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X-ray powder diffraction data for [C6Trop]+[PF6]−, C14H27NOPF6

Published online by Cambridge University Press:  11 March 2014

Zhi Jian He ,
Guo Fei Qian ,
Li Li Zhang ,
Hui Li  and
Shun Yao
Zhi Jian He
Affiliation:
College of Chemistry and Chemical Engineering, Mianyang Normal University, Mianyang 621000, China
Guo Fei Qian
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Li Li Zhang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Hui Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Shun Yao*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
*
a)Author to whom correspondence should be addressed. Electronic mail: cusack@scu.edu.cn

Abstract

Experimental X-ray powder diffraction data, unit-cell parameters, and space group for [C6Trop]+[PF6]−, C14H27NOPF6, are reported [a = 16.1879(6) Å, b = 11.4271(2) Å, c = 10.3966(5) Å, α = 66.4949(3)°, β = 94.5589(0)°, γ = 93.3092(4)°, unit-cell volume V = 1923.17 Å3, Z = 1, and space group P1]. No detectable impurities were observed.

Keywords

X-ray powder diffraction (XRD)[C6Trop]+[PF6]−C14H27NOPF6

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 29 , Issue 2 , June 2014 , pp. 190 - 192
Copyright
Copyright © International Centre for Diffraction Data 2014 

I. INTRODUCTION

[C6Trop]+[PF6]− (C14H27NOPF6, see Figure 1), systematic name 8-hexyl-3-hydroxy-8-methyl-nortropanium hexafluorophosphate is a new potential ionic liquid (IL) synthesized by us recently, which is a white powders at room temperature. The skeleton of its cation originates from 3-α-tropanol, which is an important chemical and pharmaceutical raw material (Dewick et al., Reference Dewick2009; Goodman et al., Reference Goodman, Ketchum and Kirby2010). The C6 chain on the N atom lowers the melting point of the salt. Moreover, the solubility of the IL in certain reaction and extraction mixture could be changed greatly with a small-scale variation in temperature, similar to other reported ionic liquids (Li et al., Reference Li, Gu, Yang, Song and Yao2012) with temperature-sensitive properties and broad application prospects. Benzatropine and etybenzatropine are the famous derivatives of tropanol, which is also a building block of atropine, a cholinergic drug prototypical of the muscarinic antagonist class. The title compound [C6Trop]+[PF6]− is also expected to have some biological activities and medicinal value.

Figure 1.

Structural formula of [C6Trop]+[PF6]−.

At present, the crystal structure of [C6Trop]+[PF6]− has not been reported.

II. EXPERIMENTAL

A. Sample preparation

The title compound was synthesized as the following procedure (see Figure 2):

  1. (1) 0.05 mol 3-α-tropanol (from Sigma-Aldrich, CAS No. 120-29-6, purity >97%) was dissolved in 50 ml toluene together with 0.05 mol 1-bromohexane. The solution was refluxed and reacted for 6 h, and was concentrated under vacuum to produce a white solid. The product was washed by ethyl acetate for three times to obtain [C6Trop]+[Br]−.

  2. (2) 0.01 mol [C6Trop]+[Br]− and 0.12 mol potassium hexafluorophosphate were dissolved in distilled water. Then the aqueous solution of potassium hexafluorophosphate was added to the aqueous solution of [C6Trop]+[Br]− and stirred thoroughly. Then the solid in the reaction system was filtrated and washed with distilled water to obtain a white powder of [C6Trop]+[PF6]−.

The sample was characterized by high-performance liquid chromatography, as well as by UV, IR, and NMR. UV (CH3CN, 200-400 nm) max: 204 nm. IR (KBr disc, cm-1): 3304 (-OH stretching vibration); 2960, 2931, 2925 (-CH3, -CH2 stretching vibration); 2886 (-CH stretching vibration); 1471, 1466 (-CH2 bending vibration); 1448, 1326 (-CH3 bending vibration); 1261, 1232 (C-N stretching vibration). PNMR (400M, DMSO) ppm: 1.680-1.738 (4H, m, 1,4-H, -CH2×2); 3.949 (2H, brs, 2,3-H, -CH×2); 2.134- 2.198 (4H, m, 5,6-H, -CH2×2); 3.173 (3H, s, 8-H, -CH3); 4.165 (1H, t, 9-H, -CH-O); 3.439 (1H, s, -OH); 3.268-3.310 (2H, t, 11-H, -CH2); 2.732-2.766 (2H, t, 12-H, -CH2); 1.346-1.450 (2H, t, 13-H, -CH2); 0.990 (3H, s, 14-H, -CH3). Eventually, the pure [C6Trop]+[PF6]− was recrystallized in methanol, and its melting point was determined to be 185 °C.

B. Powder diffraction data collection and reduction

The diffraction pattern for the [C6Trop]+[PF6]− powder was collected at room temperature using an X'Pert PRO diffractometer (PANalytical) with an PIXcel 1D detector and CuKα 1 radiation (λ = 1.54056 Å, generator setting: 40 kV and 40 mA). The diffraction data were collected in the angular range from 5° to 50° 2θ with a step size of 0.01313° 2θ and a counting time of 30 s/step. Data evaluation was performed using the software package Material Studio 4.2 (Accelrys Co., Ltd. USA).

The preliminary unit-cell parameters were obtained by analyzing the peak positions in the X-ray powder diffraction (XRD) pattern by the X-Cell method from the “Powder Indexing” tool. The indexing results were then refined with the type of Pawley, which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental powder XRD pattern (Harris, Reference Harris2012).

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 3. Indexing the results confirmed that [C6Trop]+[PF6]− is triclinic with space group P1 and unit-cell parameters: a = 16.1879(6) Å, b = 11.4271(2) Å, c = 10.3966(5) Å, α = 66.4949(3)°, β = 94.5589(0)°, γ = 93.3092(4)°, unit-cell volume V = 1923.17 Å3, Z = 1, and space group P1 (Table I).

Figure 2.

Synthesis procedure of [C6Trop]+[PF6]−.

Figure 3.

XRD pattern of the [C6Trop]+[PF6]−, using CuKα 1 radiation (λ = 1.54056 Å).

Table I.

Indexed XRD data of 8-hexyl-3-hydroxy-8-methyl-nortropanium hexafluorophosphate, C14H27NOPF6.

Only the peaks with I rel of 1 or greater are presented [a = 16.1879(6) Å, b = 11.4271(2) Å, c = 10.3966(5) Å, α = 66.4949(3)°, β = 94.5589(0)°, γ = 93.3092(4)°, unit-cell volume V = 1923.17 Å3, Z = 1, and space group P1]. All measured lines were indexed and are consistent with the P1 space group. The d-values were calculated using CuKα 1 radiation (λ = 1.54056 Å).

ACKNOWLEDGEMENT

Preparation of this paper was supported by the National Scientific Foundation of China (Grant Nos. 81373284 and 81102344).

References

Dewick, P. M. (2009). Medicinal Natural Products: A Biosynthetic Approach (Wiley, Chichester), 3rd ed.CrossRefGoogle Scholar
Goodman, E., Ketchum, J., and Kirby, R. (2010). Historical Contributions to the Human Toxicology of Atropine. Eximdyne. p. 120.Google Scholar
Harris, K. D. M. (2012). “Powder diffraction crystallography of molecular solids,” Top. Curr. Chem. 315, 133–178.CrossRefGoogle ScholarPubMed
Li, X., Gu, Y. Q., Yang, Y., Song, H., and Yao, S. (2012). “Novel brønsted-acidic ionic liquids based on benzothiazolium cations as catalysts for the acetalization reactions,” Adv. Mater. Res. 396, 1969–1974.Google Scholar
Figure 0

Figure 1. Structural formula of [C6Trop]+[PF6]−.

Figure 1

Figure 2. Synthesis procedure of [C6Trop]+[PF6]−.

Figure 2

Figure 3. XRD pattern of the [C6Trop]+[PF6]−, using CuKα1 radiation (λ = 1.54056 Å).

Figure 3

Table I. Indexed XRD data of 8-hexyl-3-hydroxy-8-methyl-nortropanium hexafluorophosphate, C14H27NOPF6.