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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040640/hg2281sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040640/hg2281Isup2.hkl
Contains datablock I

CCDC reference: 1140966

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.118
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
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 26.49 From the CIF: _reflns_number_total 3235 Count of symmetry unique reflns 1908 Completeness (_total/calc) 169.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1327 Fraction of Friedel pairs measured 0.695 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.79
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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).

Structure description 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.

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 m3
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 mm1
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 = 66
10667 measured reflectionsk = 2020
3235 independent reflectionsl = 2121
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 = 0.29 e Å3
226 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure 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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.118Δρmax = 0.29 e Å3
S = 0.97Δρmin = 0.33 e Å3
3235 reflectionsAbsolute structure: Flack (1983)
226 parametersAbsolute structure 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)
H20.85070.01110.07490.069*
C31.1570 (12)0.0140 (3)0.0123 (3)0.0603 (13)
H31.13550.06620.00600.072*
C41.3618 (12)0.0294 (3)0.0097 (3)0.0619 (14)
H41.47740.00610.04180.074*
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)
H180.00100.16940.40550.075*
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)

Experimental details

Crystal data
Chemical formula[Zn(C20H14N2O2)]
Mr379.72
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)5.5103 (4), 16.5871 (13), 17.3146 (13)
V3)1582.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.57
Crystal size (mm)0.16 × 0.04 × 0.02
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10667, 3235, 1906
Rint0.046
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.118, 0.97
No. of reflections3235
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.33
Absolute structureFlack (1983)
Absolute structure parameter0.05 (2)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

 

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