Dichlorido{1-[(2-hy­droxy­eth­yl)imino­meth­yl]-2-naphtho­lato}pyridine­iron(III) pyridine monosolvate

Shizheng Liu; Jie Yang; Lei Lv; Dacheng Li

doi:10.1107/S1600536810046623

. 2010 Nov 17;66(Pt 12):m1585. doi: 10.1107/S1600536810046623

Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III) pyridine monosolvate

Shizheng Liu ^a, Jie Yang ^a, Lei Lv ^a, Dacheng Li ^a,^*

PMCID: PMC3011765 PMID: 21589269

Abstract

In the title complex, [Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N, the iron(III) atom is six-coordinated by the N and O atoms from the Schiff base ligand, the N atom from a pyridine molecule and two chloride anions in a distorted octahedral geometry. The crystal packing is stabilized by intermolecular O—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For the synthesis and applications of magnetic complexes, see: Oshio et al. (2004 ▶); Aromí & Brechin (2006 ▶). For related structures, see: Goodwin et al. (2000 ▶); Qian et al. (2008 ▶); Hoshino et al. (2009 ▶).

Experimental

Crystal data

[Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N
M _r = 499.19
Monoclinic,
a = 7.8590 (6) Å
b = 10.0153 (11) Å
c = 14.4884 (16) Å
β = 90.123 (1)°
V = 1140.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 298 K
0.48 × 0.44 × 0.37 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T _min = 0.666, T _max = 0.727
5726 measured reflections
3395 independent reflections
3143 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.085
S = 1.00
3395 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 1265 Friedel pairs
Flack parameter: 0.02 (2)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046623/rz2519sup1.cif

e-66-m1585-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046623/rz2519Isup2.hkl

e-66-m1585-Isup2.hkl^{(166.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.81	2.617 (4)	168
C12—H12⋯Cgⁱ	0.93	2.71	3.594 (5)	159
C16—H16⋯Cgⁱⁱ	0.93	2.78	3.653 (6)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20671048, 21041002)

supplementary crystallographic information

Comment

The considerable current interest in magnetic complexes arises from their relevance in diverse fields ranging from bioinorganic chemistry to molecular magnetic materials (Oshio et al., 2004; Aromí et al., 2006). We report here the synthesis and crystal structure of the title compound.

In the title complex (Fig. 1), the tridentate Schiff base ligand is derived from the condensation of 2-hydroxy-1-naphthaldehyde and ethanolamine. The iron(III) metal centre is six-coordinate by the N and O atoms from the Schiff base ligand, the N atom from a pyridine molecule and two chloride anions in a distorted octahedral geometry. The Fe–O(alkoxo) bond length [Fe1–O1 = 2.105 (2) Å] is longer than the Fe–O(phenoxo) distance [Fe1–O2 = 1.897 (2) Å], which lies well within the range of values reported in the literature (Goodwin et al., 2000; Qian et al., 2008; Hoshino et al., 2009). In the crystal structure, complex molecules and pyridine solvent molecules are linked into a three-dimensional network by O—H···N hydrogen bonds and C—H···π interactions (Table 1).

Experimental

Ethanolamine (1 mmol, 61.08 mg) was dissolved in methanol (10 ml) and added dropwise to a methanol solution of 2-hydroxy-1-naphthaldehyde (1 mmol, 172.19 mg). The mixture was then stirred at 323 K for 2 h. Subsequently, an MeCN/Py solution "(3:1 v/v, 4 ml) of FeCl₃.6H₂O(1 mmol, 270.29 mg) was added dropwise and stirred for another 7 h. The resulting black solution was filtrated and was allowed to stand at room temperature for about one week, whereupon block crystals suitable for X-ray diffraction analysis were obtained.