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

Boeckmann, J.; Jess, I.; Näther, C.

doi:10.1107/S1600536808042669

metal-organic compounds

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Volume 65| Part 1| January 2009| Page m102

doi:10.1107/S1600536808042669

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

Jan Boeckmann,^a Inke Jess ^a and Christian Näther ^a ^*

^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 Fe^II 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 Mn^II and Co^II, see: Maji et al. (2005 ).

Experimental

Crystal data

[Fe(C₁₂H₆O₄)]
M_r = 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)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.087
S = 1.06
2256 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −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—O4^iv	2.1867 (11)
Fe1—O1^v	2.1908 (11)
Fe1—Fe1^vi	2.9712 (4)
Fe1—Fe1^v	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 ); cell refinement: IPDS; data reduction: IPDS; 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.

Supporting information

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

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

checkCIF report

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 Fe^II 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 Mn^II and Co^II, 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.

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

	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.]
	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.

Poly[(µ₆-naphthalene-1,4-dicarboxylato- κ⁶O¹:O^1':O^1':O⁴:O^4':O^4')iron(II)] top

Crystal data top

[Fe(C₁₂H₆O₄)]	F(000) = 544
M_r = 270.02	D_x = 1.868 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8000 reflections
a = 4.7863 (4) Å	θ = 9–26°
b = 14.8940 (9) Å	µ = 1.57 mm⁻¹
c = 13.4705 (10) Å	T = 170 K
β = 91.098 (9)°	Needle, yellow
V = 960.10 (12) Å³	0.30 × 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 tube	R_int = 0.026
Graphite monochromator	θ_max = 28.0°, θ_min = 2.7°
ϕ scans	h = −6→6
13722 measured reflections	k = −19→19
2256 independent reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0535P)² + 0.4222P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
2256 reflections	Δρ_max = 0.40 e Å⁻³
155 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

Crystal data top

[Fe(C₁₂H₆O₄)]	V = 960.10 (12) Å³
M_r = 270.02	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.7863 (4) Å	µ = 1.57 mm⁻¹
b = 14.8940 (9) Å	T = 170 K
c = 13.4705 (10) Å	0.30 × 0.04 × 0.04 mm
β = 91.098 (9)°

Data collection top

Stoe IPDS-1 diffractometer	1816 reflections with I > 2σ(I)
13722 measured reflections	R_int = 0.026
2256 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
2256 reflections	Δρ_min = −0.46 e Å⁻³
155 parameters

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

	x	y	z	U_iso*/U_eq
Fe1	0.24998 (4)	0.440859 (14)	0.501167 (14)	0.00529 (13)
O1	0.6268 (3)	0.44515 (7)	0.59098 (9)	0.0071 (2)
O2	1.0178 (2)	0.36165 (8)	0.59405 (9)	0.0095 (2)
O3	−0.0120 (2)	0.13335 (8)	0.90581 (9)	0.0099 (2)
O4	0.3838 (3)	0.05263 (7)	0.90583 (9)	0.0067 (2)
C1	0.6451 (3)	0.31639 (10)	0.69582 (11)	0.0077 (3)
C2	0.6838 (4)	0.22537 (11)	0.68337 (12)	0.0097 (3)
H2	0.8026	0.2044	0.6326	0.012*
C3	0.5492 (4)	0.16326 (11)	0.74501 (12)	0.0097 (3)
H3	0.5782	0.1008	0.7353	0.012*
C4	0.3761 (3)	0.19163 (10)	0.81920 (11)	0.0074 (3)
C5	0.1863 (4)	0.31859 (12)	0.91907 (13)	0.0165 (4)
H5	0.0869	0.2776	0.9593	0.020*
C6	0.1788 (5)	0.40864 (12)	0.94029 (14)	0.0233 (5)
H6	0.0777	0.4292	0.9959	0.028*
C7	0.3198 (5)	0.47108 (12)	0.88038 (13)	0.0199 (4)
H7	0.3155	0.5332	0.8963	0.024*
C8	0.4628 (4)	0.44215 (10)	0.79915 (13)	0.0135 (4)
H8	0.5519	0.4848	0.7579	0.016*
C9	0.4798 (3)	0.34898 (10)	0.77570 (11)	0.0081 (3)
C10	0.3413 (3)	0.28589 (11)	0.83760 (11)	0.0084 (3)
C11	0.7751 (3)	0.37880 (10)	0.62232 (11)	0.0067 (3)
C12	0.2371 (3)	0.12168 (10)	0.88160 (11)	0.0067 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.00470 (18)	0.00449 (16)	0.00679 (17)	0.00009 (8)	0.00311 (10)	0.00003 (7)
O1	0.0072 (6)	0.0065 (5)	0.0076 (5)	0.0000 (4)	0.0012 (4)	0.0020 (4)
O2	0.0071 (6)	0.0088 (5)	0.0129 (5)	0.0000 (4)	0.0048 (4)	0.0036 (4)
O3	0.0063 (6)	0.0095 (5)	0.0139 (5)	−0.0002 (4)	0.0036 (4)	0.0044 (4)
O4	0.0071 (6)	0.0056 (5)	0.0074 (5)	−0.0002 (4)	0.0009 (4)	0.0023 (4)
C1	0.0069 (7)	0.0085 (7)	0.0078 (7)	−0.0012 (6)	0.0011 (6)	0.0027 (5)
C2	0.0103 (8)	0.0096 (7)	0.0094 (7)	0.0010 (6)	0.0048 (6)	0.0017 (5)
C3	0.0116 (8)	0.0071 (7)	0.0104 (7)	0.0008 (5)	0.0032 (6)	0.0020 (6)
C4	0.0068 (8)	0.0071 (7)	0.0082 (6)	−0.0004 (5)	0.0009 (5)	0.0029 (5)
C5	0.0230 (10)	0.0120 (8)	0.0150 (8)	0.0004 (7)	0.0117 (7)	0.0020 (6)
C6	0.0367 (12)	0.0128 (9)	0.0210 (9)	0.0038 (8)	0.0183 (8)	−0.0011 (7)
C7	0.0338 (11)	0.0089 (8)	0.0173 (8)	0.0011 (7)	0.0100 (8)	−0.0005 (6)
C8	0.0207 (10)	0.0077 (8)	0.0122 (7)	−0.0020 (6)	0.0050 (7)	0.0011 (6)
C9	0.0084 (8)	0.0075 (7)	0.0083 (7)	−0.0003 (5)	0.0017 (6)	0.0017 (5)
C10	0.0091 (8)	0.0081 (7)	0.0080 (7)	0.0004 (5)	0.0025 (6)	0.0016 (5)
C11	0.0074 (8)	0.0066 (7)	0.0061 (6)	−0.0018 (5)	0.0012 (5)	0.0000 (5)
C12	0.0076 (8)	0.0070 (7)	0.0056 (6)	−0.0011 (5)	0.0015 (5)	0.0004 (5)

Geometric parameters (Å, º) top

Fe1—O3ⁱ	2.0557 (11)	C2—H2	0.9500
Fe1—O2ⁱⁱ	2.0604 (11)	C3—C4	1.377 (2)
Fe1—O1	2.1533 (13)	C3—H3	0.9500
Fe1—O4ⁱⁱⁱ	2.1550 (13)	C4—C10	1.436 (2)
Fe1—O4^iv	2.1867 (11)	C4—C12	1.502 (2)
Fe1—O1^v	2.1908 (11)	C5—C6	1.372 (3)
Fe1—Fe1^vi	2.9712 (4)	C5—C10	1.422 (2)
Fe1—Fe1^v	2.9724 (4)	C5—H5	0.9500
O1—C11	1.2835 (19)	C6—C7	1.411 (3)
O2—C11	1.256 (2)	C6—H6	0.9500
O3—C12	1.254 (2)	C7—C8	1.371 (2)
O4—C12	1.2839 (19)	C7—H7	0.9500
C1—C2	1.379 (2)	C8—C9	1.426 (2)
C1—C9	1.433 (2)	C8—H8	0.9500
C1—C11	1.502 (2)	C9—C10	1.428 (2)
C2—C3	1.407 (2)

O3ⁱ—Fe1—O2ⁱⁱ	112.54 (5)	C2—C1—C9	120.12 (14)
O3ⁱ—Fe1—O1	84.19 (5)	C2—C1—C11	118.04 (13)
O2ⁱⁱ—Fe1—O1	97.55 (5)	C9—C1—C11	121.82 (14)
O3ⁱ—Fe1—O4ⁱⁱⁱ	96.08 (5)	C1—C2—C3	120.69 (15)
O2ⁱⁱ—Fe1—O4ⁱⁱⁱ	86.89 (5)	C1—C2—H2	119.7
O1—Fe1—O4ⁱⁱⁱ	175.08 (4)	C3—C2—H2	119.7
O3ⁱ—Fe1—O4^iv	159.92 (5)	C4—C3—C2	121.01 (15)
O2ⁱⁱ—Fe1—O4^iv	85.45 (4)	C4—C3—H3	119.5
O1—Fe1—O4^iv	84.65 (4)	C2—C3—H3	119.5
O4ⁱⁱⁱ—Fe1—O4^iv	93.64 (4)	C3—C4—C10	119.93 (14)
O3ⁱ—Fe1—O1^v	84.50 (4)	C3—C4—C12	118.20 (14)
O2ⁱⁱ—Fe1—O1^v	160.39 (5)	C10—C4—C12	121.83 (13)
O1—Fe1—O1^v	93.65 (4)	C6—C5—C10	120.77 (16)
O4ⁱⁱⁱ—Fe1—O1^v	81.50 (4)	C6—C5—H5	119.6
O4^iv—Fe1—O1^v	79.61 (5)	C10—C5—H5	119.6
O3ⁱ—Fe1—Fe1^vi	140.19 (4)	C5—C6—C7	120.69 (16)
O2ⁱⁱ—Fe1—Fe1^vi	84.39 (3)	C5—C6—H6	119.7
O1—Fe1—Fe1^vi	130.85 (3)	C7—C6—H6	119.7
O4ⁱⁱⁱ—Fe1—Fe1^vi	47.26 (3)	C8—C7—C6	120.04 (16)
O4^iv—Fe1—Fe1^vi	46.37 (3)	C8—C7—H7	120.0
O1^v—Fe1—Fe1^vi	76.12 (3)	C6—C7—H7	120.0
O3ⁱ—Fe1—Fe1^v	81.72 (3)	C7—C8—C9	120.93 (15)
O2ⁱⁱ—Fe1—Fe1^v	142.14 (4)	C7—C8—H8	119.5
O1—Fe1—Fe1^v	47.35 (3)	C9—C8—H8	119.5
O4ⁱⁱⁱ—Fe1—Fe1^v	127.79 (3)	C8—C9—C10	118.82 (14)
O4^iv—Fe1—Fe1^v	78.44 (3)	C8—C9—C1	122.06 (14)
O1^v—Fe1—Fe1^v	46.30 (3)	C10—C9—C1	119.01 (14)
Fe1^vi—Fe1—Fe1^v	107.275 (14)	C5—C10—C9	118.68 (14)
C11—O1—Fe1	127.88 (10)	C5—C10—C4	122.14 (14)
C11—O1—Fe1^v	129.03 (11)	C9—C10—C4	119.07 (13)
Fe1—O1—Fe1^v	86.35 (4)	O2—C11—O1	124.47 (14)
C11—O2—Fe1^vii	125.49 (10)	O2—C11—C1	118.13 (14)
C12—O3—Fe1^viii	128.98 (10)	O1—C11—C1	117.38 (14)
C12—O4—Fe1^ix	123.36 (10)	O3—C12—O4	124.25 (14)
C12—O4—Fe1^x	126.21 (10)	O3—C12—C4	118.88 (14)
Fe1^ix—O4—Fe1^x	86.36 (4)	O4—C12—C4	116.87 (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.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₂H₆O₄)]
M_r	270.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	170
a, b, c (Å)	4.7863 (4), 14.8940 (9), 13.4705 (10)
β (°)	91.098 (9)
V (Å³)	960.10 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.30 × 0.04 × 0.04

Data collection
Diffractometer	Stoe IPDS1 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13722, 2256, 1816
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.087, 1.06
No. of reflections	2256
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O3ⁱ	2.0557 (11)	Fe1—O4^iv	2.1867 (11)
Fe1—O2ⁱⁱ	2.0604 (11)	Fe1—O1^v	2.1908 (11)
Fe1—O1	2.1533 (13)	Fe1—Fe1^vi	2.9712 (4)
Fe1—O4ⁱⁱⁱ	2.1550 (13)	Fe1—Fe1^v	2.9724 (4)

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.

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

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