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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.101
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.02
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.36 From the CIF: _reflns_number_total 4083 Count of symmetry unique reflns 2274 Completeness (_total/calc) 179.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1809 Fraction of Friedel pairs measured 0.796 Are heavy atom types Z>Si present yes PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni (3) 2.82 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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).
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) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).