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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043073/at2382sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043073/at2382Isup2.hkl
Contains datablock I

CCDC reference: 663576

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.063
  • wR factor = 0.135
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (3) 2.77
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 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 (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).

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 (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).

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).

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)]F(000) = 1664
Mr = 400.13Dx = 1.516 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3770 reflections
a = 12.648 (3) Åθ = 2.4–25.0°
b = 12.647 (3) ŵ = 1.24 mm1
c = 21.915 (4) ÅT = 298 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)
Graphite monochromatorRint = 0.065
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1616
Tmin = 0.692, Tmax = 0.707k = 1616
28592 measured reflectionsl = 2828
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.5788P]
where P = (Fo2 + 2Fc2)/3
4028 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Ni(C17H19N2O2)(NCS)]V = 3505.5 (12) Å3
Mr = 400.13Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.648 (3) ŵ = 1.24 mm1
b = 12.647 (3) ÅT = 298 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)] = 0.0630 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.16Δρmax = 0.67 e Å3
4028 reflectionsΔρmin = 0.36 e Å3
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
Ni10.10083 (3)0.38201 (3)0.331471 (19)0.03927 (16)
S10.00187 (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)
C30.0427 (3)0.6417 (3)0.40643 (17)0.0517 (9)
H30.09590.64940.37750.062*
C40.0344 (3)0.7124 (3)0.45163 (18)0.0544 (10)
H40.08130.76900.45280.065*
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, º) 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)

Experimental details

Crystal data
Chemical formula[Ni(C17H19N2O2)(NCS)]
Mr400.13
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)12.648 (3), 12.647 (3), 21.915 (4)
V3)3505.5 (12)
Z8
Radiation typeMo Kα
µ (mm1)1.24
Crystal size (mm)0.32 × 0.32 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.692, 0.707
No. of measured, independent and
observed [I > 2σ(I)] reflections
28592, 4028, 3012
Rint0.065
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.135, 1.16
No. of reflections4028
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.36

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

Selected geometric parameters (Å, º) 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)
 

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