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

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ISSN: 2056-9890

Bis{2-formyl-4-methyl-6-[(tri-2-pyridyl­meth­yl)imino­meth­yl]phenolato}nickel(II)

aDepartment of Chemistry and Chemical Engineering, Binzhou University, Binzhou 256600, People's Republic of China, bResearch Center for Eco-Environmental Sciences of the Yellow River Delta, Binzhou University, Binzhou 256600, People's Republic of China, and cDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
*Correspondence e-mail: yanqiudang@163.com

(Received 19 January 2009; accepted 20 January 2009; online 28 January 2009)

The title compound, [Ni(C25H19N4O2)2], which was obtained by the reaction of nickel(II) perchlorate with 2,6-diformyl-4-methyl­phenol and (tri-2-pyridylmeth­yl)amine in methanol solution, is a discrete monometallic complex. The NiII atom is six-coordinated by the phenolate O, imine N and pyridine N atoms from two tridentate Schiff base ligands in a distorted NiN4O2 octa­hedral geometry. The dihedral angles between the noncoordinated pyridyl rings of each ligand are 72.95 (8) and 69.59 (7)°.

Related literature

For related structures, see: Arnold et al. (2003[Arnold, P. J., Davies, S. C., Durrant, M. C., Griffiths, D. V., Hughes, D. L. & Sharpe, P. C. (2003). Inorg. Chim. Acta, 348, 143-149.]); Cumming et al. (1977[Cumming, H. J., Hall, D. & Wright, C. E. (1977). Acta Cryst. B33, 1636-1638.]); Manonmani et al. (2001[Manonmani, J., Thirumuruhan, R., Kandaswamy, M., Narayanan, V., Raj, S. S. S., Ponnuswamy, M. N., Shanmugam, G. & Fun, H. K. (2001). Polyhedron, 20, 3039-3048.]); Parker et al. (2007[Parker, D., Davies, E. S., Wilson, C. & McMaster, J. (2007). Inorg. Chim. Acta, 360, 203-211.]); Li & Gao (2007[Li, Y.-H. & Gao, J. (2007). Acta Cryst. E63, o2291-o2292.]); Tian et al. (2007[Tian, L.-J., Yang, H.-J. & Ni, Z.-H. (2007). Acta Cryst. E63, m2812.]). For background, see: Borisova et al. (2007[Borisova, N. E., Reshetova, M. D. & Ustynyuk, Y. A. (2007). Chem. Rev. 107, 46-79.]); Bruckner et al. (2000[Bruckner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100-6106.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C25H19N4O2)2]

  • Mr = 873.59

  • Monoclinic, P 21 /n

  • a = 11.9592 (2) Å

  • b = 17.6301 (2) Å

  • c = 19.6633 (3) Å

  • β = 98.202 (1)°

  • V = 4103.44 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.53 mm−1

  • T = 295 (2) K

  • 0.22 × 0.16 × 0.04 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.892, Tmax = 0.979

  • 45290 measured reflections

  • 8063 independent reflections

  • 6167 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.095

  • S = 1.02

  • 8063 reflections

  • 570 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—N3 2.0210 (17)
Ni1—O2 2.0283 (13)
Ni1—N1 2.0318 (17)
Ni1—O1 2.0322 (13)
Ni1—N2 2.1084 (16)
Ni1—N4 2.1308 (16)

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.

Supporting information


Comment top

Nickel complexes with Schiff bases have received much attention in recent years due to their pharmacological and catalytic properties (Borisova et al., 2007; Bruckner et al., 2000). 2-(Tri-2-pyridylmethyliminomethyl)phenol is a potential N4O pentadentate Schiff base ligand and its complexes with copper(II) and nickel(II) have been reported (Arnold et al., 2003; Li & Gao, 2007; Tian et al., 2007). As a continuation of the work, the synthesis and structure of the title compound, (I), now are discussed.

In this mononuclear nickel complex, the environment around the central nickel atom is a distorted octahedron (Table 1) with the three axial bond angles being 173.34 (6), 168.45 (6) and 168.03 (6)°. The two Schiff base ligands are both tridentate and coordinated in a meridional fashion. Each ligand coordinates to the metal by an NN'O donor set via an imine N, one pyridine N and a phenolate O. The other two N atoms of the pyridine rings in each Schiff base ligand are distant from the metal. The meridional coordination of each ligand leads to cis orientations of the two coordinated pyridine rings and two phenolate rings, and the trans orientation of two imine N atoms. The Ni1—N2 and Ni1—N4 (pyridine) distances are appreciably longer than those for Ni1—N1 and Ni1—N3 (imine), which is agreement with those of azido{2-[(tri-2-pyridylmethylimino)methyl]phenolato}nickel(II) (Tian et al., 2007). The Ni1—O1 and Ni1—O2 distances are almost the same as those found in the six-coordinated NiN4O2 complexes such as [N,N'-bis(2-Salicylideneaminoethyl)ethylenediamine]nickel(II) (Cumming et al., 1977), {N,N'-bis[2-Hydroxy-3-(1-morpholinioylmethyl)-5-methylbenzylidene] triethylenetetraamine}nickel(II) (Manonmani et al., 2001), and bis{2,4-dibutyl-6-[2-(dimethylamino)ethyliminomethyl]phenolato}nickel(II) (Parker et al., 2007).

Related literature top

For related structures, see: Arnold et al. (2003); Cumming et al. (1977); Manonmani et al. (2001); Parker et al. (2007); Li & Gao (2007); Tian et al. (2007). For background, see: Borisova et al. (2007); Bruckner et al. (2000).

Experimental top

2,6-Diformyl-4-methylphenol (0.164 g, 1 mmol), tri-2-pyridylmethylamine (0.262 g, 1 mmol) and Ni(ClO4)2.6H2O (0.183 g, 0.5 mmol) were stirred in methanol (20 ml) for 20 min at room temperature, and then filtered. After keeping the filtrate in air for 3 d, green plates of (I) (yield 36%) were formed.

Refinement top

The H atoms were placed at calculated positions and refined in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic and formyl H atoms, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
Bis{2-formyl-4-methyl-6-[(tri-2-pyridylmethyl)iminomethyl]phenolato}nickel(II) top
Crystal data top
[Ni(C25H19N4O2)2]F(000) = 1816
Mr = 873.59Dx = 1.414 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5403 reflections
a = 11.9592 (2) Åθ = 2.4–24.2°
b = 17.6301 (2) ŵ = 0.53 mm1
c = 19.6633 (3) ÅT = 295 K
β = 98.202 (1)°Plate, green
V = 4103.44 (10) Å30.22 × 0.16 × 0.04 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
8063 independent reflections
Radiation source: fine-focus sealed tube6167 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1314
Tmin = 0.892, Tmax = 0.979k = 2121
45290 measured reflectionsl = 2424
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0424P)2 + 1.7711P]
where P = (Fo2 + 2Fc2)/3
8063 reflections(Δ/σ)max = 0.001
570 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Ni(C25H19N4O2)2]V = 4103.44 (10) Å3
Mr = 873.59Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.9592 (2) ŵ = 0.53 mm1
b = 17.6301 (2) ÅT = 295 K
c = 19.6633 (3) Å0.22 × 0.16 × 0.04 mm
β = 98.202 (1)°
Data collection top
Bruker APEX CCD
diffractometer
8063 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
6167 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.979Rint = 0.041
45290 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.02Δρmax = 0.29 e Å3
8063 reflectionsΔρmin = 0.29 e Å3
570 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
Ni10.84948 (2)0.210253 (13)0.347678 (13)0.02795 (8)
N10.75587 (14)0.17976 (9)0.25737 (8)0.0301 (4)
N20.73935 (15)0.12926 (9)0.38088 (9)0.0329 (4)
N30.94630 (14)0.22760 (9)0.43930 (8)0.0282 (4)
N40.98414 (15)0.13255 (9)0.34153 (8)0.0308 (4)
N50.45175 (18)0.17822 (13)0.26647 (13)0.0597 (6)
N60.68774 (17)0.01602 (10)0.22315 (10)0.0468 (5)
N71.13568 (17)0.31964 (10)0.49582 (10)0.0468 (5)
N81.02199 (16)0.10063 (10)0.52511 (9)0.0416 (5)
O10.93693 (12)0.28502 (8)0.29681 (7)0.0368 (3)
O20.74379 (12)0.29381 (8)0.36981 (7)0.0348 (3)
O31.15347 (16)0.43375 (10)0.23232 (11)0.0689 (6)
O40.50123 (18)0.44825 (13)0.37676 (11)0.0829 (7)
C11.0856 (2)0.38899 (13)0.24974 (14)0.0468 (6)
H11.06960.39230.29460.056*
C21.02772 (18)0.33079 (12)0.20596 (12)0.0378 (5)
C31.0438 (2)0.32684 (13)0.13762 (12)0.0444 (6)
H31.09530.35990.12210.053*
C40.9870 (2)0.27619 (14)0.09137 (12)0.0441 (6)
C51.0004 (2)0.27696 (17)0.01588 (13)0.0613 (7)
H5A0.96380.32110.00560.092*
H5B0.96660.23220.00590.092*
H5C1.07920.27810.01140.092*
C60.91057 (19)0.22805 (13)0.11659 (11)0.0411 (5)
H60.87270.19250.08680.049*
C70.88725 (18)0.23003 (12)0.18463 (11)0.0345 (5)
C80.94957 (17)0.28117 (11)0.23330 (11)0.0326 (5)
C90.79107 (18)0.18629 (12)0.19856 (11)0.0346 (5)
H90.75070.16040.16180.042*
C100.64618 (17)0.14184 (11)0.26192 (10)0.0320 (5)
C110.62185 (18)0.07697 (11)0.20947 (11)0.0340 (5)
C120.5402 (2)0.08074 (14)0.15287 (13)0.0496 (6)
H120.49710.12440.14380.059*
C130.5230 (2)0.01863 (17)0.10944 (14)0.0615 (7)
H130.46820.02010.07090.074*
C140.5873 (2)0.04440 (14)0.12396 (15)0.0580 (7)
H140.57650.08710.09600.070*
C150.6681 (2)0.04371 (14)0.18040 (15)0.0560 (7)
H150.71210.08690.18990.067*
C160.55105 (19)0.20156 (12)0.25089 (11)0.0359 (5)
C170.5635 (2)0.27178 (14)0.22305 (14)0.0537 (7)
H170.63350.28750.21280.064*
C180.4704 (3)0.31892 (16)0.21042 (15)0.0654 (8)
H180.47740.36650.19110.079*
C190.3696 (2)0.29620 (17)0.22595 (15)0.0641 (8)
H190.30640.32740.21830.077*
C200.3639 (2)0.22536 (19)0.25341 (17)0.0712 (9)
H200.29430.20890.26370.085*
C210.65235 (18)0.10801 (11)0.33457 (11)0.0343 (5)
C220.5709 (2)0.05736 (13)0.35058 (13)0.0469 (6)
H220.51170.04250.31730.056*
C230.5793 (2)0.02946 (14)0.41659 (13)0.0528 (7)
H230.52520.00390.42860.063*
C240.6686 (2)0.05143 (14)0.46456 (13)0.0498 (6)
H240.67550.03330.50940.060*
C250.7471 (2)0.10056 (12)0.44519 (12)0.0406 (5)
H250.80800.11470.47750.049*
C260.5755 (2)0.40153 (15)0.37765 (14)0.0555 (7)
H260.58800.38180.33550.067*
C270.64642 (19)0.37361 (12)0.43790 (12)0.0397 (5)
C280.6310 (2)0.39914 (13)0.50292 (13)0.0473 (6)
H280.57410.43430.50630.057*
C290.6956 (2)0.37501 (13)0.56237 (12)0.0456 (6)
C300.6744 (3)0.40074 (17)0.63294 (14)0.0672 (8)
H30A0.61290.43620.62830.101*
H30B0.74120.42470.65630.101*
H30C0.65580.35770.65900.101*
C310.78362 (19)0.32568 (12)0.55509 (11)0.0400 (5)
H310.82990.30970.59450.048*
C320.80654 (18)0.29870 (11)0.49148 (11)0.0328 (5)
C330.73323 (18)0.31936 (11)0.42974 (11)0.0324 (5)
C340.91051 (17)0.25733 (11)0.49200 (10)0.0317 (5)
H340.95590.25160.53420.038*
C351.06421 (17)0.19974 (11)0.44743 (10)0.0292 (4)
C361.09688 (17)0.15357 (11)0.51390 (10)0.0308 (4)
C371.1988 (2)0.16159 (13)0.55531 (12)0.0423 (5)
H371.24960.19890.54620.051*
C381.2248 (2)0.11334 (14)0.61061 (13)0.0509 (6)
H381.29350.11790.63920.061*
C391.1493 (2)0.05917 (13)0.62305 (13)0.0485 (6)
H391.16480.02630.66020.058*
C401.0494 (2)0.05458 (13)0.57885 (12)0.0485 (6)
H400.99790.01720.58690.058*
C411.13974 (18)0.27056 (11)0.44456 (11)0.0347 (5)
C421.2027 (2)0.28439 (15)0.39317 (13)0.0556 (7)
H421.20230.25020.35710.067*
C431.2670 (3)0.34972 (18)0.39518 (15)0.0684 (8)
H431.31120.35950.36090.082*
C441.2651 (2)0.39930 (15)0.44755 (15)0.0622 (8)
H441.30850.44330.45040.075*
C451.1978 (2)0.38298 (13)0.49609 (15)0.0566 (7)
H451.19490.41770.53140.068*
C461.07506 (18)0.14364 (11)0.38840 (10)0.0319 (5)
C471.1755 (2)0.10534 (13)0.38571 (12)0.0456 (6)
H471.23750.11380.41910.055*
C481.1829 (2)0.05449 (14)0.33312 (13)0.0524 (7)
H481.25020.02910.33010.063*
C491.0890 (2)0.04208 (12)0.28530 (12)0.0455 (6)
H491.09120.00760.24970.055*
C500.9919 (2)0.08158 (11)0.29106 (11)0.0379 (5)
H500.92850.07290.25870.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02992 (15)0.02702 (13)0.02723 (14)0.00083 (11)0.00523 (11)0.00027 (10)
N10.0293 (9)0.0294 (8)0.0318 (9)0.0025 (7)0.0051 (8)0.0010 (7)
N20.0370 (10)0.0295 (8)0.0331 (9)0.0010 (8)0.0082 (8)0.0003 (7)
N30.0271 (9)0.0276 (8)0.0298 (9)0.0016 (7)0.0039 (7)0.0004 (7)
N40.0369 (10)0.0272 (8)0.0290 (9)0.0003 (7)0.0073 (8)0.0014 (7)
N50.0427 (13)0.0609 (13)0.0803 (16)0.0051 (11)0.0246 (12)0.0028 (12)
N60.0482 (12)0.0378 (10)0.0534 (12)0.0048 (9)0.0034 (10)0.0051 (9)
N70.0505 (13)0.0360 (10)0.0544 (12)0.0035 (9)0.0088 (10)0.0049 (9)
N80.0421 (11)0.0403 (10)0.0407 (11)0.0063 (9)0.0006 (9)0.0052 (8)
O10.0417 (9)0.0339 (7)0.0361 (8)0.0063 (7)0.0099 (7)0.0008 (6)
O20.0379 (9)0.0335 (7)0.0332 (8)0.0065 (6)0.0057 (7)0.0001 (6)
O30.0640 (13)0.0591 (11)0.0865 (14)0.0264 (10)0.0211 (11)0.0078 (10)
O40.0741 (15)0.0912 (16)0.0831 (15)0.0470 (13)0.0100 (12)0.0144 (12)
C10.0406 (14)0.0413 (13)0.0606 (16)0.0032 (11)0.0139 (12)0.0087 (11)
C20.0312 (12)0.0379 (12)0.0451 (13)0.0029 (9)0.0081 (10)0.0082 (10)
C30.0356 (13)0.0496 (14)0.0504 (14)0.0025 (11)0.0138 (11)0.0159 (11)
C40.0397 (14)0.0563 (14)0.0388 (13)0.0061 (11)0.0138 (11)0.0096 (11)
C50.0645 (18)0.0784 (19)0.0451 (15)0.0028 (15)0.0225 (14)0.0079 (13)
C60.0400 (13)0.0480 (13)0.0359 (12)0.0049 (10)0.0077 (10)0.0020 (10)
C70.0336 (12)0.0367 (11)0.0335 (11)0.0006 (9)0.0057 (10)0.0037 (9)
C80.0304 (11)0.0326 (10)0.0355 (11)0.0045 (9)0.0069 (9)0.0080 (9)
C90.0353 (12)0.0356 (11)0.0327 (11)0.0023 (9)0.0038 (10)0.0010 (9)
C100.0303 (11)0.0309 (10)0.0347 (11)0.0048 (9)0.0047 (9)0.0023 (8)
C110.0327 (12)0.0337 (11)0.0358 (12)0.0055 (9)0.0062 (10)0.0022 (9)
C120.0487 (15)0.0461 (13)0.0507 (15)0.0044 (11)0.0036 (13)0.0072 (11)
C130.0613 (18)0.0700 (18)0.0501 (16)0.0103 (15)0.0030 (14)0.0194 (14)
C140.0682 (19)0.0455 (15)0.0621 (18)0.0089 (14)0.0153 (15)0.0226 (13)
C150.0656 (18)0.0377 (13)0.0667 (17)0.0044 (12)0.0166 (15)0.0106 (12)
C160.0360 (12)0.0374 (11)0.0339 (11)0.0006 (9)0.0039 (10)0.0059 (9)
C170.0390 (14)0.0523 (15)0.0699 (18)0.0051 (12)0.0080 (13)0.0138 (13)
C180.064 (2)0.0564 (16)0.074 (2)0.0173 (15)0.0054 (16)0.0168 (14)
C190.0514 (18)0.076 (2)0.0645 (18)0.0269 (15)0.0055 (15)0.0054 (15)
C200.0457 (17)0.084 (2)0.089 (2)0.0133 (15)0.0261 (16)0.0004 (18)
C210.0371 (13)0.0302 (10)0.0365 (12)0.0026 (9)0.0082 (10)0.0026 (9)
C220.0445 (15)0.0488 (13)0.0480 (14)0.0151 (11)0.0082 (12)0.0017 (11)
C230.0535 (16)0.0509 (14)0.0569 (16)0.0174 (12)0.0181 (14)0.0068 (12)
C240.0589 (17)0.0487 (14)0.0445 (14)0.0056 (12)0.0164 (13)0.0119 (11)
C250.0454 (14)0.0388 (12)0.0380 (12)0.0018 (10)0.0075 (11)0.0040 (10)
C260.0485 (16)0.0623 (16)0.0556 (16)0.0215 (13)0.0066 (13)0.0036 (13)
C270.0378 (13)0.0356 (11)0.0469 (13)0.0063 (10)0.0101 (11)0.0004 (10)
C280.0428 (14)0.0439 (13)0.0569 (16)0.0121 (11)0.0129 (12)0.0059 (11)
C290.0493 (15)0.0471 (13)0.0427 (13)0.0078 (11)0.0149 (12)0.0090 (11)
C300.077 (2)0.0749 (19)0.0530 (16)0.0255 (16)0.0197 (15)0.0155 (14)
C310.0406 (13)0.0445 (12)0.0356 (12)0.0033 (10)0.0074 (10)0.0047 (10)
C320.0322 (12)0.0323 (10)0.0347 (11)0.0015 (9)0.0078 (9)0.0020 (9)
C330.0316 (12)0.0285 (10)0.0383 (12)0.0012 (9)0.0090 (10)0.0006 (9)
C340.0326 (12)0.0330 (10)0.0291 (11)0.0012 (9)0.0032 (9)0.0012 (8)
C350.0273 (11)0.0321 (10)0.0280 (10)0.0028 (8)0.0037 (9)0.0021 (8)
C360.0321 (12)0.0283 (10)0.0320 (11)0.0033 (9)0.0047 (9)0.0021 (8)
C370.0359 (13)0.0397 (12)0.0489 (14)0.0025 (10)0.0024 (11)0.0058 (10)
C380.0475 (15)0.0483 (14)0.0518 (15)0.0030 (12)0.0109 (12)0.0037 (12)
C390.0596 (17)0.0418 (13)0.0420 (13)0.0083 (12)0.0001 (13)0.0094 (11)
C400.0584 (17)0.0410 (13)0.0457 (14)0.0079 (12)0.0057 (13)0.0104 (11)
C410.0325 (12)0.0326 (11)0.0381 (12)0.0012 (9)0.0020 (10)0.0035 (9)
C420.0593 (17)0.0626 (16)0.0478 (15)0.0202 (14)0.0175 (13)0.0089 (12)
C430.066 (2)0.081 (2)0.0605 (18)0.0323 (16)0.0190 (15)0.0057 (16)
C440.0618 (18)0.0476 (15)0.074 (2)0.0203 (13)0.0023 (16)0.0105 (14)
C450.0627 (18)0.0355 (13)0.0703 (18)0.0051 (12)0.0046 (15)0.0073 (12)
C460.0354 (12)0.0302 (10)0.0320 (11)0.0021 (9)0.0110 (10)0.0012 (8)
C470.0393 (14)0.0524 (14)0.0452 (14)0.0117 (11)0.0065 (11)0.0051 (11)
C480.0536 (17)0.0533 (15)0.0537 (16)0.0179 (12)0.0197 (14)0.0018 (12)
C490.0667 (18)0.0359 (12)0.0372 (13)0.0077 (11)0.0196 (13)0.0040 (10)
C500.0525 (15)0.0306 (11)0.0310 (11)0.0013 (10)0.0075 (11)0.0007 (9)
Geometric parameters (Å, º) top
Ni1—N32.0210 (17)C18—C191.346 (4)
Ni1—O22.0283 (13)C18—H180.9300
Ni1—N12.0318 (17)C19—C201.366 (4)
Ni1—O12.0322 (13)C19—H190.9300
Ni1—N22.1084 (16)C20—H200.9300
Ni1—N42.1308 (16)C21—C221.390 (3)
N1—C91.291 (2)C22—C231.378 (3)
N1—C101.486 (2)C22—H220.9300
N2—C211.335 (3)C23—C241.375 (4)
N2—C251.353 (3)C23—H230.9300
N3—C341.288 (2)C24—C251.371 (3)
N3—C351.480 (2)C24—H240.9300
N4—C461.336 (3)C25—H250.9300
N4—C501.352 (3)C26—C271.442 (3)
N5—C161.333 (3)C26—H260.9300
N5—C201.335 (4)C27—C281.392 (3)
N6—C111.337 (3)C27—C331.437 (3)
N6—C151.347 (3)C28—C291.373 (3)
N7—C411.335 (3)C28—H280.9300
N7—C451.341 (3)C29—C311.389 (3)
N8—C361.333 (3)C29—C301.515 (3)
N8—C401.336 (3)C30—H30A0.9600
O1—C81.281 (2)C30—H30B0.9600
O2—C331.285 (2)C30—H30C0.9600
O3—C11.216 (3)C31—C321.401 (3)
O4—C261.210 (3)C31—H310.9300
C1—C21.450 (3)C32—C331.439 (3)
C1—H10.9300C32—C341.440 (3)
C2—C31.386 (3)C34—H340.9300
C2—C81.439 (3)C35—C361.542 (3)
C3—C41.382 (3)C35—C461.545 (3)
C3—H30.9300C35—C411.547 (3)
C4—C61.390 (3)C36—C371.373 (3)
C4—C51.516 (3)C37—C381.381 (3)
C5—H5A0.9600C37—H370.9300
C5—H5B0.9600C38—C391.360 (3)
C5—H5C0.9600C38—H380.9300
C6—C71.405 (3)C39—C401.376 (3)
C6—H60.9300C39—H390.9300
C7—C81.442 (3)C40—H400.9300
C7—C91.443 (3)C41—C421.366 (3)
C9—H90.9300C42—C431.382 (4)
C10—C111.540 (3)C42—H420.9300
C10—C211.540 (3)C43—C441.353 (4)
C10—C161.543 (3)C43—H430.9300
C11—C121.373 (3)C44—C451.364 (4)
C12—C131.386 (3)C44—H440.9300
C12—H120.9300C45—H450.9300
C13—C141.358 (4)C46—C471.386 (3)
C13—H130.9300C47—C481.381 (3)
C14—C151.363 (4)C47—H470.9300
C14—H140.9300C48—C491.376 (4)
C15—H150.9300C48—H480.9300
C16—C171.370 (3)C49—C501.372 (3)
C17—C181.384 (4)C49—H490.9300
C17—H170.9300C50—H500.9300
N3—Ni1—O289.66 (6)C19—C20—H20117.9
N3—Ni1—N1173.34 (6)N2—C21—C22121.9 (2)
O2—Ni1—N195.57 (6)N2—C21—C10116.98 (17)
N3—Ni1—O194.07 (6)C22—C21—C10121.1 (2)
O2—Ni1—O190.84 (6)C23—C22—C21118.9 (2)
N1—Ni1—O189.98 (6)C23—C22—H22120.6
N3—Ni1—N297.48 (7)C21—C22—H22120.6
O2—Ni1—N289.40 (6)C24—C23—C22119.4 (2)
N1—Ni1—N278.51 (6)C24—C23—H23120.3
O1—Ni1—N2168.45 (6)C22—C23—H23120.3
N3—Ni1—N478.83 (6)C25—C24—C23118.9 (2)
O2—Ni1—N4168.03 (6)C25—C24—H24120.6
N1—Ni1—N496.14 (7)C23—C24—H24120.6
O1—Ni1—N486.73 (6)N2—C25—C24122.5 (2)
N2—Ni1—N495.32 (6)N2—C25—H25118.7
C9—N1—C10119.83 (18)C24—C25—H25118.7
C9—N1—Ni1123.35 (15)O4—C26—C27126.1 (3)
C10—N1—Ni1116.58 (12)O4—C26—H26117.0
C21—N2—C25118.38 (18)C27—C26—H26117.0
C21—N2—Ni1116.07 (13)C28—C27—C33120.7 (2)
C25—N2—Ni1125.48 (15)C28—C27—C26120.3 (2)
C34—N3—C35117.97 (17)C33—C27—C26119.0 (2)
C34—N3—Ni1124.40 (14)C29—C28—C27123.3 (2)
C35—N3—Ni1117.51 (12)C29—C28—H28118.3
C46—N4—C50117.99 (18)C27—C28—H28118.3
C46—N4—Ni1114.47 (12)C28—C29—C31116.7 (2)
C50—N4—Ni1126.93 (15)C28—C29—C30122.7 (2)
C16—N5—C20117.8 (2)C31—C29—C30120.7 (2)
C11—N6—C15117.2 (2)C29—C30—H30A109.5
C41—N7—C45117.6 (2)C29—C30—H30B109.5
C36—N8—C40117.5 (2)H30A—C30—H30B109.5
C8—O1—Ni1125.87 (13)C29—C30—H30C109.5
C33—O2—Ni1126.68 (13)H30A—C30—H30C109.5
O3—C1—C2125.0 (2)H30B—C30—H30C109.5
O3—C1—H1117.5C29—C31—C32123.5 (2)
C2—C1—H1117.5C29—C31—H31118.2
C3—C2—C8121.3 (2)C32—C31—H31118.2
C3—C2—C1119.4 (2)C31—C32—C33119.59 (19)
C8—C2—C1119.3 (2)C31—C32—C34116.4 (2)
C4—C3—C2123.2 (2)C33—C32—C34123.74 (18)
C4—C3—H3118.4O2—C33—C27120.2 (2)
C2—C3—H3118.4O2—C33—C32123.87 (18)
C3—C4—C6116.5 (2)C27—C33—C32115.92 (18)
C3—C4—C5121.9 (2)N3—C34—C32125.9 (2)
C6—C4—C5121.5 (2)N3—C34—H34117.1
C4—C5—H5A109.5C32—C34—H34117.1
C4—C5—H5B109.5N3—C35—C36112.89 (15)
H5A—C5—H5B109.5N3—C35—C46108.19 (16)
C4—C5—H5C109.5C36—C35—C46105.11 (15)
H5A—C5—H5C109.5N3—C35—C41106.29 (15)
H5B—C5—H5C109.5C36—C35—C41112.23 (17)
C4—C6—C7123.7 (2)C46—C35—C41112.17 (16)
C4—C6—H6118.2N8—C36—C37122.31 (19)
C7—C6—H6118.2N8—C36—C35114.50 (18)
C6—C7—C8119.54 (19)C37—C36—C35122.98 (18)
C6—C7—C9116.1 (2)C36—C37—C38119.0 (2)
C8—C7—C9123.95 (18)C36—C37—H37120.5
O1—C8—C2120.34 (19)C38—C37—H37120.5
O1—C8—C7123.94 (18)C39—C38—C37119.6 (2)
C2—C8—C7115.71 (18)C39—C38—H38120.2
N1—C9—C7126.0 (2)C37—C38—H38120.2
N1—C9—H9117.0C38—C39—C40117.8 (2)
C7—C9—H9117.0C38—C39—H39121.1
N1—C10—C11112.20 (16)C40—C39—H39121.1
N1—C10—C21107.70 (16)N8—C40—C39123.8 (2)
C11—C10—C21108.25 (16)N8—C40—H40118.1
N1—C10—C16108.91 (16)C39—C40—H40118.1
C11—C10—C16110.35 (17)N7—C41—C42121.8 (2)
C21—C10—C16109.36 (16)N7—C41—C35114.29 (18)
N6—C11—C12122.2 (2)C42—C41—C35123.9 (2)
N6—C11—C10114.37 (19)C41—C42—C43119.4 (2)
C12—C11—C10123.5 (2)C41—C42—H42120.3
C11—C12—C13119.1 (2)C43—C42—H42120.3
C11—C12—H12120.4C44—C43—C42119.4 (3)
C13—C12—H12120.4C44—C43—H43120.3
C14—C13—C12119.2 (3)C42—C43—H43120.3
C14—C13—H13120.4C43—C44—C45118.2 (2)
C12—C13—H13120.4C43—C44—H44120.9
C13—C14—C15118.5 (2)C45—C44—H44120.9
C13—C14—H14120.7N7—C45—C44123.7 (2)
C15—C14—H14120.7N7—C45—H45118.2
N6—C15—C14123.7 (2)C44—C45—H45118.2
N6—C15—H15118.1N4—C46—C47121.82 (19)
C14—C15—H15118.1N4—C46—C35117.70 (17)
N5—C16—C17121.5 (2)C47—C46—C35120.5 (2)
N5—C16—C10114.86 (19)C48—C47—C46119.6 (2)
C17—C16—C10123.5 (2)C48—C47—H47120.2
C16—C17—C18118.9 (2)C46—C47—H47120.2
C16—C17—H17120.5C49—C48—C47118.8 (2)
C18—C17—H17120.5C49—C48—H48120.6
C19—C18—C17120.3 (3)C47—C48—H48120.6
C19—C18—H18119.8C50—C49—C48118.7 (2)
C17—C18—H18119.8C50—C49—H49120.6
C18—C19—C20117.3 (3)C48—C49—H49120.6
C18—C19—H19121.3N4—C50—C49123.1 (2)
C20—C19—H19121.3N4—C50—H50118.5
N5—C20—C19124.2 (3)C49—C50—H50118.5
N5—C20—H20117.9
O2—Ni1—N1—C9116.19 (16)N5—C16—C17—C180.6 (4)
O1—Ni1—N1—C925.34 (17)C10—C16—C17—C18175.0 (2)
N2—Ni1—N1—C9155.57 (17)C16—C17—C18—C190.6 (4)
N4—Ni1—N1—C961.37 (17)C17—C18—C19—C200.8 (5)
O2—Ni1—N1—C1069.48 (13)C16—N5—C20—C190.8 (5)
O1—Ni1—N1—C10160.32 (13)C18—C19—C20—N50.9 (5)
N2—Ni1—N1—C1018.77 (13)C25—N2—C21—C220.4 (3)
N4—Ni1—N1—C10112.97 (13)Ni1—N2—C21—C22177.35 (16)
N3—Ni1—N2—C21173.56 (14)C25—N2—C21—C10179.95 (18)
O2—Ni1—N2—C2183.98 (14)Ni1—N2—C21—C103.0 (2)
N1—Ni1—N2—C2111.83 (14)N1—C10—C21—N211.5 (2)
O1—Ni1—N2—C217.3 (4)C11—C10—C21—N2133.05 (19)
N4—Ni1—N2—C21107.04 (14)C16—C10—C21—N2106.7 (2)
N3—Ni1—N2—C253.14 (17)N1—C10—C21—C22168.14 (19)
O2—Ni1—N2—C2592.72 (17)C11—C10—C21—C2246.6 (3)
N1—Ni1—N2—C25171.47 (18)C16—C10—C21—C2273.7 (2)
O1—Ni1—N2—C25176.0 (3)N2—C21—C22—C231.2 (3)
N4—Ni1—N2—C2576.27 (17)C10—C21—C22—C23179.1 (2)
O2—Ni1—N3—C3423.99 (16)C21—C22—C23—C240.9 (4)
O1—Ni1—N3—C34114.82 (16)C22—C23—C24—C250.1 (4)
N2—Ni1—N3—C3465.35 (16)C21—N2—C25—C240.7 (3)
N4—Ni1—N3—C34159.33 (17)Ni1—N2—C25—C24175.90 (17)
O2—Ni1—N3—C35160.07 (13)C23—C24—C25—N21.0 (4)
O1—Ni1—N3—C3569.24 (13)O4—C26—C27—C281.5 (4)
N2—Ni1—N3—C35110.59 (13)O4—C26—C27—C33178.3 (3)
N4—Ni1—N3—C3516.61 (12)C33—C27—C28—C290.1 (4)
N3—Ni1—N4—C4614.76 (13)C26—C27—C28—C29179.9 (2)
O2—Ni1—N4—C461.5 (4)C27—C28—C29—C313.4 (4)
N1—Ni1—N4—C46169.66 (13)C27—C28—C29—C30177.3 (2)
O1—Ni1—N4—C4680.04 (13)C28—C29—C31—C321.8 (4)
N2—Ni1—N4—C46111.36 (14)C30—C29—C31—C32178.9 (2)
N3—Ni1—N4—C50174.48 (17)C29—C31—C32—C333.1 (3)
O2—Ni1—N4—C50169.3 (2)C29—C31—C32—C34170.9 (2)
N1—Ni1—N4—C501.09 (17)Ni1—O2—C33—C27173.70 (14)
O1—Ni1—N4—C5090.72 (16)Ni1—O2—C33—C328.2 (3)
N2—Ni1—N4—C5077.88 (17)C28—C27—C33—O2177.1 (2)
N3—Ni1—O1—C8150.46 (16)C26—C27—C33—O23.1 (3)
O2—Ni1—O1—C8119.82 (16)C28—C27—C33—C324.7 (3)
N1—Ni1—O1—C824.24 (16)C26—C27—C33—C32175.1 (2)
N2—Ni1—O1—C828.7 (4)C31—C32—C33—O2175.76 (19)
N4—Ni1—O1—C871.91 (16)C34—C32—C33—O210.7 (3)
N3—Ni1—O2—C3321.03 (16)C31—C32—C33—C276.1 (3)
N1—Ni1—O2—C33154.85 (16)C34—C32—C33—C27167.43 (19)
O1—Ni1—O2—C33115.09 (16)C35—N3—C34—C32168.85 (18)
N2—Ni1—O2—C3376.46 (16)Ni1—N3—C34—C3215.2 (3)
N4—Ni1—O2—C3337.0 (4)C31—C32—C34—N3179.5 (2)
O3—C1—C2—C33.9 (4)C33—C32—C34—N36.8 (3)
O3—C1—C2—C8179.7 (2)C34—N3—C35—C3644.9 (2)
C8—C2—C3—C40.2 (3)Ni1—N3—C35—C36131.33 (14)
C1—C2—C3—C4176.1 (2)C34—N3—C35—C46160.76 (17)
C2—C3—C4—C60.2 (3)Ni1—N3—C35—C4615.45 (19)
C2—C3—C4—C5175.7 (2)C34—N3—C35—C4178.6 (2)
C3—C4—C6—C71.6 (3)Ni1—N3—C35—C41105.21 (15)
C5—C4—C6—C7173.8 (2)C40—N8—C36—C370.0 (3)
C4—C6—C7—C83.8 (3)C40—N8—C36—C35174.74 (19)
C4—C6—C7—C9168.7 (2)N3—C35—C36—N847.8 (2)
Ni1—O1—C8—C2170.29 (14)C46—C35—C36—N869.9 (2)
Ni1—O1—C8—C711.2 (3)C41—C35—C36—N8167.90 (17)
C3—C2—C8—O1179.1 (2)N3—C35—C36—C37137.5 (2)
C1—C2—C8—O14.6 (3)C46—C35—C36—C37104.8 (2)
C3—C2—C8—C72.3 (3)C41—C35—C36—C3717.4 (3)
C1—C2—C8—C7174.02 (19)N8—C36—C37—C380.1 (3)
C6—C7—C8—O1177.48 (19)C35—C36—C37—C38174.5 (2)
C9—C7—C8—O110.6 (3)C36—C37—C38—C390.1 (4)
C6—C7—C8—C23.9 (3)C37—C38—C39—C400.5 (4)
C9—C7—C8—C2168.02 (19)C36—N8—C40—C390.5 (4)
C10—N1—C9—C7171.24 (19)C38—C39—C40—N80.7 (4)
Ni1—N1—C9—C714.6 (3)C45—N7—C41—C421.3 (4)
C6—C7—C9—N1179.3 (2)C45—N7—C41—C35179.0 (2)
C8—C7—C9—N18.5 (3)N3—C35—C41—N763.8 (2)
C9—N1—C10—C1133.8 (3)C36—C35—C41—N760.0 (2)
Ni1—N1—C10—C11140.70 (14)C46—C35—C41—N7178.10 (19)
C9—N1—C10—C21152.88 (18)N3—C35—C41—C42113.8 (2)
Ni1—N1—C10—C2121.66 (19)C36—C35—C41—C42122.3 (2)
C9—N1—C10—C1688.6 (2)C46—C35—C41—C424.2 (3)
Ni1—N1—C10—C1696.83 (16)N7—C41—C42—C432.1 (4)
C15—N6—C11—C122.7 (3)C35—C41—C42—C43179.6 (2)
C15—N6—C11—C10177.8 (2)C41—C42—C43—C440.9 (5)
N1—C10—C11—N670.4 (2)C42—C43—C44—C450.9 (5)
C21—C10—C11—N648.3 (2)C41—N7—C45—C440.7 (4)
C16—C10—C11—N6167.90 (18)C43—C44—C45—N71.8 (4)
N1—C10—C11—C12109.1 (2)C50—N4—C46—C470.8 (3)
C21—C10—C11—C12132.2 (2)Ni1—N4—C46—C47170.80 (16)
C16—C10—C11—C1212.6 (3)C50—N4—C46—C35177.78 (17)
N6—C11—C12—C132.0 (4)Ni1—N4—C46—C3510.6 (2)
C10—C11—C12—C13178.6 (2)N3—C35—C46—N42.4 (2)
C11—C12—C13—C140.0 (4)C36—C35—C46—N4123.30 (18)
C12—C13—C14—C151.1 (4)C41—C35—C46—N4114.48 (19)
C11—N6—C15—C141.5 (4)N3—C35—C46—C47176.19 (18)
C13—C14—C15—N60.3 (4)C36—C35—C46—C4755.3 (2)
C20—N5—C16—C170.7 (4)C41—C35—C46—C4766.9 (2)
C20—N5—C16—C10175.3 (2)N4—C46—C47—C480.4 (3)
N1—C10—C16—N5167.85 (19)C35—C46—C47—C48179.0 (2)
C11—C10—C16—N568.6 (2)C46—C47—C48—C491.3 (4)
C21—C10—C16—N550.4 (2)C47—C48—C49—C501.0 (4)
N1—C10—C16—C1716.3 (3)C46—N4—C50—C491.2 (3)
C11—C10—C16—C17107.3 (2)Ni1—N4—C50—C49169.31 (16)
C21—C10—C16—C17133.7 (2)C48—C49—C50—N40.2 (3)

Experimental details

Crystal data
Chemical formula[Ni(C25H19N4O2)2]
Mr873.59
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)11.9592 (2), 17.6301 (2), 19.6633 (3)
β (°) 98.202 (1)
V3)4103.44 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.53
Crystal size (mm)0.22 × 0.16 × 0.04
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.892, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
45290, 8063, 6167
Rint0.041
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.095, 1.02
No. of reflections8063
No. of parameters570
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.29

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top
Ni1—N32.0210 (17)Ni1—O12.0322 (13)
Ni1—O22.0283 (13)Ni1—N22.1084 (16)
Ni1—N12.0318 (17)Ni1—N42.1308 (16)
 

Acknowledgements

This work was supported by the Postdoctoral Innovation Project of Shandong Province (grant no. 200702021), the Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education (grant No. 200707) and Binzhou University University (grant No. BZXYQNLG200820).

References

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