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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1062.
Published online 2009 August 12. doi:  10.1107/S1600536809031109
PMCID: PMC2970013

Bis(2-butyl­imino­methyl-5-methoxy­phenolato-κ2 N,O 1)zinc(II)

Abstract

In the centrosymmetric title compound, [Zn(C12H16NO2)2], the ZnII centre is coordinated by two O,N-bidentate Schiff base ligands, resulting in a slightly distorted trans-ZnN2O2 square-planar geometry for the metal ion. Two short intra­molecular C—H(...)O contacts occur in the mol­ecule.

Related literature

For related structures, see: Zhu et al. (2003 [triangle]); You et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1062-scheme1.jpg

Experimental

Crystal data

  • [Zn(C12H16NO2)2]
  • M r = 477.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1062-efi1.jpg
  • a = 13.250 (4) Å
  • b = 4.8845 (15) Å
  • c = 17.858 (5) Å
  • β = 93.555 (5)°
  • V = 1153.6 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.10 mm−1
  • T = 200 K
  • 0.30 × 0.30 × 0.20 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.734, T max = 0.811
  • 13300 measured reflections
  • 2856 independent reflections
  • 2438 reflections with I > 2σ(I)
  • R int = 0.155

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.164
  • S = 1.10
  • 2856 reflections
  • 144 parameters
  • H-atom parameters constrained
  • Δρmax = 1.13 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031109/hb5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031109/hb5031Isup2.hkl

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

supplementary crystallographic information

Comment

As part of our ongoing studies of the structures of zinc(II) complexes (Zhu et al., 2003; You et al., 2003), we now report the crystal structure of the title compound, (I).

Compound (I) consists of a ZnII atom and two bidentate salicylal schiff base ligands (Fig. 1). The central ZnII atom exhibits 4-coordination by two N atoms from imine moieties and two O-anions from salicylal groups, forming a slightly distorted square planar geometry (Table 1). Ring Zn1—N1—C7—C1—C2—O1 and Ring Zn1—N1A—C7A—C1A—C2A—O1A, togethor with the two benzene rings, stand in a plane with mean deviation of 0.0489 °. Two short intramolecular C—H···O contacts occur in the molecule (Table 2).

Experimental

0.5 mmol of zinc oxide, 1 mmol of 4-methoxysalicylaldehyde and 1 mmol of butylamine were dissolved in 10 ml methanol. After 3 ml ammonia was added, the result solution was then heated to 423 K for 10 h in a sealed vessel. The reactor was cooled to room temperature at a rate of 10 K h-1. The mixture was filtered and held at room temperature for 8 d. Colourless blocks of (I) were isolated in 47% yield.

Refinement

All H atoms were placed in geometrically idealized positions (C—H = 0.95—0.99Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and dashed lines indicate hydrogen bonds. Atoms with a label A suffix are generated by the symmetry operator (1–x, 1–y, –z).

Crystal data

[Zn(C12H16NO2)2]F(000) = 504
Mr = 477.89Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2317 reflections
a = 13.250 (4) Åθ = 2.7–26.5°
b = 4.8845 (15) ŵ = 1.10 mm1
c = 17.858 (5) ÅT = 200 K
β = 93.555 (5)°Block, colorless
V = 1153.6 (6) Å30.30 × 0.30 × 0.20 mm
Z = 2

Data collection

Bruker APEX CCD diffractometer2856 independent reflections
Radiation source: fine-focus sealed tube2438 reflections with I > 2σ(I)
graphiteRint = 0.155
[var phi] and ω scansθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −17→17
Tmin = 0.734, Tmax = 0.811k = −6→6
13300 measured reflectionsl = −23→23

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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0665P)2 + 0.1817P] where P = (Fo2 + 2Fc2)/3
2856 reflections(Δ/σ)max < 0.001
144 parametersΔρmax = 1.13 e Å3
0 restraintsΔρmin = −0.67 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
C10.40796 (16)0.2347 (5)0.15609 (13)0.0375 (5)
C20.3582 (2)0.0191 (5)0.11694 (18)0.0403 (6)
C30.26490 (19)−0.0732 (6)0.14142 (16)0.0437 (6)
H30.2290−0.21360.11430.052*
C40.2254 (2)0.0377 (5)0.20399 (17)0.0425 (6)
C50.27511 (19)0.2446 (6)0.24413 (15)0.0488 (6)
H50.24750.31960.28750.059*
C60.36504 (18)0.3396 (6)0.22021 (13)0.0470 (6)
H60.39950.48110.24790.056*
C70.49911 (17)0.3519 (5)0.13234 (13)0.0392 (5)
H40.52810.49360.16310.047*
C80.63958 (19)0.4507 (5)0.06201 (16)0.0386 (5)
H8A0.63920.61920.09280.046*
H8B0.63930.50600.00870.046*
C90.73453 (16)0.2898 (5)0.08264 (15)0.0458 (6)
H9A0.73080.11050.05680.055*
H9B0.73910.25510.13740.055*
C100.8289 (2)0.4405 (6)0.0612 (2)0.0523 (7)
H10A0.82120.49140.00750.063*
H10B0.83620.61140.09090.063*
C110.92355 (19)0.2690 (8)0.0748 (2)0.0713 (10)
H11A0.93030.21310.12760.107*
H11B0.98280.37690.06280.107*
H11C0.91880.10590.04280.107*
C120.0780 (2)−0.2452 (6)0.18909 (18)0.0582 (8)
H12A0.0683−0.18950.13640.087*
H12B0.0119−0.26840.21010.087*
H12C0.1151−0.41870.19240.087*
N10.54697 (13)0.2884 (4)0.07401 (11)0.0366 (4)
O10.39291 (14)−0.0997 (5)0.05842 (11)0.0542 (5)
O20.13414 (17)−0.0399 (4)0.23031 (14)0.0539 (6)
Zn10.50000.00000.00000.0382 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0311 (11)0.0452 (13)0.0370 (11)0.0012 (10)0.0067 (9)0.0032 (9)
C20.0334 (14)0.0431 (15)0.0463 (16)0.0002 (9)0.0159 (11)0.0018 (9)
C30.0340 (12)0.0495 (13)0.0491 (15)−0.0069 (12)0.0153 (10)−0.0039 (12)
C40.0299 (13)0.0518 (15)0.0474 (16)0.0030 (10)0.0165 (11)0.0061 (11)
C50.0444 (13)0.0631 (17)0.0407 (13)0.0016 (12)0.0176 (10)−0.0046 (11)
C60.0440 (13)0.0555 (16)0.0424 (13)−0.0034 (12)0.0087 (10)−0.0067 (11)
C70.0335 (11)0.0431 (13)0.0409 (12)−0.0017 (10)0.0023 (9)−0.0012 (10)
C80.0331 (12)0.0362 (11)0.0472 (14)−0.0047 (10)0.0089 (10)0.0018 (10)
C90.0311 (11)0.0490 (14)0.0578 (15)−0.0058 (10)0.0073 (10)0.0079 (11)
C100.0332 (14)0.0565 (15)0.0681 (19)−0.0094 (13)0.0101 (12)0.0000 (15)
C110.0345 (14)0.086 (2)0.094 (2)−0.0009 (14)0.0141 (15)−0.0003 (19)
C120.0362 (13)0.0653 (19)0.075 (2)−0.0047 (13)0.0203 (13)0.0043 (15)
N10.0275 (9)0.0381 (10)0.0446 (10)−0.0016 (8)0.0068 (7)0.0031 (8)
O10.0458 (10)0.0578 (12)0.0625 (12)−0.0190 (10)0.0321 (9)−0.0203 (10)
O20.0384 (11)0.0685 (13)0.0578 (13)−0.0067 (9)0.0265 (9)−0.0022 (9)
Zn10.0311 (3)0.0394 (3)0.0457 (3)−0.00210 (13)0.0137 (2)−0.00106 (14)

Geometric parameters (Å, °)

C1—C21.405 (4)C9—C101.521 (4)
C1—C61.406 (3)C9—H9A0.9900
C1—C71.425 (3)C9—H9B0.9900
C2—O11.304 (3)C10—C111.515 (4)
C2—C31.411 (4)C10—H10A0.9900
C3—C41.374 (4)C10—H10B0.9900
C3—H30.9500C11—H11A0.9800
C4—O21.377 (3)C11—H11B0.9800
C4—C51.382 (4)C11—H11C0.9800
C5—C61.371 (3)C12—O21.426 (4)
C5—H50.9500C12—H12A0.9800
C6—H60.9500C12—H12B0.9800
C7—N11.291 (3)C12—H12C0.9800
C7—H40.9500N1—Zn12.004 (2)
C8—N11.488 (3)Zn1—O11.8769 (17)
C8—C91.510 (3)Zn1—N1i2.004 (2)
C8—H8A0.9900Zn1—O1i1.8769 (17)
C8—H8B0.9900Zn1—O1i1.8769 (17)
C2—C1—C6118.5 (2)C10—C9—H9B109.2
C2—C1—C7122.2 (2)H9A—C9—H9B107.9
C6—C1—C7119.3 (2)C11—C10—C9112.2 (3)
O1—C2—C1123.7 (3)C11—C10—H10A109.2
O1—C2—C3117.7 (2)C9—C10—H10A109.2
C1—C2—C3118.6 (3)C11—C10—H10B109.2
C4—C3—C2120.8 (3)C9—C10—H10B109.2
C4—C3—H3119.6H10A—C10—H10B107.9
C2—C3—H3119.6C10—C11—H11A109.5
C3—C4—O2123.8 (3)C10—C11—H11B109.5
C3—C4—C5121.1 (3)H11A—C11—H11B109.5
O2—C4—C5115.1 (3)C10—C11—H11C109.5
C6—C5—C4118.8 (2)H11A—C11—H11C109.5
C6—C5—H5120.6H11B—C11—H11C109.5
C4—C5—H5120.6O2—C12—H12A109.5
C5—C6—C1122.2 (2)O2—C12—H12B109.5
C5—C6—H6118.9H12A—C12—H12B109.5
C1—C6—H6118.9O2—C12—H12C109.5
N1—C7—C1127.7 (2)H12A—C12—H12C109.5
N1—C7—H4116.1H12B—C12—H12C109.5
C1—C7—H4116.1C7—N1—C8116.0 (2)
N1—C8—C9111.7 (2)C7—N1—Zn1123.59 (15)
N1—C8—H8A109.3C8—N1—Zn1120.33 (16)
C9—C8—H8A109.3C2—O1—Zn1130.26 (18)
N1—C8—H8B109.3C4—O2—C12117.3 (2)
C9—C8—H8B109.3O1i—Zn1—O1180.0
H8A—C8—H8B107.9O1i—Zn1—N1i91.74 (8)
C8—C9—C10111.9 (2)O1—Zn1—N1i88.26 (8)
C8—C9—H9A109.2O1i—Zn1—N188.26 (8)
C10—C9—H9A109.2O1—Zn1—N191.74 (8)
C8—C9—H9B109.2N1i—Zn1—N1180.0
C6—C1—C2—O1−177.6 (3)C9—C8—N1—C7104.5 (3)
C7—C1—C2—O13.3 (4)C9—C8—N1—Zn1−77.6 (2)
C6—C1—C2—C33.2 (4)C1—C2—O1—Zn1−10.8 (4)
C7—C1—C2—C3−175.9 (2)C3—C2—O1—Zn1168.5 (2)
O1—C2—C3—C4178.1 (3)C3—C4—O2—C12−0.7 (4)
C1—C2—C3—C4−2.6 (4)C5—C4—O2—C12177.6 (3)
C2—C3—C4—O2179.0 (3)C2—O1—Zn1—O1i−103.5 (2)
C2—C3—C4—C50.8 (4)C2—O1—Zn1—O1i−103.5 (2)
C3—C4—C5—C60.3 (4)C2—O1—Zn1—N1i−169.8 (3)
O2—C4—C5—C6−178.0 (2)C2—O1—Zn1—N110.2 (3)
C4—C5—C6—C10.3 (4)C7—N1—Zn1—O1i175.0 (2)
C2—C1—C6—C5−2.1 (4)C8—N1—Zn1—O1i−2.69 (17)
C7—C1—C6—C5177.0 (2)C7—N1—Zn1—O1i175.0 (2)
C2—C1—C7—N11.5 (4)C8—N1—Zn1—O1i−2.69 (17)
C6—C1—C7—N1−177.5 (2)C7—N1—Zn1—O1−5.0 (2)
N1—C8—C9—C10172.7 (2)C8—N1—Zn1—O1177.31 (17)
C8—C9—C10—C11−174.5 (3)C7—N1—Zn1—N1i104.5 (4)
C1—C7—N1—C8178.5 (2)C8—N1—Zn1—N1i−73.1 (2)
C1—C7—N1—Zn10.8 (3)

Symmetry codes: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8B···O1i0.992.342.763 (3)105
C9—H9A···O1i0.992.553.087 (3)114

Symmetry codes: (i) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5031).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • You, Z.-L., Lin, Y.-S., Liu, W.-S., Tan, M.-Y. & Zhu, H.-L. (2003). Acta Cryst. E59, m1025–m1027.
  • Zhu, H.-L., Meng, F.-J., Wang, Z.-D. & Yang, F. (2003). Z. Kristallogr. New Cryst. Struct. 218, 321–322.

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