Bis(2-imino­methyl-5-methoxy­phenolato)nickel(II)

Tang, C.

doi:10.1107/S1600536809039233

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1275

https://doi.org/10.1107/S1600536809039233

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Bis(2-iminomethyl-5-methoxyphenolato)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 24 September 2009; accepted 27 September 2009; online 3 October 2009)

The title compound, [Ni(C₈H₈NO₂)₂], is a centrosymmetric mononuclear nickel(II) complex. The Ni^II ion, lying on an inversion centre, is four-coordinated in a square-planar geometry by two phenolate O and two imine N atoms from two symmetry-related 2-iminomethyl-5-methoxyphenolate ligands. In the crystal, molecules are linked into corrugated layers parallel to (100) by N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Angulo et al. (2001 ); Dey et al. (2004 ); Edison et al. (2004 ); Ramadevi et al. (2005 ); Suh et al. (1996 ); Tang (2009 ); Kamenar et al. (1990 ); Costes et al. (1994 ).

Experimental

Crystal data

[Ni(C₈H₈NO₂)₂]
M_r = 359.02
Orthorhombic, P b c a
a = 7.5704 (16) Å
b = 11.331 (2) Å
c = 17.227 (4) Å
V = 1477.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.795, T_max = 0.805
7939 measured reflections
1620 independent reflections
1122 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.083
S = 1.01
1620 reflections
110 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.8411 (16)
Ni1—N1	1.8529 (18)

O1ⁱ—Ni1—O1	180
O1—Ni1—N1ⁱ	86.08 (6)
O1—Ni1—N1	93.92 (6)
N1ⁱ—Ni1—N1	180
Symmetry code: (i) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱⁱ	0.90 (1)	2.391 (18)	3.166 (2)	144 (2)
Symmetry code: (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039233/ci2923sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039233/ci2923Isup2.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). Recently, the author has reported a nickel(II) complex (Tang, 2009). As a continuation of this work, the title mononuclear nickel(II) complex (Fig. 1), is reported in this paper.

The title complex is a centrosymmetric mononuclear nickel(II) complex. The Ni^II ion, lying on the inversion centre, is four-coordinated in a square-planar geometry, with two phenolate O and two imine N atoms from two 2-(iminomethyl)-5-methoxyphenolate ligands. The coordination bond lengths (Table 1) are comparable to those observed in related complexes (Kamenar et al., 1990; Costes et al., 1994).

In the crytal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 2), forming zigzag layers parallel to the (100) [Fig.2].

Related literature top

For related structures, see: Angulo et al. (2001); Dey et al. (2004); Edison et al. (2004); Ramadevi et al. (2005); Suh et al. (1996); Tang (2009); Kamenar et al. (1990); Costes et al. (1994).

Experimental top

4-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg) and nickel(II) nitrate hexahydrate (0.1 mmol, 29.1 mg) were mixed in a methanol solution (20 ml) which contains small quantity of ammonia. The mixture was stirred at room temperature for 30 min to give a red solution. The solution was allowed to stand in air for 8 d, yielding red block-shaped crystals of the title complex. The absorption band indicative of the C═N double bond formation in the IR spectrum of the complex is at 1617 cm^-1.

Structure description top

In the crytal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 2), forming zigzag layers parallel to the (100) [Fig.2].

For related structures, see: Angulo et al. (2001); Dey et al. (2004); Edison et al. (2004); Ramadevi et al. (2005); Suh et al. (1996); Tang (2009); Kamenar et al. (1990); Costes et al. (1994).

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are at the symmetry position (2-x, -y, 1-z).
	Fig. 2. Packing diagram, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Bis(2-iminomethyl-5-methoxyphenolato)nickel(II) top

Crystal data top

[Ni(C₈H₈NO₂)₂]	F(000) = 744
M_r = 359.02	D_x = 1.614 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1894 reflections
a = 7.5704 (16) Å	θ = 2.3–26.2°
b = 11.331 (2) Å	µ = 1.34 mm⁻¹
c = 17.227 (4) Å	T = 298 K
V = 1477.7 (5) Å³	Block, red
Z = 4	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1620 independent reflections
Radiation source: fine-focus sealed tube	1122 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
T_min = 0.795, T_max = 0.805	k = −11→14
7939 measured reflections	l = −21→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0414P)² + 0.384P] where P = (F_o² + 2F_c²)/3
1620 reflections	(Δ/σ)_max = 0.001
110 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Ni(C₈H₈NO₂)₂]	V = 1477.7 (5) Å³
M_r = 359.02	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 7.5704 (16) Å	µ = 1.34 mm⁻¹
b = 11.331 (2) Å	T = 298 K
c = 17.227 (4) Å	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1620 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1122 reflections with I > 2σ(I)
T_min = 0.795, T_max = 0.805	R_int = 0.028
7939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.28 e Å⁻³
1620 reflections	Δρ_min = −0.29 e Å⁻³
110 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
Ni1	1.0000	0.0000	0.5000	0.03483 (14)
O1	0.98642 (18)	0.00398 (11)	0.39332 (9)	0.0407 (4)
O2	0.8757 (2)	0.14990 (13)	0.13928 (8)	0.0486 (4)
N1	0.9039 (3)	0.14925 (16)	0.51213 (9)	0.0422 (4)
C1	0.8581 (3)	0.19740 (17)	0.37798 (11)	0.0366 (5)
C2	0.9275 (3)	0.08998 (17)	0.34895 (11)	0.0352 (4)
C3	0.9336 (3)	0.07278 (17)	0.26800 (11)	0.0369 (5)
H3	0.9783	0.0026	0.2480	0.044*
C4	0.8738 (3)	0.15895 (18)	0.21830 (11)	0.0380 (5)
C5	0.8038 (3)	0.26481 (18)	0.24643 (12)	0.0457 (5)
H5	0.7634	0.3224	0.2123	0.055*
C6	0.7956 (3)	0.28230 (19)	0.32452 (12)	0.0426 (5)
H6	0.7473	0.3522	0.3433	0.051*
C7	0.8489 (3)	0.22017 (18)	0.45884 (12)	0.0423 (5)
H7	0.7997	0.2915	0.4746	0.051*
C8	0.9403 (4)	0.0435 (2)	0.10637 (13)	0.0547 (6)
H8A	1.0625	0.0338	0.1198	0.082*
H8B	0.9286	0.0467	0.0509	0.082*
H8C	0.8736	−0.0220	0.1261	0.082*
H1	0.897 (3)	0.176 (2)	0.5612 (8)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0469 (2)	0.0262 (2)	0.0314 (2)	0.00123 (15)	−0.00135 (15)	−0.00138 (14)
O1	0.0622 (10)	0.0268 (8)	0.0330 (7)	0.0072 (6)	−0.0022 (6)	0.0002 (5)
O2	0.0658 (10)	0.0432 (9)	0.0367 (8)	0.0046 (7)	−0.0027 (7)	0.0072 (7)
N1	0.0578 (12)	0.0320 (10)	0.0367 (10)	0.0037 (9)	−0.0006 (8)	−0.0044 (7)
C1	0.0413 (11)	0.0290 (10)	0.0395 (11)	−0.0004 (8)	−0.0032 (8)	−0.0019 (9)
C2	0.0384 (11)	0.0289 (11)	0.0382 (11)	−0.0038 (9)	−0.0029 (8)	0.0015 (8)
C3	0.0442 (11)	0.0284 (10)	0.0381 (11)	0.0001 (9)	0.0005 (9)	−0.0001 (8)
C4	0.0402 (12)	0.0361 (11)	0.0378 (11)	−0.0045 (9)	−0.0036 (8)	0.0045 (9)
C5	0.0532 (12)	0.0351 (12)	0.0488 (13)	0.0023 (10)	−0.0072 (10)	0.0107 (10)
C6	0.0499 (13)	0.0279 (11)	0.0500 (13)	0.0058 (9)	−0.0032 (10)	0.0007 (10)
C7	0.0516 (14)	0.0281 (11)	0.0472 (13)	0.0038 (10)	−0.0018 (10)	−0.0050 (9)
C8	0.0743 (16)	0.0515 (14)	0.0382 (12)	0.0055 (13)	−0.0010 (11)	0.0029 (11)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8411 (16)	C2—C3	1.409 (3)
Ni1—O1	1.8411 (16)	C3—C4	1.375 (3)
Ni1—N1ⁱ	1.8529 (18)	C3—H3	0.93
Ni1—N1	1.8529 (18)	C4—C5	1.398 (3)
O1—C2	1.316 (2)	C5—C6	1.361 (3)
O2—C4	1.365 (2)	C5—H5	0.93
O2—C8	1.419 (3)	C6—H6	0.93
N1—C7	1.289 (3)	C7—H7	0.93
N1—H1	0.901 (10)	C8—H8A	0.96
C1—C6	1.413 (3)	C8—H8B	0.96
C1—C2	1.417 (3)	C8—H8C	0.96
C1—C7	1.418 (3)

O1ⁱ—Ni1—O1	180	C2—C3—H3	119.8
O1ⁱ—Ni1—N1ⁱ	93.92 (6)	O2—C4—C3	124.35 (19)
O1—Ni1—N1ⁱ	86.08 (6)	O2—C4—C5	114.44 (18)
O1ⁱ—Ni1—N1	86.08 (6)	C3—C4—C5	121.21 (19)
O1—Ni1—N1	93.92 (6)	C6—C5—C4	119.00 (19)
N1ⁱ—Ni1—N1	180	C6—C5—H5	120.5
C2—O1—Ni1	128.08 (13)	C4—C5—H5	120.5
C4—O2—C8	117.75 (16)	C5—C6—C1	121.97 (19)
C7—N1—Ni1	127.97 (15)	C5—C6—H6	119.0
C7—N1—H1	116.0 (17)	C1—C6—H6	119.0
Ni1—N1—H1	116.0 (17)	N1—C7—C1	124.78 (19)
C6—C1—C2	118.63 (18)	N1—C7—H7	117.6
C6—C1—C7	119.98 (18)	C1—C7—H7	117.6
C2—C1—C7	121.40 (18)	O2—C8—H8A	109.5
O1—C2—C3	117.48 (18)	O2—C8—H8B	109.5
O1—C2—C1	123.82 (17)	H8A—C8—H8B	109.5
C3—C2—C1	118.69 (18)	O2—C8—H8C	109.5
C4—C3—C2	120.50 (19)	H8A—C8—H8C	109.5
C4—C3—H3	119.8	H8B—C8—H8C	109.5

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.90 (1)	2.39 (2)	3.166 (2)	144 (2)

Symmetry code: (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₈NO₂)₂]
M_r	359.02
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	7.5704 (16), 11.331 (2), 17.227 (4)
V (Å³)	1477.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.18 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.795, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	7939, 1620, 1122
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.083, 1.01
No. of reflections	1620
No. of parameters	110
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.29

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	1.8411 (16)	Ni1—N1	1.8529 (18)

O1ⁱ—Ni1—O1	180	O1—Ni1—N1	93.92 (6)
O1—Ni1—N1ⁱ	86.08 (6)	N1ⁱ—Ni1—N1	180

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.90 (1)	2.391 (18)	3.166 (2)	144 (2)

Symmetry code: (ii) x, −y+1/2, z+1/2.

Acknowledgements

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

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