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X-ray powder diffraction data for niclosamide, C13H8N2O4Cl2

Published online by Cambridge University Press:  13 August 2015

Liu Qi Guo ,
Kai Lin Xu ,
Xiao Li Ma ,
Shan Shan Li  and
Hui Li
Liu Qi Guo
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Kai Lin Xu
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xiao Li Ma
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Shan Shan Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Hui Li*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
*
a) Author to whom correspondence should be addressed. Electronic mail: lihuilab@sina.com

Abstract

Experimental X-ray powder diffraction data, unit-cell parameters, and space group for niclosamide, C13H8N2O4Cl2, are reported [a = 13.571(1) Å, b = 7.181(8) Å, c = 13.742(3) Å, β = 97.984(7)°, unit-cell volume V = 1326.40 Å3, Z = 4, and space group P21/c]. All measured lines were indexed and are consistent with the P21/c space group. No detectable impurity was observed.

Keywords

X-ray powder diffractionniclosamide

Information

Type
Data Reports
Information
Powder Diffraction , Volume 30 , Issue 4 , December 2015 , pp. 375 - 377
Copyright
Copyright © International Centre for Diffraction Data 2015 

I. INTRODUCTION

Niclosamide (chemical name 2, 5-dichloro-4-nitrosalicylanilide, Figure 1, hereinafter abbreviated NCL), is a frequently-used anthelmintic drug to restrain the infestation of multiple worms (Weinbach & Garbus, Reference Weinbach and Garbus1969). It is also used for therapeutic application including antibacterial and antitumour activities (Helfman, Reference Helfman2011), as well as inhibits the replication of several acute respiratory syndrome coronavirus (Wu et al., Reference Wu, Jan, Chen, Hsieh, Hwang, Liu, Liu, Huang, Chen, Hong, Lin, Chao and Hsu2004).

Figure 1.

Structural formula of NCL.

The single-crystal structure of NCL (a = 13.485(2) Å, b = 7.0669(11) Å, c = 13.510(2) Å, β = 98.345(2)°, unit-cell volume V = 1273.9(3) Å3, Z = 4, and space group P21/c) was first reported by Sanphui (Sanphui et al., Reference Sanphui, Kumar and Nangia2012). But detailed X-ray powder diffraction data for NCL have not been reported in the literature. The X-ray powder diffraction data of NCL were collected, analyzed, and evaluated in this paper.

II. EXPERIMENTAL

A. Sample preparation

The title compound, NCL (99% purity), in powder form was obtained from Chengdu Aikeda Pharmaceutical Co., Ltd, its melting range is 227–229°C and density is 1.625 g cm−3. It was recrystallized, dried, and then sieved by a 200-mesh screen to obtain the appropriate particle size (Figure 2). The NCL sample was characterized by high-performance liquid chromatography, Ultraviolet spectroscopy, and Fourier Transform Infrared Spectrometer.

Figure 2.

(Color online) Optical photomicrograph of NCL.

B. Powder Diffraction data collection and reduction

The diffraction pattern for the NCL powder was collected at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with an X'celerator detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected in the angular range from 4° to 50°2θ with a step size of 0.01313°2θ and a counting time of 100 ms step−1. Data structure solution was performed using the software package Material Studio 4.2 (Accelrys Co., Ltd., CA, USA).

Through analyzing the peak positions in the powder X-ray diffraction (PXRD) pattern by X-Cell method from “Powder Indexing”, the preliminary unit-cell parameters were obtained. The indexing results were then refined with the type of Pawley (Pan et al., Reference Pan, Guo, Duan, Cheng and Li2012), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental PXRD pattern (Harris, Reference Harris2012). In order to obtain detailed X-ray powder diffraction data, variables defining the structural model and the powder diffraction profiles from the results of Powder Indexing and the experiment powder diffraction pattern were recurrently refined by Pawley refinement (Pawley, Reference Pawley1981) techniques. After Pawley refinement, the final R wp of the spectrogram was converged to 4.20%.

III. RESULTS

The diffraction patterns of recrystallized NCL matched a pattern collected which corresponds to a pattern simulated using the single-crystal structure data (Figure 3). Indexing results confirmed that NCL is monoclinic with space group P21/c and unit-cell parameters: a = 13.571(1) Å, b = 7.181(8) Å, c = 13.742(3) Å, β = 97.984(7)°, unit-cell volume V = 1326.40 Å3, Z = 4, and space group P21/c (Table I). Using Pawley refinement, the detailed X-ray powder diffraction data of NCL was successfully determined.

Figure 3.

(Color online) Comparison of the powder diffraction pattern of NCL recrystallized in methanol (black) with the pattern simulated from the single-crystal data (red).

Table I.

X-ray powder diffraction data of NCL (C13H8N2O4Cl2).

The d-values were calculated using CuKα 1 radiation (λ = 1.540 56 Å).

ACKNOWLEDGEMENTS

We acknowledge financial support by the National Development and Reform Commission and Education of China (Grant No. 2014BW011).

SUPPLEMENTARY MATERIALS

For supplementary material for this article, please visit http://dx.doi.org/10.1017/S0885715615000615

References

Harris, K. D. M. (2012). “Powder diffraction crystallography of molecular solids,” Top. Curr. Chem. 315, 133–178.Google Scholar
Helfman, D. M. (2011). “Niclosamide: an established antihelminthic drug as a potential therapy against S100A4-mediated metastatic colon tumors,” J. Natl Cancer Instrum. 103, 991–992.Google Scholar
Pan, Q. Q., Guo, P., Duan, J., Cheng, Q., and Li, H. (2012). “Comparative crystal structure determination of griseofulvin: powder X-ray diffraction versus single-crystal X-ray diffraction,” Chin. Sci. Bull. 57, 3867–3871.Google Scholar
Pawley, G. S. (1981). “Unit-cell refinement from powder diffraction scans,” J. Appl. Crystallogr. 14(6), 357–361.Google Scholar
Sanphui, P., Kumar, S. S., and Nangia, A. (2012). “Pharmaceutical cocrystals of niclosamide,” Cryst. Growth Des. 12, 4588–4599.Google Scholar
Weinbach, E. C. and Garbus, J. (1969). “Mechanism of action of reagents that uncouple oxidative phosphorylation,” Nature 221, 1016–1018.Google Scholar
Wu, C.-J., Jan, J.-T., Chen, C.-M., Hsieh, H.-P., Hwang, D.-R., Liu, H.-W., Liu, C.-Y., Huang, H.-W., Chen, S.-C., Hong, C.-H., Lin, R.-K., Chao, Y.-S., and Hsu, J. T. A. (2004). “Inhibition of severe acute respiratory syndrome coronavirus replication by niclosamide,” Antimicrob. Agents Chemother. 48, 2693–2696.Google Scholar
Figure 0

Figure 1. Structural formula of NCL.

Figure 1

Figure 2. (Color online) Optical photomicrograph of NCL.

Figure 2

Figure 3. (Color online) Comparison of the powder diffraction pattern of NCL recrystallized in methanol (black) with the pattern simulated from the single-crystal data (red).

Figure 3

Table I. X-ray powder diffraction data of NCL (C13H8N2O4Cl2).

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