Bis[2-(3-cyano­phenyl­imino­meth­yl)phenolato]nickel(II)

Gong, X.-X.; Xia, R.; Xu, H.-J.

doi:10.1107/S1600536808004765

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m494

doi:10.1107/S1600536808004765

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Bis[2-(3-cyanophenyliminomethyl)phenolato]nickel(II)

Xing-Xuan Gong,^a Rong Xia ^a and Hai-Jun Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast UniVersity, Nanjing, 210096, People's Republic of China
^*Correspondence e-mail: xuhj@seu.edu.cn

(Received 10 January 2008; accepted 19 February 2008; online 22 February 2008)

In the title complex, [Ni(C₁₄H₉N₂O)₂], the Ni^II atom lies on an inversion center and is coordinated by the O atom and an N atom of two Schiff base 2-(3-cyanophenyliminomethyl)phenolate ligands in a square-planar geometry. The dihedral angle between the cyanophenyl and phenolate rings is 47.62 (7)°.

Related literature

For related literature, see: Adams et al. (2004 ); Bian et al. (2004 ); Brückner et al. (2000 ); Harrop et al. (2003 ); Marganian et al. (1995 ); Akkurt et al. (2006 ); Peng et al. (2006 ).

Experimental

Crystal data

[Ni(C₁₄H₉N₂O)₂]
M_r = 501.17
Monoclinic, P 2₁ /c
a = 9.0294 (18) Å
b = 8.0856 (16) Å
c = 15.644 (3) Å
β = 104.01 (3)°
V = 1108.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 (2) K
0.25 × 0.18 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.852, T_max = 1.00 (expected range = 0.723–0.849)
11052 measured reflections
2540 independent reflections
2246 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.10
2540 reflections
160 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004765/dn2310sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004765/dn2310Isup2.hkl

checkCIF report

Comment top

Schiff bases have been used extensively as ligands in the field of coordination chemistry. These complexes play an important role in the development of pharmacological and catalytic properties (Harrop et al., 2003; Brückner et al., 2000). Nickel(II) compounds with Schiff bases have received much attention in recent years (Marganian et al., 1995). Here we report the molecular and crystal structure of nickel (II) complex with a Schiff base ligand.

The Ni^IIatom in (I) lies on an inversion center and is coordinated by the two imine N and two phenolateO atoms of the two Schiff base ligands in a square-planar geometry (Fig.1). The dihedral angle between the cyanophenyl and phenyl rings is 47.62 (7)°.. The Ni—O and Ni—N bond lengths agree with the values reported for related complexes(Peng, et al., (2006); Adams et al., 2004; Bian et al., 2004).

Related literature top

For related literature, see: Adams et al. (2004); Bian et al. (2004); Brückner et al. (2000); Harrop et al. (2003); Marganian et al. (1995); Akkurt et al. (2006); Peng et al. (2006).

Experimental top

2-(3-cyanophenyliminomethyl)phenol was prepared according to the literature (Akkurt et al., 2006). NiCl₂.6H₂O(23.7 mg, 0.1 mmol) in methanol (5 ml) was added to the solution of 2-(3-cyanophenyliminomethyl)phenol (22.2 mg, 0.1 mmol)in the methanol (5 ml), the pH was then adjusted to 8–9 and the mixture was stirred for 4 h. The filtrate was kept at room temperature for about two weeks, and blue block shaped crystals of (I) suitable for for X-ray single-crystal analyses were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. [Symmetry code: (i) 1 - x, 1 - y, 1 - z]

Bis[2-(3-cyanophenyliminomethyl)phenolato]nickel(II) top

Crystal data top

[Ni(C₁₄H₉N₂O)₂]	F(000) = 516
M_r = 501.17	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10336 reflections
a = 9.0294 (18) Å	θ = 3.1–27.4°
b = 8.0856 (16) Å	µ = 0.91 mm⁻¹
c = 15.644 (3) Å	T = 293 K
β = 104.01 (3)°	Block, blue
V = 1108.1 (4) Å³	0.25 × 0.18 × 0.18 mm
Z = 2

Data collection top

Rigaku Mercury2 diffractometer	2540 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.852, T_max = 1.00	l = −20→20
11052 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0403P)² + 0.5389P] where P = (F_o² + 2F_c²)/3
2540 reflections	(Δ/σ)_max < 0.001
160 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Ni(C₁₄H₉N₂O)₂]	V = 1108.1 (4) Å³
M_r = 501.17	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0294 (18) Å	µ = 0.91 mm⁻¹
b = 8.0856 (16) Å	T = 293 K
c = 15.644 (3) Å	0.25 × 0.18 × 0.18 mm
β = 104.01 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2540 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2246 reflections with I > 2σ(I)
T_min = 0.852, T_max = 1.00	R_int = 0.035
11052 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.10	Δρ_max = 0.32 e Å⁻³
2540 reflections	Δρ_min = −0.35 e Å⁻³
160 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	0.5000	0.5000	0.5000	0.02514 (11)
O1	0.66446 (15)	0.36034 (17)	0.52053 (9)	0.0349 (3)
N1	0.41172 (16)	0.38940 (18)	0.58415 (10)	0.0266 (3)
C9	0.3215 (2)	0.6210 (2)	0.65595 (12)	0.0302 (4)
H9	0.4159	0.6714	0.6613	0.036*
C14	0.2380 (2)	0.8635 (3)	0.72431 (15)	0.0401 (5)
C1	0.5678 (2)	0.1429 (2)	0.59534 (12)	0.0283 (4)
C10	0.2087 (2)	0.6997 (2)	0.68770 (12)	0.0318 (4)
C8	0.2929 (2)	0.4678 (2)	0.61652 (12)	0.0274 (4)
C11	0.0679 (2)	0.6238 (3)	0.68133 (14)	0.0395 (5)
H11	−0.0069	0.6759	0.7034	0.047*
C3	0.7949 (2)	0.1080 (3)	0.54150 (14)	0.0383 (5)
H3	0.8663	0.1492	0.5130	0.046*
C2	0.6729 (2)	0.2098 (2)	0.55130 (11)	0.0286 (4)
C13	0.1528 (2)	0.3938 (3)	0.60894 (15)	0.0404 (5)
H13	0.1329	0.2914	0.5815	0.048*
C7	0.4475 (2)	0.2409 (2)	0.61321 (12)	0.0297 (4)
H7	0.3897	0.1942	0.6488	0.036*
C5	0.7059 (3)	−0.1167 (3)	0.61697 (15)	0.0432 (5)
H5	0.7169	−0.2245	0.6382	0.052*
N2	0.2618 (3)	0.9944 (2)	0.75059 (17)	0.0570 (6)
C12	0.0409 (2)	0.4716 (3)	0.64212 (17)	0.0461 (6)
H12	−0.0527	0.4199	0.6377	0.055*
C4	0.8094 (3)	−0.0502 (3)	0.57343 (15)	0.0430 (5)
H4	0.8904	−0.1149	0.5658	0.052*
C6	0.5875 (3)	−0.0197 (2)	0.62794 (14)	0.0366 (4)
H6	0.5184	−0.0625	0.6577	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02507 (18)	0.02233 (17)	0.03093 (19)	0.00178 (12)	0.01241 (13)	0.00362 (12)
O1	0.0309 (7)	0.0327 (7)	0.0458 (8)	0.0070 (6)	0.0182 (6)	0.0125 (6)
N1	0.0262 (7)	0.0245 (7)	0.0319 (7)	−0.0009 (6)	0.0124 (6)	−0.0003 (6)
C9	0.0294 (9)	0.0286 (9)	0.0360 (9)	−0.0003 (7)	0.0146 (8)	0.0016 (7)
C14	0.0431 (12)	0.0363 (12)	0.0480 (12)	0.0067 (9)	0.0247 (10)	0.0000 (9)
C1	0.0305 (9)	0.0236 (9)	0.0309 (9)	0.0009 (7)	0.0075 (7)	0.0007 (7)
C10	0.0348 (10)	0.0305 (9)	0.0332 (9)	0.0058 (8)	0.0140 (8)	0.0022 (8)
C8	0.0282 (9)	0.0272 (9)	0.0300 (9)	0.0015 (7)	0.0133 (7)	0.0023 (7)
C11	0.0327 (10)	0.0449 (12)	0.0461 (11)	0.0093 (9)	0.0194 (9)	0.0032 (9)
C3	0.0335 (10)	0.0412 (11)	0.0425 (11)	0.0088 (9)	0.0134 (9)	0.0043 (9)
C2	0.0294 (9)	0.0282 (9)	0.0278 (9)	0.0036 (7)	0.0064 (7)	0.0020 (7)
C13	0.0348 (10)	0.0378 (11)	0.0521 (12)	−0.0068 (9)	0.0174 (9)	−0.0090 (9)
C7	0.0315 (9)	0.0263 (9)	0.0335 (9)	−0.0034 (7)	0.0122 (7)	0.0022 (7)
C5	0.0491 (13)	0.0250 (10)	0.0528 (13)	0.0073 (9)	0.0070 (10)	0.0048 (9)
N2	0.0685 (15)	0.0369 (11)	0.0762 (15)	−0.0001 (9)	0.0379 (12)	−0.0109 (10)
C12	0.0294 (10)	0.0550 (14)	0.0592 (14)	−0.0081 (9)	0.0212 (10)	−0.0084 (11)
C4	0.0407 (12)	0.0397 (11)	0.0476 (12)	0.0173 (9)	0.0085 (9)	0.0018 (10)
C6	0.0398 (11)	0.0266 (10)	0.0437 (11)	−0.0013 (8)	0.0104 (9)	0.0045 (8)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8310 (14)	C8—C13	1.378 (3)
Ni1—O1	1.8310 (14)	C11—C12	1.371 (3)
Ni1—N1ⁱ	1.9174 (15)	C11—H11	0.9300
Ni1—N1	1.9174 (15)	C3—C4	1.368 (3)
O1—C2	1.304 (2)	C3—C2	1.413 (3)
N1—C7	1.297 (2)	C3—H3	0.9300
N1—C8	1.440 (2)	C13—C12	1.393 (3)
C9—C8	1.380 (3)	C13—H13	0.9300
C9—C10	1.391 (3)	C7—H7	0.9300
C9—H9	0.9300	C5—C6	1.370 (3)
C14—N2	1.137 (3)	C5—C4	1.390 (3)
C14—C10	1.442 (3)	C5—H5	0.9300
C1—C6	1.406 (2)	C12—H12	0.9300
C1—C2	1.409 (3)	C4—H4	0.9300
C1—C7	1.426 (3)	C6—H6	0.9300
C10—C11	1.393 (3)

O1ⁱ—Ni1—O1	180.000 (1)	C10—C11—H11	120.4
O1ⁱ—Ni1—N1ⁱ	92.65 (6)	C4—C3—C2	120.89 (19)
O1—Ni1—N1ⁱ	87.35 (6)	C4—C3—H3	119.6
O1ⁱ—Ni1—N1	87.35 (6)	C2—C3—H3	119.6
O1—Ni1—N1	92.65 (6)	O1—C2—C1	123.56 (17)
N1ⁱ—Ni1—N1	180.000 (1)	O1—C2—C3	118.75 (17)
C2—O1—Ni1	127.78 (12)	C1—C2—C3	117.68 (17)
C7—N1—C8	115.34 (15)	C8—C13—C12	120.4 (2)
C7—N1—Ni1	124.25 (13)	C8—C13—H13	119.8
C8—N1—Ni1	120.35 (12)	C12—C13—H13	119.8
C8—C9—C10	119.75 (18)	N1—C7—C1	125.63 (17)
C8—C9—H9	120.1	N1—C7—H7	117.2
C10—C9—H9	120.1	C1—C7—H7	117.2
N2—C14—C10	177.8 (2)	C6—C5—C4	118.5 (2)
C6—C1—C2	119.71 (18)	C6—C5—H5	120.7
C6—C1—C7	118.93 (18)	C4—C5—H5	120.7
C2—C1—C7	121.21 (16)	C11—C12—C13	120.4 (2)
C9—C10—C11	120.51 (18)	C11—C12—H12	119.8
C9—C10—C14	118.81 (18)	C13—C12—H12	119.8
C11—C10—C14	120.64 (18)	C3—C4—C5	121.6 (2)
C13—C8—C9	119.78 (17)	C3—C4—H4	119.2
C13—C8—N1	121.69 (17)	C5—C4—H4	119.2
C9—C8—N1	118.53 (16)	C5—C6—C1	121.6 (2)
C12—C11—C10	119.20 (19)	C5—C6—H6	119.2
C12—C11—H11	120.4	C1—C6—H6	119.2

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₉N₂O)₂]
M_r	501.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.0294 (18), 8.0856 (16), 15.644 (3)
β (°)	104.01 (3)
V (Å³)	1108.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.25 × 0.18 × 0.18

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.852, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	11052, 2540, 2246
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.10
No. of reflections	2540
No. of parameters	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.35

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

HJX acknowledges a Start-up Grant from Southeast University, People's Republic of China

References

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