[(4-Dimethyl­amino-2-methyl-5-phenyl­furan-3-yl)meth­yl]diethyl­methyl­aza­nium iodide

Armen Ayvazyan

doi:10.1107/S1600536811037743

. 2011 Sep 20;67(Pt 10):o2693. doi: 10.1107/S1600536811037743

[(4-Dimethylamino-2-methyl-5-phenylfuran-3-yl)methyl]diethylmethylazanium iodide

Armen Ayvazyan ^a,^*

PMCID: PMC3201454 PMID: 22058790

Abstract

In the title compound, C₁₉H₂₉N₂O⁺·I⁻, the dihedral angle between the mean planes of the essentially planar furan (r.m.s. deviation = 0.007 Å) and phenyl rings is 48.4 (1)°. In the crystal, cations and anions are arranged in layers lying parallel to (100).

Related literature

For the biological activities of furan derivatives, see: Chen et al. (2006 ▶); Meotti et al. (2003 ▶); Kazuo et al. (2001 ▶). For details of the synthesis, see: Manukyan et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₂₉N₂O⁺·I⁻
M _r = 428.34
Monoclinic,
a = 17.905 (4) Å
b = 7.2458 (14) Å
c = 15.732 (3) Å
β = 94.84 (3)°
V = 2033.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.58 mm⁻¹
T = 293 K
0.4 × 0.36 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (PLATON; Spek, 2009 ▶) T _min = 0.395, T _max = 0.430
6119 measured reflections
5911 independent reflections
4370 reflections with I > 2σ(I)
R _int = 0.013
3 standard reflections every 60 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.081
S = 0.99
5911 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1988 ▶); cell refinement: SETANG in CAD-4 Software (Enraf–Nonius, 1988 ▶); data reduction: HELENA (Spek, 1997 ▶); 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: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037743/lh5334sup1.cif

e-67-o2693-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037743/lh5334Isup2.hkl

e-67-o2693-Isup2.hkl^{(289.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037743/lh5334Isup3.cml

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

Acknowledgments

The title compound was provided by M. O. Manukyan, synthesized within the framework of State Committee of Science of Armenia (grant No. 11B-1d024).

supplementary crystallographic information

Comment

Compounds containing furan rings are distinguished by a number of interesting biological properties. In particular, the certain representatives of this family show antibacterial, antioxidant and anti-inflammatory activities (Chen et al., 2006, Meotti et al., 2003, Kazuo et al., 2001). Such a diversity of biological properties of these materials stimulates the interest in their structural studies. The asymmetric unit of title compound is shown in Fig.1. The molecule contains one quaternary N⁺ cation, the positive charge on which is balanced by an iodide anion. All bond lengths (Allen et al., 1987) and angles in good agreement with their standard values. In the crystal, cations and anions are arranged in layers parallel to (100) with N⁺···I^- distances in the range 4.429 (1) Å–5.332 (1) Å (see Fig. 2).

Experimental

The title compound was synthesized via Stevens rearrangement by the interaction of methyl iodide and 2-phenyl-3-dimethylamino-4-diethylamino-5-methylfuran (Manukyan et al., 2007). Single crystals were grown by slow evaporation of a solution of the title compound in ethanol at room temperature.