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Acta Cryst. (2007). E63, m1999-m2000    [ doi:10.1107/S1600536807030498 ]

Bis(dimethylformamide-2[kappa]O)bis[[mu]-1-(2-oxidobenzoyl)-2-(phenoxyacetyl)hydrazine(3-)]-1[kappa]3O,N,O':2[kappa]2N,O'';2[kappa]2N,O'':3[kappa]3O,N,O'-dipyridine-1[kappa]N,3[kappa]N-trinickel(II)

Y. Zhao, J.-H. Luo, X.-H. Huang, C.-C. Huang and D.-S. Liu

Abstract top

The trinuclear nickel(II) title compound, [Ni3(C15H12N2O4)2(C5H5N)2(C3H6NO)2], possesses a crystallographically imposed centre of symmetry. The central Ni atom adopts an axially elongated octahedral geometry, involving two N and two O atoms from two phenoxyacetylsalicylhydrazidate ligands in the equatorial plane and two O atoms from two dimethylformamide molecules in the axial positions. The inversion-related outer Ni atoms have square-planar coordination environments provided by two O atoms and one N atom of a phenoxyacetylsalicylhydrazidate ligand and by the N atom of a pyridine molecule. The shortest metal-metal separation is 4.6038 (11) Å. The molecular structure is stabilized by intramolecular C-H...O hydrogen-bonding interactions.

Comment top

Hydrazide and its analogues have found practical applications in catalysis (Chatterjee & Mitra, 1999; Chatterjee et al., 2000; Kureshy et al., 2000) and in biochemistry (Belicchi Ferrari et al., 2000; Shi et al., 2001). N-Acylsalicylhydrazides, which contain several donor atoms, are strong chelating agents and are particularly well suited for the preparation of multinuclear complexes. We report here the synthesis and crystal structure of a new trinuclear nickel(II) complex, (I), containing the N-phenoxyacetylsalicylhydrazidate ligand.

The trinuclear nickel(II) complex possesses a crystallographycally imposed centre of symmetry. In the molecule, the central nickel atom Ni2 (Fig.1) has an axially elongated octahedral coordination of Ni(ON)(ON)(O)(O) type. The Ni2—O2 and Ni2—N2 bond distances at the equatorial plane (2.007 (3) and 2.047 (3) Å respectively) are shorter than the corresponding bond lengths in similar nickel(II) complexes (Yang et al., 2003; Yang & Lin, 2005; Butcher et al., 1981; Bermejo et al., 1999). The O atoms of the two dimethylformamide molecules occupy the axial positions at longer distances [Ni2—O5 = 2.147 (3) Å]. The outer Ni atoms (Ni1, Ni1A) adopt a square-planar geometry. The Ni—N(hydrazide) and Ni—N(py) bond distances are 1.838 (4) and 1.940 (1) Å, respectively. The Ni—O(carbonyl) distances are 1.814 (36) and 1.854 (38) Å, respectively. The Ni1···Ni2 distance is 4.6038 (11) Å, whereas the Ni1···Ni1A separation is 9.208 (2) Å, which is in good agreement with the corresponding values [9.2030 (8) − 9.1876 (9) Å] reported for bis[µ-(N-butylsalicylhydrazidate)(pyridine)nickel(II)]bispyridinenickel(II) (Yang et al., 2003) and shorter than that found in bis(µ2-N'-benzoyl-2-oxybenzoylhydrazidato)-bis(dimethylformamide)- dipyridine-trinickel(ii) [9.3038 (7) Å; Yang & Lin, 2005). The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For general background, see: Belicchi Ferrari et al. (2000); Chatterjee & Mitra (1999); Chatterjee et al. (2000); Kureshy et al. (2000); Shi et al. (2001). For related structures, see: Bermejo et al. (1999); Butcher et al. (1981); Yang et al. (2003); Yang & Lin (2005).

Experimental top

Two drops of pyridine were added to a solution of N-phenoxyacetylsalicylhydrazide (0.0286 g, 0.1 mmol) and NiCl2·6H2O (0.0475 g, 0.2 mmol) in ethanol (3 ml), chloroform (7 ml) and DMF (2 ml). The resulting red solution was stirred for 2 h and then filtered. Red crystals suitable for X-ray analysis were obtained after 6 days on slow evaporation of the solvent.

Refinement top

All H atoms were placed in idealized positions an refined using the riding-model approximation, with C—H = 0.93–0.97 Å, and with Uiso (H) = 1.2Ueq(C) or 1.5 Ueq(C) for the methyl groups.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the title compound with 30% probability displacement ellipsoids. H atoms have been omitted for clarity. [symmetry code: (A) 1/2 − x, 3/2 − y, 1 − z]
Bis(dimethylformamide-2κO)bis[µ-1-(2-oxidobenzoyl)-2- (phenoxyacetyl)hydrazine(3-)]- 1κ3O,N,O':2κ2N,O'';2κ2N,O'':3κ3O,N,O'-dipyridine-1κN,3κN- trinickel(II) top
Crystal data top
[Ni3(C15H12N2O4)2(C5H5N)2(C3H6NO)2]F000 = 2168
Mr = 1046.98Dx = 1.510 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 13455 reflections
a = 28.646 (6) Åθ = 3.1–27.5º
b = 8.2490 (16) ŵ = 1.28 mm−1
c = 21.176 (4) ÅT = 298 (2) K
β = 112.98 (3)ºBlock, red
V = 4606.8 (19) Å30.21 × 0.18 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer		3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Monochromator: graphiteθmax = 27.5º
T = 298(2) Kθmin = 3.1º
ω scansh = −37→35
Absorption correction: nonek = −10→10
21350 measured reflectionsl = −27→27
5266 independent 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)] = 0.060H-atom parameters constrained
wR(F2) = 0.129  w = 1/[σ2(Fo2) + (0.008P)2 + 4.5359P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5266 reflectionsΔρmax = 0.50 e Å−3
306 parametersΔρmin = −0.64 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni3(C15H12N2O4)2(C5H5N)2(C3H6NO)2]V = 4606.8 (19) Å3
Mr = 1046.98Z = 4
Monoclinic, C2/cMo Kα
a = 28.646 (6) ŵ = 1.28 mm−1
b = 8.2490 (16) ÅT = 298 (2) K
c = 21.176 (4) Å0.21 × 0.18 × 0.18 mm
β = 112.98 (3)º
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer		5266 independent reflections
Absorption correction: none3189 reflections with I > 2σ(I)
21350 measured reflectionsRint = 0.065
Refinement top
R[F2 > 2σ(F2)] = 0.060306 parameters
wR(F2) = 0.129H-atom parameters constrained
S = 1.00Δρmax = 0.50 e Å−3
5266 reflectionsΔρmin = −0.64 e Å−3
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
Ni10.19205 (3)0.36882 (8)0.32794 (3)0.0538 (2)
Ni20.25000.75000.50000.0429 (2)
O10.13443 (13)0.4435 (4)0.26024 (17)0.0628 (10)
O20.18921 (12)0.8037 (4)0.41488 (14)0.0496 (8)
O30.25040 (12)0.2981 (4)0.39945 (15)0.0520 (8)
O40.35544 (13)0.3998 (4)0.49849 (16)0.0593 (9)
O50.29860 (14)0.8574 (4)0.45592 (17)0.0581 (9)
N10.20072 (14)0.5505 (4)0.38186 (18)0.0451 (9)
N20.24345 (14)0.5421 (4)0.44438 (17)0.0443 (9)
N30.18937 (17)0.1722 (5)0.2764 (2)0.0567 (11)
N40.37718 (18)0.9207 (5)0.4632 (2)0.0657 (12)
C10.11199 (19)0.5850 (6)0.2586 (2)0.0547 (13)
C20.12931 (17)0.7048 (6)0.3092 (2)0.0480 (11)
C30.10198 (19)0.8496 (7)0.3000 (3)0.0610 (14)
H30.11350.92940.33360.073*
C40.0593 (2)0.8768 (8)0.2436 (3)0.0835 (19)
H40.04200.97460.23850.100*
C50.0417 (2)0.7597 (8)0.1943 (3)0.087 (2)
H50.01200.77670.15590.105*
C60.0679 (2)0.6173 (8)0.2014 (3)0.0718 (16)
H60.05580.53980.16690.086*
C70.17486 (18)0.6884 (5)0.3720 (2)0.0447 (11)
C80.26588 (18)0.4049 (5)0.4479 (2)0.0439 (11)
C90.31135 (18)0.3611 (6)0.5110 (2)0.0493 (11)
H9B0.31120.42170.55020.059*
H9A0.31090.24630.52080.059*
C100.40053 (19)0.3535 (6)0.5476 (3)0.0546 (12)
C110.4439 (2)0.4055 (8)0.5393 (3)0.0760 (17)
H110.44090.46890.50160.091*
C120.4915 (3)0.3640 (9)0.5867 (4)0.094 (2)
H120.52010.40190.58080.113*
C130.4971 (3)0.2704 (9)0.6407 (4)0.091 (2)
H130.52930.24210.67190.109*
C140.4558 (3)0.2182 (8)0.6493 (3)0.0812 (18)
H140.45980.15300.68690.097*
C150.4065 (2)0.2583 (7)0.6035 (3)0.0648 (14)
H150.37850.22100.61090.078*
C160.2155 (2)0.0391 (6)0.3074 (3)0.0657 (15)
H160.23270.03960.35480.079*
C170.2178 (3)−0.0952 (7)0.2721 (3)0.0758 (17)
H170.2363−0.18500.29510.091*
C180.1931 (3)−0.0984 (8)0.2031 (4)0.087 (2)
H180.1942−0.19020.17820.105*
C190.1673 (3)0.0321 (9)0.1715 (3)0.095 (2)
H190.15120.03340.12390.114*
C200.1642 (3)0.1681 (8)0.2097 (3)0.086 (2)
H200.14420.25600.18750.104*
C210.3443 (2)0.8379 (7)0.4809 (3)0.0626 (14)
H21A0.35710.75950.51490.075*
C220.4316 (3)0.8982 (10)0.4983 (4)0.109 (3)
H22A0.43830.82000.53430.163*
H22B0.44720.99960.51750.163*
H22C0.44530.86020.46620.163*
C230.3596 (3)1.0451 (7)0.4122 (3)0.0814 (18)
H23A0.36441.01110.37170.122*
H23B0.37851.14280.42960.122*
H23C0.32431.06500.40110.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0654 (4)0.0466 (4)0.0479 (4)−0.0014 (3)0.0205 (3)−0.0051 (3)
Ni20.0505 (5)0.0389 (4)0.0367 (4)0.0024 (4)0.0142 (4)−0.0023 (4)
O10.062 (2)0.058 (2)0.053 (2)0.0038 (19)0.0064 (17)−0.0095 (17)
O20.062 (2)0.0417 (17)0.0393 (16)0.0069 (16)0.0136 (15)−0.0028 (14)
O30.064 (2)0.0437 (17)0.0460 (17)0.0045 (16)0.0189 (16)−0.0048 (15)
O40.059 (2)0.067 (2)0.0518 (19)0.0059 (19)0.0218 (17)0.0145 (18)
O50.066 (2)0.057 (2)0.054 (2)−0.0014 (19)0.0260 (18)0.0030 (17)
N10.048 (2)0.044 (2)0.0387 (19)0.0011 (18)0.0132 (17)−0.0026 (17)
N20.056 (2)0.039 (2)0.0330 (18)0.0046 (19)0.0130 (17)−0.0024 (16)
N30.072 (3)0.051 (2)0.052 (2)−0.008 (2)0.030 (2)−0.008 (2)
N40.062 (3)0.059 (3)0.084 (3)0.001 (2)0.037 (3)0.003 (2)
C10.055 (3)0.055 (3)0.049 (3)−0.005 (3)0.014 (2)−0.002 (2)
C20.043 (3)0.053 (3)0.045 (2)0.000 (2)0.014 (2)0.002 (2)
C30.052 (3)0.062 (3)0.059 (3)0.006 (3)0.011 (3)−0.007 (3)
C40.068 (4)0.075 (4)0.084 (4)0.024 (3)0.004 (3)0.001 (4)
C50.065 (4)0.086 (5)0.076 (4)0.008 (4)−0.011 (3)−0.012 (4)
C60.058 (3)0.077 (4)0.061 (3)−0.006 (3)0.002 (3)−0.012 (3)
C70.054 (3)0.043 (2)0.041 (2)0.004 (2)0.022 (2)0.002 (2)
C80.053 (3)0.042 (2)0.040 (2)0.000 (2)0.021 (2)0.003 (2)
C90.063 (3)0.045 (3)0.042 (2)0.008 (2)0.023 (2)0.005 (2)
C100.055 (3)0.053 (3)0.058 (3)0.006 (3)0.023 (3)0.000 (3)
C110.062 (4)0.080 (4)0.090 (4)−0.002 (3)0.035 (3)0.013 (4)
C120.061 (4)0.092 (5)0.127 (6)−0.004 (4)0.034 (4)−0.007 (5)
C130.069 (4)0.080 (5)0.103 (5)0.011 (4)0.011 (4)−0.010 (4)
C140.074 (4)0.083 (4)0.073 (4)0.014 (4)0.013 (3)0.009 (3)
C150.055 (3)0.075 (4)0.061 (3)0.014 (3)0.020 (3)0.009 (3)
C160.085 (4)0.051 (3)0.066 (3)−0.003 (3)0.035 (3)−0.004 (3)
C170.102 (5)0.058 (3)0.082 (4)−0.004 (3)0.051 (4)−0.016 (3)
C180.111 (6)0.071 (4)0.096 (5)−0.017 (4)0.059 (4)−0.034 (4)
C190.125 (6)0.084 (5)0.072 (4)−0.003 (5)0.033 (4)−0.019 (4)
C200.122 (6)0.073 (4)0.056 (3)−0.023 (4)0.026 (4)−0.021 (3)
C210.075 (4)0.055 (3)0.063 (3)0.010 (3)0.032 (3)0.005 (3)
C220.078 (5)0.107 (6)0.147 (7)0.007 (4)0.051 (5)0.019 (5)
C230.105 (5)0.066 (4)0.088 (4)−0.007 (4)0.054 (4)0.007 (3)
Geometric parameters (Å, °) top
Ni1—O11.820 (3)C5—H50.9300
Ni1—N11.841 (4)C6—H60.9300
Ni1—O31.858 (3)C8—C91.502 (6)
Ni1—N31.939 (4)C9—H9B0.9700
Ni2—O2i2.007 (3)C9—H9A0.9700
Ni2—O22.007 (3)C10—C151.374 (7)
Ni2—N22.047 (3)C10—C111.388 (7)
Ni2—N2i2.047 (3)C11—C121.384 (8)
Ni2—O52.147 (4)C11—H110.9300
Ni2—O5i2.147 (4)C12—C131.337 (9)
O1—C11.326 (6)C12—H120.9300
O2—C71.267 (5)C13—C141.336 (9)
O3—C81.292 (5)C13—H130.9300
O4—C101.359 (6)C14—C151.405 (7)
O4—C91.425 (6)C14—H140.9300
O5—C211.215 (6)C15—H150.9300
N1—C71.329 (5)C16—C171.353 (7)
N1—N21.411 (5)C16—H160.9300
N2—C81.289 (5)C17—C181.352 (8)
N3—C201.313 (6)C17—H170.9300
N3—C161.346 (6)C18—C191.330 (9)
N4—C211.332 (7)C18—H180.9300
N4—C231.431 (7)C19—C201.406 (8)
N4—C221.453 (7)C19—H190.9300
C1—C61.392 (7)C20—H200.9300
C1—C21.399 (6)C21—H21A0.9300
C2—C31.399 (7)C22—H22A0.9600
C2—C71.462 (6)C22—H22B0.9600
C3—C41.354 (7)C22—H22C0.9600
C3—H30.9300C23—H23A0.9600
C4—C51.366 (8)C23—H23B0.9600
C4—H40.9300C23—H23C0.9600
C5—C61.370 (8)
O1—Ni1—N194.27 (16)N1—C7—C2117.8 (4)
O1—Ni1—O3177.75 (15)N2—C8—O3123.0 (4)
N1—Ni1—O383.66 (15)N2—C8—C9120.1 (4)
O1—Ni1—N390.88 (17)O3—C8—C9116.9 (4)
N1—Ni1—N3174.67 (18)O4—C9—C8107.7 (4)
O3—Ni1—N391.21 (16)O4—C9—H9B110.2
O2i—Ni2—O2180.00 (17)C8—C9—H9B110.2
O2i—Ni2—N2100.61 (13)O4—C9—H9A110.2
O2—Ni2—N279.39 (13)C8—C9—H9A110.2
O2i—Ni2—N2i79.39 (13)H9B—C9—H9A108.5
O2—Ni2—N2i100.61 (13)O4—C10—C15125.6 (5)
N2—Ni2—N2i180.000 (1)O4—C10—C11116.5 (5)
O2i—Ni2—O589.95 (14)C15—C10—C11117.9 (5)
O2—Ni2—O590.05 (14)C12—C11—C10120.6 (6)
N2—Ni2—O591.43 (14)C12—C11—H11119.7
N2i—Ni2—O588.57 (14)C10—C11—H11119.7
O2i—Ni2—O5i90.05 (14)C13—C12—C11121.3 (7)
O2—Ni2—O5i89.95 (14)C13—C12—H12119.4
N2—Ni2—O5i88.57 (14)C11—C12—H12119.4
N2i—Ni2—O5i91.43 (14)C14—C13—C12119.0 (7)
O5—Ni2—O5i180.00 (13)C14—C13—H13120.5
C1—O1—Ni1126.9 (3)C12—C13—H13120.5
C7—O2—Ni2113.7 (3)C13—C14—C15122.3 (6)
C8—O3—Ni1110.7 (3)C13—C14—H14118.9
C10—O4—C9116.2 (4)C15—C14—H14118.9
C21—O5—Ni2121.8 (4)C10—C15—C14118.9 (6)
C7—N1—N2114.5 (4)C10—C15—H15120.5
C7—N1—Ni1131.9 (3)C14—C15—H15120.5
N2—N1—Ni1113.6 (3)N3—C16—C17122.4 (6)
C8—N2—N1109.1 (3)N3—C16—H16118.8
C8—N2—Ni2140.4 (3)C17—C16—H16118.8
N1—N2—Ni2110.5 (3)C18—C17—C16119.7 (6)
C20—N3—C16118.1 (5)C18—C17—H17120.1
C20—N3—Ni1120.8 (4)C16—C17—H17120.1
C16—N3—Ni1121.0 (3)C19—C18—C17118.8 (6)
C21—N4—C23120.1 (5)C19—C18—H18120.6
C21—N4—C22121.8 (5)C17—C18—H18120.6
C23—N4—C22117.9 (5)C18—C19—C20120.3 (6)
O1—C1—C6117.2 (5)C18—C19—H19119.9
O1—C1—C2125.3 (4)C20—C19—H19119.9
C6—C1—C2117.4 (5)N3—C20—C19120.6 (7)
C1—C2—C3119.0 (4)N3—C20—H20119.7
C1—C2—C7123.7 (4)C19—C20—H20119.7
C3—C2—C7117.2 (4)O5—C21—N4124.7 (5)
C4—C3—C2121.9 (5)O5—C21—H21A117.6
C4—C3—H3119.1N4—C21—H21A117.6
C2—C3—H3119.1N4—C22—H22A109.5
C3—C4—C5119.6 (6)N4—C22—H22B109.5
C3—C4—H4120.2H22A—C22—H22B109.5
C5—C4—H4120.2N4—C22—H22C109.5
C4—C5—C6120.0 (5)H22A—C22—H22C109.5
C4—C5—H5120.0H22B—C22—H22C109.5
C6—C5—H5120.0N4—C23—H23A109.5
C5—C6—C1122.2 (5)N4—C23—H23B109.5
C5—C6—H6118.9H23A—C23—H23B109.5
C1—C6—H6118.9N4—C23—H23C109.5
O2—C7—N1121.7 (4)H23A—C23—H23C109.5
O2—C7—C2120.5 (4)H23B—C23—H23C109.5
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.932.412.749 (5)101
C16—H16···O30.932.312.800 (6)113
C20—H20···O10.932.282.783 (8)114
C23—H23C···O50.962.342.752 (9)105
C9—H9B···O2i0.972.383.183 (6)139
C21—H21A···O2i0.932.402.968 (8)119
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.932.412.749 (5)101
C16—H16···O30.932.312.800 (6)113
C20—H20···O10.932.282.783 (8)114
C23—H23C···O50.962.342.752 (9)105
C9—H9B···O2i0.972.383.183 (6)139
C21—H21A···O2i0.932.402.968 (8)119
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.
references
References top

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