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Acta Cryst. (2008). E64, m843    [ doi:10.1107/S1600536808015390 ]

Bis[(E)-4-chloro-2-(cyclohexyliminomethyl)phenolato]nickel(II)

D.-S. Xia, W. Chen, Y.-M. Zhao and Q.-F. Zeng

Abstract top

In the title mononuclear nickel(II) complex, [Ni(C13H15ClNO)2], the NiII atom is four-coordinated in a tetrahedral geometry by the N and O atoms of the two Schiff base ligands.

Comment top

As part of our ongoing interest in the structure of nickel(II) complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new mononuclear nickel(II) complex, (I), Fig. 1, derived from the Schiff base ligand 4-chloro-2-(cyclohexyliminomethyl)phenol.

The NiII atom in (I) is four-coordinate in a tetrahedral geometry, binding to the N and two O atoms of the two Schiff base ligands. The coordinate bond values (Table 1) are comparable to values observed in other similar nickel(II) complexes (Shi et al., 2007; Li et al., 2007; Cheng et al., 2007; Qiu et al., 2006; Wang et al., 2005).

Related literature top

For related structures, see: Cheng et al. (2007); Li et al. (2007); Qiu et al. (2006); Shi et al. (2007); Wang et al. (2005); Zhu et al. (2003).

Experimental top

5-Chlorosalicylaldehyde (15.6 mg, 0.1 mmol), cyclohexylamine (9.9 mg, 0.1 mmol), and NiCl2.6H2O (23.8 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding green crystals.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.98 Å, and with Uiso(H) set at 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Bis[(E)-4-chloro-2-(cyclohexyliminomethyl)phenolato]nickel(II) top
Crystal data top
[Ni(C13H15ClNO)2]F000 = 2224
Mr = 532.13Dx = 1.402 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2013 reflections
a = 14.871 (3) Åθ = 2.3–25.3º
b = 13.563 (3) ŵ = 1.01 mm−1
c = 24.993 (5) ÅT = 298 (2) K
V = 5040.9 (17) Å3Block, green
Z = 80.42 × 0.38 × 0.37 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4693 independent reflections
Radiation source: fine-focus sealed tube2416 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 298(2) Kθmax = 25.5º
ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→18
Tmin = 0.663, Tmax = 0.686k = −15→16
4933 measured reflectionsl = −30→30
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.162  w = 1/[σ2(Fo2) + (0.0617P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4693 reflectionsΔρmax = 0.32 e Å−3
298 parametersΔρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C13H15ClNO)2]V = 5040.9 (17) Å3
Mr = 532.13Z = 8
Orthorhombic, PbcaMo Kα
a = 14.871 (3) ŵ = 1.01 mm−1
b = 13.563 (3) ÅT = 298 (2) K
c = 24.993 (5) Å0.42 × 0.38 × 0.37 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4693 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2416 reflections with I > 2σ(I)
Tmin = 0.663, Tmax = 0.686Rint = 0.023
4933 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066298 parameters
wR(F2) = 0.162H-atom parameters constrained
S = 1.04Δρmax = 0.32 e Å−3
4693 reflectionsΔρmin = −0.45 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Ni10.14197 (4)0.91723 (5)0.19419 (3)0.0418 (2)
Cl1−0.11240 (16)0.61620 (16)0.01142 (8)0.1021 (8)
Cl20.32265 (12)1.23468 (13)0.39664 (7)0.0768 (6)
O10.1603 (3)0.8322 (3)0.13420 (17)0.0644 (12)
O20.2180 (3)0.9080 (3)0.25567 (16)0.0586 (11)
N10.0151 (3)0.8732 (3)0.20947 (18)0.0460 (12)
N20.1735 (3)1.0591 (3)0.17874 (19)0.0482 (13)
C10.0059 (4)0.7796 (4)0.1256 (2)0.0473 (15)
C20.0954 (4)0.7884 (4)0.1071 (3)0.0524 (16)
C30.1154 (4)0.7475 (5)0.0575 (3)0.0618 (17)
H30.17290.75600.04350.074*
C40.0536 (5)0.6954 (5)0.0286 (3)0.069 (2)
H40.06990.6676−0.00400.083*
C5−0.0337 (5)0.6836 (5)0.0478 (3)0.0648 (19)
C6−0.0575 (4)0.7255 (4)0.0950 (2)0.0586 (17)
H6−0.11620.71870.10750.070*
C7−0.0277 (4)0.8180 (4)0.1755 (2)0.0501 (16)
H7−0.08650.80140.18440.060*
C8−0.0329 (4)0.9005 (4)0.2591 (2)0.0486 (15)
H8−0.09700.88600.25450.058*
C90.0027 (5)0.8394 (5)0.3045 (2)0.0683 (19)
H9A0.06730.84850.30720.082*
H9B−0.00860.77030.29730.082*
C10−0.0411 (5)0.8677 (5)0.3573 (3)0.083 (2)
H10A−0.10470.85200.35600.100*
H10B−0.01420.82980.38610.100*
C11−0.0291 (5)0.9768 (6)0.3682 (3)0.079 (2)
H11A−0.05920.99440.40130.095*
H11B0.03440.99200.37210.095*
C12−0.0682 (5)1.0352 (5)0.3224 (3)0.072 (2)
H12A−0.13201.02120.31950.087*
H12B−0.06121.10510.32950.087*
C13−0.0222 (4)1.0095 (4)0.2705 (3)0.0577 (17)
H13A0.04121.02590.27280.069*
H13B−0.04831.04760.24160.069*
C140.2385 (3)1.0838 (4)0.2672 (2)0.0449 (14)
C150.2402 (4)0.9843 (5)0.2852 (3)0.0498 (16)
C160.2693 (4)0.9689 (5)0.3380 (3)0.0601 (18)
H160.27190.90450.35070.072*
C170.2941 (4)1.0439 (5)0.3720 (3)0.0622 (18)
H170.31181.03040.40690.075*
C180.2920 (4)1.1408 (5)0.3530 (2)0.0530 (16)
C190.2665 (4)1.1603 (4)0.3020 (2)0.0520 (16)
H190.26741.22500.28970.062*
C200.2118 (4)1.1130 (4)0.2144 (2)0.0507 (15)
H200.22361.17810.20490.061*
C210.1556 (4)1.1016 (4)0.1257 (2)0.0551 (17)
H210.16591.17290.12750.066*
C220.2191 (4)1.0582 (5)0.0844 (2)0.0644 (19)
H22A0.21570.98680.08600.077*
H22B0.28021.07740.09310.077*
C230.1970 (4)1.0921 (6)0.0278 (2)0.076 (2)
H23A0.20831.16230.02470.092*
H23B0.23601.05840.00260.092*
C240.0995 (4)1.0709 (5)0.0138 (3)0.071 (2)
H24A0.08941.00020.01350.085*
H24B0.08631.0961−0.02170.085*
C250.0371 (4)1.1194 (5)0.0545 (3)0.0648 (19)
H25A0.04441.19040.05300.078*
H25B−0.02491.10410.04570.078*
C260.0575 (4)1.0836 (5)0.1107 (2)0.0575 (16)
H26A0.04461.01360.11310.069*
H26B0.01891.11770.13590.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0369 (4)0.0331 (4)0.0554 (5)−0.0024 (3)0.0001 (4)0.0037 (4)
Cl10.1222 (19)0.1082 (17)0.0760 (14)−0.0257 (14)−0.0106 (13)−0.0268 (12)
Cl20.0907 (13)0.0690 (12)0.0706 (12)−0.0022 (10)−0.0220 (10)−0.0051 (10)
O10.054 (3)0.055 (3)0.085 (3)−0.005 (2)0.012 (2)−0.010 (2)
O20.064 (3)0.038 (2)0.074 (3)−0.003 (2)−0.008 (2)0.006 (2)
N10.047 (3)0.039 (3)0.052 (3)−0.002 (2)0.007 (3)−0.002 (2)
N20.045 (3)0.045 (3)0.055 (3)−0.003 (2)−0.012 (2)0.006 (2)
C10.057 (4)0.039 (3)0.047 (4)0.002 (3)0.007 (3)−0.001 (3)
C20.055 (4)0.037 (3)0.065 (5)0.003 (3)0.012 (4)0.007 (3)
C30.064 (4)0.056 (4)0.066 (5)0.008 (4)0.013 (4)−0.001 (4)
C40.097 (6)0.055 (4)0.055 (4)0.016 (4)0.011 (4)−0.003 (4)
C50.090 (5)0.051 (4)0.054 (4)0.000 (4)0.000 (4)−0.006 (3)
C60.064 (4)0.059 (4)0.053 (4)0.000 (4)−0.003 (4)0.004 (3)
C70.045 (4)0.046 (4)0.059 (4)−0.005 (3)0.004 (3)0.000 (3)
C80.044 (3)0.045 (4)0.057 (4)−0.005 (3)0.002 (3)−0.003 (3)
C90.097 (5)0.052 (4)0.057 (4)0.004 (4)0.017 (4)0.001 (4)
C100.107 (6)0.074 (5)0.070 (5)0.006 (5)0.011 (5)−0.001 (4)
C110.085 (6)0.087 (6)0.064 (5)0.000 (5)0.005 (4)−0.021 (5)
C120.081 (5)0.059 (4)0.077 (5)0.002 (4)0.005 (4)−0.020 (4)
C130.057 (4)0.043 (4)0.073 (5)0.004 (3)0.009 (3)−0.010 (3)
C140.038 (3)0.043 (3)0.054 (4)−0.003 (3)−0.005 (3)0.010 (3)
C150.039 (3)0.048 (4)0.062 (4)0.003 (3)−0.001 (3)0.008 (3)
C160.054 (4)0.052 (4)0.074 (5)0.006 (3)−0.007 (4)0.026 (4)
C170.057 (4)0.072 (5)0.057 (4)−0.001 (4)−0.006 (3)0.007 (4)
C180.049 (4)0.056 (4)0.054 (4)0.000 (3)−0.009 (3)0.004 (3)
C190.046 (4)0.048 (4)0.062 (4)0.001 (3)−0.003 (3)0.007 (4)
C200.045 (3)0.044 (4)0.063 (4)0.000 (3)−0.005 (3)0.011 (3)
C210.059 (4)0.039 (4)0.067 (4)−0.004 (3)−0.019 (3)0.006 (3)
C220.045 (4)0.084 (5)0.064 (4)−0.004 (3)−0.005 (3)0.017 (4)
C230.063 (5)0.099 (6)0.067 (5)−0.013 (4)−0.007 (4)0.010 (4)
C240.069 (5)0.081 (5)0.064 (5)−0.004 (4)−0.015 (4)0.003 (4)
C250.063 (4)0.060 (4)0.072 (5)0.001 (4)−0.021 (4)0.002 (4)
C260.053 (4)0.053 (4)0.066 (4)0.004 (3)−0.009 (3)0.000 (4)
Geometric parameters (Å, °) top
Ni1—O11.911 (4)C11—H11B0.9700
Ni1—O21.911 (4)C12—C131.508 (8)
Ni1—N12.016 (5)C12—H12A0.9700
Ni1—N22.018 (5)C12—H12B0.9700
Cl1—C51.740 (7)C13—H13A0.9700
Cl2—C181.737 (6)C13—H13B0.9700
O1—C21.321 (7)C14—C191.417 (7)
O2—C151.314 (7)C14—C151.423 (7)
N1—C71.298 (7)C14—C201.434 (7)
N1—C81.478 (7)C15—C161.404 (8)
N2—C201.286 (7)C16—C171.374 (8)
N2—C211.470 (7)C16—H160.9300
C1—C21.415 (8)C17—C181.398 (8)
C1—C61.419 (8)C17—H170.9300
C1—C71.440 (7)C18—C191.356 (7)
C2—C31.390 (8)C19—H190.9300
C3—C41.366 (8)C20—H200.9300
C3—H30.9300C21—C221.516 (8)
C4—C51.394 (9)C21—C261.526 (7)
C4—H40.9300C21—H210.9800
C5—C61.358 (8)C22—C231.525 (8)
C6—H60.9300C22—H22A0.9700
C7—H70.9300C22—H22B0.9700
C8—C91.502 (8)C23—C241.520 (8)
C8—C131.514 (7)C23—H23A0.9700
C8—H80.9800C23—H23B0.9700
C9—C101.520 (8)C24—C251.527 (8)
C9—H9A0.9700C24—H24A0.9700
C9—H9B0.9700C24—H24B0.9700
C10—C111.516 (9)C25—C261.516 (8)
C10—H10A0.9700C25—H25A0.9700
C10—H10B0.9700C25—H25B0.9700
C11—C121.508 (9)C26—H26A0.9700
C11—H11A0.9700C26—H26B0.9700
O1—Ni1—O2120.45 (18)H12A—C12—H12B108.0
O1—Ni1—N195.93 (18)C12—C13—C8109.9 (5)
O2—Ni1—N1112.44 (18)C12—C13—H13A109.7
O1—Ni1—N2113.09 (19)C8—C13—H13A109.7
O2—Ni1—N294.54 (17)C12—C13—H13B109.7
N1—Ni1—N2122.42 (18)C8—C13—H13B109.7
C2—O1—Ni1124.8 (4)H13A—C13—H13B108.2
C15—O2—Ni1123.3 (4)C19—C14—C15119.7 (5)
C7—N1—C8117.2 (5)C19—C14—C20116.4 (5)
C7—N1—Ni1120.4 (4)C15—C14—C20124.0 (5)
C8—N1—Ni1122.4 (4)O2—C15—C16119.3 (6)
C20—N2—C21118.8 (5)O2—C15—C14124.4 (6)
C20—N2—Ni1120.8 (4)C16—C15—C14116.3 (6)
C21—N2—Ni1120.3 (4)C17—C16—C15123.6 (6)
C2—C1—C6119.5 (6)C17—C16—H16118.2
C2—C1—C7125.5 (6)C15—C16—H16118.2
C6—C1—C7115.0 (5)C16—C17—C18118.7 (6)
O1—C2—C3118.7 (6)C16—C17—H17120.6
O1—C2—C1123.8 (6)C18—C17—H17120.6
C3—C2—C1117.4 (6)C19—C18—C17120.6 (6)
C4—C3—C2122.2 (6)C19—C18—Cl2121.4 (5)
C4—C3—H3118.9C17—C18—Cl2118.1 (5)
C2—C3—H3118.9C18—C19—C14121.1 (6)
C3—C4—C5120.3 (6)C18—C19—H19119.5
C3—C4—H4119.8C14—C19—H19119.5
C5—C4—H4119.8N2—C20—C14127.1 (5)
C6—C5—C4119.6 (7)N2—C20—H20116.5
C6—C5—Cl1119.9 (6)C14—C20—H20116.5
C4—C5—Cl1120.5 (6)N2—C21—C22110.4 (5)
C5—C6—C1120.8 (6)N2—C21—C26109.4 (5)
C5—C6—H6119.6C22—C21—C26111.4 (5)
C1—C6—H6119.6N2—C21—H21108.5
N1—C7—C1127.2 (6)C22—C21—H21108.5
N1—C7—H7116.4C26—C21—H21108.5
C1—C7—H7116.4C21—C22—C23112.4 (5)
N1—C8—C9109.0 (5)C21—C22—H22A109.1
N1—C8—C13110.7 (5)C23—C22—H22A109.1
C9—C8—C13111.0 (5)C21—C22—H22B109.1
N1—C8—H8108.7C23—C22—H22B109.1
C9—C8—H8108.7H22A—C22—H22B107.9
C13—C8—H8108.7C24—C23—C22111.2 (5)
C8—C9—C10111.5 (5)C24—C23—H23A109.4
C8—C9—H9A109.3C22—C23—H23A109.4
C10—C9—H9A109.3C24—C23—H23B109.4
C8—C9—H9B109.3C22—C23—H23B109.4
C10—C9—H9B109.3H23A—C23—H23B108.0
H9A—C9—H9B108.0C23—C24—C25110.2 (5)
C11—C10—C9110.6 (6)C23—C24—H24A109.6
C11—C10—H10A109.5C25—C24—H24A109.6
C9—C10—H10A109.5C23—C24—H24B109.6
C11—C10—H10B109.5C25—C24—H24B109.6
C9—C10—H10B109.5H24A—C24—H24B108.1
H10A—C10—H10B108.1C26—C25—C24111.0 (5)
C12—C11—C10109.3 (6)C26—C25—H25A109.4
C12—C11—H11A109.8C24—C25—H25A109.4
C10—C11—H11A109.8C26—C25—H25B109.4
C12—C11—H11B109.8C24—C25—H25B109.4
C10—C11—H11B109.8H25A—C25—H25B108.0
H11A—C11—H11B108.3C25—C26—C21111.6 (5)
C13—C12—C11110.9 (6)C25—C26—H26A109.3
C13—C12—H12A109.5C21—C26—H26A109.3
C11—C12—H12A109.5C25—C26—H26B109.3
C13—C12—H12B109.5C21—C26—H26B109.3
C11—C12—H12B109.5H26A—C26—H26B108.0
Table 1
Selected geometric parameters (Å, °) top
Ni1—O11.911 (4)Ni1—N12.016 (5)
Ni1—O21.911 (4)Ni1—N22.018 (5)
O1—Ni1—O2120.45 (18)O1—Ni1—N2113.09 (19)
O1—Ni1—N195.93 (18)O2—Ni1—N294.54 (17)
O2—Ni1—N1112.44 (18)N1—Ni1—N2122.42 (18)
Acknowledgements top

no acknowledgements

references
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