Bis{1-[(4-methyl­phen­yl)imino­meth­yl]-2-naphtho­lato-κ2N,O}nickel(II)

Wang, Q.; Jiang, J.; Zhu, P.

doi:10.1107/S1600536811010087

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m470

doi:10.1107/S1600536811010087

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Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-κ²N,O}nickel(II)

Quanbo Wang,^a Jianzhuang Jiang ^a ^* and Peihua Zhu ^a ^*

^aSchool of Chemistry & Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: calm_tree@sohu.com, zhangxiaomei@sdu.edu.cn

(Received 8 March 2011; accepted 17 March 2011; online 23 March 2011)

In the title complex, [Ni(C₁₈H₁₄NO)₂], the Ni^II ion lies on an inversion center and is coordinated in a slightly distorted square-planar environment. The 1-[(4-methylphenyl)iminomethyl]-2-naphtholate ligands are coordinated in a trans arrangement with respect to the N and O atoms. In the symmetry-unique ligand, the dihedral angle between the naphthalene ring system and the benzene ring of the methylphenyl group is 49.03 (7)°.

Related literature

For the isostructural Cu analog and background information, see: Zhu et al. (2010 ). For a related Ni structure, see: Chang et al. (2004 ).

Experimental

Crystal data

[Ni(C₁₈H₁₄NO)₂]
M_r = 579.31
Triclinic, $[P \overline 1]$
a = 7.1159 (4) Å
b = 9.9950 (5) Å
c = 10.5803 (5) Å
α = 103.057 (4)°
β = 96.327 (4)°
γ = 103.488 (4)°
V = 702.21 (6) Å³
Z = 1
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 293 K
0.46 × 0.36 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.848, T_max = 1.0
6948 measured reflections
2753 independent reflections
2438 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.074
S = 1.07
2753 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S1600536811010087/lh5218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010087/lh5218Isup2.hkl

checkCIF report

Comment top

In a previous paper, we reported the crystal structure of Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-κ² N,O}copper(II) (Zhu et al., 2010). As part of our search for Schiff base metal complexes, the title compound, (I) (Fig. 1), was synthesized and its crystal structure is reported herein. The Ni^II ion is coordinated by two O atoms and two N atoms of two bidentate schiff base ligands to form a slightly distorted square-planar geometry with a trans arrangement. In the symmetry unique ligand the dihedral angle between the naphthalene ring [C9-C18] system and the benzene ring [C1-C6] of the methylphenyl group is 49.03 (7)°. The Ni—N and Ni—O bond lengths agree with those in a related complex (Chang et al., 2004).

Related literature top

For the isostructural Cu analog and background information, see: Zhu et al. (2010). For a related Ni structure, see: Chang et al. (2004).

Experimental top

Nickel(II) acetate hydrate (0.194 g, 0.001 mol) in methanol (50 ml) and N-(p-Tolyl)-2-hydroxy-1-naphthaldimine (0.586 g, 0.002 mol) in acetonitrile(75 ml) were mixed and heated at 333 K for 1 h. The solution was filtered and the filtrate kept in a beaker at room temperature for crystallization. Needle-shaped crystals started appearing after 3 days.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (symmetry code (A): -x+2, -y, -z).

Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato- κ²N,O}nickel(II) top

Crystal data top

[Ni(C₁₈H₁₄NO)₂]	Z = 1
M_r = 579.31	F(000) = 302
Triclinic, P1	D_x = 1.370 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1159 (4) Å	Cell parameters from 4766 reflections
b = 9.9950 (5) Å	θ = 3.2–28.8°
c = 10.5803 (5) Å	µ = 0.73 mm⁻¹
α = 103.057 (4)°	T = 293 K
β = 96.327 (4)°	Needle, colourless
γ = 103.488 (4)°	0.46 × 0.36 × 0.14 mm
V = 702.21 (6) Å³

Data collection top

Bruker SMART CCD diffractometer	2753 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.0355 pixels mm^-1	θ_max = 26.0°, θ_min = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.848, T_max = 1.0	l = −12→13
6948 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0426P)²] where P = (F_o² + 2F_c²)/3
2753 reflections	(Δ/σ)_max = 0.001
188 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Ni(C₁₈H₁₄NO)₂]	γ = 103.488 (4)°
M_r = 579.31	V = 702.21 (6) Å³
Triclinic, P1	Z = 1
a = 7.1159 (4) Å	Mo Kα radiation
b = 9.9950 (5) Å	µ = 0.73 mm⁻¹
c = 10.5803 (5) Å	T = 293 K
α = 103.057 (4)°	0.46 × 0.36 × 0.14 mm
β = 96.327 (4)°

Data collection top

Bruker SMART CCD diffractometer	2753 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2438 reflections with I > 2σ(I)
T_min = 0.848, T_max = 1.0	R_int = 0.023
6948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
2753 reflections	Δρ_min = −0.19 e Å⁻³
188 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	1.0000	0.0000	0.0000	0.03301 (12)
O1	1.13942 (16)	−0.07866 (13)	0.10420 (11)	0.0407 (3)
N1	0.86165 (19)	0.06039 (14)	0.13584 (13)	0.0333 (3)
C1	0.7670 (2)	0.17310 (17)	0.13529 (15)	0.0330 (4)
C2	0.5687 (2)	0.14945 (18)	0.13814 (16)	0.0389 (4)
H2	0.4929	0.0588	0.1347	0.047*
C3	0.4832 (3)	0.26138 (19)	0.14616 (17)	0.0442 (4)
H3	0.3494	0.2446	0.1477	0.053*
C4	0.5911 (3)	0.39724 (19)	0.15200 (17)	0.0436 (4)
C5	0.7878 (3)	0.41810 (19)	0.14396 (18)	0.0479 (5)
H5	0.8627	0.5082	0.1452	0.057*
C6	0.8752 (3)	0.30679 (19)	0.13413 (18)	0.0435 (4)
H6	1.0071	0.3221	0.1267	0.052*
C7	0.4985 (3)	0.5211 (2)	0.1706 (2)	0.0656 (6)
H7A	0.3635	0.4877	0.1285	0.098*
H7C	0.5673	0.5921	0.1321	0.098*
H7B	0.5062	0.5619	0.2629	0.098*
C8	0.8407 (2)	0.00365 (18)	0.23459 (16)	0.0362 (4)
H8	0.7570	0.0334	0.2897	0.043*
C9	0.9333 (2)	−0.09941 (17)	0.26675 (15)	0.0348 (4)
C10	0.8838 (3)	−0.16148 (18)	0.37372 (16)	0.0378 (4)
C11	0.7251 (3)	−0.1453 (2)	0.43815 (17)	0.0472 (5)
H11	0.6482	−0.0889	0.4136	0.057*
C12	0.6802 (3)	−0.2103 (2)	0.53611 (18)	0.0582 (5)
H12	0.5739	−0.1976	0.5768	0.070*
C13	0.7941 (3)	−0.2955 (2)	0.57493 (19)	0.0631 (6)
H13	0.7626	−0.3406	0.6406	0.076*
C14	0.9498 (3)	−0.3120 (2)	0.51683 (19)	0.0562 (5)
H14	1.0257	−0.3677	0.5442	0.067*
C15	1.0000 (3)	−0.24677 (19)	0.41566 (17)	0.0436 (4)
C16	1.1607 (3)	−0.2661 (2)	0.35237 (19)	0.0494 (5)
H16	1.2390	−0.3194	0.3817	0.059*
C17	1.2044 (3)	−0.2103 (2)	0.25140 (18)	0.0454 (4)
H17	1.3110	−0.2259	0.2125	0.054*
C18	1.0881 (2)	−0.12706 (17)	0.20317 (16)	0.0359 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02674 (17)	0.03779 (19)	0.03807 (18)	0.01097 (13)	0.01075 (12)	0.01204 (13)
O1	0.0334 (6)	0.0540 (8)	0.0446 (7)	0.0189 (6)	0.0146 (5)	0.0208 (6)
N1	0.0292 (7)	0.0346 (7)	0.0391 (7)	0.0109 (6)	0.0093 (6)	0.0112 (6)
C1	0.0320 (9)	0.0351 (9)	0.0329 (8)	0.0120 (7)	0.0086 (7)	0.0064 (7)
C2	0.0355 (9)	0.0368 (9)	0.0456 (10)	0.0102 (8)	0.0143 (8)	0.0087 (8)
C3	0.0352 (10)	0.0480 (11)	0.0519 (10)	0.0181 (8)	0.0145 (8)	0.0073 (9)
C4	0.0496 (11)	0.0419 (10)	0.0409 (9)	0.0222 (9)	0.0060 (8)	0.0045 (8)
C5	0.0498 (11)	0.0345 (10)	0.0569 (11)	0.0072 (8)	0.0047 (9)	0.0132 (9)
C6	0.0316 (9)	0.0440 (10)	0.0553 (11)	0.0093 (8)	0.0070 (8)	0.0149 (9)
C7	0.0751 (15)	0.0541 (13)	0.0754 (14)	0.0374 (12)	0.0151 (12)	0.0102 (11)
C8	0.0318 (9)	0.0382 (9)	0.0382 (9)	0.0088 (7)	0.0101 (7)	0.0077 (8)
C9	0.0320 (9)	0.0359 (9)	0.0359 (9)	0.0075 (7)	0.0057 (7)	0.0102 (7)
C10	0.0403 (10)	0.0350 (9)	0.0341 (9)	0.0047 (7)	0.0044 (7)	0.0075 (7)
C11	0.0482 (11)	0.0544 (12)	0.0406 (10)	0.0123 (9)	0.0106 (8)	0.0154 (9)
C12	0.0610 (13)	0.0704 (14)	0.0441 (11)	0.0107 (11)	0.0184 (10)	0.0189 (10)
C13	0.0860 (17)	0.0624 (14)	0.0445 (11)	0.0130 (12)	0.0165 (11)	0.0255 (10)
C14	0.0778 (15)	0.0503 (12)	0.0444 (11)	0.0190 (11)	0.0083 (10)	0.0196 (10)
C15	0.0533 (11)	0.0366 (10)	0.0379 (9)	0.0089 (8)	0.0030 (8)	0.0093 (8)
C16	0.0562 (12)	0.0458 (11)	0.0521 (11)	0.0236 (9)	0.0043 (9)	0.0166 (9)
C17	0.0424 (10)	0.0500 (11)	0.0505 (11)	0.0215 (9)	0.0107 (8)	0.0156 (9)
C18	0.0317 (9)	0.0360 (9)	0.0376 (9)	0.0065 (7)	0.0038 (7)	0.0086 (8)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8255 (11)	C7—H7B	0.9600
Ni1—O1	1.8255 (11)	C8—H8	0.9300
Ni1—N1	1.8964 (13)	C8—C9	1.427 (2)
Ni1—N1ⁱ	1.8964 (13)	C9—C10	1.447 (2)
O1—C18	1.302 (2)	C9—C18	1.402 (2)
N1—C1	1.4420 (18)	C10—C11	1.404 (2)
N1—C8	1.303 (2)	C10—C15	1.423 (2)
C1—C2	1.380 (2)	C11—H11	0.9300
C1—C6	1.381 (2)	C11—C12	1.370 (3)
C2—H2	0.9300	C12—H12	0.9300
C2—C3	1.383 (2)	C12—C13	1.399 (3)
C3—H3	0.9300	C13—H13	0.9300
C3—C4	1.379 (3)	C13—C14	1.350 (3)
C4—C5	1.381 (3)	C14—H14	0.9300
C4—C7	1.518 (2)	C14—C15	1.410 (3)
C5—H5	0.9300	C15—C16	1.416 (3)
C5—C6	1.386 (2)	C16—H16	0.9300
C6—H6	0.9300	C16—C17	1.345 (3)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7C	0.9600	C17—C18	1.434 (2)

O1ⁱ—Ni1—O1	180	H7C—C7—H7B	109.5
O1ⁱ—Ni1—N1	88.02 (5)	C8—N1—Ni1	123.82 (10)
O1—Ni1—N1	91.98 (5)	C8—N1—C1	114.66 (13)
O1ⁱ—Ni1—N1ⁱ	91.98 (5)	C8—C9—C10	120.43 (14)
O1—Ni1—N1ⁱ	88.02 (5)	C9—C8—H8	116.7
O1—C18—C9	124.55 (14)	C9—C18—C17	118.85 (15)
O1—C18—C17	116.56 (14)	C10—C11—H11	119.0
N1—Ni1—N1ⁱ	180)	C11—C10—C9	124.15 (15)
N1—C8—H8	116.7	C11—C10—C15	117.29 (16)
N1—C8—C9	126.64 (14)	C11—C12—H12	120.0
C1—N1—Ni1	121.52 (10)	C11—C12—C13	120.04 (19)
C1—C2—H2	120.2	C12—C11—C10	122.01 (17)
C1—C2—C3	119.58 (16)	C12—C11—H11	119.0
C1—C6—C5	120.18 (16)	C12—C13—H13	120.1
C1—C6—H6	119.9	C13—C12—H12	120.0
C2—C1—N1	120.54 (15)	C13—C14—H14	119.2
C2—C1—C6	119.37 (14)	C13—C14—C15	121.60 (18)
C2—C3—H3	119.1	C14—C13—C12	119.80 (19)
C3—C2—H2	120.2	C14—C13—H13	120.1
C3—C4—C5	117.94 (15)	C14—C15—C10	119.25 (17)
C3—C4—C7	121.20 (17)	C14—C15—C16	121.88 (16)
C4—C3—C2	121.79 (16)	C15—C10—C9	118.55 (15)
C4—C3—H3	119.1	C15—C14—H14	119.2
C4—C5—H5	119.5	C15—C16—H16	118.8
C4—C5—C6	121.00 (17)	C16—C15—C10	118.86 (16)
C4—C7—H7A	109.5	C16—C17—H17	119.7
C4—C7—H7C	109.5	C16—C17—C18	120.68 (16)
C4—C7—H7B	109.5	C17—C16—C15	122.48 (15)
C5—C4—C7	120.84 (18)	C17—C16—H16	118.8
C5—C6—H6	119.9	C18—O1—Ni1	127.72 (10)
C6—C1—N1	120.08 (14)	C18—C9—C8	118.71 (15)
C6—C5—H5	119.5	C18—C9—C10	120.46 (14)
H7A—C7—H7C	109.5	C18—C17—H17	119.7
H7A—C7—H7B	109.5

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₈H₁₄NO)₂]
M_r	579.31
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.1159 (4), 9.9950 (5), 10.5803 (5)
α, β, γ (°)	103.057 (4), 96.327 (4), 103.488 (4)
V (Å³)	702.21 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.46 × 0.36 × 0.14

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.848, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	6948, 2753, 2438
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.074, 1.07
No. of reflections	2753
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Doctoral Foundation of Shandong (grant No. 200903058).

References

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