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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1338.
Published online 2008 September 27. doi:  10.1107/S1600536808030614
PMCID: PMC2959363

catena-Poly[[(dimethyl sulfoxide-κO)zinc(II)]-μ-(E)-2-[(2-oxido-1-naphth­yl)­methyl­eneamino]propanoato-κ4 O 2,N,O 1:O 1′]

Abstract

In the title coordination polymer, [Zn(C14H11NO3)(C2H6OS)]n, each ZnII ion is five-coordinated in a slightly distorted trigonal–bipyramidal coordination environment, formed by three O atoms from two 2-[(2-oxido-1-naphth­yl)­methyl­eneamino]propanoate ligands, one O atom from a dimethyl sulfoxide mol­ecule and the N atom from the amino­propanoate ligand. The propanoate ligands bridge ZnII ions, forming a zigzag chain parallel to [010].

Related literature

For the synthesis of (E)-2-[(2-hydroxy­naphthalen-1-yl)­methyl­eneamino]propanoic acid, see: Audriceth et al. (1954 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1338-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H11NO3)(C2H6OS)]
  • M r = 384.74
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1338-efi2.jpg
  • a = 9.676 (4) Å
  • b = 7.651 (4) Å
  • c = 11.715 (5) Å
  • β = 106.256 (15)°
  • V = 832.6 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.62 mm−1
  • T = 291 (2) K
  • 0.31 × 0.28 × 0.24 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.633, T max = 0.697
  • 8191 measured reflections
  • 3729 independent reflections
  • 3533 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.056
  • S = 1.06
  • 3729 reflections
  • 211 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.19 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1675 Friedel pairs
  • Flack parameter: 0.006 (8)

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); 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: SHELXL97.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030614/ng2495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030614/ng2495Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20272011).

supplementary crystallographic information

Comment

The continuous interest in designing and making novel Schiff base ligand and transition-metal complexes have persisted because of their impressive catalytic property. In this paper, we report the new title compound, (I), synthesized by the reaction of (E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)propanoic acid ligands and Zn(OAc)2 in an aqueous solution.

As shown in Fig. 1, ZnII ion is five-coordinate in a slightly distorted trigonal-bipyramidal coordination environment, formed by four O atoms and one N atom. Each quadridentate Schiff base ligand bridge two different CuII ions, resulting in a one-dimensional polymeric structure chain (Fig. 2).

Experimental

(E)-2-((2-Hydroxynaphthalen-1-yl)methyleneamino)propanoic acid was prepared of L-alanine acid and 2-hydroxy-1-naphthaldehyde in aqueous solution (Audriceth et al., 1954). (E)-2-((2-Hydroxynaphthalen-1-yl)methyleneamino)propanoic acid (0.243 g, 1 mmol) and Zn(OAc)2 (0.190 g, 1 mmol) dissolved in hot aqueous solution (20 ml) then refluxed for 1 huor. After cooling to room temperature the solution was filtered, the residue was recrystaled in DMSO and methanol (10/1, V/V) solution, several days latter, a suitable for X-ray diffraction yellow crystal was obtained.

Refinement

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (Caromatic); C—H = 0.96 Å (methyl); C—H = 0.98 ° A (methine), and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. [Symmetry code: (I) -x + 1, 1/2 + y, -z + 1].
Fig. 2.
A partial packing view, showing the one-dimensional chain structure. H atoms have been omitted for clarity.

Crystal data

[Zn(C14H11NO3)(C2H6OS)]F(000) = 396
Mr = 384.74Dx = 1.535 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7870 reflections
a = 9.676 (4) Åθ = 3.2–27.5°
b = 7.651 (4) ŵ = 1.62 mm1
c = 11.715 (5) ÅT = 291 K
β = 106.256 (15)°Block, yellow
V = 832.6 (7) Å30.31 × 0.28 × 0.24 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer3729 independent reflections
Radiation source: fine-focus sealed tube3533 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −11→12
Tmin = 0.633, Tmax = 0.697k = −9→9
8191 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.056w = 1/[σ2(Fo2) + (0.0259P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3729 reflectionsΔρmax = 0.25 e Å3
211 parametersΔρmin = −0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 1675 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.006 (8)

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
C10.7743 (2)−0.1178 (3)0.23967 (18)0.0288 (4)
C20.66925 (19)−0.0224 (3)0.15494 (15)0.0272 (4)
C30.6855 (2)0.0055 (4)0.03564 (15)0.0304 (4)
C40.5858 (3)0.0965 (3)−0.0557 (2)0.0429 (6)
H40.50200.1392−0.04160.051*
C50.6085 (3)0.1243 (4)−0.1655 (2)0.0477 (6)
H50.54000.1837−0.22430.057*
C60.7336 (3)0.0636 (3)−0.1883 (2)0.0483 (6)
H60.75040.0859−0.26130.058*
C70.8305 (3)−0.0276 (4)−0.10433 (19)0.0445 (6)
H70.9131−0.0694−0.12090.053*
C80.8094 (2)−0.0613 (3)0.00897 (19)0.0340 (5)
C90.9098 (2)−0.1605 (4)0.0950 (2)0.0418 (5)
H90.9890−0.20750.07560.050*
C100.8947 (2)−0.1897 (3)0.2055 (2)0.0382 (5)
H100.9628−0.25680.25950.046*
C110.5465 (2)0.0524 (3)0.18248 (18)0.0292 (4)
H110.47780.10430.11980.035*
C120.3897 (2)0.1430 (3)0.29272 (17)0.0307 (4)
H120.36760.23870.23490.037*
C130.2635 (2)0.0163 (5)0.2663 (3)0.0612 (9)
H13A0.2422−0.02190.18510.092*
H13B0.18080.07380.27880.092*
H13C0.2879−0.08290.31820.092*
C140.4141 (2)0.2180 (3)0.41799 (18)0.0274 (4)
C150.7228 (3)0.4372 (3)0.3802 (3)0.0555 (7)
H15A0.68520.36180.31320.083*
H15B0.75080.54670.35340.083*
H15C0.65010.45710.42020.083*
C160.9720 (3)0.2924 (4)0.3760 (3)0.0566 (7)
H16A1.06050.23490.41610.085*
H16B0.99300.39980.34180.085*
H16C0.91610.21800.31430.085*
N10.52124 (17)0.0554 (2)0.28544 (14)0.0268 (3)
O10.77231 (16)−0.1464 (2)0.34856 (12)0.0355 (3)
O20.51906 (16)0.1680 (2)0.49919 (13)0.0372 (4)
O30.32074 (15)0.3268 (2)0.42825 (13)0.0354 (3)
O40.82733 (16)0.1620 (2)0.51567 (15)0.0422 (4)
S10.87374 (6)0.33792 (8)0.47907 (5)0.03915 (13)
Zn10.66361 (2)−0.00892 (3)0.440772 (16)0.02749 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0313 (10)0.0256 (11)0.0325 (9)−0.0010 (8)0.0141 (9)−0.0017 (8)
C20.0308 (8)0.0236 (10)0.0288 (8)0.0005 (10)0.0113 (7)−0.0007 (10)
C30.0376 (9)0.0261 (11)0.0303 (8)−0.0042 (11)0.0141 (8)−0.0031 (10)
C40.0557 (15)0.0403 (14)0.0372 (11)0.0075 (12)0.0204 (12)0.0064 (10)
C50.0727 (17)0.0373 (14)0.0331 (11)−0.0006 (13)0.0146 (12)0.0055 (10)
C60.0787 (18)0.0388 (13)0.0374 (11)−0.0155 (13)0.0323 (14)−0.0064 (10)
C70.0566 (13)0.0462 (16)0.0411 (10)−0.0114 (14)0.0308 (11)−0.0094 (12)
C80.0387 (11)0.0339 (13)0.0330 (10)−0.0073 (9)0.0162 (9)−0.0070 (8)
C90.0357 (11)0.0521 (15)0.0441 (12)0.0053 (11)0.0221 (11)−0.0068 (11)
C100.0345 (11)0.0424 (14)0.0392 (11)0.0104 (10)0.0130 (10)−0.0003 (10)
C110.0311 (10)0.0269 (10)0.0291 (9)0.0025 (8)0.0076 (9)0.0001 (7)
C120.0280 (10)0.0330 (12)0.0319 (10)0.0043 (9)0.0096 (9)−0.0071 (9)
C130.0308 (11)0.073 (2)0.0840 (18)−0.0102 (14)0.0225 (12)−0.0487 (19)
C140.0279 (10)0.0267 (10)0.0333 (10)−0.0044 (8)0.0181 (9)−0.0043 (8)
C150.0493 (14)0.0333 (14)0.088 (2)0.0012 (11)0.0255 (15)0.0115 (12)
C160.0464 (15)0.0558 (19)0.0764 (19)−0.0036 (13)0.0319 (15)−0.0019 (15)
N10.0266 (8)0.0274 (9)0.0284 (7)0.0022 (6)0.0106 (7)−0.0035 (6)
O10.0414 (8)0.0361 (9)0.0325 (7)0.0111 (7)0.0161 (7)0.0074 (6)
O20.0369 (8)0.0455 (10)0.0309 (7)0.0056 (7)0.0121 (7)−0.0044 (7)
O30.0358 (8)0.0372 (9)0.0365 (7)0.0056 (7)0.0156 (7)−0.0104 (7)
O40.0371 (8)0.0357 (9)0.0520 (9)−0.0084 (7)0.0094 (7)0.0051 (8)
S10.0388 (3)0.0311 (3)0.0503 (3)−0.0096 (2)0.0169 (3)−0.0059 (2)
Zn10.02884 (11)0.02883 (11)0.02707 (10)0.00032 (12)0.01157 (8)0.00374 (11)

Geometric parameters (Å, °)

C1—O11.300 (2)C12—C141.531 (3)
C1—C21.410 (3)C12—H120.9800
C1—C101.443 (3)C13—H13A0.9600
C2—C111.434 (3)C13—H13B0.9600
C2—C31.465 (2)C13—H13C0.9600
C3—C41.408 (3)C14—O21.242 (3)
C3—C81.416 (3)C14—O31.259 (3)
C4—C51.381 (3)C15—S11.762 (3)
C4—H40.9300C15—H15A0.9600
C5—C61.391 (4)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—C71.348 (4)C16—S11.768 (3)
C6—H60.9300C16—H16A0.9600
C7—C81.422 (3)C16—H16B0.9600
C7—H70.9300C16—H16C0.9600
C8—C91.409 (3)N1—Zn12.0119 (18)
C9—C101.361 (3)O1—Zn12.0040 (15)
C9—H90.9300O2—Zn12.1891 (16)
C10—H100.9300O3—Zn1i1.9560 (15)
C11—N11.296 (2)O4—S11.5184 (18)
C11—H110.9300O4—Zn12.0520 (17)
C12—N11.462 (2)Zn1—O3ii1.9560 (15)
C12—C131.521 (3)
O1—C1—C2124.91 (17)C12—C13—H13B109.5
O1—C1—C10116.32 (19)H13A—C13—H13B109.5
C2—C1—C10118.77 (17)C12—C13—H13C109.5
C1—C2—C11121.86 (16)H13A—C13—H13C109.5
C1—C2—C3119.89 (17)H13B—C13—H13C109.5
C11—C2—C3118.24 (18)O2—C14—O3125.85 (18)
C4—C3—C8116.96 (17)O2—C14—C12119.49 (17)
C4—C3—C2124.27 (18)O3—C14—C12114.66 (19)
C8—C3—C2118.77 (19)S1—C15—H15A109.5
C5—C4—C3122.0 (2)S1—C15—H15B109.5
C5—C4—H4119.0H15A—C15—H15B109.5
C3—C4—H4119.0S1—C15—H15C109.5
C4—C5—C6120.1 (2)H15A—C15—H15C109.5
C4—C5—H5120.0H15B—C15—H15C109.5
C6—C5—H5120.0S1—C16—H16A109.5
C7—C6—C5119.9 (2)S1—C16—H16B109.5
C7—C6—H6120.1H16A—C16—H16B109.5
C5—C6—H6120.1S1—C16—H16C109.5
C6—C7—C8121.5 (2)H16A—C16—H16C109.5
C6—C7—H7119.2H16B—C16—H16C109.5
C8—C7—H7119.2C11—N1—C12117.15 (17)
C9—C8—C3119.56 (17)C11—N1—Zn1125.29 (13)
C9—C8—C7120.97 (19)C12—N1—Zn1116.50 (12)
C3—C8—C7119.5 (2)C1—O1—Zn1126.51 (14)
C10—C9—C8122.14 (19)C14—O2—Zn1114.09 (12)
C10—C9—H9118.9C14—O3—Zn1i126.85 (14)
C8—C9—H9118.9S1—O4—Zn1134.27 (11)
C9—C10—C1120.8 (2)O4—S1—C15108.15 (11)
C9—C10—H10119.6O4—S1—C16106.05 (12)
C1—C10—H10119.6C15—S1—C1698.14 (15)
N1—C11—C2126.87 (19)O3ii—Zn1—O198.54 (7)
N1—C11—H11116.6O3ii—Zn1—N1138.57 (7)
C2—C11—H11116.6O1—Zn1—N188.32 (7)
N1—C12—C13111.01 (19)O3ii—Zn1—O4101.12 (7)
N1—C12—C14108.94 (16)O1—Zn1—O496.09 (7)
C13—C12—C14109.48 (17)N1—Zn1—O4118.82 (7)
N1—C12—H12109.1O3ii—Zn1—O293.89 (7)
C13—C12—H12109.1O1—Zn1—O2166.10 (6)
C14—C12—H12109.1N1—Zn1—O278.22 (6)
C12—C13—H13A109.5O4—Zn1—O287.52 (7)
O1—C1—C2—C11−0.5 (4)C13—C12—N1—C1189.0 (2)
C10—C1—C2—C11179.8 (2)C14—C12—N1—C11−150.37 (18)
O1—C1—C2—C3178.2 (2)C13—C12—N1—Zn1−102.1 (2)
C10—C1—C2—C3−1.4 (3)C14—C12—N1—Zn118.5 (2)
C1—C2—C3—C4179.0 (2)C2—C1—O1—Zn1−20.7 (3)
C11—C2—C3—C4−2.2 (4)C10—C1—O1—Zn1158.98 (16)
C1—C2—C3—C8−1.5 (3)O3—C14—O2—Zn1−175.97 (16)
C11—C2—C3—C8177.3 (2)C12—C14—O2—Zn14.9 (2)
C8—C3—C4—C5−1.7 (4)O2—C14—O3—Zn1i16.7 (3)
C2—C3—C4—C5177.8 (3)C12—C14—O3—Zn1i−164.18 (13)
C3—C4—C5—C6−0.8 (4)Zn1—O4—S1—C1523.79 (18)
C4—C5—C6—C72.2 (4)Zn1—O4—S1—C16−80.64 (17)
C5—C6—C7—C8−1.1 (4)C1—O1—Zn1—O3ii165.79 (17)
C4—C3—C8—C9−177.1 (2)C1—O1—Zn1—N126.85 (17)
C2—C3—C8—C93.4 (3)C1—O1—Zn1—O4−91.96 (18)
C4—C3—C8—C72.8 (3)C1—O1—Zn1—O212.5 (4)
C2—C3—C8—C7−176.7 (2)C11—N1—Zn1—O3ii−122.75 (17)
C6—C7—C8—C9178.4 (2)C12—N1—Zn1—O3ii69.40 (17)
C6—C7—C8—C3−1.4 (4)C11—N1—Zn1—O1−21.72 (17)
C3—C8—C9—C10−2.4 (4)C12—N1—Zn1—O1170.43 (14)
C7—C8—C9—C10177.7 (2)C11—N1—Zn1—O474.31 (18)
C8—C9—C10—C1−0.6 (4)C12—N1—Zn1—O4−93.54 (15)
O1—C1—C10—C9−177.2 (2)C11—N1—Zn1—O2154.80 (18)
C2—C1—C10—C92.5 (3)C12—N1—Zn1—O2−13.05 (14)
C1—C2—C11—N15.6 (4)S1—O4—Zn1—O3ii−170.20 (14)
C3—C2—C11—N1−173.2 (2)S1—O4—Zn1—O189.82 (14)
N1—C12—C14—O2−15.1 (3)S1—O4—Zn1—N1−1.61 (17)
C13—C12—C14—O2106.5 (2)S1—O4—Zn1—O2−76.72 (14)
N1—C12—C14—O3165.76 (17)C14—O2—Zn1—O3ii−134.50 (15)
C13—C12—C14—O3−72.7 (3)C14—O2—Zn1—O119.0 (4)
C2—C11—N1—C12178.6 (2)C14—O2—Zn1—N14.39 (14)
C2—C11—N1—Zn110.9 (3)C14—O2—Zn1—O4124.51 (15)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2495).

References

  • Audriceth, L. F., Scott, E. S. & Kipper, P. S. (1954). J. Org. Chem.19, 733–741.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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