metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Poly[(μ6-naphthalene-1,4-di­carboxyl­ato-κ6O1:O1′:O1′:O4:O4′:O4′)iron(II)]

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth Strasse 2, D-24098 Kiel, Germany
*Correspondence e-mail: cnaether@ac.uni-kiel.de

(Received 11 December 2008; accepted 15 December 2008; online 20 December 2008)

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[Maji, T. K., Kaneko, W., Ohba, M. & Kitagawa, S. (2005). Chem. Commun. pp. 4613-4615.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C12H6O4)]

  • Mr = 270.02

  • Monoclinic, P 21 /n

  • 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)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Fe1—O3i 2.0557 (11)
Fe1—O2ii 2.0604 (11)
Fe1—O1 2.1533 (13)
Fe1—O4iii 2.1550 (13)
Fe1—O4iv 2.1867 (11)
Fe1—O1v 2.1908 (11)
Fe1—Fe1vi 2.9712 (4)
Fe1—Fe1v 2.9724 (4)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) -x+1, -y+1, -z+1; (vi) -x, -y+1, -z+1.

Data collection: IPDS (Stoe & Cie, 1998[Stoe & Cie (1998). IPDS. Stoe & Cie, Darmstadt, Germany.]); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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

Computing details top

Data collection: IPDS (Stoe & Cie, 1998); cell refinement: IPDS (Stoe & Cie, 1998); data reduction: IPDS (Stoe & Cie, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] 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, z-1/2; (iv) -x+1/2, y+1/2, -z+3/2; (v) -x+1, -y+1, -z+1.]
[Figure 2] Fig. 2. A view of the chains formed by the Fe coordination octahedra.
[Figure 3] Fig. 3. Three-dimensional structure of the title compound viewed along the a axis.
Poly[(µ6-naphthalene-1,4-dicarboxylato- κ6O1:O1':O1':O4:O4':O4')iron(II)] top
Crystal data top
[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 top
Stoe IPDS-1
diffractometer
1816 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 28.0°, θmin = 2.7°
ϕ scansh = 66
13722 measured reflectionsk = 1919
2256 independent reflectionsl = 1717
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.087 w = 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)
Crystal data top
[Fe(C12H6O4)]V = 960.10 (12) Å3
Mr = 270.02Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.7863 (4) ŵ = 1.57 mm1
b = 14.8940 (9) ÅT = 170 K
c = 13.4705 (10) Å0.30 × 0.04 × 0.04 mm
β = 91.098 (9)°
Data collection top
Stoe IPDS-1
diffractometer
1816 reflections with I > 2σ(I)
13722 measured reflectionsRint = 0.026
2256 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.06Δρmax = 0.40 e Å3
2256 reflectionsΔρmin = 0.46 e Å3
155 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
O30.0120 (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) top
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, º) top
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, z1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z1/2; (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) x1/2, y+1/2, z+1/2; (ix) x+1/2, y+1/2, z+1/2; (x) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Fe(C12H6O4)]
Mr270.02
Crystal system, space groupMonoclinic, P21/n
Temperature (K)170
a, b, c (Å)4.7863 (4), 14.8940 (9), 13.4705 (10)
β (°) 91.098 (9)
V3)960.10 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.57
Crystal size (mm)0.30 × 0.04 × 0.04
Data collection
DiffractometerStoe IPDS1
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13722, 2256, 1816
Rint0.026
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.087, 1.06
No. of reflections2256
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.46

Computer programs: IPDS (Stoe & Cie, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Fe1—O3i2.0557 (11)Fe1—O4iv2.1867 (11)
Fe1—O2ii2.0604 (11)Fe1—O1v2.1908 (11)
Fe1—O12.1533 (13)Fe1—Fe1vi2.9712 (4)
Fe1—O4iii2.1550 (13)Fe1—Fe1v2.9724 (4)
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1/2, y+1/2, z+3/2; (v) x+1, y+1, z+1; (vi) x, y+1, z+1.
 

Acknowledgements

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

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationMaji, T. K., Kaneko, W., Ohba, M. & Kitagawa, S. (2005). Chem. Commun. pp. 4613–4615.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (1998). IPDS. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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