Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038482/bi2225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038482/bi2225Isup2.hkl |
CCDC reference: 660077
A mixture of 6-methoxysalicylaldehyde (2.0 mmol, 304 mg) and 1,3-diaminopropane (1.0 mmol, 74 mg) was dissolved in methanol (10 ml) with stirring for 10 min at room temperature, to give a clear yellow solution. A methanol solution (10 ml) of Ni(OAc)2·4H2O (1.0 mmol, 249 mg) was then added. The mixture was refluxed for a further 50 min and then filtered. After keeping the filtrate in air for 5 d, red block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent, in about 70% yield.
All H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å and with Uiso(H) = 1.2 or 1.5 times Ueq(C).
Nickel(II) complexes with N2O2 Schiff-base ligands derived from salicylaldehyde have long been used as homogenous catalysts (Gosden et al., 1981; Healy & Pletcher, 1978). Recently we reported the structure of a copper(II) complex with the N,N'-bis(6-methoxysalicylidene)-1,3-diaminopropane ligand (Habibi et al., 2007). The title compound is isostructural with its CuII analogue.
In the title compound (Figure 1), the Ni—O and Ni—N distances are larger than the comparable mean distances of 1.829 and 1.859 Å, respectively, in N,N'-ethylenebis(salicylideneiminato)nickel(II) (Shkol'nikova et al., 1970) and 1.849 (2) and 1.840 (2) Å, respectively, in N,N'-ethylenebis[(2-hydroxy-1-naphthyl)methaniminato]nickel(II) (Akhtar, 1981).
For the isostructural CuII compound, see: Habibi et al. (2007). For related literature, see: Gosden et al. (1981); Healy & Pletcher (1978); Shkol'nikova et al. (1970); Akhtar (1981).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXTL and local programs.
Fig. 1. The molecular structure with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
[Ni(C19H20N2O4)] | F(000) = 832 |
Mr = 399.08 | Dx = 1.544 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 7044 reflections |
a = 13.677 (2) Å | θ = 2.2–28.3° |
b = 12.7319 (18) Å | µ = 1.16 mm−1 |
c = 9.8561 (14) Å | T = 150 K |
V = 1716.3 (4) Å3 | Block, red |
Z = 4 | 0.34 × 0.30 × 0.30 mm |
Bruker SMART 1K CCD diffractometer | 4083 independent reflections |
Radiation source: sealed tube | 3384 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
thin–slice ω scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −17→17 |
Tmin = 0.690, Tmax = 0.725 | k = −16→17 |
13065 measured reflections | l = −13→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.6306P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.68 e Å−3 |
4083 reflections | Δρmin = −0.53 e Å−3 |
238 parameters | Extinction correction: SHELXTL (Sheldrick, 2005), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0025 (7) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1870 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (2) |
[Ni(C19H20N2O4)] | V = 1716.3 (4) Å3 |
Mr = 399.08 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 13.677 (2) Å | µ = 1.16 mm−1 |
b = 12.7319 (18) Å | T = 150 K |
c = 9.8561 (14) Å | 0.34 × 0.30 × 0.30 mm |
Bruker SMART 1K CCD diffractometer | 4083 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 3384 reflections with I > 2σ(I) |
Tmin = 0.690, Tmax = 0.725 | Rint = 0.040 |
13065 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.101 | Δρmax = 0.68 e Å−3 |
S = 1.06 | Δρmin = −0.53 e Å−3 |
4083 reflections | Absolute structure: Flack (1983), with 1870 Friedel pairs |
238 parameters | Absolute structure parameter: 0.00 (2) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Ni | 0.82396 (2) | 0.25163 (3) | 0.10277 (8) | 0.01355 (10) | |
O1 | 0.8627 (2) | −0.12162 (17) | −0.1557 (3) | 0.0282 (6) | |
O2 | 0.93677 (17) | 0.21919 (17) | 0.0070 (2) | 0.0190 (5) | |
O3 | 0.90841 (15) | 0.34683 (16) | 0.1831 (2) | 0.0176 (5) | |
O4 | 0.69303 (16) | 0.5363 (2) | 0.4694 (3) | 0.0254 (5) | |
N1 | 0.76069 (19) | 0.12822 (18) | 0.0450 (3) | 0.0163 (5) | |
N2 | 0.71214 (18) | 0.31603 (19) | 0.1800 (3) | 0.0147 (5) | |
C1 | 0.8822 (3) | −0.2066 (3) | −0.2485 (4) | 0.0347 (9) | |
H1A | 0.8303 | −0.2593 | −0.2411 | 0.052* | |
H1B | 0.9452 | −0.2389 | −0.2259 | 0.052* | |
H1C | 0.8844 | −0.1794 | −0.3414 | 0.052* | |
C2 | 0.9282 (3) | −0.0402 (2) | −0.1530 (3) | 0.0208 (7) | |
C3 | 1.0159 (3) | −0.0395 (3) | −0.2224 (3) | 0.0244 (7) | |
H3A | 1.0353 | −0.0979 | −0.2761 | 0.029* | |
C4 | 1.0754 (3) | 0.0490 (3) | −0.2116 (4) | 0.0254 (7) | |
H4A | 1.1356 | 0.0501 | −0.2597 | 0.031* | |
C5 | 1.0507 (2) | 0.1349 (3) | −0.1343 (3) | 0.0222 (7) | |
H5A | 1.0942 | 0.1928 | −0.1278 | 0.027* | |
C6 | 0.9602 (2) | 0.1368 (2) | −0.0644 (3) | 0.0178 (6) | |
C7 | 0.8979 (2) | 0.0481 (3) | −0.0745 (3) | 0.0179 (6) | |
C8 | 0.8006 (2) | 0.0511 (2) | −0.0200 (3) | 0.0185 (6) | |
H8A | 0.7615 | −0.0098 | −0.0331 | 0.022* | |
C9 | 0.6564 (2) | 0.1131 (2) | 0.0811 (3) | 0.0195 (7) | |
H9A | 0.6497 | 0.1051 | 0.1806 | 0.023* | |
H9B | 0.6310 | 0.0487 | 0.0373 | 0.023* | |
C10 | 0.5990 (2) | 0.2076 (3) | 0.0335 (4) | 0.0199 (7) | |
H10A | 0.5292 | 0.1885 | 0.0243 | 0.024* | |
H10B | 0.6232 | 0.2299 | −0.0567 | 0.024* | |
C11 | 0.6092 (2) | 0.2977 (3) | 0.1331 (3) | 0.0174 (7) | |
H11A | 0.5845 | 0.3627 | 0.0899 | 0.021* | |
H11B | 0.5676 | 0.2832 | 0.2132 | 0.021* | |
C12 | 0.7151 (2) | 0.3884 (2) | 0.2731 (3) | 0.0154 (6) | |
H12A | 0.6537 | 0.4113 | 0.3069 | 0.018* | |
C13 | 0.7990 (2) | 0.4375 (2) | 0.3308 (3) | 0.0153 (6) | |
C14 | 0.8929 (2) | 0.4154 (2) | 0.2787 (3) | 0.0154 (6) | |
C15 | 0.9741 (2) | 0.4713 (2) | 0.3329 (3) | 0.0200 (7) | |
H15A | 1.0382 | 0.4565 | 0.3009 | 0.024* | |
C16 | 0.9607 (2) | 0.5459 (2) | 0.4306 (4) | 0.0209 (7) | |
H16A | 1.0160 | 0.5819 | 0.4657 | 0.025* | |
C17 | 0.8673 (2) | 0.5711 (2) | 0.4810 (3) | 0.0194 (6) | |
H17A | 0.8594 | 0.6237 | 0.5485 | 0.023* | |
C18 | 0.7876 (2) | 0.5181 (2) | 0.4304 (3) | 0.0173 (6) | |
C19 | 0.6746 (3) | 0.6213 (3) | 0.5603 (4) | 0.0255 (8) | |
H19A | 0.6041 | 0.6268 | 0.5769 | 0.038* | |
H19B | 0.6984 | 0.6868 | 0.5201 | 0.038* | |
H19C | 0.7085 | 0.6085 | 0.6463 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.01077 (16) | 0.01476 (16) | 0.01513 (17) | −0.00103 (14) | 0.0011 (2) | −0.00126 (15) |
O1 | 0.0344 (14) | 0.0200 (11) | 0.0301 (14) | 0.0000 (10) | 0.0024 (11) | −0.0091 (10) |
O2 | 0.0152 (11) | 0.0200 (10) | 0.0218 (12) | 0.0006 (9) | 0.0038 (9) | −0.0030 (9) |
O3 | 0.0112 (10) | 0.0186 (11) | 0.0229 (12) | −0.0027 (8) | 0.0008 (9) | −0.0038 (9) |
O4 | 0.0096 (10) | 0.0312 (12) | 0.0354 (15) | 0.0022 (9) | 0.0021 (10) | −0.0172 (11) |
N1 | 0.0155 (13) | 0.0165 (12) | 0.0168 (13) | −0.0028 (10) | 0.0004 (10) | −0.0001 (10) |
N2 | 0.0085 (12) | 0.0175 (12) | 0.0182 (14) | −0.0014 (10) | −0.0017 (10) | −0.0001 (10) |
C1 | 0.043 (2) | 0.0250 (18) | 0.036 (2) | 0.0011 (17) | 0.0013 (19) | −0.0158 (16) |
C2 | 0.0258 (18) | 0.0209 (15) | 0.0156 (16) | 0.0046 (13) | −0.0049 (13) | −0.0009 (13) |
C3 | 0.0289 (19) | 0.0268 (16) | 0.0176 (16) | 0.0100 (15) | −0.0004 (14) | −0.0048 (13) |
C4 | 0.0206 (17) | 0.0349 (18) | 0.0209 (17) | 0.0083 (14) | 0.0014 (14) | −0.0011 (15) |
C5 | 0.0205 (16) | 0.0258 (16) | 0.0203 (17) | 0.0023 (13) | 0.0010 (13) | −0.0003 (13) |
C6 | 0.0177 (15) | 0.0201 (14) | 0.0155 (15) | 0.0026 (12) | −0.0014 (12) | 0.0002 (12) |
C7 | 0.0185 (16) | 0.0205 (16) | 0.0146 (15) | 0.0045 (12) | −0.0015 (12) | −0.0004 (12) |
C8 | 0.0210 (16) | 0.0168 (14) | 0.0177 (16) | 0.0005 (12) | −0.0017 (12) | 0.0017 (12) |
C9 | 0.0159 (14) | 0.0216 (14) | 0.0212 (19) | −0.0053 (11) | 0.0027 (13) | −0.0013 (12) |
C10 | 0.0150 (15) | 0.0225 (15) | 0.0223 (17) | −0.0036 (13) | −0.0014 (13) | −0.0048 (13) |
C11 | 0.0059 (13) | 0.0240 (15) | 0.0222 (19) | −0.0016 (11) | −0.0026 (11) | −0.0030 (12) |
C12 | 0.0076 (13) | 0.0209 (14) | 0.0176 (15) | 0.0027 (11) | 0.0009 (11) | −0.0012 (12) |
C13 | 0.0098 (14) | 0.0164 (14) | 0.0196 (16) | −0.0005 (11) | −0.0004 (12) | −0.0007 (12) |
C14 | 0.0125 (15) | 0.0167 (14) | 0.0170 (16) | 0.0010 (12) | 0.0022 (12) | 0.0018 (12) |
C15 | 0.0101 (15) | 0.0234 (15) | 0.0266 (18) | −0.0019 (12) | 0.0022 (13) | −0.0025 (13) |
C16 | 0.0146 (15) | 0.0210 (15) | 0.0270 (18) | −0.0041 (12) | −0.0040 (14) | −0.0034 (14) |
C17 | 0.0163 (15) | 0.0201 (14) | 0.0218 (16) | −0.0012 (12) | −0.0002 (13) | −0.0060 (12) |
C18 | 0.0100 (14) | 0.0204 (15) | 0.0214 (16) | 0.0028 (11) | 0.0004 (12) | −0.0034 (12) |
C19 | 0.0202 (16) | 0.0280 (17) | 0.028 (2) | 0.0039 (13) | 0.0039 (13) | −0.0105 (13) |
Ni—O2 | 1.855 (2) | C6—C7 | 1.418 (4) |
Ni—O3 | 1.852 (2) | C7—C8 | 1.436 (5) |
Ni—N1 | 1.882 (2) | C8—H8A | 0.950 |
Ni—N2 | 1.895 (3) | C9—H9A | 0.990 |
O1—C1 | 1.441 (4) | C9—H9B | 0.990 |
O1—C2 | 1.370 (4) | C9—C10 | 1.512 (5) |
O2—C6 | 1.303 (4) | C10—H10A | 0.990 |
O3—C14 | 1.302 (4) | C10—H10B | 0.990 |
O4—C18 | 1.369 (4) | C10—C11 | 1.516 (4) |
O4—C19 | 1.427 (4) | C11—H11A | 0.990 |
N1—C8 | 1.294 (4) | C11—H11B | 0.990 |
N1—C9 | 1.482 (4) | C12—H12A | 0.950 |
N2—C11 | 1.500 (4) | C12—C13 | 1.425 (4) |
N2—C12 | 1.301 (4) | C13—C14 | 1.411 (4) |
C1—H1A | 0.980 | C13—C18 | 1.428 (4) |
C1—H1B | 0.980 | C14—C15 | 1.424 (4) |
C1—H1C | 0.980 | C15—H15A | 0.950 |
C2—C3 | 1.381 (5) | C15—C16 | 1.365 (4) |
C2—C7 | 1.427 (4) | C16—H16A | 0.950 |
C3—H3A | 0.950 | C16—C17 | 1.408 (4) |
C3—C4 | 1.394 (5) | C17—H17A | 0.950 |
C4—H4A | 0.950 | C17—C18 | 1.376 (4) |
C4—C5 | 1.375 (5) | C19—H19A | 0.980 |
C5—H5A | 0.950 | C19—H19B | 0.980 |
C5—C6 | 1.416 (4) | C19—H19C | 0.980 |
O2—Ni—O3 | 81.06 (10) | N1—C9—H9B | 109.9 |
O2—Ni—N1 | 92.44 (11) | N1—C9—C10 | 108.8 (2) |
O2—Ni—N2 | 166.39 (10) | H9A—C9—H9B | 108.3 |
O3—Ni—N1 | 164.26 (10) | H9A—C9—C10 | 109.9 |
O3—Ni—N2 | 92.77 (10) | H9B—C9—C10 | 109.9 |
N1—Ni—N2 | 96.42 (11) | C9—C10—H10A | 109.5 |
C1—O1—C2 | 117.4 (3) | C9—C10—H10B | 109.5 |
Ni—O2—C6 | 131.2 (2) | C9—C10—C11 | 110.7 (3) |
Ni—O3—C14 | 130.3 (2) | H10A—C10—H10B | 108.1 |
C18—O4—C19 | 118.2 (2) | H10A—C10—C11 | 109.5 |
Ni—N1—C8 | 126.2 (2) | H10B—C10—C11 | 109.5 |
Ni—N1—C9 | 118.56 (19) | N2—C11—C10 | 113.8 (3) |
C8—N1—C9 | 115.2 (3) | N2—C11—H11A | 108.8 |
Ni—N2—C11 | 124.5 (2) | N2—C11—H11B | 108.8 |
Ni—N2—C12 | 124.4 (2) | C10—C11—H11A | 108.8 |
C11—N2—C12 | 110.9 (3) | C10—C11—H11B | 108.8 |
O1—C1—H1A | 109.5 | H11A—C11—H11B | 107.7 |
O1—C1—H1B | 109.5 | N2—C12—H12A | 115.9 |
O1—C1—H1C | 109.5 | N2—C12—C13 | 128.1 (3) |
H1A—C1—H1B | 109.5 | H12A—C12—C13 | 115.9 |
H1A—C1—H1C | 109.5 | C12—C13—C14 | 120.0 (3) |
H1B—C1—H1C | 109.5 | C12—C13—C18 | 120.1 (3) |
O1—C2—C3 | 124.2 (3) | C14—C13—C18 | 119.6 (3) |
O1—C2—C7 | 114.7 (3) | O3—C14—C13 | 123.1 (3) |
C3—C2—C7 | 121.1 (3) | O3—C14—C15 | 118.7 (3) |
C2—C3—H3A | 120.9 | C13—C14—C15 | 118.3 (3) |
C2—C3—C4 | 118.3 (3) | C14—C15—H15A | 119.7 |
H3A—C3—C4 | 120.9 | C14—C15—C16 | 120.5 (3) |
C3—C4—H4A | 118.6 | H15A—C15—C16 | 119.7 |
C3—C4—C5 | 122.8 (3) | C15—C16—H16A | 119.0 |
H4A—C4—C5 | 118.6 | C15—C16—C17 | 122.0 (3) |
C4—C5—H5A | 120.1 | H16A—C16—C17 | 119.0 |
C4—C5—C6 | 119.9 (3) | C16—C17—H17A | 120.7 |
H5A—C5—C6 | 120.1 | C16—C17—C18 | 118.6 (3) |
O2—C6—C5 | 119.4 (3) | H17A—C17—C18 | 120.7 |
O2—C6—C7 | 122.1 (3) | O4—C18—C13 | 114.7 (3) |
C5—C6—C7 | 118.5 (3) | O4—C18—C17 | 124.3 (3) |
C2—C7—C6 | 119.4 (3) | C13—C18—C17 | 121.0 (3) |
C2—C7—C8 | 119.5 (3) | O4—C19—H19A | 109.5 |
C6—C7—C8 | 120.7 (3) | O4—C19—H19B | 109.5 |
N1—C8—C7 | 126.6 (3) | O4—C19—H19C | 109.5 |
N1—C8—H8A | 116.7 | H19A—C19—H19B | 109.5 |
C7—C8—H8A | 116.7 | H19A—C19—H19C | 109.5 |
N1—C9—H9A | 109.9 | H19B—C19—H19C | 109.5 |
O3—Ni—O2—C6 | 161.9 (3) | C3—C2—C7—C6 | −1.8 (5) |
N1—Ni—O2—C6 | −3.7 (3) | C3—C2—C7—C8 | 171.0 (3) |
N2—Ni—O2—C6 | −134.3 (5) | Ni—N1—C8—C7 | −7.3 (5) |
O2—Ni—O3—C14 | −179.7 (3) | C9—N1—C8—C7 | 175.7 (3) |
N1—Ni—O3—C14 | −113.2 (4) | C2—C7—C8—N1 | −175.1 (3) |
N2—Ni—O3—C14 | 12.5 (3) | C6—C7—C8—N1 | −2.4 (5) |
O2—Ni—N1—C8 | 8.9 (3) | Ni—N1—C9—C10 | 54.3 (3) |
O2—Ni—N1—C9 | −174.2 (2) | C8—N1—C9—C10 | −128.4 (3) |
O3—Ni—N1—C8 | −56.2 (6) | N1—C9—C10—C11 | −80.6 (3) |
O3—Ni—N1—C9 | 120.8 (4) | Ni—N2—C11—C10 | 10.4 (4) |
N2—Ni—N1—C8 | 178.5 (3) | C12—N2—C11—C10 | −174.9 (3) |
N2—Ni—N1—C9 | −4.5 (2) | C9—C10—C11—N2 | 45.3 (4) |
O2—Ni—N2—C11 | 101.5 (5) | Ni—N2—C12—C13 | 3.4 (5) |
O2—Ni—N2—C12 | −72.5 (6) | C11—N2—C12—C13 | −171.3 (3) |
O3—Ni—N2—C11 | 164.0 (2) | N2—C12—C13—C14 | 5.6 (5) |
O3—Ni—N2—C12 | −10.0 (3) | N2—C12—C13—C18 | 178.4 (3) |
N1—Ni—N2—C11 | −28.8 (2) | Ni—O3—C14—C13 | −7.5 (4) |
N1—Ni—N2—C12 | 157.2 (3) | Ni—O3—C14—C15 | 172.9 (2) |
C1—O1—C2—C3 | −7.0 (5) | C12—C13—C14—O3 | −3.7 (4) |
C1—O1—C2—C7 | 171.3 (3) | C12—C13—C14—C15 | 175.9 (3) |
O1—C2—C3—C4 | 179.5 (3) | C18—C13—C14—O3 | −176.5 (3) |
C7—C2—C3—C4 | 1.3 (5) | C18—C13—C14—C15 | 3.0 (4) |
C2—C3—C4—C5 | 0.5 (5) | O3—C14—C15—C16 | 178.2 (3) |
C3—C4—C5—C6 | −1.7 (5) | C13—C14—C15—C16 | −1.4 (5) |
Ni—O2—C6—C5 | 176.4 (2) | C14—C15—C16—C17 | −0.4 (5) |
Ni—O2—C6—C7 | −3.7 (5) | C15—C16—C17—C18 | 0.5 (5) |
C4—C5—C6—O2 | −179.0 (3) | C19—O4—C18—C13 | −175.0 (3) |
C4—C5—C6—C7 | 1.1 (5) | C19—O4—C18—C17 | 5.2 (5) |
O2—C6—C7—C2 | −179.3 (3) | C16—C17—C18—O4 | −179.0 (3) |
O2—C6—C7—C8 | 8.0 (5) | C16—C17—C18—C13 | 1.2 (5) |
C5—C6—C7—C2 | 0.6 (5) | C12—C13—C18—O4 | 4.4 (4) |
C5—C6—C7—C8 | −172.1 (3) | C12—C13—C18—C17 | −175.8 (3) |
O1—C2—C7—C6 | 179.8 (3) | C14—C13—C18—O4 | 177.2 (3) |
O1—C2—C7—C8 | −7.4 (4) | C14—C13—C18—C17 | −3.0 (5) |
Experimental details
Crystal data | |
Chemical formula | [Ni(C19H20N2O4)] |
Mr | 399.08 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 150 |
a, b, c (Å) | 13.677 (2), 12.7319 (18), 9.8561 (14) |
V (Å3) | 1716.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.16 |
Crystal size (mm) | 0.34 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.690, 0.725 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13065, 4083, 3384 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.06 |
No. of reflections | 4083 |
No. of parameters | 238 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.53 |
Absolute structure | Flack (1983), with 1870 Friedel pairs |
Absolute structure parameter | 0.00 (2) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2005), DIAMOND (Brandenburg, 2007), SHELXTL and local programs.
Ni—O2 | 1.855 (2) | Ni—N1 | 1.882 (2) |
Ni—O3 | 1.852 (2) | Ni—N2 | 1.895 (3) |
O2—Ni—O3 | 81.06 (10) | O3—Ni—N1 | 164.26 (10) |
O2—Ni—N1 | 92.44 (11) | O3—Ni—N2 | 92.77 (10) |
O2—Ni—N2 | 166.39 (10) | N1—Ni—N2 | 96.42 (11) |
Nickel(II) complexes with N2O2 Schiff-base ligands derived from salicylaldehyde have long been used as homogenous catalysts (Gosden et al., 1981; Healy & Pletcher, 1978). Recently we reported the structure of a copper(II) complex with the N,N'-bis(6-methoxysalicylidene)-1,3-diaminopropane ligand (Habibi et al., 2007). The title compound is isostructural with its CuII analogue.
In the title compound (Figure 1), the Ni—O and Ni—N distances are larger than the comparable mean distances of 1.829 and 1.859 Å, respectively, in N,N'-ethylenebis(salicylideneiminato)nickel(II) (Shkol'nikova et al., 1970) and 1.849 (2) and 1.840 (2) Å, respectively, in N,N'-ethylenebis[(2-hydroxy-1-naphthyl)methaniminato]nickel(II) (Akhtar, 1981).