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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m102.
Published online 2008 December 20. doi:  10.1107/S1600536808042669
PMCID: PMC2968007

Poly[(μ6-naphthalene-1,4-dicarboxyl­ato-κ6 O 1:O 1′:O 1′:O 4:O 4′:O 4′)iron(II)]

Abstract

In the title compound, [Fe(C12H6O4)]n, the FeII atom is coordinated by six O atoms from six symmetrically equivalent naphthalene-1,4-dicarboxyl­ate ligands in a strongly distorted octa­hedral geometry. These octa­hedra are connected via common edges into chains that elongate along the a axis, with Fe(...)Fe distances of 2.9712 (4) and 2.9724 (4) Å. The chains are linked via the naphthalene-1,4-dicarboxyl­ate ligands into a three-dimensional coordination network.

Related literature

For isotypical structures with MnII and CoII, see: Maji et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m102-scheme1.jpg

Experimental

Crystal data

  • [Fe(C12H6O4)]
  • M r = 270.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m102-efi10.jpg
  • a = 4.7863 (4) Å
  • b = 14.8940 (9) Å
  • c = 13.4705 (10) Å
  • β = 91.098 (9)°
  • V = 960.10 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.57 mm−1
  • T = 170 (2) K
  • 0.30 × 0.04 × 0.04 mm

Data collection

  • Stoe IPDS-1 diffractometer
  • Absorption correction: none
  • 13722 measured reflections
  • 2256 independent reflections
  • 1816 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.087
  • S = 1.06
  • 2256 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: IPDS (Stoe & Cie, 1998 [triangle]); cell refinement: IPDS; data reduction: IPDS; 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]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042669/hy2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042669/hy2174Isup2.hkl

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

Acknowledgments

This work was supported by the State of Schleswig-Holstein. We thank Professor Dr Wolfgang Bensch for the facility to use his equipment.

supplementary crystallographic information

Comment

The structure determination of the title compound was performed as a part of a project on the synthesis of new metal–organic frameworks. In this project we have reacted iron(II) sulfate with naphthalene-1,4-dicarboxylic acid in potassium hydroxide and water, which leads to the formation of a naphthalene-1,4-dicarboxylate iron(II) coordination polymer.

The title compound is isostructural to the manganese(II) and cobalt(II) complexes of naphthalene-1,4-dicarboxylate (Maji et al., 2005). In the title compound, the FeII atom is surrounded by six O atoms from six crystallographically equivalent naphthalene-1,4-dicarboxylate ligands in a distorted octahedral coordination environment (Fig. 1 and Table 1). The Fe atoms are linked by O atoms of the carboxylate groups in a µ3-O:O':O' mode into chains, which elongate along the a axis (Fig. 2). Within these chains the Fe coordination octahedra are connected via common edges. These chains are connected by the naphthalene-1,4-dicarboxylate ligands into a three-dimensional network.

Experimental

A mixture of FeSO4.7H2O (0.139 g, 0.5 mmol), naphthalene-1,4-dicarboxylic acid (0.108 g, 0.5 mmol), KOH (0.112 g, 1 mmol) and water (5 ml) was transfered into a glass tube and heated to 423 K for 4 d. On cooling, yellow needle crystals of the title compound were obtained.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The structure of the title compound, together with symmetry-related atoms to complete the Fe coordination. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) x+1/2, -y+1/2, z-1/2; (ii) x-1, y, z; (iii) x-1/2, -y+1/2, ...
Fig. 2.
A view of the chains formed by the Fe coordination octahedra.
Fig. 3.
Three-dimensional structure of the title compound viewed along the a axis.

Crystal data

[Fe(C12H6O4)]F(000) = 544
Mr = 270.02Dx = 1.868 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8000 reflections
a = 4.7863 (4) Åθ = 9–26°
b = 14.8940 (9) ŵ = 1.57 mm1
c = 13.4705 (10) ÅT = 170 K
β = 91.098 (9)°Needle, yellow
V = 960.10 (12) Å30.30 × 0.04 × 0.04 mm
Z = 4

Data collection

Stoe IPDS-1 diffractometer1816 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 28.0°, θmin = 2.7°
[var phi] scansh = −6→6
13722 measured reflectionsk = −19→19
2256 independent reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4222P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
2256 reflectionsΔρmax = 0.40 e Å3
155 parametersΔρmin = −0.46 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Fe10.24998 (4)0.440859 (14)0.501167 (14)0.00529 (13)
O10.6268 (3)0.44515 (7)0.59098 (9)0.0071 (2)
O21.0178 (2)0.36165 (8)0.59405 (9)0.0095 (2)
O3−0.0120 (2)0.13335 (8)0.90581 (9)0.0099 (2)
O40.3838 (3)0.05263 (7)0.90583 (9)0.0067 (2)
C10.6451 (3)0.31639 (10)0.69582 (11)0.0077 (3)
C20.6838 (4)0.22537 (11)0.68337 (12)0.0097 (3)
H20.80260.20440.63260.012*
C30.5492 (4)0.16326 (11)0.74501 (12)0.0097 (3)
H30.57820.10080.73530.012*
C40.3761 (3)0.19163 (10)0.81920 (11)0.0074 (3)
C50.1863 (4)0.31859 (12)0.91907 (13)0.0165 (4)
H50.08690.27760.95930.020*
C60.1788 (5)0.40864 (12)0.94029 (14)0.0233 (5)
H60.07770.42920.99590.028*
C70.3198 (5)0.47108 (12)0.88038 (13)0.0199 (4)
H70.31550.53320.89630.024*
C80.4628 (4)0.44215 (10)0.79915 (13)0.0135 (4)
H80.55190.48480.75790.016*
C90.4798 (3)0.34898 (10)0.77570 (11)0.0081 (3)
C100.3413 (3)0.28589 (11)0.83760 (11)0.0084 (3)
C110.7751 (3)0.37880 (10)0.62232 (11)0.0067 (3)
C120.2371 (3)0.12168 (10)0.88160 (11)0.0067 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.00470 (18)0.00449 (16)0.00679 (17)0.00009 (8)0.00311 (10)0.00003 (7)
O10.0072 (6)0.0065 (5)0.0076 (5)0.0000 (4)0.0012 (4)0.0020 (4)
O20.0071 (6)0.0088 (5)0.0129 (5)0.0000 (4)0.0048 (4)0.0036 (4)
O30.0063 (6)0.0095 (5)0.0139 (5)−0.0002 (4)0.0036 (4)0.0044 (4)
O40.0071 (6)0.0056 (5)0.0074 (5)−0.0002 (4)0.0009 (4)0.0023 (4)
C10.0069 (7)0.0085 (7)0.0078 (7)−0.0012 (6)0.0011 (6)0.0027 (5)
C20.0103 (8)0.0096 (7)0.0094 (7)0.0010 (6)0.0048 (6)0.0017 (5)
C30.0116 (8)0.0071 (7)0.0104 (7)0.0008 (5)0.0032 (6)0.0020 (6)
C40.0068 (8)0.0071 (7)0.0082 (6)−0.0004 (5)0.0009 (5)0.0029 (5)
C50.0230 (10)0.0120 (8)0.0150 (8)0.0004 (7)0.0117 (7)0.0020 (6)
C60.0367 (12)0.0128 (9)0.0210 (9)0.0038 (8)0.0183 (8)−0.0011 (7)
C70.0338 (11)0.0089 (8)0.0173 (8)0.0011 (7)0.0100 (8)−0.0005 (6)
C80.0207 (10)0.0077 (8)0.0122 (7)−0.0020 (6)0.0050 (7)0.0011 (6)
C90.0084 (8)0.0075 (7)0.0083 (7)−0.0003 (5)0.0017 (6)0.0017 (5)
C100.0091 (8)0.0081 (7)0.0080 (7)0.0004 (5)0.0025 (6)0.0016 (5)
C110.0074 (8)0.0066 (7)0.0061 (6)−0.0018 (5)0.0012 (5)0.0000 (5)
C120.0076 (8)0.0070 (7)0.0056 (6)−0.0011 (5)0.0015 (5)0.0004 (5)

Geometric parameters (Å, °)

Fe1—O3i2.0557 (11)C2—H20.9500
Fe1—O2ii2.0604 (11)C3—C41.377 (2)
Fe1—O12.1533 (13)C3—H30.9500
Fe1—O4iii2.1550 (13)C4—C101.436 (2)
Fe1—O4iv2.1867 (11)C4—C121.502 (2)
Fe1—O1v2.1908 (11)C5—C61.372 (3)
Fe1—Fe1vi2.9712 (4)C5—C101.422 (2)
Fe1—Fe1v2.9724 (4)C5—H50.9500
O1—C111.2835 (19)C6—C71.411 (3)
O2—C111.256 (2)C6—H60.9500
O3—C121.254 (2)C7—C81.371 (2)
O4—C121.2839 (19)C7—H70.9500
C1—C21.379 (2)C8—C91.426 (2)
C1—C91.433 (2)C8—H80.9500
C1—C111.502 (2)C9—C101.428 (2)
C2—C31.407 (2)
O3i—Fe1—O2ii112.54 (5)C2—C1—C9120.12 (14)
O3i—Fe1—O184.19 (5)C2—C1—C11118.04 (13)
O2ii—Fe1—O197.55 (5)C9—C1—C11121.82 (14)
O3i—Fe1—O4iii96.08 (5)C1—C2—C3120.69 (15)
O2ii—Fe1—O4iii86.89 (5)C1—C2—H2119.7
O1—Fe1—O4iii175.08 (4)C3—C2—H2119.7
O3i—Fe1—O4iv159.92 (5)C4—C3—C2121.01 (15)
O2ii—Fe1—O4iv85.45 (4)C4—C3—H3119.5
O1—Fe1—O4iv84.65 (4)C2—C3—H3119.5
O4iii—Fe1—O4iv93.64 (4)C3—C4—C10119.93 (14)
O3i—Fe1—O1v84.50 (4)C3—C4—C12118.20 (14)
O2ii—Fe1—O1v160.39 (5)C10—C4—C12121.83 (13)
O1—Fe1—O1v93.65 (4)C6—C5—C10120.77 (16)
O4iii—Fe1—O1v81.50 (4)C6—C5—H5119.6
O4iv—Fe1—O1v79.61 (5)C10—C5—H5119.6
O3i—Fe1—Fe1vi140.19 (4)C5—C6—C7120.69 (16)
O2ii—Fe1—Fe1vi84.39 (3)C5—C6—H6119.7
O1—Fe1—Fe1vi130.85 (3)C7—C6—H6119.7
O4iii—Fe1—Fe1vi47.26 (3)C8—C7—C6120.04 (16)
O4iv—Fe1—Fe1vi46.37 (3)C8—C7—H7120.0
O1v—Fe1—Fe1vi76.12 (3)C6—C7—H7120.0
O3i—Fe1—Fe1v81.72 (3)C7—C8—C9120.93 (15)
O2ii—Fe1—Fe1v142.14 (4)C7—C8—H8119.5
O1—Fe1—Fe1v47.35 (3)C9—C8—H8119.5
O4iii—Fe1—Fe1v127.79 (3)C8—C9—C10118.82 (14)
O4iv—Fe1—Fe1v78.44 (3)C8—C9—C1122.06 (14)
O1v—Fe1—Fe1v46.30 (3)C10—C9—C1119.01 (14)
Fe1vi—Fe1—Fe1v107.275 (14)C5—C10—C9118.68 (14)
C11—O1—Fe1127.88 (10)C5—C10—C4122.14 (14)
C11—O1—Fe1v129.03 (11)C9—C10—C4119.07 (13)
Fe1—O1—Fe1v86.35 (4)O2—C11—O1124.47 (14)
C11—O2—Fe1vii125.49 (10)O2—C11—C1118.13 (14)
C12—O3—Fe1viii128.98 (10)O1—C11—C1117.38 (14)
C12—O4—Fe1ix123.36 (10)O3—C12—O4124.25 (14)
C12—O4—Fe1x126.21 (10)O3—C12—C4118.88 (14)
Fe1ix—O4—Fe1x86.36 (4)O4—C12—C4116.87 (14)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1; (vii) x+1, y, z; (viii) x−1/2, −y+1/2, z+1/2; (ix) x+1/2, −y+1/2, z+1/2; (x) −x+1/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2174).

References

  • Brandenburg, K. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Maji, T. K., Kaneko, W., Ohba, M. & Kitagawa, S. (2005). Chem. Commun. pp. 4613–4615. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (1998). IPDS Stoe & Cie, Darmstadt, Germany.

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