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Acta Cryst. (2007). E63, m2494    [ doi:10.1107/S1600536807043073 ]

{1-[(2-Morpholin-4-ylethylimino-[kappa]2N,N')methyl]naphthalen-2-olato-[kappa]O}(thiocyanato-N)nickel(II)

Y.-P. Diao, Y.-Z. Wang, M.-D. Wang and K. Li

Abstract top

In the title mononuclear nickel(II) complex, [Ni(C17H19N2O2)(NCS)], the NiII atom is four-coordinated by the phenolate O, imine N and amine N atoms of one Schiff base ligand, and by the terminal N atom of a thiocyanate ligand, forming 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 (Harrop et al., 2003; Brückner et al., 2000; 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. We have recently reported a few transition metal complexes (Diao, 2007a,b; Diao, Huang et al., 2007; Diao, Shu et al., 2007; Li, Huang et al., 2007). In order to further develop the coordination chemistry of such nickel complexes, we report herein the title new nickel(II) compound.

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 atoms of one Schiff base ligand and one terminal N atom of a thiocyanate ligand (Fig. 1). All the bond values (Table 1) subtended at the metal centre are comparable with the values observed in other Schiff base nickel(II) complexes (Arıcı et al., 2005; Usman et al., 2003; Van Hecke et al., 2007; Li, Jiang et al., 2007).

Related literature top

For related literature, see: Arıcı et al. (2005); Brückner et al. (2000); Diao (2007a,b); Diao, Huang et al. (2007); Diao, Shu et al. (2007); Harrop et al. (2003); Li, Huang et al. (2007); Li, Jiang et al. (2007); Marganian et al. (1995); Ren et al. (2002); Usman et al. (2003); Van Hecke et al. (2007).

Experimental top

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.0 mg), 2-morpholin-4-ylethylamine (0.1 mmol, 13.0 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 8 days, 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 (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The structure of the title complex with 30% probability level.
{1-[(2-Morpholin-4-ylethylimino-κ2N,N')methyl]naphthalen-2-olato-κO} (thiocyanato-N)nickel(II) top
Crystal data top
[Ni(C17H19N2O2)(NCS)]F000 = 1664
Mr = 400.13Dx = 1.516 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3770 reflections
a = 12.648 (3) Åθ = 2.4–25.0º
b = 12.647 (3) ŵ = 1.24 mm−1
c = 21.915 (4) ÅT = 298 (2) K
V = 3505.5 (12) Å3Block, red
Z = 80.32 × 0.32 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4028 independent reflections
Radiation source: fine-focus sealed tube3012 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.065
T = 298(2) Kθmax = 27.5º
ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −16→16
Tmin = 0.692, Tmax = 0.707k = −16→16
28592 measured reflectionsl = −28→28
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)] = 0.063H-atom parameters constrained
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0577P)2 + 0.5788P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
4028 reflectionsΔρmax = 0.67 e Å−3
226 parametersΔρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C17H19N2O2)(NCS)]V = 3505.5 (12) Å3
Mr = 400.13Z = 8
Orthorhombic, PbcaMo Kα
a = 12.648 (3) ŵ = 1.24 mm−1
b = 12.647 (3) ÅT = 298 (2) K
c = 21.915 (4) Å0.32 × 0.32 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4028 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3012 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.707Rint = 0.065
28592 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063226 parameters
wR(F2) = 0.135H-atom parameters constrained
S = 1.16Δρmax = 0.67 e Å−3
4028 reflectionsΔρmin = −0.36 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
Ni10.10083 (3)0.38201 (3)0.331471 (19)0.03927 (16)
S1−0.00187 (9)0.45522 (8)0.13251 (5)0.0641 (3)
O10.02168 (18)0.49703 (19)0.35297 (11)0.0469 (6)
O20.2686 (2)0.1258 (2)0.21262 (13)0.0623 (7)
N10.1692 (2)0.3770 (2)0.40509 (13)0.0442 (7)
N20.17885 (19)0.2534 (2)0.30999 (12)0.0393 (6)
N30.0480 (3)0.3984 (2)0.25161 (14)0.0513 (7)
C10.1016 (2)0.5384 (3)0.44931 (15)0.0408 (8)
C20.0287 (3)0.5548 (3)0.40201 (16)0.0436 (8)
C3−0.0427 (3)0.6417 (3)0.40643 (17)0.0517 (9)
H3−0.09590.64940.37750.062*
C4−0.0344 (3)0.7124 (3)0.45163 (18)0.0544 (10)
H4−0.08130.76900.45280.065*
C50.0436 (3)0.7039 (3)0.49775 (18)0.0513 (9)
C60.0570 (4)0.7847 (4)0.5416 (2)0.0680 (12)
H60.01260.84330.54070.082*
C70.1325 (4)0.7786 (4)0.5847 (2)0.0785 (14)
H70.14220.83380.61220.094*
C80.1962 (4)0.6884 (4)0.5877 (2)0.0780 (14)
H80.24620.68260.61870.094*
C90.1860 (3)0.6079 (3)0.54553 (17)0.0615 (11)
H90.22940.54870.54830.074*
C100.1111 (3)0.6147 (3)0.49864 (17)0.0475 (9)
C110.1660 (3)0.4476 (3)0.44838 (16)0.0467 (8)
H110.21030.43700.48170.056*
C120.2429 (3)0.2881 (3)0.41236 (17)0.0585 (10)
H12A0.24120.26210.45400.070*
H12B0.31450.31040.40300.070*
C130.2089 (3)0.2043 (3)0.36966 (17)0.0549 (10)
H13A0.14890.16650.38650.066*
H13B0.26600.15420.36350.066*
C140.2734 (3)0.2859 (3)0.27331 (17)0.0493 (9)
H14A0.32000.32790.29880.059*
H14B0.25040.33000.23960.059*
C150.3346 (3)0.1926 (3)0.24830 (19)0.0617 (11)
H15A0.39260.21810.22340.074*
H15B0.36420.15230.28190.074*
C160.1853 (3)0.0866 (3)0.24931 (19)0.0565 (10)
H16A0.21450.04760.28350.068*
H16B0.14220.03840.22550.068*
C170.1176 (2)0.1755 (3)0.27276 (18)0.0465 (9)
H17A0.08560.21190.23840.056*
H17B0.06110.14640.29750.056*
C180.0284 (3)0.4230 (3)0.20196 (17)0.0430 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0335 (2)0.0431 (3)0.0412 (3)0.00581 (18)−0.00355 (18)0.00764 (19)
S10.0890 (8)0.0573 (6)0.0461 (6)0.0087 (6)−0.0121 (5)0.0034 (5)
O10.0439 (13)0.0504 (14)0.0465 (14)0.0116 (11)−0.0066 (11)0.0027 (11)
O20.0501 (15)0.0656 (18)0.0712 (19)0.0054 (14)0.0113 (14)−0.0084 (14)
N10.0367 (15)0.0514 (17)0.0446 (16)0.0023 (13)−0.0017 (13)0.0118 (14)
N20.0274 (13)0.0441 (15)0.0465 (16)0.0031 (12)0.0006 (12)0.0077 (12)
N30.0552 (19)0.0501 (18)0.0487 (18)0.0145 (15)−0.0099 (15)0.0016 (14)
C10.0363 (17)0.0443 (19)0.0417 (18)−0.0075 (15)0.0050 (15)0.0078 (15)
C20.0400 (18)0.045 (2)0.045 (2)−0.0005 (15)0.0063 (15)0.0062 (16)
C30.047 (2)0.058 (2)0.050 (2)0.0087 (18)0.0027 (17)0.0069 (18)
C40.054 (2)0.049 (2)0.060 (2)0.0030 (18)0.016 (2)0.0007 (19)
C50.049 (2)0.051 (2)0.054 (2)−0.0148 (18)0.0178 (18)−0.0001 (18)
C60.064 (3)0.070 (3)0.069 (3)−0.015 (2)0.019 (2)−0.018 (2)
C70.082 (3)0.087 (3)0.066 (3)−0.026 (3)0.015 (3)−0.022 (3)
C80.066 (3)0.107 (4)0.061 (3)−0.027 (3)−0.002 (2)−0.009 (3)
C90.053 (2)0.077 (3)0.055 (2)−0.015 (2)0.0034 (19)−0.001 (2)
C100.0417 (19)0.057 (2)0.0439 (19)−0.0160 (17)0.0093 (16)0.0058 (17)
C110.0385 (19)0.060 (2)0.0421 (19)−0.0090 (17)−0.0025 (15)0.0122 (17)
C120.054 (2)0.068 (2)0.054 (2)0.022 (2)−0.0087 (19)0.011 (2)
C130.054 (2)0.056 (2)0.054 (2)0.0185 (18)−0.0025 (18)0.0146 (19)
C140.0321 (17)0.053 (2)0.063 (2)−0.0059 (16)−0.0003 (16)0.0034 (18)
C150.0330 (19)0.077 (3)0.075 (3)0.0027 (18)0.0057 (19)0.002 (2)
C160.054 (2)0.043 (2)0.072 (3)0.0026 (18)−0.003 (2)0.0028 (19)
C170.0309 (17)0.044 (2)0.065 (2)0.0000 (15)0.0008 (16)0.0087 (17)
C180.0428 (18)0.0341 (17)0.052 (2)0.0083 (15)−0.0041 (17)−0.0044 (16)
Geometric parameters (Å, °) top
Ni1—O11.828 (2)C6—C71.345 (6)
Ni1—N11.832 (3)C6—H60.9300
Ni1—N31.885 (3)C7—C81.398 (7)
Ni1—N21.959 (3)C7—H70.9300
S1—C181.621 (4)C8—C91.382 (6)
O1—C21.302 (4)C8—H80.9300
O2—C161.416 (4)C9—C101.401 (5)
O2—C151.421 (5)C9—H90.9300
N1—C111.303 (4)C11—H110.9300
N1—C121.470 (4)C12—C131.478 (5)
N2—C171.496 (4)C12—H12A0.9700
N2—C131.497 (4)C12—H12B0.9700
N2—C141.498 (4)C13—H13A0.9700
N3—C181.158 (4)C13—H13B0.9700
C1—C21.403 (5)C14—C151.514 (5)
C1—C111.407 (5)C14—H14A0.9700
C1—C101.454 (5)C14—H14B0.9700
C2—C31.426 (5)C15—H15A0.9700
C3—C41.339 (5)C15—H15B0.9700
C3—H30.9300C16—C171.504 (5)
C4—C51.416 (5)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C61.413 (5)C17—H17A0.9700
C5—C101.415 (5)C17—H17B0.9700
O1—Ni1—N193.38 (12)C10—C9—H9119.7
O1—Ni1—N387.57 (11)C9—C10—C5117.8 (4)
N1—Ni1—N3171.51 (13)C9—C10—C1124.1 (4)
O1—Ni1—N2176.66 (11)C5—C10—C1118.0 (3)
N1—Ni1—N286.86 (12)N1—C11—C1125.9 (3)
N3—Ni1—N292.69 (12)N1—C11—H11117.0
C2—O1—Ni1128.4 (2)C1—C11—H11117.0
C16—O2—C15109.4 (3)N1—C12—C13107.2 (3)
C11—N1—C12117.7 (3)N1—C12—H12A110.3
C11—N1—Ni1127.1 (2)C13—C12—H12A110.3
C12—N1—Ni1114.9 (2)N1—C12—H12B110.3
C17—N2—C13109.5 (3)C13—C12—H12B110.3
C17—N2—C14107.5 (3)H12A—C12—H12B108.5
C13—N2—C14112.3 (3)C12—C13—N2109.2 (3)
C17—N2—Ni1114.65 (18)C12—C13—H13A109.8
C13—N2—Ni1105.2 (2)N2—C13—H13A109.8
C14—N2—Ni1107.7 (2)C12—C13—H13B109.8
C18—N3—Ni1167.9 (3)N2—C13—H13B109.8
C2—C1—C11119.4 (3)H13A—C13—H13B108.3
C2—C1—C10120.3 (3)N2—C14—C15112.9 (3)
C11—C1—C10120.3 (3)N2—C14—H14A109.0
O1—C2—C1124.9 (3)C15—C14—H14A109.0
O1—C2—C3116.4 (3)N2—C14—H14B109.0
C1—C2—C3118.7 (3)C15—C14—H14B109.0
C4—C3—C2121.0 (4)H14A—C14—H14B107.8
C4—C3—H3119.5O2—C15—C14111.3 (3)
C2—C3—H3119.5O2—C15—H15A109.4
C3—C4—C5122.2 (4)C14—C15—H15A109.4
C3—C4—H4118.9O2—C15—H15B109.4
C5—C4—H4118.9C14—C15—H15B109.4
C6—C5—C4120.9 (4)H15A—C15—H15B108.0
C6—C5—C10119.7 (4)O2—C16—C17110.8 (3)
C4—C5—C10119.4 (4)O2—C16—H16A109.5
C7—C6—C5121.4 (5)C17—C16—H16A109.5
C7—C6—H6119.3O2—C16—H16B109.5
C5—C6—H6119.3C17—C16—H16B109.5
C6—C7—C8119.3 (4)H16A—C16—H16B108.1
C6—C7—H7120.3N2—C17—C16112.6 (3)
C8—C7—H7120.3N2—C17—H17A109.1
C9—C8—C7121.0 (4)C16—C17—H17A109.1
C9—C8—H8119.5N2—C17—H17B109.1
C7—C8—H8119.5C16—C17—H17B109.1
C8—C9—C10120.6 (4)H17A—C17—H17B107.8
C8—C9—H9119.7N3—C18—S1178.4 (4)
Table 1
Selected geometric parameters (Å, °) top
Ni1—O11.828 (2)Ni1—N31.885 (3)
Ni1—N11.832 (3)Ni1—N21.959 (3)
O1—Ni1—N193.38 (12)O1—Ni1—N2176.66 (11)
O1—Ni1—N387.57 (11)N1—Ni1—N286.86 (12)
N1—Ni1—N3171.51 (13)N3—Ni1—N292.69 (12)
Acknowledgements top

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

references
References top

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