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

Tang, C.

doi:10.1107/S1600536809006084

metal-organic compounds

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Volume 65| Part 3| March 2009| Page m317

doi:10.1107/S1600536809006084

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

Chunbao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@126.com

(Received 11 February 2009; accepted 19 February 2009; online 25 February 2009)

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.

Related literature

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

Crystal data

[Ni(C₂₀H₂₀N₂O₂)]
M_r = 379.09
Monoclinic, P 2₁ /c
a = 7.6193 (8) Å
b = 19.118 (2) Å
c = 11.5459 (12) Å
β = 90.907 (1)°
V = 1681.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.721, T_max = 0.735
9694 measured reflections
3650 independent reflections
3023 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.05
3650 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.8897 (12)
Ni1—O2	1.9125 (12)
Ni1—N1	1.9435 (15)
Ni1—N2	1.9507 (14)

O1—Ni1—O2	89.22 (5)
O1—Ni1—N1	93.76 (5)
O2—Ni1—N1	175.27 (6)
O1—Ni1—N2	177.83 (6)
O2—Ni1—N2	92.71 (5)
N1—Ni1—N2	84.25 (6)

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006084/bq2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006084/bq2125Isup2.hkl

checkCIF report

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).

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

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
M_r = 379.09	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6193 (8) Å	Cell parameters from 3779 reflections
b = 19.118 (2) Å	θ = 2.6–28.6°
c = 11.5459 (12) Å	µ = 1.17 mm⁻¹
β = 90.907 (1)°	T = 298 K
V = 1681.6 (3) Å³	Block, red
Z = 4	0.30 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3650 independent reflections
Radiation source: fine-focus sealed tube	3023 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.721, T_max = 0.735	k = −24→24
9694 measured reflections	l = −14→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.033P)² + 0.2023P] where P = (F_o² + 2F_c²)/3
3650 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Ni(C₂₀H₂₀N₂O₂)]	V = 1681.6 (3) Å³
M_r = 379.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6193 (8) Å	µ = 1.17 mm⁻¹
b = 19.118 (2) Å	T = 298 K
c = 11.5459 (12) Å	0.30 × 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)
T_min = 0.721, T_max = 0.735	R_int = 0.022
9694 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
3650 reflections	Δρ_min = −0.22 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

	x	y	z	U_iso*/U_eq
Ni1	0.80232 (3)	0.468244 (10)	0.481224 (17)	0.03293 (8)
O1	0.86946 (19)	0.37326 (6)	0.49143 (10)	0.0477 (3)
O2	0.89546 (18)	0.48282 (6)	0.63411 (11)	0.0484 (3)
N1	0.6899 (2)	0.45709 (7)	0.33007 (12)	0.0378 (3)
N2	0.7259 (2)	0.56527 (7)	0.46659 (12)	0.0386 (3)
C1	0.8626 (2)	0.32645 (9)	0.40841 (15)	0.0395 (4)
C2	0.9388 (3)	0.26009 (9)	0.42918 (17)	0.0472 (5)
H2	0.9899	0.2508	0.5012	0.057*
C3	0.9392 (3)	0.20924 (9)	0.34579 (18)	0.0500 (5)
H3	0.9903	0.1661	0.3625	0.060*
C4	0.8651 (3)	0.22058 (10)	0.23682 (18)	0.0526 (5)
H4	0.8671	0.1859	0.1804	0.063*
C5	0.7887 (3)	0.28423 (9)	0.21422 (17)	0.0488 (5)
H5	0.7383	0.2923	0.1415	0.059*
C6	0.7842 (2)	0.33781 (9)	0.29806 (15)	0.0386 (4)
C7	0.6995 (2)	0.40218 (9)	0.26570 (15)	0.0412 (4)
H7	0.6473	0.4044	0.1924	0.049*
C8	0.5917 (3)	0.52030 (8)	0.29253 (16)	0.0401 (4)
H8	0.4767	0.5185	0.3292	0.048*
C9	0.5592 (3)	0.52841 (9)	0.16326 (16)	0.0482 (5)
H9A	0.4894	0.4895	0.1346	0.058*
H9B	0.6703	0.5281	0.1233	0.058*
C10	0.4630 (3)	0.59708 (10)	0.13887 (18)	0.0565 (5)
H10A	0.4499	0.6032	0.0558	0.068*
H10B	0.3464	0.5947	0.1712	0.068*
C11	0.5588 (3)	0.65940 (10)	0.18949 (17)	0.0555 (5)
H11A	0.4900	0.7013	0.1755	0.067*
H11B	0.6703	0.6649	0.1512	0.067*
C12	0.5911 (3)	0.65080 (9)	0.31981 (16)	0.0488 (5)
H12A	0.6590	0.6901	0.3490	0.059*
H12B	0.4797	0.6502	0.3594	0.059*
C13	0.6899 (2)	0.58284 (9)	0.34426 (15)	0.0419 (4)
H13	0.8032	0.5860	0.3056	0.050*
C14	0.7157 (2)	0.60977 (9)	0.54952 (16)	0.0423 (4)
H14	0.6733	0.6541	0.5315	0.051*
C15	0.7650 (2)	0.59611 (9)	0.66825 (15)	0.0397 (4)
C16	0.7300 (3)	0.64851 (10)	0.75078 (17)	0.0478 (5)
H16	0.6726	0.6890	0.7268	0.057*
C17	0.7777 (3)	0.64176 (10)	0.86443 (17)	0.0551 (5)
H17	0.7512	0.6766	0.9175	0.066*
C18	0.8670 (3)	0.58153 (11)	0.89957 (17)	0.0547 (5)
H18	0.9010	0.5764	0.9768	0.066*
C19	0.9054 (3)	0.52957 (10)	0.82153 (16)	0.0478 (5)
H19	0.9663	0.4902	0.8469	0.057*
C20	0.8544 (2)	0.53471 (8)	0.70409 (15)	0.0398 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03599 (14)	0.03109 (12)	0.03155 (13)	0.00174 (9)	−0.00469 (9)	−0.00265 (8)
O1	0.0670 (9)	0.0363 (6)	0.0396 (7)	0.0052 (6)	−0.0079 (6)	−0.0018 (5)
O2	0.0549 (9)	0.0475 (7)	0.0424 (7)	0.0133 (6)	−0.0129 (6)	−0.0091 (6)
N1	0.0390 (9)	0.0359 (7)	0.0382 (8)	−0.0005 (6)	−0.0033 (6)	−0.0002 (6)
N2	0.0408 (9)	0.0366 (7)	0.0383 (8)	0.0000 (6)	−0.0041 (6)	−0.0020 (6)
C1	0.0409 (10)	0.0362 (9)	0.0415 (10)	−0.0038 (7)	0.0029 (8)	0.0004 (7)
C2	0.0541 (12)	0.0384 (9)	0.0491 (11)	0.0025 (8)	−0.0001 (9)	0.0025 (8)
C3	0.0547 (13)	0.0345 (9)	0.0609 (13)	0.0020 (8)	0.0081 (10)	0.0003 (8)
C4	0.0640 (14)	0.0391 (10)	0.0548 (13)	−0.0022 (9)	0.0059 (10)	−0.0113 (9)
C5	0.0580 (13)	0.0442 (10)	0.0442 (11)	−0.0040 (9)	−0.0020 (9)	−0.0057 (8)
C6	0.0406 (10)	0.0365 (9)	0.0388 (9)	−0.0046 (7)	0.0013 (8)	−0.0021 (7)
C7	0.0441 (11)	0.0425 (9)	0.0369 (10)	−0.0049 (8)	−0.0055 (8)	−0.0036 (8)
C8	0.0400 (10)	0.0393 (9)	0.0410 (10)	0.0001 (7)	−0.0040 (8)	0.0013 (7)
C9	0.0525 (12)	0.0489 (11)	0.0429 (11)	0.0013 (9)	−0.0084 (9)	−0.0008 (8)
C10	0.0652 (14)	0.0527 (11)	0.0511 (12)	0.0051 (10)	−0.0157 (10)	0.0055 (9)
C11	0.0613 (14)	0.0498 (11)	0.0550 (12)	0.0024 (10)	−0.0072 (10)	0.0114 (9)
C12	0.0562 (13)	0.0391 (10)	0.0507 (11)	0.0022 (9)	−0.0070 (9)	0.0029 (8)
C13	0.0437 (11)	0.0412 (9)	0.0408 (10)	−0.0031 (8)	−0.0016 (8)	0.0030 (7)
C14	0.0443 (11)	0.0349 (9)	0.0476 (11)	−0.0004 (8)	−0.0023 (8)	−0.0030 (8)
C15	0.0389 (10)	0.0396 (9)	0.0406 (10)	−0.0043 (8)	0.0003 (8)	−0.0051 (7)
C16	0.0510 (12)	0.0420 (10)	0.0506 (12)	−0.0018 (9)	0.0021 (9)	−0.0090 (8)
C17	0.0660 (14)	0.0536 (11)	0.0458 (12)	−0.0066 (10)	0.0056 (10)	−0.0159 (9)
C18	0.0616 (14)	0.0647 (13)	0.0377 (11)	−0.0109 (10)	−0.0017 (9)	−0.0072 (9)
C19	0.0515 (12)	0.0506 (11)	0.0413 (11)	−0.0033 (9)	−0.0053 (9)	−0.0010 (8)
C20	0.0376 (10)	0.0426 (9)	0.0391 (10)	−0.0050 (8)	−0.0010 (8)	−0.0047 (8)

Geometric parameters (Å, º) top

Ni1—O1	1.8897 (12)	C9—C10	1.528 (2)
Ni1—O2	1.9125 (12)	C9—H9A	0.9700
Ni1—N1	1.9435 (15)	C9—H9B	0.9700
Ni1—N2	1.9507 (14)	C10—C11	1.510 (3)
O1—C1	1.312 (2)	C10—H10A	0.9700
O2—C20	1.320 (2)	C10—H10B	0.9700
N1—C7	1.289 (2)	C11—C12	1.530 (3)
N1—C8	1.483 (2)	C11—H11A	0.9700
N2—C14	1.284 (2)	C11—H11B	0.9700
N2—C13	1.473 (2)	C12—C13	1.526 (2)
C1—C2	1.414 (2)	C12—H12A	0.9700
C1—C6	1.415 (2)	C12—H12B	0.9700
C2—C3	1.368 (2)	C13—H13	0.9800
C2—H2	0.9300	C14—C15	1.439 (2)
C3—C4	1.388 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.411 (2)
C4—C5	1.372 (3)	C15—C20	1.416 (2)
C4—H4	0.9300	C16—C17	1.362 (3)
C5—C6	1.410 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.394 (3)
C6—C7	1.437 (2)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.376 (3)
C8—C9	1.517 (2)	C18—H18	0.9300
C8—C13	1.527 (2)	C19—C20	1.408 (3)
C8—H8	0.9800	C19—H19	0.9300

O1—Ni1—O2	89.22 (5)	H9A—C9—H9B	108.2
O1—Ni1—N1	93.76 (5)	C11—C10—C9	112.26 (17)
O2—Ni1—N1	175.27 (6)	C11—C10—H10A	109.2
O1—Ni1—N2	177.83 (6)	C9—C10—H10A	109.2
O2—Ni1—N2	92.71 (5)	C11—C10—H10B	109.2
N1—Ni1—N2	84.25 (6)	C9—C10—H10B	109.2
C1—O1—Ni1	127.04 (11)	H10A—C10—H10B	107.9
C20—O2—Ni1	125.90 (11)	C10—C11—C12	111.42 (16)
C7—N1—C8	121.87 (15)	C10—C11—H11A	109.3
C7—N1—Ni1	125.39 (12)	C12—C11—H11A	109.3
C8—N1—Ni1	112.73 (10)	C10—C11—H11B	109.3
C14—N2—C13	123.45 (15)	C12—C11—H11B	109.3
C14—N2—Ni1	125.94 (13)	H11A—C11—H11B	108.0
C13—N2—Ni1	110.53 (10)	C13—C12—C11	110.17 (16)
O1—C1—C2	118.46 (16)	C13—C12—H12A	109.6
O1—C1—C6	124.38 (16)	C11—C12—H12A	109.6
C2—C1—C6	117.16 (16)	C13—C12—H12B	109.6
C3—C2—C1	121.58 (18)	C11—C12—H12B	109.6
C3—C2—H2	119.2	H12A—C12—H12B	108.1
C1—C2—H2	119.2	N2—C13—C12	117.09 (15)
C2—C3—C4	121.41 (18)	N2—C13—C8	106.20 (13)
C2—C3—H3	119.3	C12—C13—C8	110.91 (15)
C4—C3—H3	119.3	N2—C13—H13	107.4
C5—C4—C3	118.45 (18)	C12—C13—H13	107.4
C5—C4—H4	120.8	C8—C13—H13	107.4
C3—C4—H4	120.8	N2—C14—C15	124.88 (16)
C4—C5—C6	121.89 (19)	N2—C14—H14	117.6
C4—C5—H5	119.1	C15—C14—H14	117.6
C6—C5—H5	119.1	C16—C15—C20	119.10 (16)
C5—C6—C1	119.49 (16)	C16—C15—C14	117.73 (16)
C5—C6—C7	117.35 (16)	C20—C15—C14	123.08 (15)
C1—C6—C7	123.16 (15)	C17—C16—C15	122.23 (18)
N1—C7—C6	125.24 (16)	C17—C16—H16	118.9
N1—C7—H7	117.4	C15—C16—H16	118.9
C6—C7—H7	117.4	C16—C17—C18	118.67 (18)
N1—C8—C9	116.41 (14)	C16—C17—H17	120.7
N1—C8—C13	106.37 (14)	C18—C17—H17	120.7
C9—C8—C13	112.08 (15)	C19—C18—C17	120.90 (19)
N1—C8—H8	107.2	C19—C18—H18	119.5
C9—C8—H8	107.2	C17—C18—H18	119.5
C13—C8—H8	107.2	C18—C19—C20	121.48 (18)
C8—C9—C10	109.85 (15)	C18—C19—H19	119.3
C8—C9—H9A	109.7	C20—C19—H19	119.3
C10—C9—H9A	109.7	O2—C20—C19	118.21 (16)
C8—C9—H9B	109.7	O2—C20—C15	124.17 (16)
C10—C9—H9B	109.7	C19—C20—C15	117.61 (16)

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₂₀N₂O₂)]
M_r	379.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.6193 (8), 19.118 (2), 11.5459 (12)
β (°)	90.907 (1)
V (Å³)	1681.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.30 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.721, 0.735
No. of measured, independent and observed [I > 2σ(I)] reflections	9694, 3650, 3023
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.05
No. of reflections	3650
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	1.8897 (12)	Ni1—N1	1.9435 (15)
Ni1—O2	1.9125 (12)	Ni1—N2	1.9507 (14)

O1—Ni1—O2	89.22 (5)	O1—Ni1—N2	177.83 (6)
O1—Ni1—N1	93.76 (5)	O2—Ni1—N2	92.71 (5)
O2—Ni1—N1	175.27 (6)	N1—Ni1—N2	84.25 (6)

Acknowledgements

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

References

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