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Acta Cryst. (2007). E63, m1946    [ doi:10.1107/S1600536807029340 ]

{2-[2-(Piperidin-1-yl)ethyliminomethyl]phenolato-[kappa]3N,N',O}(thiocyanato-[kappa]N)nickel(II)

S.-X. Wang

Abstract top

In the title compound, [Ni(C14H19N2O)(NCS)], a mononuclear Schiff base nickel(II) complex, the Ni atom is four-coordinated by one imine N atom, one amine N atom and one phenolate O atom of the Schiff base ligand, and by one terminal N atom of the thiocyanate ligand, forming a square-planar geometry. The piperidine ring adopts a chair conformation. No significant hydrogen bonding or [pi]-[pi] interactions are observed in the crystal structure.

Comment top

Nickel(II) complexes derived from Schiff base ligands have been studied extensively due to their interesting structures and numerous applications (Mukhopadhyay et al., 2003; Kraihanzel et al., 1981; Di Bella et al., 1997; Loeb et al., 1984; Costes et al., 2005). Previously, the author has reported the crystal structure of a Schiff base zinc(II) complex (Wang, 2007). As part of a further investigation of Schiff base complexes, the structure of the title compound, a mononuclear nickel(II) complex, is reported here.

The square-planar coordination environment of NiII atom in the title compound is formed by one imine N atom, one amine N atom, and one phenolate O atom of the Schiff base ligand, and by one terminal N atom of the thiocyanate ligand (Fig. 1). The coordination bond distances (Table 1) are typical and comparable with the values in similar nickel(II) complexes (Zhu et al., 2004; Liu et al., 2006; Fu et al., 2007).

Related literature top

For related literature, see: Costes et al. (2005); Di Bella et al. (1997); Fu et al. (2007); Kraihanzel et al. (1981); Liu et al. (2006); Loeb et al. (1984); Mukhopadhyay et al. (2003); Wang (2007); Zhu et al. (2004).

Experimental top

The title compound was obtained by stirring of salicylaldehyde (0.1 mmol, 12.1 mg), 2-piperidin-1-ylethylamine (0.1 mmol, 12.8 mg), ammonium thiocyanate (0.1 mmol, 7.6 mg), and nickel(II) nitrate (0.1 mmol, 29.1 mg) in methanol (20 ml) for 30 min. The reaction mixture was then filtered. Red block-shaped single crystals suitable for X-ray diffraction were formed from the filtrate after 5 d.

Refinement top

H atoms were positioned geometrically (C—H = 0.93 or 0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level
{2-[2-(Piperidin-1-yl)ethyliminomethyl]phenolato-κ3N,N',O}(thiocyanato- κN)nickel(II) top
Crystal data top
[Ni(C14H19N2O)(NCS)]F000 = 1456
Mr = 348.10Dx = 1.465 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3068 reflections
a = 12.997 (3) Åθ = 2.5–25.4º
b = 12.525 (3) ŵ = 1.36 mm−1
c = 19.386 (4) ÅT = 298 (2) K
V = 3155.8 (11) Å3Block, red
Z = 80.37 × 0.32 × 0.30 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer		3587 independent reflections
Radiation source: fine-focus sealed tube2494 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.054
T = 298(2) Kθmax = 27.5º
ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→16
Tmin = 0.618, Tmax = 0.670k = −16→16
18388 measured reflectionsl = −16→25
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.107  w = 1/[σ2(Fo2) + (0.0516P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3587 reflectionsΔρmax = 0.51 e Å−3
190 parametersΔρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C14H19N2O)(NCS)]V = 3155.8 (11) Å3
Mr = 348.10Z = 8
Orthorhombic, PbcaMo Kα
a = 12.997 (3) ŵ = 1.36 mm−1
b = 12.525 (3) ÅT = 298 (2) K
c = 19.386 (4) Å0.37 × 0.32 × 0.30 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer		3587 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2494 reflections with I > 2σ(I)
Tmin = 0.618, Tmax = 0.670Rint = 0.054
18388 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043190 parameters
wR(F2) = 0.107H-atom parameters constrained
S = 1.02Δρmax = 0.51 e Å−3
3587 reflectionsΔρmin = −0.35 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
Ni10.11596 (2)0.56364 (3)0.162861 (19)0.03658 (13)
S1−0.00585 (8)0.49582 (7)0.38329 (4)0.0652 (3)
O10.05319 (15)0.43892 (14)0.13658 (11)0.0459 (5)
N10.18173 (17)0.58278 (17)0.07974 (12)0.0409 (6)
N20.18420 (15)0.69534 (17)0.19361 (12)0.0373 (5)
N30.05700 (18)0.54126 (18)0.25004 (14)0.0465 (6)
C10.1120 (2)0.4304 (2)0.01950 (16)0.0428 (7)
C20.0550 (2)0.3924 (2)0.07622 (15)0.0382 (6)
C3−0.0010 (2)0.2974 (2)0.06736 (16)0.0455 (7)
H3−0.03930.27070.10400.055*
C4−0.0004 (2)0.2436 (2)0.00622 (16)0.0508 (8)
H4−0.03790.18070.00210.061*
C50.0552 (2)0.2813 (3)−0.05009 (17)0.0563 (9)
H50.05520.2442−0.09170.068*
C60.1096 (2)0.3739 (3)−0.04300 (16)0.0523 (8)
H60.14610.4001−0.08060.063*
C70.1740 (2)0.5242 (2)0.02556 (16)0.0462 (7)
H70.21190.5446−0.01290.055*
C80.2543 (2)0.6728 (2)0.07842 (17)0.0511 (8)
H8A0.25660.70430.03270.061*
H8B0.32290.64870.09050.061*
C90.2168 (2)0.7523 (2)0.12972 (14)0.0475 (7)
H9A0.15910.79170.11070.057*
H9B0.27120.80260.14050.057*
C100.2741 (2)0.6595 (2)0.23558 (16)0.0450 (7)
H10A0.32010.61860.20630.054*
H10B0.24970.61230.27180.054*
C110.3344 (2)0.7504 (3)0.26836 (16)0.0535 (8)
H11A0.36690.79250.23250.064*
H11B0.38810.72120.29750.064*
C120.2646 (2)0.8218 (3)0.31126 (18)0.0597 (9)
H12A0.23780.78220.35030.072*
H12B0.30350.88220.32870.072*
C130.1766 (2)0.8611 (2)0.26675 (17)0.0512 (8)
H13A0.13020.90400.29450.061*
H13B0.20340.90580.23010.061*
C140.11822 (19)0.7684 (2)0.23584 (16)0.0422 (7)
H14A0.08680.72770.27280.051*
H14B0.06340.79610.20700.051*
C150.0307 (2)0.5216 (2)0.30525 (16)0.0405 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0351 (2)0.0358 (2)0.0388 (2)−0.00503 (14)0.00431 (15)0.00423 (16)
S10.0955 (7)0.0548 (5)0.0454 (5)0.0077 (5)0.0229 (5)0.0067 (4)
O10.0569 (13)0.0419 (11)0.0388 (12)−0.0127 (9)0.0085 (10)0.0004 (9)
N10.0376 (12)0.0401 (13)0.0448 (15)−0.0040 (10)0.0058 (11)0.0084 (11)
N20.0307 (11)0.0364 (12)0.0448 (14)−0.0035 (9)0.0010 (10)0.0048 (11)
N30.0522 (15)0.0421 (14)0.0451 (16)−0.0119 (11)0.0063 (12)0.0000 (12)
C10.0447 (16)0.0452 (17)0.0386 (17)0.0032 (13)0.0001 (13)0.0036 (14)
C20.0373 (14)0.0391 (15)0.0380 (17)0.0060 (12)−0.0026 (12)0.0036 (13)
C30.0475 (16)0.0443 (16)0.0448 (18)−0.0041 (13)−0.0035 (14)0.0025 (15)
C40.0528 (17)0.0485 (18)0.051 (2)−0.0015 (15)−0.0117 (16)−0.0030 (16)
C50.066 (2)0.060 (2)0.042 (2)0.0033 (17)−0.0084 (16)−0.0080 (16)
C60.0557 (18)0.064 (2)0.0369 (18)0.0027 (16)0.0013 (14)0.0019 (16)
C70.0455 (17)0.0488 (17)0.0441 (18)0.0010 (14)0.0128 (14)0.0110 (15)
C80.0512 (17)0.0498 (19)0.052 (2)−0.0133 (14)0.0111 (15)0.0096 (15)
C90.0443 (16)0.0425 (16)0.056 (2)−0.0094 (13)0.0004 (14)0.0098 (16)
C100.0353 (14)0.0427 (16)0.057 (2)0.0033 (12)−0.0036 (13)0.0043 (14)
C110.0348 (14)0.063 (2)0.062 (2)−0.0071 (14)−0.0099 (14)0.0069 (18)
C120.0524 (19)0.061 (2)0.066 (2)−0.0174 (16)−0.0054 (16)−0.0108 (17)
C130.0463 (16)0.0372 (16)0.070 (2)−0.0025 (13)0.0010 (16)−0.0051 (15)
C140.0330 (13)0.0384 (16)0.055 (2)0.0009 (11)−0.0015 (13)−0.0005 (14)
C150.0441 (15)0.0291 (14)0.0484 (19)−0.0019 (12)0.0036 (14)−0.0033 (14)
Geometric parameters (Å, °) top
Ni1—O11.8344 (19)C6—H60.93
Ni1—N11.840 (2)C7—H70.93
Ni1—N31.877 (3)C8—C91.490 (4)
Ni1—N21.965 (2)C8—H8A0.97
S1—C151.619 (3)C8—H8B0.97
O1—C21.307 (3)C9—H9A0.97
N1—C71.285 (4)C9—H9B0.97
N1—C81.470 (3)C10—C111.521 (4)
N2—C91.491 (3)C10—H10A0.97
N2—C101.493 (3)C10—H10B0.97
N2—C141.498 (3)C11—C121.522 (4)
N3—C151.150 (3)C11—H11A0.97
C1—C61.404 (4)C11—H11B0.97
C1—C21.409 (4)C12—C131.515 (4)
C1—C71.429 (4)C12—H12A0.97
C2—C31.405 (4)C12—H12B0.97
C3—C41.363 (4)C13—C141.511 (4)
C3—H30.93C13—H13A0.97
C4—C51.392 (4)C13—H13B0.97
C4—H40.93C14—H14A0.97
C5—C61.365 (4)C14—H14B0.97
C5—H50.93
O1—Ni1—N194.26 (10)N1—C8—H8B110.3
O1—Ni1—N386.63 (9)C9—C8—H8B110.3
N1—Ni1—N3176.32 (10)H8A—C8—H8B108.6
O1—Ni1—N2178.33 (9)C8—C9—N2109.1 (2)
N1—Ni1—N286.94 (10)C8—C9—H9A109.9
N3—Ni1—N292.09 (10)N2—C9—H9A109.9
C2—O1—Ni1128.31 (18)C8—C9—H9B109.9
C7—N1—C8118.3 (2)N2—C9—H9B109.9
C7—N1—Ni1127.2 (2)H9A—C9—H9B108.3
C8—N1—Ni1114.41 (19)N2—C10—C11113.9 (2)
C9—N2—C10112.0 (2)N2—C10—H10A108.8
C9—N2—C14108.9 (2)C11—C10—H10A108.8
C10—N2—C14109.5 (2)N2—C10—H10B108.8
C9—N2—Ni1106.12 (17)C11—C10—H10B108.8
C10—N2—Ni1105.41 (16)H10A—C10—H10B107.7
C14—N2—Ni1114.86 (15)C10—C11—C12111.2 (2)
C15—N3—Ni1172.4 (2)C10—C11—H11A109.4
C6—C1—C2119.4 (3)C12—C11—H11A109.4
C6—C1—C7119.9 (3)C10—C11—H11B109.4
C2—C1—C7120.7 (3)C12—C11—H11B109.4
O1—C2—C3118.5 (3)H11A—C11—H11B108.0
O1—C2—C1123.9 (3)C13—C12—C11109.3 (3)
C3—C2—C1117.6 (3)C13—C12—H12A109.8
C4—C3—C2121.5 (3)C11—C12—H12A109.8
C4—C3—H3119.3C13—C12—H12B109.8
C2—C3—H3119.3C11—C12—H12B109.8
C3—C4—C5121.1 (3)H12A—C12—H12B108.3
C3—C4—H4119.4C14—C13—C12110.8 (2)
C5—C4—H4119.4C14—C13—H13A109.5
C6—C5—C4118.6 (3)C12—C13—H13A109.5
C6—C5—H5120.7C14—C13—H13B109.5
C4—C5—H5120.7C12—C13—H13B109.5
C5—C6—C1121.8 (3)H13A—C13—H13B108.1
C5—C6—H6119.1N2—C14—C13113.5 (2)
C1—C6—H6119.1N2—C14—H14A108.9
N1—C7—C1125.5 (3)C13—C14—H14A108.9
N1—C7—H7117.3N2—C14—H14B108.9
C1—C7—H7117.3C13—C14—H14B108.9
N1—C8—C9106.9 (2)H14A—C14—H14B107.7
N1—C8—H8A110.3N3—C15—S1179.2 (3)
C9—C8—H8A110.3
Table 1
Selected geometric parameters (Å, °) top
Ni1—O11.8344 (19)Ni1—N31.877 (3)
Ni1—N11.840 (2)Ni1—N21.965 (2)
O1—Ni1—N194.26 (10)O1—Ni1—N2178.33 (9)
O1—Ni1—N386.63 (9)N1—Ni1—N286.94 (10)
N1—Ni1—N3176.32 (10)N3—Ni1—N292.09 (10)
references
References top

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