[2,6-Bis(6-methyl­quinolin-2-yl)pyridine-κ3 N,N′,N′′]dichloridoiron(II)

Xiao-Ping Li; Jian-She Zhao; Seik Weng Ng

doi:10.1107/S1600536810037049

. 2010 Sep 25;66(Pt 10):m1299. doi: 10.1107/S1600536810037049

[2,6-Bis(6-methylquinolin-2-yl)pyridine-κ³ N,N′,N′′]dichloridoiron(II)

Xiao-Ping Li ^a, Jian-She Zhao ^a, Seik Weng Ng ^b,^*

PMCID: PMC2983294 PMID: 21587438

Abstract

In the molecule of the title compound, [FeCl₂(C₂₅H₁₉N₃)], the three N atoms span the axial–equatorial–axial sites of the trigonal-bipyramidal coordination polyhedron; the geometry of the Fe^II atom is 32% distorted from trigonal-bipyramidal (towards square-pyramidal along the Berry pseudorotation pathway). One of the Cl atoms is disordered over two positions in a 0.938 (11):0.062 (11) ratio. Intermolecular C—H⋯Cl hydrogen bonding occurs in the crystal structure.

Related literature

For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965 ▶). For a related structure, see: Li et al. (2010 ▶).

Experimental

Crystal data

[FeCl₂(C₂₅H₁₉N₃)]
M _r = 488.18
Triclinic,
a = 9.6228 (7) Å
b = 10.2558 (8) Å
c = 10.7324 (8) Å
α = 94.352 (1)°
β = 95.481 (1)°
γ = 96.121 (1)°
V = 1044.35 (14) Å³
Z = 2
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.754, T _max = 0.952
9910 measured reflections
4757 independent reflections
3954 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.108
S = 1.05
4757 reflections
292 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037049/xu5032sup1.cif

e-66-m1299-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037049/xu5032Isup2.hkl

e-66-m1299-Isup2.hkl^{(233KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Fe1—N1	2.2386 (19)
Fe1—N2	2.103 (2)
Fe1—N3	2.2523 (19)
Fe1—Cl1	2.3636 (8)
Fe1—Cl2	2.2748 (7)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl2ⁱ	0.95	2.70	3.561 (2)	151
C17—H17⋯Cl1ⁱⁱ	0.95	2.73	3.538 (4)	144

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

Acknowledgments

We thank the Graduate Experimental Research Fund of Northwest University (project No. 09YSY22), the National Natural Science Foundation of China (No.20971104) and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

A recent study reported the chromium(III) chloride adduct of 2,6-bis(p-bromphenylimino)pyridine; the N-heterocycle chelates to the metal atom in a terdentate manner (Li et al., 2010). Bis[2'-(6-methylquinolinyl)]pyridine has a similar set of donor sites capable of binding in this manner, as demonstrated in the present iron dichloride adduct (Scheme I, Fig. 1 and Table 1). In the molecule of FeCl₂(C₂₅H₁₉N₃), the three N atoms span the axial–equatorial-axial sites of the trigonal bipyramidal coordination polyhedron; the geometry of Fe is 32% distorted from the trigonal bipyramid along the Berry pseudorotation pathway. Intermolecular C—H···Cl hydrogen bonding occurs in the crystal structure (Table 2).

Experimental

The ligand was synthesized by using a literature procedure (Buu-Hoi et al., 1965).

Bis[2'-(6-methylquinolinyl)]pyridine (0.018 g, 0.05 mmol), and ferrous chloride tetrahydrate (0.02 g, 0.05 mmol) along with five drops of 1 M hydrochloric acid were dissolved in ethanol (10 ml). The mixture was heated in a Teflon-lined, stainless-steel Parr bomb at 363 K for 120 h. The bomb was cooled at 5 K per hour. Black crystals were isolated.