metal-organic compounds
The NiII center in the monomeric complex, [NiBr2(C20H18N4O4)], is covalently bonded to two Br atoms and datively bonded to two N atoms of the Schiff base in a tetrahedral geometry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019775/hy2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019775/hy2004Isup2.hkl |
CCDC reference: 613732
Computing details top
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
Dibromo[bis(trans-2-nitrocinnamaldehyde)ethylenediimine-N,N']nickel(II) top
Crystal data top
[NiBr2(C20H18N4O4)] | F(000) = 1184 |
Mr = 596.91 | Dx = 1.725 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4873 reflections |
a = 7.6644 (3) Å | θ = 2.2–24.0° |
b = 16.3219 (6) Å | µ = 4.36 mm−1 |
c = 18.5582 (7) Å | T = 293 K |
β = 98.204 (1)° | Plate, purple |
V = 2297.8 (3) Å3 | 0.45 × 0.30 × 0.15 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 6270 independent reflections |
Radiation source: fine-focus sealed tube | 3365 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 29.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.231, Tmax = 0.522 | k = −22→22 |
25133 measured reflections | l = −25→25 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3 |
6270 reflections | (Δ/σ)max = 0.001 |
309 parameters | Δρmax = 0.51 e Å−3 |
9 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.63307 (4) | 0.67773 (2) | 0.57976 (2) | 0.0530 (1) | |
Br1 | 0.7657 (4) | 0.7481 (2) | 0.6837 (1) | 0.076 (1) | 0.63 (3) |
Br1' | 0.799 (3) | 0.7425 (6) | 0.6757 (7) | 0.116 (2) | 0.37 (3) |
Br2 | 0.75872 (5) | 0.63921 (2) | 0.47531 (2) | 0.0764 (1) | |
O1 | 0.1206 (6) | 1.1309 (4) | 0.4859 (3) | 0.105 (2) | 0.65 (1) |
O2 | 0.0398 (5) | 1.0518 (4) | 0.5664 (2) | 0.073 (2) | 0.65 (1) |
O1' | 0.129 (1) | 1.0660 (8) | 0.4749 (3) | 0.084 (4) | 0.35 (1) |
O2' | 0.040 (1) | 1.1163 (8) | 0.5687 (5) | 0.111 (5) | 0.35 (1) |
O3 | 0.9222 (4) | 0.2773 (2) | 0.6390 (2) | 0.088 (1) | |
O4 | 1.0986 (4) | 0.2085 (2) | 0.7173 (2) | 0.123 (1) | |
N1 | 0.1534 (3) | 1.0899 (1) | 0.5390 (1) | 0.060 (1) | |
N2 | 0.3896 (3) | 0.7153 (2) | 0.5443 (1) | 0.052 (1) | |
N3 | 0.5148 (3) | 0.5750 (2) | 0.6043 (1) | 0.055 (1) | |
N4 | 1.0410 (4) | 0.2729 (2) | 0.6898 (2) | 0.077 (1) | |
C1 | 0.3371 (4) | 1.0838 (2) | 0.5761 (2) | 0.053 (1) | |
C2 | 0.4117 (4) | 1.1579 (2) | 0.6013 (2) | 0.065 (1) | |
C3 | 0.5833 (5) | 1.1580 (2) | 0.6357 (2) | 0.074 (1) | |
C4 | 0.6768 (4) | 1.0860 (2) | 0.6440 (2) | 0.071 (1) | |
C5 | 0.6001 (4) | 1.0132 (2) | 0.6196 (2) | 0.064 (1) | |
C6 | 0.4254 (3) | 1.0095 (2) | 0.5847 (2) | 0.052 (1) | |
C7 | 0.3395 (4) | 0.9321 (2) | 0.5599 (2) | 0.056 (1) | |
C8 | 0.4177 (4) | 0.8593 (2) | 0.5625 (2) | 0.058 (1) | |
C9 | 0.3193 (4) | 0.7862 (2) | 0.5403 (2) | 0.056 (1) | |
C10 | 0.2823 (4) | 0.6423 (2) | 0.5253 (2) | 0.066 (1) | |
C11 | 0.3218 (4) | 0.5830 (2) | 0.5875 (2) | 0.068 (1) | |
C12 | 0.5834 (4) | 0.5080 (2) | 0.6302 (2) | 0.055 (1) | |
C13 | 0.7701 (4) | 0.4990 (2) | 0.6510 (2) | 0.056 (1) | |
C14 | 0.8450 (4) | 0.4319 (2) | 0.6833 (2) | 0.054 (1) | |
C15 | 1.0332 (4) | 0.4243 (2) | 0.7115 (2) | 0.053 (1) | |
C16 | 1.1283 (4) | 0.4932 (2) | 0.7370 (2) | 0.059 (1) | |
C17 | 1.3023 (4) | 0.4891 (2) | 0.7686 (2) | 0.072 (1) | |
C18 | 1.3863 (4) | 0.4146 (3) | 0.7769 (2) | 0.078 (1) | |
C19 | 1.2976 (4) | 0.3441 (2) | 0.7530 (2) | 0.072 (1) | |
C20 | 1.1249 (4) | 0.3495 (2) | 0.7196 (2) | 0.059 (1) | |
H2 | 0.3472 | 1.2063 | 0.5952 | 0.078* | |
H3 | 0.6359 | 1.2068 | 0.6532 | 0.088* | |
H4 | 0.7932 | 1.0865 | 0.6665 | 0.085* | |
H5 | 0.6656 | 0.9652 | 0.6262 | 0.076* | |
H7 | 0.2206 | 0.9342 | 0.5408 | 0.068* | |
H8 | 0.5379 | 0.8555 | 0.5788 | 0.070* | |
H9 | 0.2000 | 0.7909 | 0.5225 | 0.068* | |
H10a | 0.3114 | 0.6181 | 0.4808 | 0.080* | |
H10b | 0.1581 | 0.6564 | 0.5181 | 0.080* | |
H11a | 0.2738 | 0.6031 | 0.6297 | 0.082* | |
H11b | 0.2691 | 0.5301 | 0.5740 | 0.082* | |
H12 | 0.5102 | 0.4637 | 0.6358 | 0.066* | |
H13 | 0.8429 | 0.5421 | 0.6416 | 0.068* | |
H14 | 0.7729 | 0.3870 | 0.6882 | 0.065* | |
H16 | 1.0729 | 0.5440 | 0.7327 | 0.071* | |
H17 | 1.3627 | 0.5367 | 0.7842 | 0.086* | |
H18 | 1.5032 | 0.4117 | 0.7987 | 0.093* | |
H19 | 1.3532 | 0.2935 | 0.7593 | 0.087* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0375 (2) | 0.0493 (2) | 0.0679 (3) | −0.0013 (2) | −0.0070 (2) | 0.0045 (2) |
Br1 | 0.0751 (9) | 0.082 (1) | 0.064 (1) | −0.003 (1) | −0.015 (1) | −0.005 (1) |
Br1' | 0.102 (4) | 0.115 (3) | 0.111 (3) | −0.039 (2) | −0.049 (2) | −0.009 (2) |
Br2 | 0.0673 (2) | 0.0749 (3) | 0.0896 (3) | 0.0031 (2) | 0.0198 (2) | 0.0019 (2) |
O1 | 0.085 (3) | 0.093 (5) | 0.122 (4) | 0.000 (3) | −0.031 (3) | 0.056 (4) |
O2 | 0.045 (2) | 0.091 (4) | 0.081 (3) | 0.011 (2) | 0.003 (2) | −0.016 (2) |
O1' | 0.068 (5) | 0.106 (9) | 0.072 (5) | 0.025 (5) | −0.011 (4) | 0.019 (5) |
O2' | 0.068 (5) | 0.14 (1) | 0.122 (7) | 0.047 (6) | 0.002 (4) | −0.066 (7) |
O3 | 0.071 (2) | 0.074 (2) | 0.114 (2) | −0.008 (1) | 0.000 (2) | −0.013 (2) |
O4 | 0.102 (2) | 0.059 (2) | 0.203 (4) | 0.019 (2) | 0.004 (2) | 0.020 (2) |
N1 | 0.051 (2) | 0.057 (2) | 0.069 (2) | 0.003 (1) | −0.006 (1) | 0.002 (2) |
N2 | 0.041 (1) | 0.051 (1) | 0.063 (2) | 0.003 (1) | −0.004 (1) | 0.005 (1) |
N3 | 0.041 (1) | 0.053 (2) | 0.069 (2) | −0.002 (1) | −0.002 (1) | 0.005 (1) |
N4 | 0.057 (2) | 0.060 (2) | 0.113 (3) | 0.005 (1) | 0.016 (2) | 0.004 (2) |
C1 | 0.046 (2) | 0.057 (2) | 0.055 (2) | 0.002 (1) | 0.004 (1) | 0.003 (1) |
C2 | 0.065 (2) | 0.059 (2) | 0.071 (2) | −0.004 (2) | 0.007 (2) | −0.005 (2) |
C3 | 0.069 (2) | 0.076 (2) | 0.075 (2) | −0.022 (2) | 0.007 (2) | −0.012 (2) |
C4 | 0.045 (2) | 0.096 (3) | 0.069 (2) | −0.010 (2) | −0.004 (1) | −0.005 (2) |
C5 | 0.046 (2) | 0.075 (2) | 0.067 (2) | 0.004 (2) | −0.003 (1) | 0.005 (2) |
C6 | 0.042 (2) | 0.056 (2) | 0.056 (2) | 0.001 (1) | 0.000 (1) | 0.005 (1) |
C7 | 0.043 (2) | 0.057 (2) | 0.066 (2) | 0.006 (1) | −0.003 (1) | 0.004 (2) |
C8 | 0.045 (2) | 0.057 (2) | 0.070 (2) | 0.006 (1) | −0.001 (1) | 0.007 (2) |
C9 | 0.041 (2) | 0.058 (2) | 0.066 (2) | 0.006 (1) | −0.006 (1) | 0.007 (2) |
C10 | 0.042 (2) | 0.062 (2) | 0.088 (2) | 0.002 (1) | −0.014 (2) | 0.000 (2) |
C11 | 0.042 (2) | 0.058 (2) | 0.100 (2) | 0.000 (1) | −0.002 (2) | 0.010 (2) |
C12 | 0.050 (2) | 0.051 (2) | 0.064 (2) | 0.001 (1) | 0.005 (1) | 0.006 (2) |
C13 | 0.050 (2) | 0.053 (2) | 0.064 (2) | −0.001 (1) | 0.003 (1) | 0.009 (2) |
C14 | 0.047 (2) | 0.058 (2) | 0.057 (2) | 0.001 (1) | 0.008 (1) | 0.003 (1) |
C15 | 0.047 (2) | 0.064 (2) | 0.047 (2) | 0.006 (1) | 0.007 (1) | 0.008 (1) |
C16 | 0.059 (2) | 0.061 (2) | 0.056 (2) | 0.002 (2) | 0.004 (1) | 0.004 (2) |
C17 | 0.057 (2) | 0.087 (3) | 0.068 (2) | −0.009 (2) | 0.000 (2) | −0.009 (2) |
C18 | 0.049 (2) | 0.103 (3) | 0.076 (2) | 0.005 (2) | −0.007 (2) | 0.005 (2) |
C19 | 0.051 (2) | 0.082 (3) | 0.082 (2) | 0.018 (2) | 0.005 (2) | 0.016 (2) |
C20 | 0.052 (2) | 0.060 (2) | 0.066 (2) | 0.007 (1) | 0.008 (1) | 0.012 (2) |
Geometric parameters (Å, º) top
Ni1—N2 | 1.985 (2) | C12—C13 | 1.436 (4) |
Ni1—N3 | 1.990 (2) | C13—C14 | 1.338 (4) |
Ni1—Br1 | 2.349 (2) | C14—C15 | 1.468 (4) |
Ni1—Br2 | 2.369 (1) | C15—C16 | 1.387 (4) |
Ni1—Br1' | 2.294 (5) | C15—C20 | 1.406 (4) |
O1—N1 | 1.187 (4) | C16—C17 | 1.379 (4) |
O2—N1 | 1.238 (4) | C17—C18 | 1.375 (5) |
O1'—N1 | 1.240 (6) | C18—C19 | 1.376 (5) |
O2'—N1 | 1.175 (6) | C19—C20 | 1.382 (4) |
O3—N4 | 1.216 (4) | C2—H2 | 0.93 |
O4—N4 | 1.223 (4) | C3—H3 | 0.93 |
N1—C1 | 1.480 (4) | C4—H4 | 0.93 |
N2—C9 | 1.274 (4) | C5—H5 | 0.93 |
N2—C10 | 1.462 (4) | C7—H7 | 0.93 |
N3—C12 | 1.277 (4) | C8—H8 | 0.93 |
N3—C11 | 1.473 (4) | C9—H9 | 0.93 |
N4—C20 | 1.477 (4) | C10—H10a | 0.97 |
C1—C6 | 1.387 (4) | C10—H10b | 0.97 |
C1—C2 | 1.390 (4) | C11—H11a | 0.97 |
C2—C3 | 1.377 (5) | C11—H11b | 0.97 |
C3—C4 | 1.373 (5) | C12—H12 | 0.93 |
C4—C5 | 1.374 (5) | C13—H13 | 0.93 |
C5—C6 | 1.403 (4) | C14—H14 | 0.93 |
C6—C7 | 1.468 (4) | C16—H16 | 0.93 |
C7—C8 | 1.329 (4) | C17—H17 | 0.93 |
C8—C9 | 1.440 (4) | C18—H18 | 0.93 |
C10—C11 | 1.503 (4) | C19—H19 | 0.93 |
N2—Ni1—N3 | 84.2 (1) | C17—C16—C15 | 122.3 (3) |
N2—Ni1—Br1 | 113.4 (1) | C16—C17—C18 | 120.0 (3) |
N2—Ni1—Br2 | 106.4 (1) | C19—C18—C17 | 120.1 (3) |
N3—Ni1—Br1 | 112.5 (1) | C18—C19—C20 | 119.3 (3) |
N3—Ni1—Br2 | 102.4 (1) | C19—C20—C15 | 122.3 (3) |
Br1—Ni1—Br2 | 128.5 (1) | C19—C20—N4 | 116.9 (3) |
N2—Ni1—Br1' | 120.5 (6) | C15—C20—N4 | 120.7 (3) |
N3—Ni1—Br1' | 115.6 (3) | C3—C2—H2 | 120.8 |
Br1'—Ni1—Br2 | 120.8 (7) | C1—C2—H2 | 120.8 |
O1—N1—O2 | 123.1 (4) | C4—C3—H3 | 120.0 |
O2'—N1—O1' | 123.1 (6) | C2—C3—H3 | 120.0 |
O2'—N1—C1 | 121.5 (5) | C3—C4—H4 | 119.6 |
O1—N1—C1 | 120.0 (3) | C5—C4—H4 | 119.6 |
O2—N1—C1 | 116.9 (3) | C4—C5—H5 | 119.2 |
O1'—N1—C1 | 115.4 (4) | C6—C5—H5 | 119.2 |
C9—N2—C10 | 120.5 (2) | C8—C7—H7 | 117.3 |
C9—N2—Ni1 | 132.0 (2) | C6—C7—H7 | 117.3 |
C10—N2—Ni1 | 107.3 (2) | C7—C8—H8 | 119.5 |
C12—N3—C11 | 120.2 (3) | C9—C8—H8 | 119.5 |
C12—N3—Ni1 | 129.1 (2) | N2—C9—H9 | 118.8 |
C11—N3—Ni1 | 110.7 (2) | C8—C9—H9 | 118.8 |
O3—N4—O4 | 124.1 (3) | N2—C10—H10a | 110.3 |
O3—N4—C20 | 118.6 (3) | C11—C10—H10a | 110.3 |
O4—N4—C20 | 117.4 (3) | N2—C10—H10b | 110.3 |
C6—C1—C2 | 123.5 (3) | C11—C10—H10b | 110.3 |
C6—C1—N1 | 121.9 (2) | H10a—C10—H10b | 108.5 |
C2—C1—N1 | 114.6 (2) | N3—C11—H11a | 110.1 |
C3—C2—C1 | 118.4 (3) | C10—C11—H11a | 110.1 |
C4—C3—C2 | 120.0 (3) | N3—C11—H11b | 110.1 |
C3—C4—C5 | 120.7 (3) | C10—C11—H11b | 110.1 |
C4—C5—C6 | 121.6 (3) | H11a—C11—H11b | 108.5 |
C1—C6—C5 | 115.7 (3) | N3—C12—H12 | 119.0 |
C1—C6—C7 | 121.8 (2) | C13—C12—H12 | 119.0 |
C5—C6—C7 | 122.5 (3) | C14—C13—H13 | 118.3 |
C8—C7—C6 | 125.4 (3) | C12—C13—H13 | 118.3 |
C7—C8—C9 | 121.0 (3) | C13—C14—H14 | 117.8 |
N2—C9—C8 | 122.4 (3) | C15—C14—H14 | 117.8 |
N2—C10—C11 | 107.2 (2) | C17—C16—H16 | 118.8 |
N3—C11—C10 | 107.8 (3) | C15—C16—H16 | 118.8 |
N3—C12—C13 | 122.0 (3) | C16—C17—H17 | 120.0 |
C14—C13—C12 | 123.5 (3) | C18—C17—H17 | 120.0 |
C13—C14—C15 | 124.4 (3) | C19—C18—H18 | 120.0 |
C16—C15—C20 | 115.9 (3) | C17—C18—H18 | 120.0 |
C16—C15—C14 | 119.7 (3) | C18—C19—H19 | 120.3 |
C20—C15—C14 | 124.2 (3) | C20—C19—H19 | 120.3 |
N3—Ni1—N2—C9 | 150.5 (3) | C4—C5—C6—C7 | −178.3 (3) |
Br1'—Ni1—N2—C9 | 34.2 (5) | C1—C6—C7—C8 | 176.0 (3) |
Br1—Ni1—N2—C9 | 38.5 (3) | C5—C6—C7—C8 | −5.1 (5) |
Br2—Ni1—N2—C9 | −108.2 (3) | C6—C7—C8—C9 | 176.6 (3) |
N3—Ni1—N2—C10 | −25.0 (2) | C10—N2—C9—C8 | 176.3 (3) |
Br1'—Ni1—N2—C10 | −141.3 (4) | Ni1—N2—C9—C8 | 1.2 (5) |
Br1—Ni1—N2—C10 | −137.0 (2) | C7—C8—C9—N2 | −177.8 (3) |
Br2—Ni1—N2—C10 | 76.3 (2) | C9—N2—C10—C11 | −128.8 (3) |
N2—Ni1—N3—C12 | 176.5 (3) | Ni1—N2—C10—C11 | 47.3 (3) |
Br1'—Ni1—N3—C12 | −62.4 (7) | C12—N3—C11—C10 | −150.1 (3) |
Br1—Ni1—N3—C12 | −70.5 (3) | Ni1—N3—C11—C10 | 29.2 (3) |
Br2—Ni1—N3—C12 | 70.9 (3) | N2—C10—C11—N3 | −50.2 (3) |
N2—Ni1—N3—C11 | −2.7 (2) | C11—N3—C12—C13 | −176.6 (3) |
Br1'—Ni1—N3—C11 | 118.4 (7) | Ni1—N3—C12—C13 | 4.3 (4) |
Br1—Ni1—N3—C11 | 110.3 (2) | N3—C12—C13—C14 | 174.9 (3) |
Br2—Ni1—N3—C11 | −108.3 (2) | C12—C13—C14—C15 | −173.8 (3) |
O2'—N1—C1—C6 | 120.9 (8) | C13—C14—C15—C16 | 30.0 (4) |
O1—N1—C1—C6 | −119.8 (5) | C13—C14—C15—C20 | −154.8 (3) |
O2—N1—C1—C6 | 61.1 (4) | C20—C15—C16—C17 | 0.0 (4) |
O1'—N1—C1—C6 | −59.6 (7) | C14—C15—C16—C17 | 175.5 (3) |
O2'—N1—C1—C2 | −59.0 (7) | C15—C16—C17—C18 | −1.3 (5) |
O1—N1—C1—C2 | 60.3 (5) | C16—C17—C18—C19 | 0.7 (5) |
O2—N1—C1—C2 | −118.8 (4) | C17—C18—C19—C20 | 1.1 (5) |
O1'—N1—C1—C2 | 120.5 (7) | C18—C19—C20—C15 | −2.5 (5) |
C6—C1—C2—C3 | 1.1 (5) | C18—C19—C20—N4 | 175.2 (3) |
N1—C1—C2—C3 | −179.0 (3) | C16—C15—C20—C19 | 1.9 (4) |
C1—C2—C3—C4 | 0.3 (5) | C14—C15—C20—C19 | −173.4 (3) |
C2—C3—C4—C5 | −1.1 (5) | C16—C15—C20—N4 | −175.7 (3) |
C3—C4—C5—C6 | 0.6 (5) | C14—C15—C20—N4 | 9.0 (5) |
C2—C1—C6—C5 | −1.5 (4) | O3—N4—C20—C19 | −153.2 (3) |
N1—C1—C6—C5 | 178.6 (3) | O4—N4—C20—C19 | 25.5 (5) |
C2—C1—C6—C7 | 177.5 (3) | O3—N4—C20—C15 | 24.6 (5) |
N1—C1—C6—C7 | −2.4 (4) | O4—N4—C20—C15 | −156.7 (3) |
C4—C5—C6—C1 | 0.6 (5) |