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Acta Cryst. (2007). E63, m2396    [ doi:10.1107/S1600536807040640 ]

{2,2'-[o-Phenylenebis(nitrilomethylidyne)]diphenolato}zinc(II)

Y.-Q. Liu, X.-R. Zeng, Q.-Y. Luo and Y.-P. Xu

Abstract top

The title complex, [Zn(C20H14N2O2)], is a mononuclear zinc(II) compound. The zinc(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from one 2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolate Schiff base ligand. No strong hydrogen bonds were found in the crystal.

Comment top

In the title complex, each zinc(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from the Schiff base 1,2-bis{[(2-hydroxy-phenyl)-methyl]-imino}benzene (Fig. 1). The Zn—N and Zn—O bond lengths are Zn1—N1 1.859 (4) Å, Zn1—N2 1.852 (4) Å, Zn1—O1 1.839 (3) Å and Zn1—O2 1.831 (4) Å. Atoms O1, O2, N1 and N2 are approximately coplanar with the central Zn1 ion, the maximum deviation from the least-squares plane through all five atoms being 0.0140 Å for atom O1. No strong hydrogen bonds are found to exist in the crystal.

Experimental top

A mixture of 1,2-bis{[(2-hydroxy-phenyl)-methyl]-imino}benzene (0.341 g,0.001 mol) and ZnSO4 (0.161 g, 0.001 mol) was added to methanol. The mixture was heated for 5 h under reflux with stirring. The resulting solution was then filtered off. Single crystals suitable for X-ray diffraction analysis formed after a week by slow evaporation of the solvent.

Refinement top

All H atoms were located at calculated positions and refined as riding on their parent C atoms with the C—H bond length fixed to 0.93 Å with Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing diagram of (I), viewed along the a axis.
{2,2'-[o-Phenylenebis(nitrilomethylidyne)]diphenolato}zinc(II) top
Crystal data top
[Zn(C20H14N2O2)]F(000) = 776.0
Mr = 379.72Dx = 1.594 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2762 reflections
a = 5.5103 (4) Åθ = 2.5–22.3°
b = 16.5871 (13) ŵ = 1.57 mm−1
c = 17.3146 (13) ÅT = 293 K
V = 1582.6 (2) Å3Block, colourless
Z = 40.16 × 0.04 × 0.02 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 26.5°, θmin = 2.4°
φ and ω scansh = −6→6
10667 measured reflectionsk = −20→20
3235 independent reflectionsl = −21→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0632P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3235 reflectionsΔρmax = 0.28 e Å−3
226 parametersΔρmin = −0.33 e Å−3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (2)
Crystal data top
[Zn(C20H14N2O2)]V = 1582.6 (2) Å3
Mr = 379.72Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.5103 (4) ŵ = 1.57 mm−1
b = 16.5871 (13) ÅT = 293 K
c = 17.3146 (13) Å0.16 × 0.04 × 0.02 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1906 reflections with I > 2σ(I)
10667 measured reflectionsRint = 0.046
3235 independent reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.118Δρmax = 0.28 e Å−3
S = 0.97Δρmin = −0.33 e Å−3
3235 reflectionsAbsolute structure: Flack (1983)
226 parametersFlack parameter: 0.05 (2)
0 restraints
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
C11.0111 (11)0.0983 (3)0.0897 (3)0.0547 (13)
C20.9856 (10)0.0192 (3)0.0609 (3)0.0574 (14)
H20.8507−0.01110.07490.069*
C31.1570 (12)−0.0140 (3)0.0123 (3)0.0603 (13)
H31.1355−0.0662−0.00600.072*
C41.3618 (12)0.0294 (3)−0.0097 (3)0.0619 (14)
H41.47740.0061−0.04180.074*
C51.3912 (11)0.1057 (3)0.0160 (3)0.0587 (15)
H51.52640.13490.00030.070*
C61.2217 (10)0.1421 (3)0.0663 (3)0.0537 (14)
C71.2639 (9)0.2214 (3)0.0924 (3)0.0518 (12)
H71.40210.24720.07390.062*
C81.1889 (11)0.3417 (3)0.1633 (3)0.0516 (13)
C91.3812 (11)0.3882 (3)0.1364 (3)0.0565 (14)
H91.48560.36800.09890.068*
C101.4155 (11)0.4645 (3)0.1659 (3)0.0599 (15)
H101.54440.49560.14820.072*
C111.2633 (11)0.4950 (3)0.2206 (3)0.0602 (16)
H111.29200.54640.23990.072*
C121.0689 (11)0.4519 (3)0.2478 (3)0.0570 (15)
H120.96260.47420.28370.068*
C131.0345 (10)0.3726 (3)0.2200 (3)0.0524 (13)
C140.7065 (10)0.3357 (3)0.3027 (3)0.0531 (13)
H140.73280.38410.32850.064*
C150.5211 (10)0.2870 (3)0.3292 (3)0.0552 (13)
C160.3782 (11)0.3131 (3)0.3946 (3)0.0609 (15)
H160.41750.36150.41870.073*
C170.1874 (10)0.2691 (3)0.4223 (3)0.0639 (14)
H170.09910.28690.46470.077*
C180.1295 (12)0.1991 (3)0.3868 (3)0.0626 (15)
H18−0.00100.16940.40550.075*
C190.2578 (10)0.1699 (3)0.3234 (3)0.0594 (15)
H190.21090.12190.30000.071*
C200.4579 (10)0.2129 (3)0.2946 (3)0.0547 (13)
Zn10.84969 (12)0.22299 (3)0.18870 (3)0.0573 (2)
N11.1265 (8)0.2622 (2)0.1402 (2)0.0489 (10)
N20.8498 (9)0.3188 (2)0.2436 (2)0.0498 (10)
O10.8500 (7)0.12647 (18)0.13644 (18)0.0567 (9)
O20.5762 (7)0.18339 (18)0.2353 (2)0.0543 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.062 (4)0.052 (3)0.050 (3)0.000 (3)0.001 (3)−0.003 (2)
C20.067 (4)0.053 (3)0.053 (3)0.000 (3)0.002 (3)−0.002 (3)
C30.070 (4)0.056 (3)0.055 (3)0.004 (3)0.000 (3)−0.006 (2)
C40.068 (4)0.061 (3)0.057 (3)0.006 (3)0.002 (3)−0.006 (2)
C50.064 (4)0.059 (3)0.053 (3)0.004 (3)0.002 (3)−0.004 (3)
C60.061 (4)0.052 (3)0.049 (3)0.001 (3)0.001 (3)−0.002 (2)
C70.061 (3)0.049 (3)0.046 (3)0.000 (3)−0.001 (2)0.002 (3)
C80.064 (4)0.046 (3)0.044 (3)0.001 (3)−0.005 (3)0.001 (2)
C90.069 (4)0.051 (3)0.049 (3)−0.003 (3)−0.003 (3)0.000 (2)
C100.071 (4)0.053 (3)0.055 (3)−0.006 (3)−0.001 (3)−0.001 (2)
C110.073 (4)0.051 (3)0.057 (3)−0.005 (3)−0.002 (3)−0.002 (3)
C120.070 (5)0.049 (3)0.052 (3)0.000 (3)−0.002 (3)0.000 (2)
C130.064 (4)0.046 (3)0.047 (3)0.003 (3)−0.004 (3)0.003 (2)
C140.061 (4)0.050 (3)0.048 (3)0.009 (2)−0.003 (3)0.004 (2)
C150.060 (4)0.055 (3)0.052 (3)0.011 (3)0.001 (3)0.004 (2)
C160.065 (4)0.064 (3)0.055 (3)0.011 (3)0.003 (3)0.002 (2)
C170.064 (4)0.069 (4)0.058 (3)0.011 (4)0.005 (3)0.008 (3)
C180.061 (4)0.065 (4)0.062 (3)0.010 (3)0.005 (3)0.013 (3)
C190.059 (4)0.057 (3)0.062 (4)0.012 (3)0.002 (3)0.010 (3)
C200.057 (4)0.051 (3)0.057 (3)0.012 (3)0.002 (3)0.007 (3)
Zn10.0659 (4)0.0518 (3)0.0543 (3)0.0037 (3)0.0003 (3)0.0012 (3)
N10.061 (3)0.044 (2)0.041 (2)0.000 (2)−0.005 (2)0.0025 (18)
N20.060 (3)0.044 (2)0.045 (2)0.006 (2)−0.005 (3)0.0060 (18)
O10.060 (2)0.0532 (19)0.057 (2)−0.004 (2)0.004 (2)−0.0051 (16)
O20.057 (3)0.0471 (18)0.058 (2)0.0070 (16)0.0021 (19)0.0035 (16)
Geometric parameters (Å, º) top
C1—O11.289 (6)C11—H110.9300
C1—C21.411 (7)C12—C131.415 (6)
C1—C61.427 (7)C12—H120.9300
C2—C31.379 (7)C13—N21.414 (7)
C2—H20.9300C14—N21.322 (6)
C3—C41.392 (7)C14—C151.381 (7)
C3—H30.9300C14—H140.9300
C4—C51.351 (6)C15—C201.410 (7)
C4—H40.9300C15—C161.446 (7)
C5—C61.412 (7)C16—C171.367 (8)
C5—H50.9300C16—H160.9300
C6—C71.411 (7)C17—C181.350 (7)
C7—N11.309 (6)C17—H170.9300
C7—H70.9300C18—C191.394 (7)
C8—C91.391 (7)C18—H180.9300
C8—C131.396 (7)C19—C201.404 (7)
C8—N11.420 (6)C19—H190.9300
C9—C101.377 (6)C20—O21.311 (6)
C9—H90.9300Zn1—O21.831 (4)
C10—C111.363 (7)Zn1—O11.839 (3)
C10—H100.9300Zn1—N21.852 (4)
C11—C121.372 (7)Zn1—N11.858 (4)
O1—C1—C2119.4 (5)C8—C13—C12120.0 (5)
O1—C1—C6123.7 (4)N2—C13—C12125.7 (5)
C2—C1—C6116.9 (5)N2—C14—C15125.1 (5)
C3—C2—C1121.3 (5)N2—C14—H14117.4
C3—C2—H2119.4C15—C14—H14117.4
C1—C2—H2119.4C14—C15—C20123.5 (5)
C2—C3—C4121.1 (5)C14—C15—C16119.2 (5)
C2—C3—H3119.5C20—C15—C16117.3 (5)
C4—C3—H3119.5C17—C16—C15122.2 (5)
C5—C4—C3119.4 (5)C17—C16—H16118.9
C5—C4—H4120.3C15—C16—H16118.9
C3—C4—H4120.3C18—C17—C16118.8 (5)
C4—C5—C6121.6 (5)C18—C17—H17120.6
C4—C5—H5119.2C16—C17—H17120.6
C6—C5—H5119.2C17—C18—C19122.5 (6)
C7—C6—C5119.2 (5)C17—C18—H18118.8
C7—C6—C1121.2 (5)C19—C18—H18118.8
C5—C6—C1119.7 (5)C18—C19—C20120.1 (5)
N1—C7—C6126.0 (5)C18—C19—H19120.0
N1—C7—H7117.0C20—C19—H19120.0
C6—C7—H7117.0O2—C20—C19118.6 (5)
C9—C8—C13119.7 (5)O2—C20—C15122.4 (5)
C9—C8—N1127.3 (5)C19—C20—C15119.0 (5)
C13—C8—N1113.0 (5)O2—Zn1—O184.56 (15)
C10—C9—C8119.3 (5)O2—Zn1—N294.70 (18)
C10—C9—H9120.3O1—Zn1—N2178.58 (15)
C8—C9—H9120.3O2—Zn1—N1179.15 (16)
C11—C10—C9121.0 (5)O1—Zn1—N194.66 (16)
C11—C10—H10119.5N2—Zn1—N186.09 (19)
C9—C10—H10119.5C7—N1—C8121.1 (5)
C10—C11—C12121.7 (5)C7—N1—Zn1125.4 (3)
C10—C11—H11119.1C8—N1—Zn1113.3 (3)
C12—C11—H11119.1C14—N2—C13121.4 (4)
C11—C12—C13118.2 (5)C14—N2—Zn1125.3 (4)
C11—C12—H12120.9C13—N2—Zn1113.1 (3)
C13—C12—H12120.9C1—O1—Zn1128.7 (3)
C8—C13—N2114.3 (4)C20—O2—Zn1128.3 (3)
Acknowledgements top

The authors are grateful for support from the Natural Science Foundation of Jiangxi Province (grants 0520036 and 0620029) for this work.

references
References top

Bruker (1997). SMART (Version 5.044) and SAINT (Version 5.01). Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Siemens (1996). SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.