Bis{1-[(4-methyl­phen­yl)imino­meth­yl]-2-naphtho­lato-κ² N,O}nickel(II)

Abstract

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,

• 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) ų

• 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[F ² > 2σ(F ²)] = 0.029

• wR(F ²) = 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.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Hydrogen atoms were placed in calculated positions and refined using a riding-model approximation with C—H = 0.93 Å, U_iso = 1.2U_eq(C) for aromatic H atoms and C—H = 0.96 Å, U_iso = 1.5U_eq(C) for methyl H atoms.

Figures

Fig. 1.

The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (symmetry code (A): -x+2, -y, -z).

Crystal data

[Ni(C18H14NO)2]	Z = 1
Mr = 579.31	F(000) = 302
Triclinic, P1	Dx = 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

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

Refinement

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(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
2753 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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 codes: (i) −x+2, −y, −z.