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Acta Cryst. (2007). E63, m2426
https://doi.org/10.1107/S1600536807041505
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{1-[2-(Piperidin-1-yl)ethyl­imino­meth­yl]-2-naphtholato}thio­cyanato­nickel(II)

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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041505/sj2338sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041505/sj2338Isup2.hkl
Contains datablock I

CCDC reference: 660170

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.072
  • wR factor = 0.179
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found




Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.134
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (3)       2.73


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
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).

Structure description 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).

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).

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)]F(000) = 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 = 2.3–24.5°
b = 12.530 (3) ŵ = 1.19 mm−1
c = 13.484 (3) ÅT = 298 K
β = 111.77 (3)°Block, 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)
Graphite monochromatorRint = 0.134
ω scansθmax = 27.5°, θmin = 1.9°
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 F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0415P)2]
where P = (Fo2 + 2Fc2)/3
4144 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
[Ni(C18H21N2O)(NCS)]V = 1830.0 (6) Å3
Mr = 398.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.663 (2) ŵ = 1.19 mm−1
b = 12.530 (3) ÅT = 298 K
c = 13.484 (3) Å0.20 × 0.20 × 0.17 mm
β = 111.77 (3)°
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)] = 0.0720 restraints
wR(F2) = 0.179H-atom parameters constrained
S = 0.97Δρmax = 0.36 e Å−3
4144 reflectionsΔρmin = −0.34 e Å−3
226 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
Ni10.81734 (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, º) 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)

Experimental details

Crystal data
Chemical formula[Ni(C18H21N2O)(NCS)]
Mr398.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.663 (2), 12.530 (3), 13.484 (3)
β (°) 111.77 (3)
V (Å3)1830.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)1.19
Crystal size (mm)0.20 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.797, 0.824
No. of measured, independent and
observed [I > 2σ(I)] reflections		15376, 4144, 2157
Rint0.134
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.179, 0.97
No. of reflections4144
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.36, −0.34

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

 

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