Bis{2-[imino­(phen­yl)meth­yl]-5-meth­oxy­phenolato-κ2N,O1}nickel(II)

Xiao, Y.; Li, Z.-Q.; Peng, X.Y.

doi:10.1107/S1600536812043061

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1387

doi:10.1107/S1600536812043061

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Bis{2-[imino(phenyl)methyl]-5-methoxyphenolato-κ²N,O¹}nickel(II)

Yu Xiao,^a ^* Zhong-Qiu Li ^a and Xue Yan Peng ^a

^aCollege of Environmental Science and Engineering, Guilin University of Technology, Guangxi Key Laboratory of Environmental Engineering, Protection and Assessment, Guilin 541004, People's Republic of China
^*Correspondence e-mail: 657683458@qq.com

(Received 9 October 2012; accepted 16 October 2012; online 20 October 2012)

The title complex, [Ni(C₁₄H₁₂NO₂)₂], lies about an inversion center. The Ni^II atom is coordinated in a slightly distorted square-planar geometry by two O atoms and two N atoms from two 2-[imino(phenyl)methyl]-5-methoxyphenolate ligands. The dihedral angle between the symmetry-unique phenyl and benzene rings is 73.2 (1)°.

Related literature

For background to 2-imino(methyl)phenol compounds, see: Zhang et al. (2008 , 2009 ); Jiang et al. (2003 ); Liu et al. (2009 ). For a related structure, see: Bernès (2010).

Experimental

Crystal data

[Ni(C₁₄H₁₂NO₂)₂]
M_r = 511.20
Monoclinic, P 2₁ /n
a = 11.882 (2) Å
b = 5.4983 (10) Å
c = 17.494 (3) Å
β = 91.913 (2)°
V = 1142.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 296 K
0.24 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.244, T_max = 0.453
5526 measured reflections
2010 independent reflections
1680 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.064
S = 1.03
2010 reflections
161 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 I, global. DOI: 10.1107/S1600536812043061/lh5543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043061/lh5543Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043061/lh5543Isup3.cdx

checkCIF report

Comment top

2-Imino(methyl)phenol compounds have been studied for many years (Jiang et al., 2003; Zhang et al., 2008, 2009; Bernés 2010; Liu et al., 2009) and have attracted interest because of their magnetic properties. The crystal structure of the title compound (I) is presented herein.

The molecular structure of (I) is shown in Fig .1. The Ni^II ion lies on a centre of inversion and is coordinated by two O atoms and two N atoms from two bidentate ligands, forming a slightly distorted square-planar geometry. The dihedral angle between the symmetry unique phenyl and benzene rings is 73.2 (1) °.

Related literature top

For background to 2-imino(methyl)phenol compounds, see: Zhang et al. (2008, 2009); Jiang et al. (2003); Liu et al. (2009). For a related structure, see: Bernès (2010).

Experimental top

Complex (I) was prepared from a mixture of 2-hydroxy-4-methoxy benzophenone (1 mmol, 0.228 g), ammonia (25%, 0.5 ml), triethylamine (0.5 ml), nickel(II) acetate tetrahydrate (0.5 mmol, 0.127 g) and methanol(8 mL) sealed in a 15 mL teflon-lined stainless steel bomb, and kept at 393 K for 120 h under autogenous pressure. After the reaction was slowly cooled to room temperature, green rectangular plates were produced (yield: 63%, based on Nickel). Anal. Calcd for C₂₈H₂₄N₂NiO₄(%): C, 65.78; H, 4.73; N, 5.48. Found(%): C, 65.72; H, 4.76; N, 5.53.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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), showing 30 % probability displacement ellipsoids. H atoms bonded to atoms are not shown. Symmetry code (a); 1-x, -y, 2-z.

Bis{2-[imino(phenyl)methyl]-5-methoxyphenolato- κ²N,O¹}nickel(II) top

Crystal data top

[Ni(C₁₄H₁₂NO₂)₂]	F(000) = 532
M_r = 511.20	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2010 reflections
a = 11.882 (2) Å	θ = 2.0–25.0°
b = 5.4983 (10) Å	µ = 0.89 mm⁻¹
c = 17.494 (3) Å	T = 296 K
β = 91.913 (2)°	Plate, green
V = 1142.3 (4) Å³	0.24 × 0.15 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	2010 independent reflections
Radiation source: fine-focus sealed tube	1680 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→11
T_min = 0.244, T_max = 0.453	k = −6→6
5526 measured reflections	l = −20→20

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0308P)² + 0.224P] where P = (F_o² + 2F_c²)/3
2010 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

[Ni(C₁₄H₁₂NO₂)₂]	V = 1142.3 (4) Å³
M_r = 511.20	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.882 (2) Å	µ = 0.89 mm⁻¹
b = 5.4983 (10) Å	T = 296 K
c = 17.494 (3) Å	0.24 × 0.15 × 0.10 mm
β = 91.913 (2)°

Data collection top

Bruker SMART CCD diffractometer	2010 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1680 reflections with I > 2σ(I)
T_min = 0.244, T_max = 0.453	R_int = 0.021
5526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	2 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
2010 reflections	Δρ_min = −0.15 e Å⁻³
161 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.47072 (17)	0.1107 (4)	0.71936 (11)	0.0451 (5)
H1	0.5182	−0.0211	0.7290	0.054*
C2	0.41390 (18)	0.1315 (4)	0.64899 (11)	0.0538 (5)
H2	0.4237	0.0140	0.6116	0.065*
C3	0.34319 (17)	0.3250 (4)	0.63443 (11)	0.0514 (5)
H3	0.3044	0.3374	0.5875	0.062*
C4	0.33005 (16)	0.4994 (4)	0.68923 (12)	0.0495 (5)
H4	0.2828	0.6311	0.6792	0.059*
C5	0.38659 (15)	0.4814 (3)	0.75956 (11)	0.0428 (5)
H5	0.3773	0.6012	0.7963	0.051*
C6	0.45685 (14)	0.2859 (3)	0.77523 (9)	0.0338 (4)
C7	0.50867 (14)	0.2546 (3)	0.85404 (9)	0.0346 (4)
C8	0.59499 (14)	0.4187 (3)	0.88197 (9)	0.0336 (4)
C9	0.63412 (15)	0.4204 (3)	0.96059 (10)	0.0359 (4)
C10	0.71438 (15)	0.5983 (4)	0.98239 (10)	0.0410 (4)
H10	0.7376	0.6093	1.0336	0.049*
C11	0.75958 (15)	0.7561 (4)	0.93082 (11)	0.0411 (4)
C12	0.72465 (16)	0.7507 (4)	0.85333 (10)	0.0428 (5)
H12	0.7555	0.8556	0.8180	0.051*
C13	0.64357 (15)	0.5853 (4)	0.83168 (10)	0.0389 (4)
H13	0.6191	0.5830	0.7806	0.047*
C14	0.88453 (18)	1.0924 (4)	0.91151 (13)	0.0564 (6)
H14A	0.9237	1.0160	0.8708	0.085*
H14B	0.9358	1.1940	0.9406	0.085*
H14C	0.8241	1.1898	0.8904	0.085*
Ni1	0.5000	0.0000	1.0000	0.03463 (12)
N1	0.47005 (13)	0.0801 (3)	0.89494 (8)	0.0404 (4)
H1A	0.4234	−0.0153	0.8712	0.048*
O2	0.84011 (12)	0.9107 (3)	0.96004 (8)	0.0573 (4)
O1	0.60041 (10)	0.2698 (2)	1.01257 (7)	0.0437 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0554 (12)	0.0395 (11)	0.0399 (10)	0.0065 (10)	−0.0067 (9)	0.0015 (9)
C2	0.0702 (14)	0.0538 (14)	0.0369 (11)	−0.0003 (12)	−0.0086 (10)	−0.0047 (10)
C3	0.0531 (12)	0.0599 (14)	0.0401 (11)	−0.0120 (11)	−0.0150 (9)	0.0128 (10)
C4	0.0407 (11)	0.0483 (12)	0.0587 (13)	0.0024 (10)	−0.0116 (9)	0.0105 (11)
C5	0.0416 (10)	0.0390 (11)	0.0475 (11)	0.0029 (9)	−0.0031 (8)	−0.0009 (9)
C6	0.0330 (9)	0.0353 (10)	0.0329 (9)	−0.0041 (8)	−0.0017 (7)	0.0061 (8)
C7	0.0343 (9)	0.0371 (10)	0.0322 (9)	0.0030 (8)	0.0011 (7)	−0.0004 (8)
C8	0.0350 (10)	0.0356 (9)	0.0301 (9)	0.0030 (8)	−0.0002 (7)	0.0006 (7)
C9	0.0369 (10)	0.0369 (10)	0.0339 (9)	0.0031 (8)	0.0009 (8)	0.0010 (8)
C10	0.0449 (11)	0.0458 (11)	0.0320 (9)	−0.0028 (9)	−0.0037 (8)	−0.0015 (9)
C11	0.0365 (10)	0.0430 (11)	0.0439 (10)	−0.0048 (9)	0.0016 (8)	−0.0052 (9)
C12	0.0426 (10)	0.0463 (12)	0.0397 (10)	−0.0081 (9)	0.0045 (8)	0.0035 (9)
C13	0.0400 (10)	0.0433 (11)	0.0334 (10)	0.0005 (9)	0.0001 (8)	0.0030 (8)
C14	0.0523 (13)	0.0493 (12)	0.0680 (14)	−0.0138 (11)	0.0090 (11)	−0.0067 (11)
Ni1	0.0386 (2)	0.0381 (2)	0.02698 (17)	−0.00429 (15)	−0.00215 (12)	0.00705 (14)
N1	0.0476 (9)	0.0416 (9)	0.0316 (7)	−0.0113 (7)	−0.0048 (7)	0.0054 (7)
O2	0.0616 (9)	0.0619 (9)	0.0483 (8)	−0.0262 (8)	−0.0007 (7)	−0.0050 (7)
O1	0.0501 (8)	0.0482 (8)	0.0323 (6)	−0.0107 (6)	−0.0051 (5)	0.0080 (6)

Geometric parameters (Å, º) top

C1—C6	1.387 (3)	C9—C10	1.410 (3)
C1—C2	1.389 (3)	C10—C11	1.374 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.374 (3)	C11—O2	1.366 (2)
C2—H2	0.9300	C11—C12	1.405 (3)
C3—C4	1.369 (3)	C12—C13	1.369 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.385 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—O2	1.424 (3)
C5—C6	1.383 (2)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.501 (2)	C14—H14C	0.9600
C7—N1	1.290 (2)	Ni1—N1	1.9118 (14)
C7—C8	1.439 (2)	Ni1—N1ⁱ	1.9118 (14)
C8—C13	1.407 (3)	Ni1—O1	1.9120 (13)
C8—C9	1.437 (2)	Ni1—O1ⁱ	1.9120 (13)
C9—O1	1.303 (2)	N1—H1A	0.8600

C6—C1—C2	120.12 (19)	C11—C10—H10	118.8
C6—C1—H1	119.9	C9—C10—H10	118.8
C2—C1—H1	119.9	O2—C11—C10	115.56 (16)
C3—C2—C1	120.3 (2)	O2—C11—C12	123.72 (17)
C3—C2—H2	119.9	C10—C11—C12	120.71 (17)
C1—C2—H2	119.9	C13—C12—C11	117.63 (17)
C4—C3—C2	119.73 (18)	C13—C12—H12	121.2
C4—C3—H3	120.1	C11—C12—H12	121.2
C2—C3—H3	120.1	C12—C13—C8	123.98 (16)
C3—C4—C5	120.59 (19)	C12—C13—H13	118.0
C3—C4—H4	119.7	C8—C13—H13	118.0
C5—C4—H4	119.7	O2—C14—H14A	109.5
C6—C5—C4	120.21 (18)	O2—C14—H14B	109.5
C6—C5—H5	119.9	H14A—C14—H14B	109.5
C4—C5—H5	119.9	O2—C14—H14C	109.5
C5—C6—C1	119.06 (16)	H14A—C14—H14C	109.5
C5—C6—C7	119.85 (16)	H14B—C14—H14C	109.5
C1—C6—C7	120.87 (16)	N1—Ni1—N1ⁱ	180.00 (2)
N1—C7—C8	122.72 (15)	N1—Ni1—O1	91.56 (6)
N1—C7—C6	116.88 (15)	N1ⁱ—Ni1—O1	88.44 (6)
C8—C7—C6	120.39 (15)	N1—Ni1—O1ⁱ	88.44 (6)
C13—C8—C9	117.89 (16)	N1ⁱ—Ni1—O1ⁱ	91.56 (6)
C13—C8—C7	119.90 (15)	O1—Ni1—O1ⁱ	180.0
C9—C8—C7	122.21 (16)	C7—N1—Ni1	130.26 (13)
O1—C9—C10	118.23 (15)	C7—N1—H1A	114.9
O1—C9—C8	124.53 (16)	Ni1—N1—H1A	114.9
C10—C9—C8	117.24 (16)	C11—O2—C14	118.83 (16)
C11—C10—C9	122.44 (17)	C9—O1—Ni1	128.17 (11)

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₂NO₂)₂]
M_r	511.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.882 (2), 5.4983 (10), 17.494 (3)
β (°)	91.913 (2)
V (Å³)	1142.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.24 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.244, 0.453
No. of measured, independent and observed [I > 2σ(I)] reflections	5526, 2010, 1680
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.064, 1.03
No. of reflections	2010
No. of parameters	161
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported financially by the Natural Science Foundation of Guangxi Province of China (No. 2010GXNSFA013014).

References

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