Acta Cryst. (2007). E63, m1791 [ doi:10.1107/S160053680702689X ]
The title compound, [Ni(C10H8Br2NO)2], is a mononuclear nickel(II) complex. The NiII atom, located on an inversion centre, exhibits a square-planar coordination geometry. The metal atom is bonded to two phenolate O atoms and two imine N atoms from two Schiff base ligands.
3,5-Dibromosalicylaldehyde (0.2 mmol, 56.4 mg) and cyclopropylamine (0.2 mmol, 11.5 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at room temperature for 30 min, giving a clear yellow solution. To this solution was added a methanol solution (5 ml) of Ni(NO3)2·6H2O (0.1 mmol, 29.1 mg) with stirring. The resulting mixture was stirred for a further 30 min at room temperature, giving a clear red solution. After allowing the solution to stand in air for a week, red block-shaped crystals were formed.
H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C–H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
| [Ni(C10H8Br2NO)2] | F000 = 668 |
| Mr = 694.70 | Dx = 2.217 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| a = 8.0170 (16) Å | Cell parameters from 1834 reflections |
| b = 9.2420 (18) Å | θ = 2.5–25.3º |
| c = 14.088 (3) Å | µ = 8.63 mm−1 |
| β = 94.62 (3)º | T = 298 (2) K |
| V = 1040.4 (4) Å3 | Block, red |
| Z = 2 | 0.23 × 0.20 × 0.17 mm |
| Bruker SMART CCD area-detector diffractometer | 2362 independent reflections |
| Radiation source: fine-focus sealed tube | 1801 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.041 |
| T = 298(2) K | θmax = 27.5º |
| ω scan | θmin = 2.6º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
| Tmin = 0.152, Tmax = 0.241 | k = −12→11 |
| 8738 measured reflections | l = −18→17 |
| 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)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0393P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2362 reflections | Δρmax = 0.51 e Å−3 |
| 133 parameters | Δρmin = −0.56 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Ni(C10H8Br2NO)2] | V = 1040.4 (4) Å3 |
| Mr = 694.70 | Z = 2 |
| Monoclinic, P21/c | Mo Kα |
| a = 8.0170 (16) Å | µ = 8.63 mm−1 |
| b = 9.2420 (18) Å | T = 298 (2) K |
| c = 14.088 (3) Å | 0.23 × 0.20 × 0.17 mm |
| β = 94.62 (3)º |
| Bruker SMART CCD area-detector diffractometer | 2362 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1801 reflections with I > 2σ(I) |
| Tmin = 0.152, Tmax = 0.241 | Rint = 0.041 |
| 8738 measured reflections |
| R[F2 > 2σ(F2)] = 0.036 | 133 parameters |
| wR(F2) = 0.084 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.51 e Å−3 |
| 2362 reflections | Δρmin = −0.56 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 > 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. |
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.5000 | 0.0000 | 0.5000 | 0.02886 (18) | |
| Br1 | 0.91324 (5) | −0.02357 (5) | 0.26991 (3) | 0.04253 (15) | |
| Br2 | 1.30178 (6) | 0.38800 (5) | 0.48338 (3) | 0.05101 (16) | |
| O1 | 0.6838 (3) | 0.0172 (3) | 0.43016 (19) | 0.0342 (6) | |
| N1 | 0.6038 (4) | 0.1142 (3) | 0.6033 (2) | 0.0283 (7) | |
| C1 | 0.8438 (5) | 0.1940 (4) | 0.5221 (3) | 0.0298 (8) | |
| C2 | 0.8144 (5) | 0.0988 (4) | 0.4431 (3) | 0.0292 (8) | |
| C3 | 0.9399 (5) | 0.0995 (4) | 0.3777 (3) | 0.0294 (8) | |
| C4 | 1.0802 (5) | 0.1830 (4) | 0.3890 (3) | 0.0327 (9) | |
| H4 | 1.1601 | 0.1782 | 0.3448 | 0.039* | |
| C5 | 1.1037 (5) | 0.2754 (4) | 0.4667 (3) | 0.0335 (9) | |
| C6 | 0.9869 (5) | 0.2807 (4) | 0.5324 (3) | 0.0357 (9) | |
| H6 | 1.0030 | 0.3426 | 0.5844 | 0.043* | |
| C7 | 0.7349 (5) | 0.1926 (4) | 0.5975 (3) | 0.0323 (9) | |
| H7 | 0.7619 | 0.2553 | 0.6481 | 0.039* | |
| C8 | 0.5247 (5) | 0.1218 (4) | 0.6926 (3) | 0.0327 (9) | |
| H8 | 0.4104 | 0.1602 | 0.6872 | 0.039* | |
| C9 | 0.5548 (6) | 0.0033 (5) | 0.7635 (3) | 0.0435 (11) | |
| H9A | 0.6342 | −0.0716 | 0.7498 | 0.052* | |
| H9B | 0.4606 | −0.0298 | 0.7968 | 0.052* | |
| C10 | 0.6219 (5) | 0.1516 (5) | 0.7862 (3) | 0.0431 (11) | |
| H10A | 0.7417 | 0.1664 | 0.7860 | 0.052* | |
| H10B | 0.5680 | 0.2082 | 0.8330 | 0.052* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0286 (4) | 0.0337 (4) | 0.0244 (4) | −0.0010 (3) | 0.0028 (3) | −0.0023 (3) |
| Br1 | 0.0411 (3) | 0.0576 (3) | 0.0295 (2) | 0.0009 (2) | 0.00693 (18) | −0.00779 (19) |
| Br2 | 0.0382 (3) | 0.0608 (3) | 0.0544 (3) | −0.0152 (2) | 0.0063 (2) | 0.0010 (2) |
| O1 | 0.0311 (15) | 0.0441 (17) | 0.0282 (15) | −0.0076 (13) | 0.0066 (12) | −0.0065 (12) |
| N1 | 0.0308 (18) | 0.0289 (17) | 0.0258 (16) | −0.0011 (14) | 0.0059 (13) | −0.0026 (13) |
| C1 | 0.031 (2) | 0.029 (2) | 0.030 (2) | 0.0037 (17) | 0.0048 (16) | 0.0030 (16) |
| C2 | 0.031 (2) | 0.033 (2) | 0.0234 (19) | 0.0064 (17) | 0.0015 (15) | 0.0053 (16) |
| C3 | 0.032 (2) | 0.035 (2) | 0.0219 (19) | 0.0047 (17) | 0.0021 (15) | −0.0017 (15) |
| C4 | 0.026 (2) | 0.043 (2) | 0.030 (2) | 0.0045 (18) | 0.0067 (16) | 0.0054 (17) |
| C5 | 0.028 (2) | 0.035 (2) | 0.037 (2) | −0.0020 (17) | 0.0028 (17) | 0.0078 (18) |
| C6 | 0.039 (2) | 0.038 (2) | 0.030 (2) | −0.0029 (19) | 0.0013 (17) | −0.0016 (17) |
| C7 | 0.037 (2) | 0.034 (2) | 0.0257 (19) | 0.0017 (18) | 0.0021 (16) | −0.0052 (16) |
| C8 | 0.035 (2) | 0.039 (2) | 0.025 (2) | −0.0066 (18) | 0.0084 (17) | −0.0064 (16) |
| C9 | 0.048 (3) | 0.050 (3) | 0.033 (2) | 0.002 (2) | 0.012 (2) | −0.0020 (19) |
| C10 | 0.042 (3) | 0.057 (3) | 0.032 (2) | −0.011 (2) | 0.0080 (19) | −0.009 (2) |
| Ni1—O1 | 1.844 (3) | C4—C5 | 1.389 (5) |
| Ni1—O1i | 1.844 (3) | C4—H4 | 0.9300 |
| Ni1—N1i | 1.931 (3) | C5—C6 | 1.370 (5) |
| Ni1—N1 | 1.931 (3) | C6—H6 | 0.9300 |
| Br1—C3 | 1.896 (4) | C7—H7 | 0.9300 |
| Br2—C5 | 1.898 (4) | C8—C9 | 1.489 (6) |
| O1—C2 | 1.291 (4) | C8—C10 | 1.502 (5) |
| N1—C7 | 1.284 (5) | C8—H8 | 0.9800 |
| N1—C8 | 1.456 (5) | C9—C10 | 1.498 (6) |
| C1—C6 | 1.398 (5) | C9—H9A | 0.9700 |
| C1—C2 | 1.423 (5) | C9—H9B | 0.9700 |
| C1—C7 | 1.429 (5) | C10—H10A | 0.9700 |
| C2—C3 | 1.418 (5) | C10—H10B | 0.9700 |
| C3—C4 | 1.363 (5) | ||
| O1—Ni1—O1i | 180.0 | C5—C6—C1 | 120.6 (4) |
| O1—Ni1—N1i | 87.67 (12) | C5—C6—H6 | 119.7 |
| O1i—Ni1—N1i | 92.33 (12) | C1—C6—H6 | 119.7 |
| O1—Ni1—N1 | 92.33 (12) | N1—C7—C1 | 127.2 (3) |
| O1i—Ni1—N1 | 87.67 (12) | N1—C7—H7 | 116.4 |
| N1i—Ni1—N1 | 180.0 | C1—C7—H7 | 116.4 |
| C2—O1—Ni1 | 130.5 (2) | N1—C8—C9 | 119.1 (3) |
| C7—N1—C8 | 116.3 (3) | N1—C8—C10 | 122.4 (3) |
| C7—N1—Ni1 | 124.5 (3) | C9—C8—C10 | 60.1 (3) |
| C8—N1—Ni1 | 119.1 (2) | N1—C8—H8 | 114.8 |
| C6—C1—C2 | 121.3 (4) | C9—C8—H8 | 114.8 |
| C6—C1—C7 | 118.2 (4) | C10—C8—H8 | 114.8 |
| C2—C1—C7 | 120.2 (3) | C8—C9—C10 | 60.4 (3) |
| O1—C2—C3 | 121.4 (3) | C8—C9—H9A | 117.7 |
| O1—C2—C1 | 123.6 (3) | C10—C9—H9A | 117.7 |
| C3—C2—C1 | 115.1 (3) | C8—C9—H9B | 117.7 |
| C4—C3—C2 | 123.3 (3) | C10—C9—H9B | 117.7 |
| C4—C3—Br1 | 118.2 (3) | H9A—C9—H9B | 114.9 |
| C2—C3—Br1 | 118.5 (3) | C9—C10—C8 | 59.5 (3) |
| C3—C4—C5 | 119.9 (3) | C9—C10—H10A | 117.8 |
| C3—C4—H4 | 120.1 | C8—C10—H10A | 117.8 |
| C5—C4—H4 | 120.1 | C9—C10—H10B | 117.8 |
| C6—C5—C4 | 119.9 (4) | C8—C10—H10B | 117.8 |
| C6—C5—Br2 | 120.5 (3) | H10A—C10—H10B | 115.0 |
| C4—C5—Br2 | 119.6 (3) |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| Ni1—O1 | 1.844 (3) | Ni1—N1 | 1.931 (3) |
| O1—Ni1—O1i | 180.0 | O1—Ni1—N1 | 92.33 (12) |
| O1—Ni1—N1i | 87.67 (12) |
| Symmetry codes: (i) −x+1, −y, −z+1. |
The project is sponsored by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (BZYO 7002).
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![[Figure 1]](./gk2080fig1thm.gif)
Schiff base complexes have been of great interest for a long time (Chaturvedi, 1977; Archer & Wang, 1990; Costamagna et al., 1992; Yamada, 1999). These complexes play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. Recently, we have reported a few transition metal complexes (Wang & Li, 2007a,b; Li & Wang, 2007a). As an extension of the work on the structural investigation of these complexes, the title nickel(II) complex is reported here.
The title complex is a centrosymmetric mononuclear nickel(II) complex. The NiII atom, lying on the inversion centre, is four-coordinated and shows a square planar coordination geometry. It is bonded to two phenolate O and two imine N atoms from two Schiff base ligands. The Ni–O and Ni–N bond lengths are comparable to the corresponding values observed in other Schiff base nickel(II) complexes.