (4)
O6—H6A0.821 (10)C2—H2B0.9300
O9—C231.361 (4)C12—C131.399 (4)
O9—H90.818 (10)C20—H20A0.9700
C23—H23A0.9600C20—H20B0.9700
C23—H23B0.9600C15—C141.409 (5)
C23—H23C0.9600C15—H15A0.9300
C1—C21.408 (4)C4—C31.385 (4)
C1—C61.421 (4)C4—H4A0.9300
C17—C121.393 (4)C13—C141.381 (4)
C17—C161.406 (4)C13—H13A0.9300
C17—C181.471 (4)C14—H14A0.9300
C11—C81.537 (4)C3—H3B0.9300
C11—H11A0.9700
O1—Ni1—O589.72 (9)C8—C10—H10B109.7
O1—Ni1—N190.92 (10)H10A—C10—H10B108.2
O5—Ni1—N198.84 (10)O8—C22—C19109.1 (3)
O1—Ni1—N295.34 (9)O8—C22—H22A109.9
O5—Ni1—N291.56 (10)C19—C22—H22A109.9
N1—Ni1—N2167.90 (12)O8—C22—H22B109.9
O1—Ni1—O4170.66 (9)C19—C22—H22B109.9
O5—Ni1—O487.67 (9)H22A—C22—H22B108.3
N1—Ni1—O480.64 (11)N1—C8—C10115.0 (3)
N2—Ni1—O493.69 (10)N1—C8—C11106.9 (3)
O1—Ni1—O794.71 (9)C10—C8—C11108.4 (3)
O5—Ni1—O7169.10 (10)N1—C8—C9107.3 (3)
N1—Ni1—O791.05 (11)C10—C8—C9110.0 (3)
N2—Ni1—O778.14 (11)C11—C8—C9109.1 (3)
O4—Ni1—O789.45 (10)N2—C18—C17126.6 (3)
C7—N1—C8118.9 (3)N2—C18—H18A116.7
C7—N1—Ni1124.7 (2)C17—C18—H18A116.7
C8—N1—Ni1116.40 (19)C5—C6—C1119.5 (3)
C18—N2—C19121.2 (3)C5—C6—C7116.1 (3)
C18—N2—Ni1122.2 (2)C1—C6—C7124.4 (3)
C19—N2—Ni1116.0 (2)C4—C5—C6122.5 (4)
C21—O7—Ni1110.8 (2)C4—C5—H5A118.8
C21—O7—H7B109 (2)C6—C5—H5A118.8
Ni1—O7—H7B123 (2)N1—C7—C6126.6 (3)
C11—O4—Ni1110.07 (19)N1—C7—H7A116.7
C11—O4—H4B108 (2)C6—C7—H7A116.7
Ni1—O4—H4B121 (2)O7—C21—C19108.6 (3)
C1—O1—Ni1127.3 (2)O7—C21—H21A110.0
C12—O5—Ni1124.8 (2)C19—C21—H21A110.0
C10—O3—H3A115 (3)O7—C21—H21B110.0
C22—O8—H8A113 (3)C19—C21—H21B110.0
C9—O2—H2A106 (3)H21A—C21—H21B108.4
C20—O6—H6A111 (3)O2—C9—C8113.2 (3)
C23—O9—H9108 (3)O2—C9—H9A108.9
O9—C23—H23A109.5C8—C9—H9A108.9
O9—C23—H23B109.5O2—C9—H9B108.9
H23A—C23—H23B109.5C8—C9—H9B108.9
O9—C23—H23C109.5H9A—C9—H9B107.8
H23A—C23—H23C109.5C3—C2—C1121.8 (4)
H23B—C23—H23C109.5C3—C2—H2B119.1
O1—C1—C2119.9 (3)C1—C2—H2B119.1
O1—C1—C6123.3 (3)O5—C12—C17123.6 (3)
C2—C1—C6116.8 (3)O5—C12—C13118.4 (4)
C12—C17—C16120.3 (3)C17—C12—C13117.9 (3)
C12—C17—C18124.8 (3)O6—C20—C19111.5 (3)
C16—C17—C18114.7 (4)O6—C20—H20A109.3
O4—C11—C8112.4 (3)C19—C20—H20A109.3
O4—C11—H11A109.1O6—C20—H20B109.3
C8—C11—H11A109.1C19—C20—H20B109.3
O4—C11—H11B109.1H20A—C20—H20B108.0
C8—C11—H11B109.1C16—C15—C14116.5 (4)
H11A—C11—H11B107.9C16—C15—H15A121.8
N2—C19—C22114.3 (3)C14—C15—H15A121.8
N2—C19—C21104.8 (3)C5—C4—C3117.9 (4)
C22—C19—C21109.8 (3)C5—C4—H4A121.1
N2—C19—C20109.3 (3)C3—C4—H4A121.1
C22—C19—C20109.7 (3)C14—C13—C12120.5 (4)
C21—C19—C20108.6 (3)C14—C13—H13A119.7
C15—C16—C17122.6 (4)C12—C13—H13A119.7
C15—C16—H16A118.7C13—C14—C15122.3 (4)
C17—C16—H16A118.7C13—C14—H14A118.9
O3—C10—C8109.8 (3)C15—C14—H14A118.9
O3—C10—H10A109.7C2—C3—C4121.6 (4)
C8—C10—H10A109.7C2—C3—H3B119.2
O3—C10—H10B109.7C4—C3—H3B119.2
O1—Ni1—N1—C7−14.5 (3)C20—C19—C22—O861.9 (3)
O5—Ni1—N1—C7−104.4 (3)C7—N1—C8—C10−29.8 (4)
N2—Ni1—N1—C7106.7 (5)Ni1—N1—C8—C10149.3 (2)
O4—Ni1—N1—C7169.5 (3)C7—N1—C8—C11−150.2 (3)
O7—Ni1—N1—C780.2 (3)Ni1—N1—C8—C1128.9 (3)
O1—Ni1—N1—C8166.4 (2)C7—N1—C8—C992.9 (3)
O5—Ni1—N1—C876.6 (2)Ni1—N1—C8—C9−88.0 (3)
N2—Ni1—N1—C8−72.3 (5)O3—C10—C8—N1−49.7 (4)
O4—Ni1—N1—C8−9.6 (2)O3—C10—C8—C1169.9 (3)
O7—Ni1—N1—C8−98.8 (2)O3—C10—C8—C9−170.9 (2)
O1—Ni1—N2—C18−111.1 (3)O4—C11—C8—N1−40.6 (4)
O5—Ni1—N2—C18−21.2 (3)O4—C11—C8—C10−165.2 (3)
N1—Ni1—N2—C18128.1 (5)O4—C11—C8—C975.1 (3)
O4—Ni1—N2—C1866.5 (3)C19—N2—C18—C17179.0 (3)
O7—Ni1—N2—C18155.2 (3)Ni1—N2—C18—C178.9 (5)
O1—Ni1—N2—C1978.3 (2)C12—C17—C18—N28.3 (6)
O5—Ni1—N2—C19168.17 (19)C16—C17—C18—N2−176.3 (3)
N1—Ni1—N2—C19−42.5 (5)O1—C1—C6—C5179.3 (3)
O4—Ni1—N2—C19−104.1 (2)C2—C1—C6—C5−0.8 (5)
O7—Ni1—N2—C19−15.40 (19)O1—C1—C6—C7−2.8 (5)
O1—Ni1—O7—C21−108.8 (2)C2—C1—C6—C7177.1 (3)
O5—Ni1—O7—C214.9 (6)C1—C6—C5—C4−0.3 (5)
N1—Ni1—O7—C21160.2 (2)C7—C6—C5—C4−178.4 (3)
N2—Ni1—O7—C21−14.3 (2)C8—N1—C7—C6−174.6 (3)
O4—Ni1—O7—C2179.6 (2)Ni1—N1—C7—C66.4 (5)
O1—Ni1—O4—C11−39.2 (7)C5—C6—C7—N1−176.3 (3)
O5—Ni1—O4—C11−113.1 (2)C1—C6—C7—N15.7 (5)
N1—Ni1—O4—C11−13.7 (2)Ni1—O7—C21—C1939.6 (3)
N2—Ni1—O4—C11155.5 (2)N2—C19—C21—O7−50.3 (3)
O7—Ni1—O4—C1177.4 (2)C22—C19—C21—O7−173.5 (2)
O5—Ni1—O1—C1116.5 (3)C20—C19—C21—O766.4 (3)
N1—Ni1—O1—C117.7 (3)N1—C8—C9—O2−55.7 (3)
N2—Ni1—O1—C1−151.9 (3)C10—C8—C9—O270.0 (3)
O4—Ni1—O1—C142.8 (7)C11—C8—C9—O2−171.3 (3)
O7—Ni1—O1—C1−73.4 (3)O1—C1—C2—C3−179.2 (3)
O1—Ni1—O5—C12122.4 (2)C6—C1—C2—C31.0 (5)
N1—Ni1—O5—C12−146.7 (2)Ni1—O5—C12—C17−19.4 (4)
N2—Ni1—O5—C1227.1 (2)Ni1—O5—C12—C13162.8 (2)
O4—Ni1—O5—C12−66.6 (2)C16—C17—C12—O5−177.8 (3)
O7—Ni1—O5—C128.2 (6)C18—C17—C12—O5−2.7 (5)
Ni1—O1—C1—C2168.0 (2)C16—C17—C12—C13−0.1 (5)
Ni1—O1—C1—C6−12.2 (5)C18—C17—C12—C13175.0 (3)
Ni1—O4—C11—C833.7 (3)N2—C19—C20—O6−67.4 (3)
C18—N2—C19—C22−10.7 (4)C22—C19—C20—O658.7 (3)
Ni1—N2—C19—C22160.0 (2)C21—C19—C20—O6178.8 (3)
C18—N2—C19—C21−131.0 (3)C17—C16—C15—C140.2 (6)
Ni1—N2—C19—C2139.7 (3)C6—C5—C4—C31.3 (5)
C18—N2—C19—C20112.7 (3)O5—C12—C13—C14178.4 (3)
Ni1—N2—C19—C20−76.6 (3)C17—C12—C13—C140.6 (5)
C12—C17—C16—C15−0.3 (6)C12—C13—C14—C15−0.7 (6)
C18—C17—C16—C15−175.9 (3)C16—C15—C14—C130.3 (6)
N2—C19—C22—O8−174.9 (3)C1—C2—C3—C40.0 (6)
C21—C19—C22—O8−57.5 (3)C5—C4—C3—C2−1.2 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O5i0.829 (10)1.763 (11)2.587 (3)173 (4)
O7—H7B···O2i0.823 (10)2.019 (11)2.841 (4)177 (3)
O8—H8A···O1ii0.824 (10)1.795 (11)2.616 (3)174 (4)
O2—H2A···O3iii0.816 (10)1.895 (12)2.705 (3)172 (4)
O6—H6A···O8iv0.821 (10)1.936 (12)2.749 (4)171 (4)
O4—H4B···O90.813 (10)2.032 (12)2.831 (3)167 (3)
O9—H9···O6v0.818 (10)2.20 (2)2.931 (3)148 (4)
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O5i0.829 (10)1.763 (11)2.587 (3)173 (4)
O7—H7B···O2i0.823 (10)2.019 (11)2.841 (4)177 (3)
O8—H8A···O1ii0.824 (10)1.795 (11)2.616 (3)174 (4)
O2—H2A···O3iii0.816 (10)1.895 (12)2.705 (3)172 (4)
O6—H6A···O8iv0.821 (10)1.936 (12)2.749 (4)171 (4)
O4—H4B···O90.813 (10)2.032 (12)2.831 (3)167 (3)
O9—H9···O6v0.818 (10)2.20 (2)2.931 (3)148 (4)
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2.
references
References top

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Mackay, S., Gilmore, C. J., Edwards, C., Tremayne, M., Stuart, N. & Shankland, K. (1998). maXus. University of Glasgow, Scotland, Nonius BV, Delft, The Netherlands, and MacScience Co. Ltd,, Yokohama, Japan.

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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.