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Acta Cryst. (2007). E63, m2426    [ doi:10.1107/S1600536807041505 ]

{1-[2-(Piperidin-1-yl)ethyliminomethyl]-2-naphtholato}thiocyanatonickel(II)

Y.-P. Diao, K. Li, S.-S. Huang, L. Lu and K.-X. Liu

Abstract top

In the title mononuclear nickel(II) complex, [Ni(C18H21N2O)(NCS)], the NiII atom is four-coordinated by the phenolate O, imine N and amine N atoms of the Schiff base ligand, and by the terminal N atom of a thiocyanate anion in a square-planar geometry.

Comment top

Nickel(II) complexes with Schiff base ligands have received much attention in recent years (Marganian et al., 1995). Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Nickel is also present in the active sites of several important classes of metalloproteins, as either a homodinuclear or a heterodinuclear species. As part of our research programme on metal complexes of Schiff base ligands (Diao et al., 2007; Diao, 2007; Li, Huang et al., 2007) we report here the structure of the title compound (I) Fig.1.

The NiII atom in the mononuclear complex is four-coordinate in a square-planar geometry with one phenolate O, one imine N, and one amine N atom of the Schiff base ligand and one terminal N atom of a thiocyanate anion in the coordination sphere (Fig. 1). Bond lengths and angles about the Ni(II) centre are comparable with the values observed in other Schiff base Ni(II) complexes (Arıcı et al., 2005; Li, Jiang et al., 2007; Li, Huang et al., 2007; Usman et al., 2003; Van Hecke et al., 2007).

Related literature top

For the coordination chemistry and biological properties of nickel(II) complexes with Schiff base ligands, see Brückner et al. (2000); Harrop et al. (2003); Marganian et al. (1995); Ren et al. (2002). For related structures, see Arıcı et al. (2005); Diao (2007); Diao et al. (2007); Li, Huang et al. (2007); Li, Jiang et al. (2007); Usman et al. (2003); Van Hecke et al. (2007).

Experimental top

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.0 mg), 2-piperidin-1-ylethylamine (0.1 mmol, 12.7 mg), ammonium thiocyanate (0.1 mmol, 7.5 mg), and Ni(NO3)2·6H2O (0.1 mmol, 29.0 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 30 min to give a red solution. After keeping the solution in air for a week, red block-like crystals were formed.

Refinement top

H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the complex with displacement parameters drawn at the 30% probability level.
{1-[2-(Piperidin-1-yl)ethyliminomethyl]-2-naphtholato}thiocyanatonickel(II) top
Crystal data top
[Ni(C18H21N2O)(NCS)]F000 = 832
Mr = 398.16Dx = 1.445 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 539 reflections
a = 11.663 (2) Åθ = 2.3–24.5º
b = 12.530 (3) ŵ = 1.19 mm−1
c = 13.484 (3) ÅT = 298 (2) K
β = 111.77 (3)ºBlock, red
V = 1830.0 (6) Å30.20 × 0.20 × 0.17 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		4144 independent reflections
Radiation source: fine-focus sealed tube2157 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.134
T = 298(2) Kθmax = 27.5º
ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −14→15
Tmin = 0.797, Tmax = 0.824k = −15→16
15376 measured reflectionsl = −17→17
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)] = 0.072H-atom parameters constrained
wR(F2) = 0.179  w = 1/[σ2(Fo2) + (0.0415P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
4144 reflectionsΔρmax = 0.36 e Å−3
226 parametersΔρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C18H21N2O)(NCS)]V = 1830.0 (6) Å3
Mr = 398.16Z = 4
Monoclinic, P21/cMo Kα
a = 11.663 (2) ŵ = 1.19 mm−1
b = 12.530 (3) ÅT = 298 (2) K
c = 13.484 (3) Å0.20 × 0.20 × 0.17 mm
β = 111.77 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4144 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2157 reflections with I > 2σ(I)
Tmin = 0.797, Tmax = 0.824Rint = 0.134
15376 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.072226 parameters
wR(F2) = 0.179H-atom parameters constrained
S = 0.97Δρmax = 0.36 e Å−3
4144 reflectionsΔρmin = −0.34 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 > 2sigma(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
Ni10.81734 (6)0.61182 (5)0.21941 (5)0.0371 (2)
S11.23098 (15)0.52220 (16)0.36976 (15)0.0681 (5)
O10.7816 (3)0.5295 (3)0.0990 (3)0.0444 (10)
N10.6722 (4)0.6864 (3)0.1645 (3)0.0389 (11)
N20.8531 (4)0.6987 (3)0.3496 (3)0.0361 (10)
N30.9770 (5)0.5519 (4)0.2725 (4)0.0507 (13)
C10.5878 (4)0.6076 (4)−0.0116 (4)0.0335 (12)
C20.6857 (5)0.5347 (4)0.0089 (4)0.0360 (12)
C30.6827 (5)0.4611 (5)−0.0724 (5)0.0478 (15)
H30.74440.4097−0.05780.057*
C40.5922 (5)0.4642 (5)−0.1701 (5)0.0476 (15)
H40.59450.4159−0.22170.057*
C50.4938 (5)0.5387 (4)−0.1970 (4)0.0438 (14)
C60.4020 (6)0.5438 (5)−0.3007 (5)0.0590 (18)
H60.40580.4970−0.35290.071*
C70.3085 (7)0.6156 (6)−0.3258 (6)0.074 (2)
H70.24920.6186−0.39460.089*
C80.3022 (6)0.6849 (6)−0.2471 (6)0.071 (2)
H80.23710.7330−0.26350.085*
C90.3904 (5)0.6832 (5)−0.1457 (5)0.0532 (16)
H90.38450.7310−0.09500.064*
C100.4894 (5)0.6110 (4)−0.1168 (4)0.0404 (13)
C110.5856 (5)0.6796 (4)0.0688 (4)0.0396 (13)
H110.51810.72520.05270.048*
C120.6534 (5)0.7687 (5)0.2368 (5)0.0501 (16)
H12A0.56710.77230.22800.060*
H12B0.67890.83840.22110.060*
C130.7314 (5)0.7350 (5)0.3487 (5)0.0517 (16)
H13A0.74250.79450.39740.062*
H13B0.69120.67750.37150.062*
C140.9339 (5)0.7901 (4)0.3413 (4)0.0392 (13)
H14A1.00820.76110.33550.047*
H14B0.89030.82970.27640.047*
C150.9699 (5)0.8657 (4)0.4346 (4)0.0470 (15)
H15A0.89680.90230.43490.056*
H15B1.02600.91900.42620.056*
C161.0315 (6)0.8091 (4)0.5405 (4)0.0506 (16)
H16A1.04340.85890.59850.061*
H16B1.11200.78310.54580.061*
C170.9519 (6)0.7147 (5)0.5505 (4)0.0524 (16)
H17A0.99680.67440.61460.063*
H17B0.87680.74150.55650.063*
C180.9195 (6)0.6420 (4)0.4537 (4)0.0483 (15)
H18A0.99470.61080.45190.058*
H18B0.86780.58430.46120.058*
C191.0826 (6)0.5392 (4)0.3121 (4)0.0397 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0348 (4)0.0382 (4)0.0377 (4)0.0019 (3)0.0127 (3)−0.0044 (3)
S10.0411 (10)0.0882 (14)0.0700 (12)0.0021 (9)0.0149 (9)−0.0089 (10)
O10.037 (2)0.047 (2)0.045 (2)0.0026 (18)0.0097 (19)−0.0137 (18)
N10.040 (3)0.039 (3)0.036 (3)0.004 (2)0.012 (2)−0.003 (2)
N20.037 (3)0.037 (3)0.040 (3)−0.002 (2)0.020 (2)−0.004 (2)
N30.039 (3)0.061 (3)0.042 (3)0.012 (3)0.004 (2)−0.009 (2)
C10.033 (3)0.033 (3)0.034 (3)−0.004 (3)0.012 (2)0.001 (2)
C20.036 (3)0.036 (3)0.039 (3)−0.005 (3)0.017 (3)−0.004 (2)
C30.046 (4)0.048 (4)0.054 (4)0.001 (3)0.023 (3)−0.012 (3)
C40.049 (4)0.049 (4)0.045 (4)−0.006 (3)0.017 (3)−0.017 (3)
C50.051 (4)0.040 (3)0.042 (3)−0.012 (3)0.019 (3)−0.002 (3)
C60.068 (5)0.056 (4)0.039 (4)−0.019 (4)0.003 (3)−0.004 (3)
C70.069 (5)0.067 (5)0.061 (5)−0.014 (4)−0.005 (4)0.005 (4)
C80.065 (5)0.062 (5)0.063 (5)0.004 (4)−0.003 (4)0.007 (4)
C90.055 (4)0.056 (4)0.042 (4)−0.007 (3)0.010 (3)0.003 (3)
C100.041 (3)0.039 (3)0.046 (3)−0.004 (3)0.021 (3)0.006 (3)
C110.039 (3)0.038 (3)0.043 (3)0.003 (3)0.015 (3)0.003 (3)
C120.045 (4)0.046 (4)0.061 (4)0.005 (3)0.022 (3)−0.021 (3)
C130.046 (4)0.062 (4)0.053 (4)−0.003 (3)0.024 (3)−0.015 (3)
C140.043 (3)0.039 (3)0.039 (3)−0.006 (3)0.018 (3)−0.002 (3)
C150.048 (4)0.043 (4)0.044 (3)−0.002 (3)0.010 (3)−0.003 (3)
C160.064 (4)0.040 (3)0.040 (4)−0.007 (3)0.010 (3)−0.006 (3)
C170.072 (4)0.050 (4)0.038 (3)−0.002 (3)0.023 (3)−0.004 (3)
C180.062 (4)0.044 (4)0.041 (3)−0.007 (3)0.022 (3)0.008 (3)
C190.053 (4)0.035 (3)0.029 (3)0.007 (3)0.013 (3)−0.007 (2)
Geometric parameters (Å, °) top
Ni1—N11.832 (4)C7—H70.9300
Ni1—O11.836 (3)C8—C91.373 (8)
Ni1—N31.886 (5)C8—H80.9300
Ni1—N21.975 (4)C9—C101.404 (8)
S1—C191.627 (6)C9—H90.9300
O1—C21.314 (6)C11—H110.9300
N1—C111.314 (6)C12—C131.505 (8)
N1—C121.489 (6)C12—H12A0.9700
N2—C131.486 (7)C12—H12B0.9700
N2—C181.506 (6)C13—H13A0.9700
N2—C141.513 (6)C13—H13B0.9700
N3—C191.157 (7)C14—C151.505 (7)
C1—C21.407 (7)C14—H14A0.9700
C1—C111.418 (7)C14—H14B0.9700
C1—C101.457 (7)C15—C161.516 (7)
C2—C31.423 (7)C15—H15A0.9700
C3—C41.349 (7)C15—H15B0.9700
C3—H30.9300C16—C171.540 (8)
C4—C51.418 (8)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C61.412 (8)C17—C181.519 (7)
C5—C101.425 (7)C17—H17A0.9700
C6—C71.357 (9)C17—H17B0.9700
C6—H60.9300C18—H18A0.9700
C7—C81.394 (10)C18—H18B0.9700
N1—Ni1—O193.25 (18)N1—C11—C1124.5 (5)
N1—Ni1—N3172.3 (2)N1—C11—H11117.7
O1—Ni1—N388.87 (18)C1—C11—H11117.7
N1—Ni1—N286.38 (18)N1—C12—C13106.3 (4)
O1—Ni1—N2178.83 (17)N1—C12—H12A110.5
N3—Ni1—N291.64 (19)C13—C12—H12A110.5
C2—O1—Ni1128.8 (3)N1—C12—H12B110.5
C11—N1—C12116.2 (4)C13—C12—H12B110.5
C11—N1—Ni1128.5 (4)H12A—C12—H12B108.7
C12—N1—Ni1115.3 (3)N2—C13—C12108.4 (4)
C13—N2—C18108.1 (4)N2—C13—H13A110.0
C13—N2—C14112.8 (4)C12—C13—H13A110.0
C18—N2—C14107.9 (4)N2—C13—H13B110.0
C13—N2—Ni1106.0 (3)C12—C13—H13B110.0
C18—N2—Ni1115.8 (3)H13A—C13—H13B108.4
C14—N2—Ni1106.5 (3)C15—C14—N2113.8 (4)
C19—N3—Ni1164.1 (5)C15—C14—H14A108.8
C2—C1—C11120.4 (5)N2—C14—H14A108.8
C2—C1—C10119.9 (5)C15—C14—H14B108.8
C11—C1—C10119.7 (5)N2—C14—H14B108.8
O1—C2—C1124.4 (5)H14A—C14—H14B107.7
O1—C2—C3116.7 (5)C14—C15—C16112.4 (5)
C1—C2—C3118.9 (5)C14—C15—H15A109.1
C4—C3—C2121.3 (5)C16—C15—H15A109.1
C4—C3—H3119.3C14—C15—H15B109.1
C2—C3—H3119.3C16—C15—H15B109.1
C3—C4—C5122.3 (5)H15A—C15—H15B107.9
C3—C4—H4118.8C15—C16—C17110.6 (5)
C5—C4—H4118.8C15—C16—H16A109.5
C6—C5—C4121.8 (6)C17—C16—H16A109.5
C6—C5—C10119.7 (6)C15—C16—H16B109.5
C4—C5—C10118.5 (5)C17—C16—H16B109.5
C7—C6—C5121.4 (6)H16A—C16—H16B108.1
C7—C6—H6119.3C18—C17—C16110.6 (5)
C5—C6—H6119.3C18—C17—H17A109.5
C6—C7—C8119.1 (6)C16—C17—H17A109.5
C6—C7—H7120.4C18—C17—H17B109.5
C8—C7—H7120.4C16—C17—H17B109.5
C9—C8—C7121.2 (7)H17A—C17—H17B108.1
C9—C8—H8119.4N2—C18—C17113.3 (5)
C7—C8—H8119.4N2—C18—H18A108.9
C8—C9—C10121.4 (6)C17—C18—H18A108.9
C8—C9—H9119.3N2—C18—H18B108.9
C10—C9—H9119.3C17—C18—H18B108.9
C9—C10—C5117.2 (5)H18A—C18—H18B107.7
C9—C10—C1123.9 (5)N3—C19—S1179.0 (5)
C5—C10—C1118.9 (5)
Acknowledgements top

This project was supported by a research grant from Dalian Medical University.

references
References top

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