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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m907–m908.
Published online 2009 July 11. doi:  10.1107/S160053680902621X
PMCID: PMC2977203

trans-Bis(2-benzoyl­benzoato-κO 1)bis­(ethanol-κO)bis­(1H-imidazole-κN 3)nickel(II)

Abstract

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C14H9O3)2(C3H4N2)2(CH3CH2OH)2], the central NiII ion lies on an inversion centre and is octa­hedrally coordinated. The equatorial plane is formed by two O atoms from two symmetry-related 2-benzoyl­benzoate ligands and two N atoms from two symmetry-related imidazole ligands, whereas the axial positions are occupied by two O atoms from two ethanol ligands. Intramolecular O---H...O hydrogen bonds stabilize this arrangement. The mol­ecules are linked into chains running along the b axis by N—H(...)O hydrogen bonds.

Related literature

For crystal structures with 2-benzoyl­benzoate ligands, see: Diop et al. (2006 [triangle], 2007 [triangle]); Foreman et al. (2001 [triangle]); Jones et al. (1996 [triangle]); Martin & Valente (1998 [triangle]); Prout et al. (1996 [triangle]); Song et al. (2005 [triangle]); Yıldırım et al. (2009 [triangle]). For the crystal structure of 2-benzoyl­benzoic acid, see: Lalancette et al. (1990 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m907-scheme1.jpg

Experimental

Crystal data

  • [Ni(C14H9O3)2(C3H4N2)2(C2H6O)2]
  • M r = 737.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m907-efi2.jpg
  • a = 12.8914 (8) Å
  • b = 8.3908 (5) Å
  • c = 16.4590 (11) Å
  • β = 90.832 (5)°
  • V = 1780.17 (19) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.60 mm−1
  • T = 296 K
  • 0.43 × 0.25 × 0.14 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.809, T max = 0.921
  • 15078 measured reflections
  • 3889 independent reflections
  • 2704 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.150
  • S = 1.11
  • 3889 reflections
  • 235 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902621X/ci2845sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902621X/ci2845Isup2.hkl

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

Acknowledgments

The authors thank Professor Dr Orhan Büyükgüngör for his help with the data collection and acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

We have previously reported the crystal structure of [Cu(2-byba)2(bim)2] (bim = benzimidazole, 2-byba = 2-benzoylbenzoate) (Yıldırım et al., 2009). As an extension of this study, we now report the structure of a new nickel(II) complex with the 2-byba ligand.

In the title complex, the NiII ion lies on a centre of symmetry and has a octahedral coordination geometry formed by 2-byba, imidazole (im), ethanol ligands and their symmetry-related equivalents. All ligands are monodentate with the 2-byba coordinates through a carboxylate O atom, im coordinates through the aromatic N atom and ethanol coordinates through the O atom. Intramolecular O—H···O hydrogen bonds are observed.

The molecular packing is mainly stabilized by strong intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2). Atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H2, to atom O3 in the molecule at (x, y - 1, z) forming C(8) chains with R22(16) rings (Bernstein et al., 1995). These chains run parallel to the [010] (Fig. 2).

Experimental

A solution of 2-benzoylbenzoate (0.45 g, 2 mmol) in ethanol (10 ml) was added to a solution of nickel acetate tetrahydrate (0.25 g, 1 mmol) in ethanol (10 ml) and the solution was stirred for 15 min at 333 K. To this solution, a solution of imidazole (0.23 g, 2 mmol) in ethanol (10 ml) was added and the resultant solution was left to evaporate slowly at room temperature. After one week, single crystals of the title complex were isolated.

Refinement

Alcohol H atom was located in a difference Fourier map and its positional parameters were refined. The remaining H atoms were placed in calculated positions and constrained to ride on their parents atoms, with C-H = 0.93-0.97 Å, N-H = 0.86 Å and Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability. Symmetry code: (i) 1 -x, 1 -y, 1 -z.
Fig. 2.
Part of the crystal structure of the title compound showing the chain of R22(16) rings along [010] generated by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.Symmetry ...

Crystal data

[Ni(C14H9O3)2(C3H4N2)2(C2H6O)2]F(000) = 772
Mr = 737.43Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15078 reflections
a = 12.8914 (8) Åθ = 1.6–27.6°
b = 8.3908 (5) ŵ = 0.60 mm1
c = 16.4590 (11) ÅT = 296 K
β = 90.832 (5)°Prism, green
V = 1780.17 (19) Å30.43 × 0.25 × 0.14 mm
Z = 2

Data collection

Stoe IPDSII diffractometer3889 independent reflections
Radiation source: fine-focus sealed tube2704 reflections with I > 2σ(I)
graphiteRint = 0.046
Detector resolution: 6.67 pixels mm-1θmax = 27.0°, θmin = 1.6°
ω scansh = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −10→10
Tmin = 0.809, Tmax = 0.921l = −20→20
15078 measured reflections

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0435P)2 + 2.752P] where P = (Fo2 + 2Fc2)/3
3889 reflections(Δ/σ)max = 0.004
235 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.26 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
C10.3658 (4)0.5474 (6)0.3388 (3)0.0630 (13)
H1A0.30570.48820.35680.076*
H1B0.41380.47230.31510.076*
C20.3320 (5)0.6663 (8)0.2749 (3)0.0848 (18)
H2A0.29930.61120.23030.127*
H2B0.39150.72310.25580.127*
H2C0.28380.74020.29790.127*
C30.5546 (4)0.1822 (5)0.4290 (3)0.0525 (11)
H30.62480.20740.43300.063*
C40.4127 (4)0.0507 (6)0.4036 (3)0.0623 (13)
H40.3661−0.02840.38790.075*
C50.3897 (4)0.1970 (6)0.4334 (3)0.0563 (11)
H50.32300.23560.44160.068*
C60.6557 (3)0.6330 (5)0.3827 (2)0.0448 (9)
C70.7620 (3)0.6345 (5)0.3466 (2)0.0452 (9)
C80.7755 (4)0.7083 (5)0.2710 (3)0.0548 (11)
H80.71920.75600.24480.066*
C90.8715 (4)0.7106 (6)0.2352 (3)0.0660 (13)
H90.88000.76170.18560.079*
C100.9537 (4)0.6380 (7)0.2724 (3)0.0724 (15)
H101.01810.63910.24770.087*
C110.9426 (4)0.5622 (6)0.3471 (3)0.0658 (13)
H110.99910.51240.37200.079*
C120.8466 (3)0.5616 (5)0.3841 (2)0.0454 (9)
C130.8422 (3)0.4876 (6)0.4681 (2)0.0481 (9)
C140.8461 (3)0.3113 (5)0.4742 (3)0.0463 (10)
C150.8481 (4)0.2143 (6)0.4068 (3)0.0616 (12)
H150.84460.25870.35510.074*
C160.8554 (5)0.0506 (6)0.4159 (4)0.0829 (17)
H160.8574−0.01500.37040.100*
C170.8597 (4)−0.0149 (7)0.4934 (4)0.0815 (16)
H170.8650−0.12490.49930.098*
C180.8564 (5)0.0769 (7)0.5591 (4)0.0770 (16)
H180.85850.03060.61040.092*
C190.8498 (4)0.2423 (6)0.5516 (3)0.0613 (12)
H190.84790.30620.59780.074*
N10.4796 (3)0.2796 (4)0.44961 (19)0.0431 (8)
N20.5184 (3)0.0434 (4)0.4016 (2)0.0601 (10)
H20.5548−0.03620.38570.072*
Ni10.50000.50000.50000.0385 (2)
O10.4142 (2)0.6220 (4)0.40705 (17)0.0489 (7)
O20.6371 (2)0.5278 (3)0.43480 (16)0.0462 (7)
O30.5923 (2)0.7370 (4)0.35828 (19)0.0566 (8)
O40.8429 (3)0.5724 (4)0.52801 (18)0.0585 (8)
H10.465 (4)0.665 (7)0.395 (3)0.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.080 (3)0.056 (3)0.052 (3)−0.004 (2)−0.011 (2)−0.007 (2)
C20.106 (5)0.099 (5)0.049 (3)0.009 (4)−0.017 (3)0.005 (3)
C30.062 (3)0.041 (2)0.054 (2)−0.002 (2)0.007 (2)−0.003 (2)
C40.071 (3)0.046 (3)0.070 (3)−0.008 (2)−0.009 (2)−0.009 (2)
C50.058 (3)0.050 (3)0.061 (3)−0.001 (2)−0.003 (2)−0.007 (2)
C60.053 (2)0.036 (2)0.045 (2)0.0040 (19)0.0011 (18)−0.0035 (18)
C70.055 (2)0.040 (2)0.041 (2)−0.0023 (19)0.0071 (18)−0.0004 (17)
C80.067 (3)0.051 (3)0.047 (2)−0.001 (2)0.006 (2)0.004 (2)
C90.075 (3)0.070 (3)0.054 (3)−0.010 (3)0.017 (2)0.008 (2)
C100.067 (3)0.083 (4)0.068 (3)−0.010 (3)0.025 (3)0.001 (3)
C110.056 (3)0.069 (3)0.073 (3)0.005 (2)0.014 (2)0.004 (3)
C120.047 (2)0.042 (2)0.047 (2)−0.0058 (18)0.0040 (18)−0.0009 (18)
C130.044 (2)0.049 (2)0.051 (2)−0.001 (2)0.0021 (16)−0.002 (2)
C140.042 (2)0.041 (2)0.056 (2)−0.0002 (18)0.0046 (18)0.0022 (19)
C150.071 (3)0.052 (3)0.062 (3)−0.003 (2)0.007 (2)−0.006 (2)
C160.096 (4)0.045 (3)0.108 (5)0.001 (3)0.017 (4)−0.020 (3)
C170.081 (4)0.044 (3)0.120 (5)0.000 (3)0.016 (3)0.015 (3)
C180.090 (4)0.059 (3)0.082 (4)−0.001 (3)0.005 (3)0.022 (3)
C190.071 (3)0.051 (3)0.062 (3)−0.004 (2)0.002 (2)0.006 (2)
N10.0491 (19)0.0369 (18)0.0434 (17)−0.0001 (16)0.0029 (15)−0.0017 (14)
N20.078 (3)0.042 (2)0.061 (2)0.0093 (19)0.0084 (19)−0.0090 (17)
Ni10.0424 (4)0.0347 (4)0.0384 (3)0.0010 (4)0.0027 (3)−0.0022 (3)
O10.0534 (18)0.0486 (19)0.0446 (15)0.0003 (14)−0.0038 (13)−0.0035 (13)
O20.0521 (16)0.0393 (17)0.0474 (14)0.0011 (13)0.0080 (12)0.0042 (12)
O30.0580 (19)0.0476 (18)0.0644 (18)0.0100 (15)0.0056 (15)0.0074 (15)
O40.078 (2)0.0487 (18)0.0485 (17)0.0015 (16)−0.0019 (15)−0.0077 (14)

Geometric parameters (Å, °)

C1—O11.423 (5)C10—H100.93
C1—C21.509 (7)C11—C121.387 (6)
C1—H1A0.97C11—H110.93
C1—H1B0.97C12—C131.517 (6)
C2—H2A0.96C13—O41.216 (5)
C2—H2B0.96C13—C141.483 (6)
C2—H2C0.96C14—C151.377 (6)
C3—N11.315 (5)C14—C191.400 (6)
C3—N21.331 (5)C15—C161.384 (7)
C3—H30.93C15—H150.93
C4—C51.356 (6)C16—C171.389 (8)
C4—N21.365 (6)C16—H160.93
C4—H40.93C17—C181.329 (8)
C5—N11.373 (5)C17—H170.93
C5—H50.93C18—C191.396 (7)
C6—O21.257 (5)C18—H180.93
C6—O31.257 (5)C19—H190.93
C6—C71.502 (6)N1—Ni12.042 (3)
C7—C121.388 (6)N2—H20.8600
C7—C81.403 (6)Ni1—N1i2.042 (3)
C8—C91.378 (6)Ni1—O2i2.094 (3)
C8—H80.93Ni1—O22.094 (3)
C9—C101.361 (7)Ni1—O1i2.136 (3)
C9—H90.93Ni1—O12.136 (3)
C10—C111.394 (7)O1—H10.78 (5)
O1—C1—C2112.2 (4)C14—C13—C12117.9 (4)
O1—C1—H1A109.2C15—C14—C19119.2 (4)
C2—C1—H1A109.2C15—C14—C13122.4 (4)
O1—C1—H1B109.2C19—C14—C13118.4 (4)
C2—C1—H1B109.2C14—C15—C16120.1 (5)
H1A—C1—H1B107.9C14—C15—H15119.9
C1—C2—H2A109.5C16—C15—H15119.9
C1—C2—H2B109.5C15—C16—C17119.6 (6)
H2A—C2—H2B109.5C15—C16—H16120.2
C1—C2—H2C109.5C17—C16—H16120.2
H2A—C2—H2C109.5C18—C17—C16121.1 (6)
H2B—C2—H2C109.5C18—C17—H17119.5
N1—C3—N2112.0 (4)C16—C17—H17119.5
N1—C3—H3124.0C17—C18—C19120.5 (6)
N2—C3—H3124.0C17—C18—H18119.8
C5—C4—N2105.8 (4)C19—C18—H18119.8
C5—C4—H4127.1C18—C19—C14119.5 (5)
N2—C4—H4127.1C18—C19—H19120.2
C4—C5—N1109.8 (4)C14—C19—H19120.2
C4—C5—H5125.1C3—N1—C5105.0 (4)
N1—C5—H5125.1C3—N1—Ni1125.2 (3)
O2—C6—O3125.1 (4)C5—N1—Ni1129.8 (3)
O2—C6—C7117.4 (4)C3—N2—C4107.4 (4)
O3—C6—C7117.4 (4)C3—N2—H2126.3
C12—C7—C8118.9 (4)C4—N2—H2126.3
C12—C7—C6122.4 (4)N1i—Ni1—N1180.0
C8—C7—C6118.7 (4)N1i—Ni1—O2i89.87 (12)
C9—C8—C7120.6 (5)N1—Ni1—O2i90.13 (12)
C9—C8—H8119.7N1i—Ni1—O290.13 (12)
C7—C8—H8119.7N1—Ni1—O289.87 (12)
C10—C9—C8120.0 (5)O2i—Ni1—O2180.0
C10—C9—H9120.0N1i—Ni1—O1i94.64 (12)
C8—C9—H9120.0N1—Ni1—O1i85.36 (12)
C9—C10—C11120.7 (5)O2i—Ni1—O1i90.65 (11)
C9—C10—H10119.6O2—Ni1—O1i89.35 (11)
C11—C10—H10119.6N1i—Ni1—O185.36 (12)
C12—C11—C10119.6 (5)N1—Ni1—O194.64 (12)
C12—C11—H11120.2O2i—Ni1—O189.35 (11)
C10—C11—H11120.2O2—Ni1—O190.65 (11)
C11—C12—C7120.2 (4)O1i—Ni1—O1180.0
C11—C12—C13116.6 (4)C1—O1—Ni1124.9 (3)
C7—C12—C13123.1 (4)C1—O1—H1112 (4)
O4—C13—C14121.9 (4)Ni1—O1—H188 (4)
O4—C13—C12120.0 (4)C6—O2—Ni1126.8 (3)
N2—C4—C5—N10.0 (5)C17—C18—C19—C140.4 (8)
O2—C6—C7—C12−20.1 (6)C15—C14—C19—C180.6 (7)
O3—C6—C7—C12160.0 (4)C13—C14—C19—C18−178.3 (4)
O2—C6—C7—C8158.0 (4)N2—C3—N1—C5−0.6 (5)
O3—C6—C7—C8−21.9 (6)N2—C3—N1—Ni1176.6 (3)
C12—C7—C8—C9−1.1 (7)C4—C5—N1—C30.3 (5)
C6—C7—C8—C9−179.2 (4)C4—C5—N1—Ni1−176.7 (3)
C7—C8—C9—C101.4 (8)N1—C3—N2—C40.7 (5)
C8—C9—C10—C11−0.7 (8)C5—C4—N2—C3−0.4 (5)
C9—C10—C11—C12−0.4 (8)C3—N1—Ni1—O2i−147.8 (3)
C10—C11—C12—C70.7 (7)C5—N1—Ni1—O2i28.7 (4)
C10—C11—C12—C13−175.6 (5)C3—N1—Ni1—O232.2 (3)
C8—C7—C12—C110.0 (6)C5—N1—Ni1—O2−151.3 (4)
C6—C7—C12—C11178.1 (4)C3—N1—Ni1—O1i−57.2 (3)
C8—C7—C12—C13176.1 (4)C5—N1—Ni1—O1i119.3 (4)
C6—C7—C12—C13−5.9 (6)C3—N1—Ni1—O1122.8 (3)
C11—C12—C13—O4100.0 (5)C5—N1—Ni1—O1−60.7 (4)
C7—C12—C13—O4−76.2 (5)C2—C1—O1—Ni1−167.2 (3)
C11—C12—C13—C14−74.9 (5)N1i—Ni1—O1—C1−179.8 (4)
C7—C12—C13—C14108.9 (5)N1—Ni1—O1—C10.2 (4)
O4—C13—C14—C15−178.2 (4)O2i—Ni1—O1—C1−89.8 (3)
C12—C13—C14—C15−3.4 (6)O2—Ni1—O1—C190.2 (3)
O4—C13—C14—C190.6 (6)O3—C6—O2—Ni1−3.1 (6)
C12—C13—C14—C19175.4 (4)C7—C6—O2—Ni1177.0 (2)
C19—C14—C15—C16−1.0 (7)N1i—Ni1—O2—C6−61.3 (3)
C13—C14—C15—C16177.8 (5)N1—Ni1—O2—C6118.7 (3)
C14—C15—C16—C170.6 (9)O1i—Ni1—O2—C6−155.9 (3)
C15—C16—C17—C180.4 (9)O1—Ni1—O2—C624.1 (3)
C16—C17—C18—C19−0.8 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O30.78 (5)1.86 (5)2.627 (4)170 (6)
N2—H2···O3ii0.862.022.837 (5)159

Symmetry codes: (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2845).

References

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