metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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 NiII 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[Adams, H., Clunas, S. & Fenton, D. E. (2004). Acta Cryst. E60, m338-m339.]); Bian et al. (2004[Bian, H.-D., Yang, X.-E., Yu, Q., Liang, H. & Wang, H.-G. (2004). Acta Cryst. E60, m685-m686.]); Brückner et al. (2000[Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100-6106.]); Harrop et al. (2003[Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410-411.]); Marganian et al. (1995[Marganian, C. A., Vazir, H., Baidya, N., Olmstead, M. M. & Mascharak, P. K. (1995). J. Am. Chem. Soc. 117, 1584-1594.]); Akkurt et al. (2006[Akkurt, M., Karaca, S., Jarrahpour, A. A., Rezaei, S. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2156-o2157.]); Peng et al. (2006[Peng, S., Zhou, C. & Yang, T. (2006). Acta Cryst. E62, m1066-m1068.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C14H9N2O)2]

  • Mr = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.852, Tmax = 1.00 (expected range = 0.723–0.849)

  • 11052 measured reflections

  • 2540 independent reflections

  • 2246 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.10

  • 2540 reflections

  • 160 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 NiII atom 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.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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
Mr = 501.17Dx = 1.502 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10336 reflections
a = 9.0294 (18) Åθ = 3.1–27.4°
b = 8.0856 (16) ŵ = 0.91 mm1
c = 15.644 (3) ÅT = 293 K
β = 104.01 (3)°Block, blue
V = 1108.1 (4) Å30.25 × 0.18 × 0.18 mm
Z = 2
Data collection top
Rigaku Mercury2
diffractometer
2540 independent reflections
Radiation source: fine-focus sealed tube2246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1010
Tmin = 0.852, Tmax = 1.00l = 2020
11052 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.5389P]
where P = (Fo2 + 2Fc2)/3
2540 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
[Ni(C14H9N2O)2]V = 1108.1 (4) Å3
Mr = 501.17Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.0294 (18) ŵ = 0.91 mm1
b = 8.0856 (16) ÅT = 293 K
c = 15.644 (3) Å0.25 × 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)
Tmin = 0.852, Tmax = 1.00Rint = 0.035
11052 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.10Δρmax = 0.32 e Å3
2540 reflectionsΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
Ni10.50000.50000.50000.02514 (11)
O10.66446 (15)0.36034 (17)0.52053 (9)0.0349 (3)
N10.41172 (16)0.38940 (18)0.58415 (10)0.0266 (3)
C90.3215 (2)0.6210 (2)0.65595 (12)0.0302 (4)
H90.41590.67140.66130.036*
C140.2380 (2)0.8635 (3)0.72431 (15)0.0401 (5)
C10.5678 (2)0.1429 (2)0.59534 (12)0.0283 (4)
C100.2087 (2)0.6997 (2)0.68770 (12)0.0318 (4)
C80.2929 (2)0.4678 (2)0.61652 (12)0.0274 (4)
C110.0679 (2)0.6238 (3)0.68133 (14)0.0395 (5)
H110.00690.67590.70340.047*
C30.7949 (2)0.1080 (3)0.54150 (14)0.0383 (5)
H30.86630.14920.51300.046*
C20.6729 (2)0.2098 (2)0.55130 (11)0.0286 (4)
C130.1528 (2)0.3938 (3)0.60894 (15)0.0404 (5)
H130.13290.29140.58150.048*
C70.4475 (2)0.2409 (2)0.61321 (12)0.0297 (4)
H70.38970.19420.64880.036*
C50.7059 (3)0.1167 (3)0.61697 (15)0.0432 (5)
H50.71690.22450.63820.052*
N20.2618 (3)0.9944 (2)0.75059 (17)0.0570 (6)
C120.0409 (2)0.4716 (3)0.64212 (17)0.0461 (6)
H120.05270.41990.63770.055*
C40.8094 (3)0.0502 (3)0.57343 (15)0.0430 (5)
H40.89040.11490.56580.052*
C60.5875 (3)0.0197 (2)0.62794 (14)0.0366 (4)
H60.51840.06250.65770.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02507 (18)0.02233 (17)0.03093 (19)0.00178 (12)0.01241 (13)0.00362 (12)
O10.0309 (7)0.0327 (7)0.0458 (8)0.0070 (6)0.0182 (6)0.0125 (6)
N10.0262 (7)0.0245 (7)0.0319 (7)0.0009 (6)0.0124 (6)0.0003 (6)
C90.0294 (9)0.0286 (9)0.0360 (9)0.0003 (7)0.0146 (8)0.0016 (7)
C140.0431 (12)0.0363 (12)0.0480 (12)0.0067 (9)0.0247 (10)0.0000 (9)
C10.0305 (9)0.0236 (9)0.0309 (9)0.0009 (7)0.0075 (7)0.0007 (7)
C100.0348 (10)0.0305 (9)0.0332 (9)0.0058 (8)0.0140 (8)0.0022 (8)
C80.0282 (9)0.0272 (9)0.0300 (9)0.0015 (7)0.0133 (7)0.0023 (7)
C110.0327 (10)0.0449 (12)0.0461 (11)0.0093 (9)0.0194 (9)0.0032 (9)
C30.0335 (10)0.0412 (11)0.0425 (11)0.0088 (9)0.0134 (9)0.0043 (9)
C20.0294 (9)0.0282 (9)0.0278 (9)0.0036 (7)0.0064 (7)0.0020 (7)
C130.0348 (10)0.0378 (11)0.0521 (12)0.0068 (9)0.0174 (9)0.0090 (9)
C70.0315 (9)0.0263 (9)0.0335 (9)0.0034 (7)0.0122 (7)0.0022 (7)
C50.0491 (13)0.0250 (10)0.0528 (13)0.0073 (9)0.0070 (10)0.0048 (9)
N20.0685 (15)0.0369 (11)0.0762 (15)0.0001 (9)0.0379 (12)0.0109 (10)
C120.0294 (10)0.0550 (14)0.0592 (14)0.0081 (9)0.0212 (10)0.0084 (11)
C40.0407 (12)0.0397 (11)0.0476 (12)0.0173 (9)0.0085 (9)0.0018 (10)
C60.0398 (11)0.0266 (10)0.0437 (11)0.0013 (8)0.0104 (9)0.0045 (8)
Geometric parameters (Å, º) top
Ni1—O1i1.8310 (14)C8—C131.378 (3)
Ni1—O11.8310 (14)C11—C121.371 (3)
Ni1—N1i1.9174 (15)C11—H110.9300
Ni1—N11.9174 (15)C3—C41.368 (3)
O1—C21.304 (2)C3—C21.413 (3)
N1—C71.297 (2)C3—H30.9300
N1—C81.440 (2)C13—C121.393 (3)
C9—C81.380 (3)C13—H130.9300
C9—C101.391 (3)C7—H70.9300
C9—H90.9300C5—C61.370 (3)
C14—N21.137 (3)C5—C41.390 (3)
C14—C101.442 (3)C5—H50.9300
C1—C61.406 (2)C12—H120.9300
C1—C21.409 (3)C4—H40.9300
C1—C71.426 (3)C6—H60.9300
C10—C111.393 (3)
O1i—Ni1—O1180.000 (1)C10—C11—H11120.4
O1i—Ni1—N1i92.65 (6)C4—C3—C2120.89 (19)
O1—Ni1—N1i87.35 (6)C4—C3—H3119.6
O1i—Ni1—N187.35 (6)C2—C3—H3119.6
O1—Ni1—N192.65 (6)O1—C2—C1123.56 (17)
N1i—Ni1—N1180.000 (1)O1—C2—C3118.75 (17)
C2—O1—Ni1127.78 (12)C1—C2—C3117.68 (17)
C7—N1—C8115.34 (15)C8—C13—C12120.4 (2)
C7—N1—Ni1124.25 (13)C8—C13—H13119.8
C8—N1—Ni1120.35 (12)C12—C13—H13119.8
C8—C9—C10119.75 (18)N1—C7—C1125.63 (17)
C8—C9—H9120.1N1—C7—H7117.2
C10—C9—H9120.1C1—C7—H7117.2
N2—C14—C10177.8 (2)C6—C5—C4118.5 (2)
C6—C1—C2119.71 (18)C6—C5—H5120.7
C6—C1—C7118.93 (18)C4—C5—H5120.7
C2—C1—C7121.21 (16)C11—C12—C13120.4 (2)
C9—C10—C11120.51 (18)C11—C12—H12119.8
C9—C10—C14118.81 (18)C13—C12—H12119.8
C11—C10—C14120.64 (18)C3—C4—C5121.6 (2)
C13—C8—C9119.78 (17)C3—C4—H4119.2
C13—C8—N1121.69 (17)C5—C4—H4119.2
C9—C8—N1118.53 (16)C5—C6—C1121.6 (2)
C12—C11—C10119.20 (19)C5—C6—H6119.2
C12—C11—H11120.4C1—C6—H6119.2
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C14H9N2O)2]
Mr501.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.0294 (18), 8.0856 (16), 15.644 (3)
β (°) 104.01 (3)
V3)1108.1 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.91
Crystal size (mm)0.25 × 0.18 × 0.18
Data collection
DiffractometerRigaku Mercury2
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.852, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
11052, 2540, 2246
Rint0.035
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.090, 1.10
No. of reflections2540
No. of parameters160
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationAdams, H., Clunas, S. & Fenton, D. E. (2004). Acta Cryst. E60, m338–m339.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAkkurt, M., Karaca, S., Jarrahpour, A. A., Rezaei, S. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2156–o2157.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBian, H.-D., Yang, X.-E., Yu, Q., Liang, H. & Wang, H.-G. (2004). Acta Cryst. E60, m685–m686.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBrückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100–6106.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHarrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411.  Web of Science CSD CrossRef Google Scholar
First citationMarganian, C. A., Vazir, H., Baidya, N., Olmstead, M. M. & Mascharak, P. K. (1995). J. Am. Chem. Soc. 117, 1584–1594.  CSD CrossRef CAS Web of Science Google Scholar
First citationPeng, S., Zhou, C. & Yang, T. (2006). Acta Cryst. E62, m1066–m1068.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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