2-[(R)-Hydr­oxy(6-methoxy­quinolinium-4-yl)meth­yl]-8-vinyl-1-azoniabicyclo­[2.2.2]octane tetra­chloridoferrate(III) chloride monohydrate

Li-Zhuang Chen; Mei-Na Huang

doi:10.1107/S1600536810007889

. 2010 Mar 6;66(Pt 4):m377. doi: 10.1107/S1600536810007889

2-[(R)-Hydroxy(6-methoxyquinolinium-4-yl)methyl]-8-vinyl-1-azoniabicyclo[2.2.2]octane tetrachloridoferrate(III) chloride monohydrate

Li-Zhuang Chen ^a,^*, Mei-Na Huang ^a

PMCID: PMC2983884 PMID: 21580488

Abstract

In the title salt, (C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O, the Fe^III atom exists in a tetrahedral coordination environment. The cation, anions and water molecules are linked by N—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen bonds into a layer network.

Related literature

For ferroelectricity and SHG of chiral coordination compounds, see: Fu et al. (2007 ▶); Qu et al. (2003 ▶). For related transition-metal complexes, see: Zhao et al. (2003 ▶).

Experimental

Crystal data

(C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O
M _r = 577.54
Monoclinic,
a = 6.6838 (10) Å
b = 18.843 (2) Å
c = 10.8716 (10) Å
β = 104.918 (17)°
V = 1323.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.22 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.82, T _max = 0.88
12145 measured reflections
5166 independent reflections
3650 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.118
S = 1.01
5166 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 2490 Friedel pairs
Flack parameter: 0.01 (2)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007889/ng2725sup1.cif

e-66-0m377-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007889/ng2725Isup2.hkl

e-66-0m377-Isup2.hkl^{(253KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl5	0.96	2.10	3.023 (4)	161
N2—H2C⋯Cl5ⁱ	0.96	2.08	3.039 (4)	173
O2—H2B⋯O3	0.85	2.00	2.799 (6)	156
O3—H3B⋯Cl5ⁱⁱ	0.85	2.71	3.070 (6)	108

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

Acknowledgments

This work was supported by a start-up grant from Jiangsu University of Science and Technology

supplementary crystallographic information

Comment

The existence of a chiral centre in an organic ligand is very important for the construction noncentrosymmetric or chiral coordination polymers that exhibit desirable physical properties such as ferroelectricity (Fu et al., 2007), Chiral quinine has a chiral centre which have shown tremendous scope in the synthesis of transition-metal complexes (Zhao et al., 2003; Qu et al.,2003). The construction of new members of this family of ligands is an important direction in the development of modern coordination chemistry. We report here the crystal structure of the title compound

The asymmetric unit of the title compound,C₂₀H₂₆N₂O₂.FeCl₄.Cl.H₂O(Fig.1), consists of one protoned quinine and a tetrachloro-ironanion with the Fe^III ion in a slightly distorted tetrahedral coordination environment, The crystal structure is stabilized by intermolecular N—H···Cl, O—H···Cl and O—H···O hydrogen bonds.The H-bonds form of1D chain viewedalong the a-axis (Fig.2).

Experimental

A mixture of quinine (1 mmol, 0.324 g ), FeCl₃(1 mmol, 0.156 g) and 10% aqueous HCl (6 ml) were mixed and dissolved in 20 ml water by heating to 353 K (0.5 h) forming a clear solution. The reaction mixture was cooled slowly to room temperature, crystals of the title compound were formed after 11 days.