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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1295.
Published online 2009 October 3. doi:  10.1107/S1600536809037015
PMCID: PMC2971112

Chlorido[2-meth­oxy-6-(2-pyridyl­methyl­imino­meth­yl)phenolato]zinc(II)

Abstract

In the title mol­ecule, [Zn(C14H13N2O2)Cl], the Zn(II) ion is coordinated by one O and two N atoms from the Schiff base ligand, and a chloride anion in a distorted square-planar geometry. In the crystal structure, π–π inter­actions link the approximately planar (mean deviation 0.0569 Å) mol­ecules into stacks parallel to the a axis.

Related literature

For properties of transition metal complexes with Schiff base ligands, see: Ghosh et al. (2006 [triangle]); Singh et al. (2007 [triangle]); Ward (2007 [triangle]). For details of the synthesis of the ligand, see Kannappan et al. (2005 [triangle]). For related structures, see: Li & Zhang (2004 [triangle]); Chen (2005 [triangle]); You (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1295-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H13N2O2)Cl]
  • M r = 342.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1295-efi1.jpg
  • a = 7.1013 (5) Å
  • b = 18.2673 (14) Å
  • c = 10.3241 (8) Å
  • β = 104.789 (1)°
  • V = 1294.89 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.10 mm−1
  • T = 293 K
  • 0.31 × 0.25 × 0.23 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.562, T max = 0.643
  • 6845 measured reflections
  • 2538 independent reflections
  • 2263 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.082
  • S = 1.06
  • 2538 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 1998 [triangle]); software used to prepare material for publication: XP.

Table 1
Selected interatomic distances (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037015/cv2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037015/cv2598Isup2.hkl

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

Acknowledgments

This work was supported by Jining University, China.

supplementary crystallographic information

Comment

Transition metal-Schiff based complexes have been intensively focused on owing to their excellent physical and chemical properties including magnetic, optics and catalysis (Ghosh et al., 2006; Singh et al., 2007; Ward et al., 2007). Additionally, their intriguing biological activites also attract a lot of attentions. Herein, we report the structure of a new zinc complex with asymmetric tridentate Schiff base ligand.

In the title compound, (I) (Fig. 1), the Zn(II) ion is four coordinated with a slightly distorted square planar coordination sphere formed by two N atoms and one O atom from the asymmetric tridentate Schiff base ligand, and the fourth position is occupied by one Cl anion. The mean deviation of the plane formed by ZnN2OCl unit is 0.0569 Å. The Zn—O, Zn—N and Zn—Cl bond lengths are all comparable to those found in other Zn Schiff base complexes (You, 2005; Chen, 2005; Li, et al., 2004). It is worthing noting that the asymmetric unit can be linked into one-dimensional supermolecular structure via the π···π interactions (Table 1).

Experimental

The Schiff base was synthesized according to the literature method (Kannappan et al., 2005). The synthesis of the title complex was carried out by reacting ZnCl2 and the schiff-base ligand (1:1, molar ratio) in methanol under the refelux condition. The cooled solution was filtrated and left for slow evaperation in air to obtain single-crystal suitable for X-ray diffraction.

Refinement

All H atoms were geometrically positioned (C—H = 0.93 - 0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All H-atoms were omitted for clarity.

Crystal data

[Zn(C14H13N2O2)Cl]F(000) = 696
Mr = 342.08Dx = 1.755 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.1013 (5) ÅCell parameters from 3850 reflections
b = 18.2673 (14) Åθ = 3.0–26.0°
c = 10.3241 (8) ŵ = 2.10 mm1
β = 104.789 (1)°T = 293 K
V = 1294.89 (17) Å3Block, colourless
Z = 40.31 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer2538 independent reflections
Radiation source: fine-focus sealed tube2263 reflections with I > 2σ(I)
graphiteRint = 0.017
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −8→8
Tmin = 0.562, Tmax = 0.643k = −18→22
6845 measured reflectionsl = −12→10

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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0487P)2 + 0.6563P] where P = (Fo2 + 2Fc2)/3
2538 reflections(Δ/σ)max = 0.006
182 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.31 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
Zn10.33329 (4)0.484815 (14)0.11005 (3)0.02880 (12)
Cl10.45273 (10)0.40303 (3)0.27143 (6)0.04062 (17)
O10.2046 (2)0.40698 (8)−0.00080 (16)0.0324 (4)
O20.0568 (3)0.28355 (9)−0.10946 (17)0.0389 (4)
N10.4516 (3)0.57415 (10)0.21313 (18)0.0272 (4)
N20.2579 (3)0.55672 (10)−0.03049 (19)0.0276 (4)
C10.0718 (3)0.47592 (12)−0.2000 (2)0.0282 (5)
C20.1050 (3)0.41075 (12)−0.1239 (2)0.0265 (5)
C30.0236 (3)0.34459 (12)−0.1884 (2)0.0295 (5)
C4−0.0793 (3)0.34472 (14)−0.3194 (2)0.0334 (5)
H4−0.12960.3011−0.36050.040*
C5−0.1094 (3)0.40998 (15)−0.3922 (2)0.0356 (5)
H5−0.18030.4094−0.48140.043*
C6−0.0367 (3)0.47439 (13)−0.3345 (2)0.0325 (5)
H6−0.05880.5175−0.38400.039*
C70.1495 (3)0.54479 (13)−0.1478 (2)0.0303 (5)
H70.11830.5850−0.20460.036*
C8−0.0093 (4)0.21497 (13)−0.1699 (3)0.0433 (6)
H8A−0.14600.2180−0.21280.065*
H8B0.01280.1776−0.10240.065*
H8C0.06080.2032−0.23530.065*
C90.4324 (3)0.63695 (12)0.1444 (2)0.0281 (5)
C100.5065 (3)0.70331 (13)0.2015 (3)0.0340 (5)
H100.49360.74560.14990.041*
C110.5983 (4)0.70499 (14)0.3345 (3)0.0388 (6)
H110.64960.74840.37600.047*
C120.6133 (4)0.64061 (15)0.4060 (3)0.0393 (6)
H120.67220.64060.49740.047*
C130.5419 (3)0.57673 (14)0.3432 (2)0.0338 (5)
H130.55690.53370.39290.041*
C140.3226 (4)0.63242 (12)0.0026 (2)0.0325 (5)
H14A0.21040.6646−0.01330.039*
H14B0.40450.6481−0.05430.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03695 (18)0.02365 (17)0.02486 (17)0.00029 (10)0.00615 (12)0.00196 (10)
Cl10.0635 (4)0.0280 (3)0.0268 (3)0.0019 (3)0.0049 (3)0.0074 (2)
O10.0444 (9)0.0229 (8)0.0246 (8)−0.0019 (7)−0.0010 (7)0.0024 (6)
O20.0494 (10)0.0228 (8)0.0374 (9)−0.0037 (7)−0.0017 (8)−0.0012 (7)
N10.0300 (9)0.0251 (9)0.0270 (9)0.0010 (7)0.0082 (8)0.0000 (8)
N20.0343 (10)0.0211 (9)0.0271 (9)0.0011 (8)0.0073 (8)0.0032 (7)
C10.0271 (11)0.0309 (12)0.0257 (11)0.0035 (9)0.0051 (9)0.0031 (9)
C20.0238 (10)0.0285 (11)0.0263 (11)0.0013 (9)0.0051 (8)−0.0008 (9)
C30.0291 (11)0.0269 (11)0.0322 (12)0.0013 (9)0.0076 (9)−0.0007 (9)
C40.0316 (12)0.0368 (13)0.0306 (12)−0.0017 (10)0.0057 (10)−0.0078 (10)
C50.0311 (12)0.0480 (15)0.0250 (12)0.0023 (11)0.0022 (9)−0.0006 (10)
C60.0336 (12)0.0365 (13)0.0256 (11)0.0040 (10)0.0043 (10)0.0052 (10)
C70.0356 (12)0.0272 (12)0.0273 (11)0.0044 (9)0.0069 (9)0.0067 (10)
C80.0450 (15)0.0260 (12)0.0523 (16)−0.0036 (10)0.0002 (12)−0.0053 (11)
C90.0294 (11)0.0247 (11)0.0322 (12)0.0003 (9)0.0119 (9)−0.0015 (9)
C100.0365 (12)0.0254 (11)0.0415 (13)−0.0019 (10)0.0128 (10)−0.0028 (10)
C110.0344 (12)0.0363 (13)0.0463 (14)−0.0088 (11)0.0116 (11)−0.0129 (12)
C120.0348 (12)0.0480 (15)0.0338 (13)−0.0062 (11)0.0062 (10)−0.0084 (11)
C130.0354 (12)0.0358 (12)0.0286 (12)−0.0022 (10)0.0052 (10)0.0017 (10)
C140.0490 (14)0.0183 (10)0.0304 (12)0.0009 (9)0.0106 (10)0.0022 (9)

Geometric parameters (Å, °)

Zn1—O11.9059 (16)C5—C61.360 (4)
Zn1—N21.9288 (18)C5—H50.9300
Zn1—N12.0112 (19)C6—H60.9300
Zn1—Cl12.2373 (6)C7—H70.9300
O1—C21.289 (3)C8—H8A0.9600
O2—C31.366 (3)C8—H8B0.9600
O2—C81.425 (3)C8—H8C0.9600
N1—C131.333 (3)C9—C101.391 (3)
N1—C91.337 (3)C9—C141.475 (3)
N2—C71.277 (3)C10—C111.362 (4)
N2—C141.470 (3)C10—H100.9300
C1—C61.406 (3)C11—C121.378 (4)
C1—C21.412 (3)C11—H110.9300
C1—C71.423 (3)C12—C131.368 (4)
C2—C31.429 (3)C12—H120.9300
C3—C41.363 (3)C13—H130.9300
C4—C51.396 (4)C14—H14A0.9700
C4—H40.9300C14—H14B0.9700
Cg1···Cg2i3.566 (4)Cg1···Cg2ii3.767 (7)
O1—Zn1—N293.32 (7)C1—C6—H6120.0
O1—Zn1—N1174.02 (7)N2—C7—C1126.3 (2)
N2—Zn1—N181.01 (8)N2—C7—H7116.9
O1—Zn1—Cl188.94 (5)C1—C7—H7116.9
N2—Zn1—Cl1173.99 (6)O2—C8—H8A109.5
N1—Zn1—Cl196.89 (6)O2—C8—H8B109.5
C2—O1—Zn1127.63 (14)H8A—C8—H8B109.5
C3—O2—C8117.96 (19)O2—C8—H8C109.5
C13—N1—C9117.5 (2)H8A—C8—H8C109.5
C13—N1—Zn1126.18 (16)H8B—C8—H8C109.5
C9—N1—Zn1116.30 (15)N1—C9—C10123.1 (2)
C7—N2—C14117.25 (19)N1—C9—C14115.78 (19)
C7—N2—Zn1125.56 (16)C10—C9—C14121.1 (2)
C14—N2—Zn1117.11 (14)C11—C10—C9118.6 (2)
C6—C1—C2120.3 (2)C11—C10—H10120.7
C6—C1—C7117.0 (2)C9—C10—H10120.7
C2—C1—C7122.7 (2)C10—C11—C12118.2 (2)
O1—C2—C1124.4 (2)C10—C11—H11120.9
O1—C2—C3118.0 (2)C12—C11—H11120.9
C1—C2—C3117.6 (2)C13—C12—C11120.4 (2)
C4—C3—O2124.1 (2)C13—C12—H12119.8
C4—C3—C2120.8 (2)C11—C12—H12119.8
O2—C3—C2115.12 (19)N1—C13—C12122.2 (2)
C3—C4—C5120.4 (2)N1—C13—H13118.9
C3—C4—H4119.8C12—C13—H13118.9
C5—C4—H4119.8N2—C14—C9109.77 (18)
C6—C5—C4120.9 (2)N2—C14—H14A109.7
C6—C5—H5119.5C9—C14—H14A109.7
C4—C5—H5119.5N2—C14—H14B109.7
C5—C6—C1120.1 (2)C9—C14—H14B109.7
C5—C6—H6120.0H14A—C14—H14B108.2

Symmetry codes: (i) −x+1, y+3/2, −z+1/2; (ii) −x, y+3/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2598).

References

  • Bruker (2001). SAINT-Plus Bruker AXS Inc., Madison,Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, Y. (2005). Acta Cryst. E61, m2716–m2717.
  • Ghosh, R., Rahaman, S. H., Lin, C. N., Lu, T. H. & Ghosh, B. K. (2006). Polyhedron, 25, 3104–3112.
  • Kannappan, R., Tanase, S., Mutikaninen, I., Turpeinen, U. & Reedijk, J. (2005). Inorg. Chim. Acta, 358, 383–388.
  • Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017–m1019.
  • Sheldrick, G. M. (1998). XP Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
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  • You, Z.-L. (2005). Acta Cryst. C61, m456–m458. [PubMed]

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