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Acta Cryst. (2008). E64, m592    [ doi:10.1107/S160053680800809X ]

Bis(2-ethoxy-6-formylphenolato-[kappa]2O1,O6)nickel(II)

Z.-Q. Han

Abstract top

The title compound, [Ni(C9H9O3)2], was synthesized by the reaction of 3-ethoxysalicylaldehyde with nickel(II) nitrate in methanol solution. The asymmetric unit onsists of two half-molecules; each Ni atom lies on a centre of symmetry. The NiII ions are coordinated by four O atoms from two deprotonated 3-ethoxysalicylaldehyde ligands in a slightly distorted square-planar coordination environment.

Comment top

The authors interest in nickel(II) complexes arises from the fact that Ni(II) is the active center of the urease enzyme (Carlsson et al., 2004; Volkmer et al., 1996). The author reports herein the crystal structure of the title nickel(II) complex.

In the asymmetric unit of the title compound, there are two independent complex (Fig. 1). Each NiII ion lies on an inversion center and is coordinated by four O atoms from two deprotonated 3-ethoxysalicylaldehyde ligands. The coordinate bond values (Table 1) in each molecule are comparable to each other between the two independent complex molecules. The structure is similar to other nickel(II) complexes derived from the derivatives of salicylaldehyde (Li & Chen, 2006; Mounts & Fernando, 1974).

Related literature top

For related literature, see: Carlsson et al. (2004); Li & Chen (2006); Mounts & Fernando (1974); Volkmer et al. (1996).

Experimental top

All chemicals were of AR grade. 3-Ethoxysalicylaldehyde (33.2 mg, 0.2 mmol) and nickel(II) nitrate hexahydrate (29.0 mg, 0.1 mmol) were refluxed for 30 min in 10 ml methanol solution. The mixture was cooled to room temperature and filtered. Keeping the filtrate in air for a week, yielded red block crystals suitable for X-ray analysis.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(methyl C). Although no significant density was located in the solvent accessible VOIDS of 47.00 Å3, these might be able to accommodate disordered water molecules.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structures of the two centrosymmetric independent molecules, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The unlabeled atoms are related by the symmetry operators (-x, -y+1, -z) and (-x, -y, -z) for the molecules containing Ni1 and Ni2 respectively.
Bis(2-ethoxy-6-formylphenolato-κ2O1,O6)nickel(II) top
Crystal data top
[Ni(C9H9O3)2]Z = 2
Mr = 389.03F(000) = 404
Triclinic, P1Dx = 1.429 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.448 (2) ÅCell parameters from 2386 reflections
b = 10.123 (2) Åθ = 2.2–27.9°
c = 11.919 (3) ŵ = 1.10 mm−1
α = 111.175 (2)°T = 298 K
β = 97.377 (2)°Block, red
γ = 102.431 (3)°0.32 × 0.32 × 0.30 mm
V = 904.1 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		3993 independent reflections
Radiation source: fine-focus sealed tube3187 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→8
Tmin = 0.719, Tmax = 0.733k = −13→13
5465 measured reflectionsl = −11→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0596P)2 + 0.672P]
where P = (Fo2 + 2Fc2)/3
3993 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.65 e Å−3
0 restraintsΔρmin = −0.66 e Å−3
Crystal data top
[Ni(C9H9O3)2]γ = 102.431 (3)°
Mr = 389.03V = 904.1 (4) Å3
Triclinic, P1Z = 2
a = 8.448 (2) ÅMo Kα radiation
b = 10.123 (2) ŵ = 1.10 mm−1
c = 11.919 (3) ÅT = 298 K
α = 111.175 (2)°0.32 × 0.32 × 0.30 mm
β = 97.377 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3993 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3187 reflections with I > 2σ(I)
Tmin = 0.719, Tmax = 0.733Rint = 0.013
5465 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.116Δρmax = 0.65 e Å−3
S = 1.02Δρmin = −0.66 e Å−3
3993 reflectionsAbsolute structure: ?
231 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.00000.50000.00000.02805 (13)
Ni20.00000.00000.00000.02920 (14)
O10.0505 (2)−0.0121 (2)0.15045 (16)0.0363 (4)
O2−0.0576 (3)0.1741 (2)0.0663 (2)0.0506 (5)
O30.1596 (3)−0.0689 (2)0.33683 (18)0.0484 (5)
O40.0529 (3)0.3494 (3)−0.1190 (2)0.0513 (5)
O50.1989 (2)0.63719 (19)0.02863 (17)0.0350 (4)
O60.4541 (3)0.8659 (2)0.1053 (2)0.0552 (6)
C10.3232 (3)0.4873 (3)−0.1220 (3)0.0366 (6)
C20.3219 (3)0.6192 (3)−0.0278 (2)0.0328 (5)
C30.4641 (3)0.7438 (3)0.0107 (3)0.0416 (7)
C40.5959 (4)0.7345 (4)−0.0462 (3)0.0534 (8)
H40.68720.8170−0.02140.064*
C50.5940 (4)0.6031 (4)−0.1404 (3)0.0583 (9)
H50.68370.5983−0.17790.070*
C60.4608 (4)0.4814 (4)−0.1777 (3)0.0508 (8)
H60.46060.3938−0.24030.061*
C70.1866 (3)0.3570 (3)−0.1613 (3)0.0387 (6)
H70.19460.2713−0.22200.046*
C80.5934 (4)0.9930 (4)0.1562 (4)0.0630 (10)
H8A0.61621.03040.09390.076*
H8B0.69100.96870.18590.076*
C90.5528 (5)1.1062 (5)0.2603 (4)0.0745 (11)
H9A0.45231.12510.23080.112*
H9B0.64241.19590.29330.112*
H9C0.53751.07060.32380.112*
C100.0426 (4)0.2306 (3)0.2817 (3)0.0403 (6)
C110.0741 (3)0.0937 (3)0.2595 (2)0.0344 (6)
C120.1373 (4)0.0681 (3)0.3646 (3)0.0408 (6)
C130.1716 (5)0.1762 (4)0.4812 (3)0.0603 (9)
H130.21430.15820.54840.072*
C140.1433 (6)0.3135 (4)0.5010 (3)0.0737 (12)
H140.16890.38660.58060.088*
C150.0782 (5)0.3389 (4)0.4027 (3)0.0604 (10)
H150.05710.42920.41580.073*
C16−0.0311 (4)0.2596 (3)0.1806 (3)0.0390 (6)
H16−0.06170.34670.19960.047*
C170.2484 (5)−0.0970 (4)0.4322 (3)0.0552 (8)
H17A0.1831−0.09920.49300.066*
H17B0.3528−0.02020.47330.066*
C180.2804 (6)−0.2441 (5)0.3720 (4)0.0832 (14)
H18A0.1769−0.32080.34140.125*
H18B0.3527−0.26060.43150.125*
H18C0.3322−0.24490.30470.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0239 (2)0.0277 (2)0.0327 (2)0.00622 (17)0.00861 (17)0.01208 (19)
Ni20.0308 (2)0.0285 (2)0.0283 (2)0.00865 (18)0.00732 (18)0.01098 (18)
O10.0484 (11)0.0311 (9)0.0290 (9)0.0129 (8)0.0067 (8)0.0113 (8)
O20.0517 (13)0.0484 (12)0.0514 (13)0.0158 (10)0.0160 (10)0.0173 (10)
O30.0639 (14)0.0438 (12)0.0361 (10)0.0201 (10)0.0001 (10)0.0152 (9)
O40.0470 (12)0.0502 (13)0.0537 (13)0.0132 (10)0.0147 (10)0.0164 (11)
O50.0277 (9)0.0310 (9)0.0459 (11)0.0057 (7)0.0132 (8)0.0149 (8)
O60.0374 (11)0.0432 (12)0.0731 (16)−0.0024 (9)0.0148 (11)0.0170 (11)
C10.0303 (13)0.0484 (16)0.0388 (14)0.0144 (12)0.0129 (11)0.0225 (12)
C20.0246 (12)0.0412 (14)0.0404 (14)0.0104 (10)0.0093 (10)0.0238 (12)
C30.0300 (13)0.0469 (17)0.0530 (18)0.0070 (12)0.0110 (12)0.0272 (15)
C40.0316 (15)0.061 (2)0.072 (2)0.0021 (14)0.0163 (15)0.0362 (18)
C50.0380 (17)0.079 (3)0.069 (2)0.0179 (17)0.0286 (16)0.036 (2)
C60.0414 (16)0.065 (2)0.0521 (18)0.0205 (15)0.0228 (14)0.0239 (16)
C70.0367 (14)0.0426 (15)0.0386 (14)0.0161 (12)0.0154 (12)0.0132 (12)
C80.0436 (18)0.055 (2)0.076 (3)−0.0064 (16)0.0034 (17)0.0253 (19)
C90.073 (3)0.060 (2)0.064 (2)−0.008 (2)0.005 (2)0.0134 (19)
C100.0472 (16)0.0387 (15)0.0354 (14)0.0168 (13)0.0131 (12)0.0114 (12)
C110.0318 (13)0.0374 (14)0.0314 (13)0.0086 (11)0.0091 (10)0.0110 (11)
C120.0423 (15)0.0421 (15)0.0341 (14)0.0127 (12)0.0064 (12)0.0115 (12)
C130.084 (3)0.064 (2)0.0297 (15)0.030 (2)0.0049 (16)0.0120 (15)
C140.114 (3)0.064 (2)0.0347 (17)0.041 (2)0.0089 (19)0.0036 (16)
C150.093 (3)0.0484 (19)0.0391 (17)0.0340 (19)0.0151 (17)0.0092 (14)
C160.0474 (16)0.0345 (14)0.0392 (15)0.0176 (12)0.0166 (12)0.0139 (12)
C170.062 (2)0.065 (2)0.0424 (17)0.0247 (17)0.0015 (15)0.0249 (16)
C180.118 (4)0.077 (3)0.062 (2)0.057 (3)0.000 (2)0.027 (2)
Geometric parameters (Å, º) top
Ni1—O51.837 (2)C6—H60.9300
Ni1—O5i1.837 (2)C7—H70.9300
Ni1—O41.852 (2)C8—C91.491 (5)
Ni1—O4i1.852 (2)C8—H8A0.9700
Ni2—O11.843 (2)C8—H8B0.9700
Ni2—O1ii1.843 (2)C9—H9A0.9600
Ni2—O2ii1.851 (2)C9—H9B0.9600
Ni2—O21.851 (2)C9—H9C0.9600
O1—C111.309 (3)C10—C111.405 (4)
O2—C161.282 (3)C10—C151.406 (4)
O3—C121.365 (3)C10—C161.438 (4)
O3—C171.429 (3)C11—C121.430 (4)
O4—C71.294 (3)C12—C131.369 (4)
O5—C21.319 (3)C13—C141.402 (5)
O6—C31.367 (4)C13—H130.9300
O6—C81.417 (4)C14—C151.362 (5)
C1—C21.404 (4)C14—H140.9300
C1—C61.412 (4)C15—H150.9300
C1—C71.432 (4)C16—H160.9300
C2—C31.426 (4)C17—C181.502 (5)
C3—C41.380 (4)C17—H17A0.9700
C4—C51.391 (5)C17—H17B0.9700
C4—H40.9300C18—H18A0.9600
C5—C61.364 (5)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
O5—Ni1—O5i180O6—C8—H8B110.2
O5—Ni1—O494.16 (9)C9—C8—H8B110.2
O5i—Ni1—O485.84 (9)H8A—C8—H8B108.5
O5—Ni1—O4i85.84 (9)C8—C9—H9A109.5
O5i—Ni1—O4i94.16 (9)C8—C9—H9B109.5
O4—Ni1—O4i180H9A—C9—H9B109.5
O1—Ni2—O1ii180C8—C9—H9C109.5
O1—Ni2—O2ii86.30 (9)H9A—C9—H9C109.5
O1ii—Ni2—O2ii93.70 (9)H9B—C9—H9C109.5
O1—Ni2—O293.70 (9)C11—C10—C15120.7 (3)
O1ii—Ni2—O286.30 (9)C11—C10—C16120.0 (2)
O2ii—Ni2—O2180C15—C10—C16119.3 (3)
C11—O1—Ni2126.59 (17)O1—C11—C10125.3 (2)
C16—O2—Ni2127.6 (2)O1—C11—C12117.4 (2)
C12—O3—C17118.6 (2)C10—C11—C12117.3 (2)
C7—O4—Ni1127.6 (2)O3—C12—C13125.1 (3)
C2—O5—Ni1127.62 (17)O3—C12—C11114.3 (2)
C3—O6—C8118.6 (3)C13—C12—C11120.5 (3)
C2—C1—C6120.1 (3)C12—C13—C14121.2 (3)
C2—C1—C7120.5 (2)C12—C13—H13119.4
C6—C1—C7119.4 (3)C14—C13—H13119.4
O5—C2—C1125.0 (2)C15—C14—C13119.4 (3)
O5—C2—C3117.0 (2)C15—C14—H14120.3
C1—C2—C3118.0 (2)C13—C14—H14120.3
O6—C3—C4125.7 (3)C14—C15—C10120.9 (3)
O6—C3—C2114.0 (2)C14—C15—H15119.6
C4—C3—C2120.3 (3)C10—C15—H15119.6
C3—C4—C5120.8 (3)O2—C16—C10124.7 (3)
C3—C4—H4119.6O2—C16—H16117.6
C5—C4—H4119.6C10—C16—H16117.6
C6—C5—C4120.2 (3)O3—C17—C18107.2 (3)
C6—C5—H5119.9O3—C17—H17A110.3
C4—C5—H5119.9C18—C17—H17A110.3
C5—C6—C1120.6 (3)O3—C17—H17B110.3
C5—C6—H6119.7C18—C17—H17B110.3
C1—C6—H6119.7H17A—C17—H17B108.5
O4—C7—C1125.0 (3)C17—C18—H18A109.5
O4—C7—H7117.5C17—C18—H18B109.5
C1—C7—H7117.5H18A—C18—H18B109.5
O6—C8—C9107.6 (3)C17—C18—H18C109.5
O6—C8—H8A110.2H18A—C18—H18C109.5
C9—C8—H8A110.2H18B—C18—H18C109.5
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z.
Selected geometric parameters (Å, º) top
Ni1—O51.837 (2)Ni2—O11.843 (2)
Ni1—O41.852 (2)Ni2—O21.851 (2)
O5—Ni1—O5i180O1—Ni2—O1ii180
O5—Ni1—O494.16 (9)O1—Ni2—O293.70 (9)
O5i—Ni1—O485.84 (9)O1ii—Ni2—O286.30 (9)
O4—Ni1—O4i180O2ii—Ni2—O2180
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z.
Acknowledgements top

The author acknowledges Qiqihar University for a research grant.

references
References top

Bruker (1998). SMART (Version 5.628) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.

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Li, Y.-G. & Chen, H.-J. (2006). Acta Cryst. E62, m1038–m1039.

Mounts, R. D. & Fernando, Q. (1974). Acta Cryst. B30, 542–543.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Volkmer, D., Hommerich, B., Griesar, K., Haase, W. & Krebs, B. (1996). Inorg. Chem. 35, 3792–3803.