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Acta Cryst. (2009). E65, m317    [ doi:10.1107/S1600536809006084 ]

{2,2'-[Cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)

C. Tang

Abstract top

In the title mononuclear nickel(II) complex, [Ni(C20H20N2O2)], the Ni atom is four-coordinated in a square-planar geometry by the four donor atoms of the Schiff base ligand. The dihedral angle between the two benzene rings is 9.4 (2)°. The cyclohexyl group adopts a C-form chair conformation.

Comment top

Nickel(II) complexes play an important role in both bioinorganic chemistry and coordination chemistry (Suh et al., 1996; Dey et al., 2004; Angulo et al., 2001; Ramadevi et al., 2005; Edison et al., 2004). As a further study of the structures of such complexes, the title mononuclear nickel(II) complex, (I), is reported in this paper.

In (I), the Ni atom is four-coordinated in a square planar geometry by the four donor atoms of the Schiff base ligand. The dihedral angle between the two benzene rings is 9.4 (2)°. The cyclohexyl group adopts C-form chair conformation with the generalized puckering coordinates; q(3)=-0.569 (1)Å, q(2)=0.009 (1)Å and φ=96.288 (1)° (Cremer & Pople, 1975) (Fig. 1).

Related literature top

For nickel(II) complexes in bio-inorganic chemistry and

coordination chemistry, see: Angulo et al. (2001); Dey et al. (2004); Edison et al. (2004); Ramadevi et al. (2005); Suh et al. (1996). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Salicylaldehyde (0.2 mmol, 24.5 mg) and cyclohexyl-1,2-diamine (0.1 mmol, 11.4 mg) were dissolved in 10 ml methanol. To the mixture was added dropwise a 5 ml me thanol solution of nickel(II) nitrate hexahydrate (0.2 mmol, 58.2 mg) with stirring. The final solution was allowed to stand in air for two weeks, yielding red block-shaped crystals of (I).

Refinement top

H atoms were constrained to ideal geometries, with C—H = 0.93–0.97Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
{2,2'-[Cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) top
Crystal data top
[Ni(C20H20N2O2)]F(000) = 792
Mr = 379.09Dx = 1.497 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.6193 (8) ÅCell parameters from 3779 reflections
b = 19.118 (2) Åθ = 2.6–28.6°
c = 11.5459 (12) ŵ = 1.17 mm−1
β = 90.907 (1)°T = 298 K
V = 1681.6 (3) Å3Block, red
Z = 40.30 × 0.30 × 0.28 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3650 independent reflections
Radiation source: fine-focus sealed tube3023 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.721, Tmax = 0.735k = −24→24
9694 measured reflectionsl = −14→9
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.033P)2 + 0.2023P]
where P = (Fo2 + 2Fc2)/3
3650 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
[Ni(C20H20N2O2)]V = 1681.6 (3) Å3
Mr = 379.09Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.6193 (8) ŵ = 1.17 mm−1
b = 19.118 (2) ÅT = 298 K
c = 11.5459 (12) Å0.30 × 0.30 × 0.28 mm
β = 90.907 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3650 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3023 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 0.735Rint = 0.022
9694 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.28 e Å−3
S = 1.05Δρmin = −0.22 e Å−3
3650 reflectionsAbsolute structure: ?
226 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Ni10.80232 (3)0.468244 (10)0.481224 (17)0.03293 (8)
O10.86946 (19)0.37326 (6)0.49143 (10)0.0477 (3)
O20.89546 (18)0.48282 (6)0.63411 (11)0.0484 (3)
N10.6899 (2)0.45709 (7)0.33007 (12)0.0378 (3)
N20.7259 (2)0.56527 (7)0.46659 (12)0.0386 (3)
C10.8626 (2)0.32645 (9)0.40841 (15)0.0395 (4)
C20.9388 (3)0.26009 (9)0.42918 (17)0.0472 (5)
H20.98990.25080.50120.057*
C30.9392 (3)0.20924 (9)0.34579 (18)0.0500 (5)
H30.99030.16610.36250.060*
C40.8651 (3)0.22058 (10)0.23682 (18)0.0526 (5)
H40.86710.18590.18040.063*
C50.7887 (3)0.28423 (9)0.21422 (17)0.0488 (5)
H50.73830.29230.14150.059*
C60.7842 (2)0.33781 (9)0.29806 (15)0.0386 (4)
C70.6995 (2)0.40218 (9)0.26570 (15)0.0412 (4)
H70.64730.40440.19240.049*
C80.5917 (3)0.52030 (8)0.29253 (16)0.0401 (4)
H80.47670.51850.32920.048*
C90.5592 (3)0.52841 (9)0.16326 (16)0.0482 (5)
H9A0.48940.48950.13460.058*
H9B0.67030.52810.12330.058*
C100.4630 (3)0.59708 (10)0.13887 (18)0.0565 (5)
H10A0.44990.60320.05580.068*
H10B0.34640.59470.17120.068*
C110.5588 (3)0.65940 (10)0.18949 (17)0.0555 (5)
H11A0.49000.70130.17550.067*
H11B0.67030.66490.15120.067*
C120.5911 (3)0.65080 (9)0.31981 (16)0.0488 (5)
H12A0.65900.69010.34900.059*
H12B0.47970.65020.35940.059*
C130.6899 (2)0.58284 (9)0.34426 (15)0.0419 (4)
H130.80320.58600.30560.050*
C140.7157 (2)0.60977 (9)0.54952 (16)0.0423 (4)
H140.67330.65410.53150.051*
C150.7650 (2)0.59611 (9)0.66825 (15)0.0397 (4)
C160.7300 (3)0.64851 (10)0.75078 (17)0.0478 (5)
H160.67260.68900.72680.057*
C170.7777 (3)0.64176 (10)0.86443 (17)0.0551 (5)
H170.75120.67660.91750.066*
C180.8670 (3)0.58153 (11)0.89957 (17)0.0547 (5)
H180.90100.57640.97680.066*
C190.9054 (3)0.52957 (10)0.82153 (16)0.0478 (5)
H190.96630.49020.84690.057*
C200.8544 (2)0.53471 (8)0.70409 (15)0.0398 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03599 (14)0.03109 (12)0.03155 (13)0.00174 (9)−0.00469 (9)−0.00265 (8)
O10.0670 (9)0.0363 (6)0.0396 (7)0.0052 (6)−0.0079 (6)−0.0018 (5)
O20.0549 (9)0.0475 (7)0.0424 (7)0.0133 (6)−0.0129 (6)−0.0091 (6)
N10.0390 (9)0.0359 (7)0.0382 (8)−0.0005 (6)−0.0033 (6)−0.0002 (6)
N20.0408 (9)0.0366 (7)0.0383 (8)0.0000 (6)−0.0041 (6)−0.0020 (6)
C10.0409 (10)0.0362 (9)0.0415 (10)−0.0038 (7)0.0029 (8)0.0004 (7)
C20.0541 (12)0.0384 (9)0.0491 (11)0.0025 (8)−0.0001 (9)0.0025 (8)
C30.0547 (13)0.0345 (9)0.0609 (13)0.0020 (8)0.0081 (10)0.0003 (8)
C40.0640 (14)0.0391 (10)0.0548 (13)−0.0022 (9)0.0059 (10)−0.0113 (9)
C50.0580 (13)0.0442 (10)0.0442 (11)−0.0040 (9)−0.0020 (9)−0.0057 (8)
C60.0406 (10)0.0365 (9)0.0388 (9)−0.0046 (7)0.0013 (8)−0.0021 (7)
C70.0441 (11)0.0425 (9)0.0369 (10)−0.0049 (8)−0.0055 (8)−0.0036 (8)
C80.0400 (10)0.0393 (9)0.0410 (10)0.0001 (7)−0.0040 (8)0.0013 (7)
C90.0525 (12)0.0489 (11)0.0429 (11)0.0013 (9)−0.0084 (9)−0.0008 (8)
C100.0652 (14)0.0527 (11)0.0511 (12)0.0051 (10)−0.0157 (10)0.0055 (9)
C110.0613 (14)0.0498 (11)0.0550 (12)0.0024 (10)−0.0072 (10)0.0114 (9)
C120.0562 (13)0.0391 (10)0.0507 (11)0.0022 (9)−0.0070 (9)0.0029 (8)
C130.0437 (11)0.0412 (9)0.0408 (10)−0.0031 (8)−0.0016 (8)0.0030 (7)
C140.0443 (11)0.0349 (9)0.0476 (11)−0.0004 (8)−0.0023 (8)−0.0030 (8)
C150.0389 (10)0.0396 (9)0.0406 (10)−0.0043 (8)0.0003 (8)−0.0051 (7)
C160.0510 (12)0.0420 (10)0.0506 (12)−0.0018 (9)0.0021 (9)−0.0090 (8)
C170.0660 (14)0.0536 (11)0.0458 (12)−0.0066 (10)0.0056 (10)−0.0159 (9)
C180.0616 (14)0.0647 (13)0.0377 (11)−0.0109 (10)−0.0017 (9)−0.0072 (9)
C190.0515 (12)0.0506 (11)0.0413 (11)−0.0033 (9)−0.0053 (9)−0.0010 (8)
C200.0376 (10)0.0426 (9)0.0391 (10)−0.0050 (8)−0.0010 (8)−0.0047 (8)
Geometric parameters (Å, °) top
Ni1—O11.8897 (12)C9—C101.528 (2)
Ni1—O21.9125 (12)C9—H9A0.9700
Ni1—N11.9435 (15)C9—H9B0.9700
Ni1—N21.9507 (14)C10—C111.510 (3)
O1—C11.312 (2)C10—H10A0.9700
O2—C201.320 (2)C10—H10B0.9700
N1—C71.289 (2)C11—C121.530 (3)
N1—C81.483 (2)C11—H11A0.9700
N2—C141.284 (2)C11—H11B0.9700
N2—C131.473 (2)C12—C131.526 (2)
C1—C21.414 (2)C12—H12A0.9700
C1—C61.415 (2)C12—H12B0.9700
C2—C31.368 (2)C13—H130.9800
C2—H20.9300C14—C151.439 (2)
C3—C41.388 (3)C14—H140.9300
C3—H30.9300C15—C161.411 (2)
C4—C51.372 (3)C15—C201.416 (2)
C4—H40.9300C16—C171.362 (3)
C5—C61.410 (2)C16—H160.9300
C5—H50.9300C17—C181.394 (3)
C6—C71.437 (2)C17—H170.9300
C7—H70.9300C18—C191.376 (3)
C8—C91.517 (2)C18—H180.9300
C8—C131.527 (2)C19—C201.408 (3)
C8—H80.9800C19—H190.9300
O1—Ni1—O289.22 (5)H9A—C9—H9B108.2
O1—Ni1—N193.76 (5)C11—C10—C9112.26 (17)
O2—Ni1—N1175.27 (6)C11—C10—H10A109.2
O1—Ni1—N2177.83 (6)C9—C10—H10A109.2
O2—Ni1—N292.71 (5)C11—C10—H10B109.2
N1—Ni1—N284.25 (6)C9—C10—H10B109.2
C1—O1—Ni1127.04 (11)H10A—C10—H10B107.9
C20—O2—Ni1125.90 (11)C10—C11—C12111.42 (16)
C7—N1—C8121.87 (15)C10—C11—H11A109.3
C7—N1—Ni1125.39 (12)C12—C11—H11A109.3
C8—N1—Ni1112.73 (10)C10—C11—H11B109.3
C14—N2—C13123.45 (15)C12—C11—H11B109.3
C14—N2—Ni1125.94 (13)H11A—C11—H11B108.0
C13—N2—Ni1110.53 (10)C13—C12—C11110.17 (16)
O1—C1—C2118.46 (16)C13—C12—H12A109.6
O1—C1—C6124.38 (16)C11—C12—H12A109.6
C2—C1—C6117.16 (16)C13—C12—H12B109.6
C3—C2—C1121.58 (18)C11—C12—H12B109.6
C3—C2—H2119.2H12A—C12—H12B108.1
C1—C2—H2119.2N2—C13—C12117.09 (15)
C2—C3—C4121.41 (18)N2—C13—C8106.20 (13)
C2—C3—H3119.3C12—C13—C8110.91 (15)
C4—C3—H3119.3N2—C13—H13107.4
C5—C4—C3118.45 (18)C12—C13—H13107.4
C5—C4—H4120.8C8—C13—H13107.4
C3—C4—H4120.8N2—C14—C15124.88 (16)
C4—C5—C6121.89 (19)N2—C14—H14117.6
C4—C5—H5119.1C15—C14—H14117.6
C6—C5—H5119.1C16—C15—C20119.10 (16)
C5—C6—C1119.49 (16)C16—C15—C14117.73 (16)
C5—C6—C7117.35 (16)C20—C15—C14123.08 (15)
C1—C6—C7123.16 (15)C17—C16—C15122.23 (18)
N1—C7—C6125.24 (16)C17—C16—H16118.9
N1—C7—H7117.4C15—C16—H16118.9
C6—C7—H7117.4C16—C17—C18118.67 (18)
N1—C8—C9116.41 (14)C16—C17—H17120.7
N1—C8—C13106.37 (14)C18—C17—H17120.7
C9—C8—C13112.08 (15)C19—C18—C17120.90 (19)
N1—C8—H8107.2C19—C18—H18119.5
C9—C8—H8107.2C17—C18—H18119.5
C13—C8—H8107.2C18—C19—C20121.48 (18)
C8—C9—C10109.85 (15)C18—C19—H19119.3
C8—C9—H9A109.7C20—C19—H19119.3
C10—C9—H9A109.7O2—C20—C19118.21 (16)
C8—C9—H9B109.7O2—C20—C15124.17 (16)
C10—C9—H9B109.7C19—C20—C15117.61 (16)
Table 1
Selected geometric parameters (Å, °) top
Ni1—O11.8897 (12)Ni1—N11.9435 (15)
Ni1—O21.9125 (12)Ni1—N21.9507 (14)
O1—Ni1—O289.22 (5)O1—Ni1—N2177.83 (6)
O1—Ni1—N193.76 (5)O2—Ni1—N292.71 (5)
O2—Ni1—N1175.27 (6)N1—Ni1—N284.25 (6)
Acknowledgements top

Financial support from the Jiaying University research fund is gratefully acknowledged.

references
References top

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