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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1253.
Published online 2008 September 6. doi:  10.1107/S1600536808028171
PMCID: PMC2959330

(2-{[2-(4-Chlorophenoxy)-1-oxido­ethyl­idene-κO 1]hydrazono­methyl}­phenol­ato-κ2 N 1,O)(1H-imidazole-κN 3)nickel(II)

Abstract

In the title complex, [Ni(C15H11ClN2O3)(C3H4N2)], the NiII ion is coordinated by a phenolate O, hydrazine N and carbonyl O atom from the hydrazone ligand and by an N atom from the imidazole mol­ecule, forming a distorted square-planar geometry. Inter­molecular N—H(...)N hydrogen bonds link neighboring molecules into extended chains parallel to [100].

Related literature

For general background, see: Liu & Gao (1998 [triangle]); Ma et al. (1989 [triangle]); Sur et al. (1993 [triangle]); Sun et al. (2005 [triangle]). For related structures, see: Chen & Liu (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1253-scheme1.jpg

Experimental

Crystal data

  • [Ni(C15H11ClN2O3)(C3H4N2)]
  • M r = 429.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1253-efi1.jpg
  • a = 18.745 (5) Å
  • b = 6.6054 (14) Å
  • c = 29.230 (8) Å
  • V = 3619.2 (16) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.25 mm−1
  • T = 293 (2) K
  • 0.65 × 0.21 × 0.15 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 [triangle]) T min = 0.498, T max = 0.835
  • 29384 measured reflections
  • 4146 independent reflections
  • 2947 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.087
  • S = 0.96
  • 4146 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: TEXRAY (Molecular Structure Corporation, 1999 [triangle]); cell refinement: TEXRAY; data reduction: TEXSAN (Mol­ec­ular Structure Corporation, 1999 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEX (McArdle, 1995 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028171/bv2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028171/bv2105Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Hydrazones are of interest owing to their capacity for chelating to transition (Sur et al., 1993; Sun et al., 2005), lanthanide (Ma et al., 1989) and main group (Liu & Gao 1998) metals. Here we report the crystal structure of the title complex, (I) (Fig. 1). The Ni(II) ion exists in a square-planar N2O2 coordination geometry defined by the phenolate O1, hydrazine N1, and carbonyl O2 atom of the hydrazone ligand, and N3 atom from the 1H-imidazole molecule. The hydrazone ligand in the title complex is distorted, the dihedral angle between the two phenyl rings being 50.56 (9)°. The corresponding dihedral angle is about 87° in the complex [Co(C15H12N2O3)(C5H7O2)(C3H7NO)] (Chen & Liu, 2006) with the ligand of salicylaldehyde phenoxyacylhydrazone. In the title complex, an extended one-dimensional chain structure is formed via intermolecular hydrogen bonds between the 1H-imidazole N—H groups and the uncoordinated N-atom of the hydrazone ligand (Fig. 2). The N4···N2(A) distance and the N4—H···N2(A) angle are 2.916 (3) Å and 171.92°, respectively [Symmetry code: (A) x - 1/2, y, -z + 1/2].

Experimental

The hydrazone ligand was prepared by the reaction of salicylaldehyde and 4-chloro-phenoxyacetylhydrazine in a molar ratio of 1:1 under reflux in ethanol for 2 h. The yellow product obtained on cooling was recrystallized from methanol. Salicylaldehyde 4-chloro-phenoxyacetylhydrazone (1 mmol), [Ni(OAc)2].4H2O (1 mmol), imidazole (1 mmol), N,N-dimethylformamide (5 ml), and methanol (10 ml) were stirred for 2 h. The solution was filtered and allowed to stand at room temperature for one week, and red crystals of complex (I) were obtained.

Refinement

All H atoms were placed in idealized positions and treated as riding with N—H = 0.86 Å, C—H = 0.93–0.97Å and Uiso(H) = 1.2Ueq(C/N).

Figures

Fig. 1.
The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
Extended chain structure of (I).

Crystal data

[Ni(C15H11ClN2O3)(C3H4N2)]F(000) = 1760
Mr = 429.50Dx = 1.576 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2947 reflections
a = 18.745 (5) Åθ = 3.0–27.5°
b = 6.6054 (14) ŵ = 1.25 mm1
c = 29.230 (8) ÅT = 293 K
V = 3619.2 (16) Å3Prism, red
Z = 80.65 × 0.21 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer4146 independent reflections
Radiation source: fine-focus sealed tube2947 reflections with I > 2σ(I)
graphiteRint = 0.058
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)h = −24→24
Tmin = 0.498, Tmax = 0.835k = −8→8
29384 measured reflectionsl = −37→37

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0475P)2] where P = (Fo2 + 2Fc2)/3
4146 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

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)

xyzUiso*/Ueq
Ni10.160819 (13)0.65045 (4)0.262178 (8)0.03514 (10)
O10.11416 (8)0.6681 (2)0.31655 (5)0.0519 (4)
O20.20944 (7)0.63914 (19)0.20727 (4)0.0397 (3)
O30.30335 (9)0.7513 (2)0.14068 (5)0.0524 (4)
N10.25009 (9)0.6404 (2)0.28711 (5)0.0344 (3)
N20.30584 (9)0.6336 (2)0.25500 (6)0.0381 (4)
N30.07133 (9)0.6479 (2)0.23119 (6)0.0403 (4)
N4−0.04380 (10)0.6469 (3)0.21963 (6)0.0489 (4)
H4A−0.08890.65190.22500.059*
Cl10.44937 (4)0.82246 (10)−0.03563 (2)0.0718 (2)
C10.14251 (12)0.6600 (3)0.35761 (7)0.0433 (5)
C20.21615 (12)0.6403 (3)0.36618 (7)0.0393 (4)
C30.24043 (14)0.6287 (3)0.41153 (7)0.0508 (6)
H3A0.28900.61430.41710.061*
C40.19446 (16)0.6382 (3)0.44779 (8)0.0580 (6)
H4B0.21140.62850.47760.070*
C50.12234 (16)0.6625 (4)0.43930 (8)0.0589 (6)
H5A0.09080.67130.46380.071*
C60.09647 (14)0.6737 (4)0.39544 (8)0.0575 (6)
H6A0.04780.69060.39070.069*
C70.26712 (11)0.6330 (3)0.32997 (7)0.0396 (4)
H7A0.31510.62240.33760.048*
C80.27699 (11)0.6312 (3)0.21432 (7)0.0376 (4)
C90.32487 (11)0.6078 (3)0.17375 (7)0.0430 (5)
H9A0.37410.63120.18250.052*
H9B0.32100.47190.16140.052*
C100.33961 (11)0.7564 (3)0.10033 (7)0.0432 (5)
C110.32289 (16)0.9148 (4)0.07150 (9)0.0694 (8)
H11A0.28901.00990.08040.083*
C120.35588 (16)0.9335 (4)0.02962 (9)0.0709 (8)
H12A0.34401.03990.01020.085*
C130.40604 (13)0.7950 (3)0.01670 (7)0.0505 (5)
C140.42323 (14)0.6372 (3)0.04485 (7)0.0533 (6)
H14A0.45730.54310.03570.064*
C150.39005 (13)0.6170 (3)0.08685 (7)0.0481 (5)
H15A0.40180.50940.10600.058*
C160.05887 (13)0.6245 (4)0.18536 (8)0.0545 (6)
H16A0.09380.61070.16300.065*
C17−0.01198 (13)0.6245 (4)0.17777 (8)0.0619 (7)
H17A−0.03480.61170.14970.074*
C180.00820 (11)0.6595 (3)0.25023 (8)0.0418 (5)
H18A0.00080.67480.28150.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.02247 (14)0.04455 (16)0.03838 (15)−0.00093 (10)0.00212 (10)0.00103 (11)
O10.0303 (8)0.0837 (11)0.0416 (8)0.0012 (8)0.0047 (6)0.0011 (7)
O20.0259 (7)0.0523 (8)0.0408 (7)−0.0004 (6)0.0013 (6)0.0006 (6)
O30.0488 (10)0.0576 (9)0.0507 (8)0.0156 (8)0.0168 (7)0.0097 (7)
N10.0259 (8)0.0354 (8)0.0419 (9)0.0007 (7)0.0018 (7)0.0000 (7)
N20.0249 (8)0.0471 (9)0.0422 (9)0.0004 (7)0.0043 (7)0.0010 (7)
N30.0268 (9)0.0488 (9)0.0453 (9)−0.0028 (7)0.0023 (7)−0.0002 (8)
N40.0238 (9)0.0643 (11)0.0585 (11)0.0004 (8)−0.0006 (8)0.0004 (9)
Cl10.0848 (5)0.0815 (4)0.0491 (3)0.0023 (4)0.0225 (3)0.0045 (3)
C10.0442 (13)0.0457 (11)0.0400 (10)−0.0037 (10)0.0040 (9)0.0005 (9)
C20.0423 (12)0.0345 (9)0.0413 (10)0.0001 (9)0.0003 (9)0.0005 (8)
C30.0533 (15)0.0526 (13)0.0467 (12)0.0052 (11)−0.0053 (11)−0.0010 (10)
C40.0749 (19)0.0589 (14)0.0401 (11)0.0025 (14)0.0010 (12)0.0006 (10)
C50.0646 (18)0.0688 (15)0.0433 (12)−0.0019 (13)0.0152 (12)−0.0017 (11)
C60.0441 (14)0.0787 (16)0.0497 (12)−0.0033 (12)0.0116 (11)0.0007 (12)
C70.0305 (11)0.0434 (10)0.0448 (11)0.0030 (9)−0.0038 (9)0.0021 (9)
C80.0282 (10)0.0399 (10)0.0448 (11)0.0005 (8)0.0034 (9)0.0026 (9)
C90.0302 (11)0.0569 (12)0.0418 (11)0.0031 (9)0.0044 (9)0.0037 (10)
C100.0353 (12)0.0492 (11)0.0450 (11)−0.0007 (9)0.0067 (9)0.0012 (10)
C110.0705 (19)0.0652 (15)0.0725 (17)0.0248 (14)0.0267 (15)0.0204 (14)
C120.076 (2)0.0674 (15)0.0692 (16)0.0195 (15)0.0218 (15)0.0269 (14)
C130.0502 (14)0.0613 (13)0.0400 (10)−0.0037 (11)0.0074 (10)0.0007 (10)
C140.0522 (14)0.0614 (14)0.0463 (12)0.0104 (12)0.0085 (11)−0.0039 (10)
C150.0456 (13)0.0551 (13)0.0436 (11)0.0105 (11)0.0018 (10)0.0046 (10)
C160.0335 (12)0.0849 (17)0.0452 (11)−0.0035 (12)0.0035 (10)−0.0045 (11)
C170.0363 (13)0.100 (2)0.0490 (13)−0.0063 (13)−0.0056 (10)−0.0039 (13)
C180.0267 (10)0.0506 (11)0.0480 (11)0.0006 (9)0.0016 (9)−0.0035 (10)

Geometric parameters (Å, °)

Ni1—O11.8178 (14)C4—C51.384 (4)
Ni1—N11.8264 (17)C4—H4B0.9300
Ni1—O21.8473 (14)C5—C61.373 (3)
Ni1—N31.9064 (18)C5—H5A0.9300
O1—C11.314 (3)C6—H6A0.9300
O2—C81.284 (2)C7—H7A0.9300
O3—C101.362 (2)C8—C91.495 (3)
O3—C91.413 (2)C9—H9A0.9700
N1—C71.294 (3)C9—H9B0.9700
N1—N21.405 (2)C10—C151.377 (3)
N2—C81.307 (3)C10—C111.380 (3)
N3—C181.310 (3)C11—C121.377 (3)
N3—C161.368 (3)C11—H11A0.9300
N4—C181.326 (3)C12—C131.365 (4)
N4—C171.369 (3)C12—H12A0.9300
N4—H4A0.8600C13—C141.367 (3)
Cl1—C131.741 (2)C14—C151.383 (3)
C1—C61.406 (3)C14—H14A0.9300
C1—C21.409 (3)C15—H15A0.9300
C2—C31.404 (3)C16—C171.347 (3)
C2—C71.427 (3)C16—H16A0.9300
C3—C41.367 (3)C17—H17A0.9300
C3—H3A0.9300C18—H18A0.9300
O1—Ni1—N195.41 (7)N1—C7—H7A118.3
O1—Ni1—O2178.45 (7)C2—C7—H7A118.3
N1—Ni1—O283.87 (7)O2—C8—N2123.63 (19)
O1—Ni1—N389.58 (7)O2—C8—C9117.97 (18)
N1—Ni1—N3174.52 (7)N2—C8—C9118.34 (18)
O2—Ni1—N391.20 (7)O3—C9—C8107.58 (16)
C1—O1—Ni1126.98 (15)O3—C9—H9A110.2
C8—O2—Ni1110.41 (13)C8—C9—H9A110.2
C10—O3—C9117.83 (16)O3—C9—H9B110.2
C7—N1—N2117.51 (17)C8—C9—H9B110.2
C7—N1—Ni1127.87 (14)H9A—C9—H9B108.5
N2—N1—Ni1114.59 (12)O3—C10—C15125.01 (19)
C8—N2—N1107.48 (16)O3—C10—C11115.7 (2)
C18—N3—C16105.56 (19)C15—C10—C11119.2 (2)
C18—N3—Ni1126.33 (15)C12—C11—C10120.6 (2)
C16—N3—Ni1128.04 (15)C12—C11—H11A119.7
C18—N4—C17106.83 (19)C10—C11—H11A119.7
C18—N4—H4A126.6C13—C12—C11119.7 (2)
C17—N4—H4A126.6C13—C12—H12A120.1
O1—C1—C6117.9 (2)C11—C12—H12A120.1
O1—C1—C2124.22 (19)C12—C13—C14120.5 (2)
C6—C1—C2117.9 (2)C12—C13—Cl1119.65 (18)
C3—C2—C1119.4 (2)C14—C13—Cl1119.89 (19)
C3—C2—C7118.8 (2)C13—C14—C15120.1 (2)
C1—C2—C7121.83 (19)C13—C14—H14A119.9
C4—C3—C2121.7 (2)C15—C14—H14A119.9
C4—C3—H3A119.2C10—C15—C14119.9 (2)
C2—C3—H3A119.2C10—C15—H15A120.1
C3—C4—C5118.8 (2)C14—C15—H15A120.1
C3—C4—H4B120.6C17—C16—N3109.2 (2)
C5—C4—H4B120.6C17—C16—H16A125.4
C6—C5—C4121.3 (2)N3—C16—H16A125.4
C6—C5—H5A119.4C16—C17—N4106.4 (2)
C4—C5—H5A119.4C16—C17—H17A126.8
C5—C6—C1121.0 (2)N4—C17—H17A126.8
C5—C6—H6A119.5N3—C18—N4112.0 (2)
C1—C6—H6A119.5N3—C18—H18A124.0
N1—C7—C2123.49 (19)N4—C18—H18A124.0
N1—Ni1—O1—C1−3.95 (18)C2—C1—C6—C5−1.8 (3)
O2—Ni1—O1—C1−66 (2)N2—N1—C7—C2179.46 (15)
N3—Ni1—O1—C1173.78 (18)Ni1—N1—C7—C2−2.8 (3)
O1—Ni1—O2—C862 (2)C3—C2—C7—N1179.26 (18)
N1—Ni1—O2—C8−0.19 (13)C1—C2—C7—N1−1.2 (3)
N3—Ni1—O2—C8−177.80 (13)Ni1—O2—C8—N2−0.8 (2)
O1—Ni1—N1—C74.62 (17)Ni1—O2—C8—C9176.13 (13)
O2—Ni1—N1—C7−176.76 (16)N1—N2—C8—O21.6 (3)
N3—Ni1—N1—C7−150.9 (7)N1—N2—C8—C9−175.36 (16)
O1—Ni1—N1—N2−177.59 (11)C10—O3—C9—C8−179.55 (18)
O2—Ni1—N1—N21.03 (11)O2—C8—C9—O348.3 (2)
N3—Ni1—N1—N226.9 (8)N2—C8—C9—O3−134.64 (19)
C7—N1—N2—C8176.44 (17)C9—O3—C10—C158.3 (3)
Ni1—N1—N2—C8−1.59 (17)C9—O3—C10—C11−172.1 (2)
O1—Ni1—N3—C180.86 (18)O3—C10—C11—C12−179.4 (3)
N1—Ni1—N3—C18156.5 (6)C15—C10—C11—C120.3 (4)
O2—Ni1—N3—C18−177.80 (17)C10—C11—C12—C13−0.6 (5)
O1—Ni1—N3—C16−175.8 (2)C11—C12—C13—C140.6 (4)
N1—Ni1—N3—C16−20.2 (8)C11—C12—C13—Cl1−178.4 (2)
O2—Ni1—N3—C165.55 (19)C12—C13—C14—C15−0.3 (4)
Ni1—O1—C1—C6−179.05 (14)Cl1—C13—C14—C15178.68 (19)
Ni1—O1—C1—C21.5 (3)O3—C10—C15—C14179.7 (2)
O1—C1—C2—C3−178.61 (18)C11—C10—C15—C140.0 (4)
C6—C1—C2—C32.0 (3)C13—C14—C15—C100.0 (4)
O1—C1—C2—C71.8 (3)C18—N3—C16—C170.6 (3)
C6—C1—C2—C7−177.61 (18)Ni1—N3—C16—C17177.80 (16)
C1—C2—C3—C4−0.7 (3)N3—C16—C17—N4−0.4 (3)
C7—C2—C3—C4178.91 (19)C18—N4—C17—C160.1 (3)
C2—C3—C4—C5−0.9 (3)C16—N3—C18—N4−0.6 (2)
C3—C4—C5—C61.1 (4)Ni1—N3—C18—N4−177.83 (13)
C4—C5—C6—C10.3 (4)C17—N4—C18—N30.3 (2)
O1—C1—C6—C5178.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···N2i0.862.062.916 (3)172

Symmetry codes: (i) x−1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2105).

References

  • Chen, X.-H. & Liu, S.-X. (2006). Acta Cryst. E62, m2869–m2871.
  • Liu, S.-X. & Gao, S. (1998). Polyhedron, 17, 81–84.
  • Ma, Y.-X., Ma, Z.-Q., Zhao, G., Ma, Y. & Yang, M. (1989). Polyhedron, 8, 2105–2108.
  • McArdle, P. (1995). J. Appl. Cryst.28, 65.
  • Molecular Structure Corporation (1999). TEXRAY and TEXSAN MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, M.-M., Li, W.-P. & Liu, S.-X. (2005). Acta Cryst. E61, m1818–m1820.
  • Sur, H., Roychowdhuri, S. & Seth, S. (1993). Acta Cryst. C49, 870–873.

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