Acta Cryst. (2008). E64, m494 [ doi:10.1107/S1600536808004765 ]
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)°.
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.
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).
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).
![[Figure 1]](./dn2310fig1thm.gif)
| 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] |
| [Ni(C14H9N2O1)2] | F000 = 516 |
| Mr = 501.17 | Dx = 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 = 3.1–27.4º |
| b = 8.0856 (16) Å | µ = 0.91 mm−1 |
| c = 15.644 (3) Å | T = 293 (2) K |
| β = 104.01 (3)º | Block, blue |
| V = 1108.1 (4) Å3 | 0.25 × 0.18 × 0.18 mm |
| Z = 2 |
| Rigaku Mercury2 diffractometer | 2540 independent reflections |
| Radiation source: fine-focus sealed tube | 2246 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5º |
| T = 293(2) K | θmin = 3.1º |
| ω scans | h = −11→11 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −10→10 |
| Tmin = 0.852, Tmax = 1.00 | l = −20→20 |
| 11052 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0403P)2 + 0.5389P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max < 0.001 |
| 2540 reflections | Δρmax = 0.32 e Å−3 |
| 160 parameters | Δρmin = −0.35 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Ni(C14H9N2O1)2] | V = 1108.1 (4) Å3 |
| Mr = 501.17 | Z = 2 |
| Monoclinic, P21/c | Mo Kα |
| a = 9.0294 (18) Å | µ = 0.91 mm−1 |
| b = 8.0856 (16) Å | T = 293 (2) K |
| c = 15.644 (3) Å | 0.25 × 0.18 × 0.18 mm |
| β = 104.01 (3)º |
| Rigaku Mercury2 diffractometer | 2540 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2246 reflections with I > 2σ(I) |
| Tmin = 0.852, Tmax = 1.00 | Rint = 0.035 |
| 11052 measured reflections |
| R[F2 > 2σ(F2)] = 0.034 | 160 parameters |
| wR(F2) = 0.090 | H-atom parameters constrained |
| S = 1.10 | Δρmax = 0.32 e Å−3 |
| 2540 reflections | Δρmin = −0.35 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| 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* |
| 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) |
| 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 codes: (i) −x+1, −y+1, −z+1. |
HJX acknowledges a Start-up Grant from Southeast University, People's Republic of China
Adams, H., Clunas, S. & Fenton, D. E. (2004). Acta Cryst. E60, m338–m339.
Akkurt, M., Karaca, S., Jarrahpour, A. A., Rezaei, S. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2156–o2157.
Bian, H.-D., Yang, X.-E., Yu, Q., Liang, H. & Wang, H.-G. (2004). Acta Cryst. E60, m685–m686.
Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100–6106.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411.
Marganian, C. A., Vazir, H., Baidya, N., Olmstead, M. M. & Mascharak, P. K. (1995). J. Am. Chem. Soc. 117, 1584–1594.
Peng, S., Zhou, C. & Yang, T. (2006). Acta Cryst. E62, m1066–m1068.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
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).