Hostname: page-component-74656f9884-8r8nv Total loading time: 0 Render date: 2026-11-06T22:56:50.952Z Has data issue: false hasContentIssue false
  • English
  • Français

X-ray powder diffraction data for norandrostenedione

Published online by Cambridge University Press:  29 May 2013

Pei Xiao Tang ,
Xiao Qing Wu ,
Qing Qing Pan ,
Li Li Zhang ,
Qiang Cheng  and
Hui Li
Pei Xiao Tang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xiao Qing Wu
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qing Qing Pan
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Li Li Zhang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qiang Cheng
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

X-ray powder diffraction data, unit-cell parameters, and space group for norandrostenedione, C18H24O2, are reported [a = 26.3955(15) Å, b = 8.0476(4) Å, c = 7.3002(3) Å, α = β = γ = 90°, unit-cell volume V = 1550.71 Å3, Z = 4, and space group P212121]. All measured lines were indexed and are consistent with the P212121 space group. No detectable impurity was observed.

Keywords

X-ray powder diffractionnorandrostenedioneanabolic steroid

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 28 , Issue 4 , December 2013 , pp. 302 - 304
Copyright
Copyright © International Centre for Diffraction Data 2013 

I. INTRODUCTION

The title compound norandrostenedione (Figure 1), systematic name 19-norandrost-4-ene-3, 17-dione, an anabolic steroid whose use in sport is prohibited by the World Anti-Doping Agency (WADA), is an intermediate for contraceptive drugs such as norethindrone, androlin, and nandrolone benzyl propionate. In the process of synthesizing norethindrone from the norandrostenedione matrix, norandrostenedione makes the synthesized compounds impure and leaves residues in norethisterone tablets (Walker, Reference Walker, Cowan, James, Lau and Kicman2009). Therefore, it is very important to detect and control the percentage of norandrostenedione as well as make certain of its crystal structure.

Figure 1.

Structural formula of norandrostenedione.

Our lab has reported the crystal structure of normethisterone and gestonoronacetat (Wu et al., Reference Wu, Tang, Pan, Cheng and Li2013). Both of them are steroid progestational hormones. The three compounds have a similar parent structure, but their crystal structures have many differences.

Presently, the crystal structure of norandrostenedione has not been reported.

II. EXPERIMENTAL

A. Sample preparation

The title compound was obtained from Zhejiang Guangersheng Import & Export Co., Ltd. It was re-crystallized in 95% ethanol, then, dried and ground into powder. The structure of norandrostenedione was characterized by IR, UV, and high-performance liquid chromatography (HPLC).

B. Diffraction data collection and reduction

The diffraction pattern for the title compound was collected at room temperature using an X'Pert PRO diffractometer (PANalytical) with an X'celerator detector and CuKα 1 radiation (λ = 1.540 56 Å, generator setting: 40 kV, 40 mA). The diffraction data were collected over the angular range from 5 to 50°2θ with a step size of 0.013 13°2θ and a counting time of 10.16 ms/step. Data evaluation was performed using the software package Material Studio 4.2 (Accelrys Co. Ltd, USA).

The first stage of structure determination involves determination of the unit cell {a, b, c, α, β, γ} by analysis of the peak positions in the powder XRD pattern [this task is referred to as “indexing” the powder pattern, and involves assigning the Miller indices (h, k, l) to each observed peak in the experimental powder XRD pattern] (Harris, Reference Harris2012). Indexing was carried out using peak positions obtained from the powder diffraction profiles by the X-cell method then the indexing result was refined with the type of Pawley (Pan et al., Reference Pan, Guo, Duan, Cheng and Li2012). MC/SA search algorithm in Powder Solve package (Engle et al., Reference Engle, Wilke, König, Harris and Leusen1999) was used to constantly adjust the conformation, position, and orientation of the trial model in the unit cell of norandrostenedione, and then the result of Powder Solve was refined by Rietveld refinement techniques based on the experimental X-ray powder diffraction pattern. In the Rietveld refinement (Young, Reference Young1993), variables defining the structural model and the powder diffraction profile were adjusted by least squares methods in order to obtain an optimal fit between the experimental pattern and the calculated pattern. After Rietveld refinement, the final R wp of the structure was converged at 9.66%.

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 2. Indexing results show that norandrostenedione is orthorhombic with the space group P212121 and unit-cell parameters: a = 26.3955(15) Å, b = 8.0476(4) Å, c = 7.3002(3) Å, α = β = γ = 90°, unit-cell volume V = 1550.71 Å3, Z = 4, and space group P212121 (Table I). After Rietveld refinement, the structure of norandrostenedione was solved. The final results were compared with single-crystal data, which were collected on an Oxford Diffraction Xcalibur Nova system with MoKα radiation (λ = 0.710 73 Å) at room temperature and the θ from 3.05–28.77°, the deviations of the two methods were between 0.011% and 0.039%. All lines of powder and single-crystal data were indexed and are consistent with the P212121 space group.

Figure 2.

X-ray powder diffraction pattern of norandrostenedione, using CuKα 1 radiation (λ = 1.540 56 Å).

Table I.

Indexed X-ray powder diffraction data of norandrostenedione, C18H24O2. Only the peaks with I rel of 1 or greater are presented reported [a = 26.3955(15) Å, b = 8.0476(4) Å, c = 7.3002(3) Å, α = β = γ = 90°, unit-cell volume V = 1550.71 Å3, Z = 4, and space group P212121]. All measured lines were indexed and are consistent with the P212121 space group. The d-values were calculated using CuKα1 radiation (λ = 1.540 56 Å).

References

Engle, G. E., Wilke, S., König, O., Harris, K. D. M., and Leusen, F. J. J. (1999). “Powder solve-a complete package for crystal structure solution from powder diffraction patterns,” J. Appl. Crystal. 32, 1169–1179.CrossRefGoogle Scholar
Harris, K. D. M. (2012). “Powder diffraction crystallography of moleculars,” Top. Curr. Chem. 315, 133–178. [DOI: i10.1007/128_2011_251].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.CrossRefGoogle Scholar
Walker, C. J., Cowan, D. A., James, V. H., Lau, J. C., Kicman, A. T. (2009). “Doping in sport-2. Quantification of the impurity 19-norandrostenedione in pharmaceutical preparations of norethisterone,” Steroids 74(3), 335–340.CrossRefGoogle ScholarPubMed
Wu, X. Q., Tang, P. X., Pan, Q. Q., Cheng, Q., & Li, H. (2013). “Crystal structure determination of three polycyclic compounds and comparative rietveld refinement between MS and GSAS programs,” Chin, Sci. Bull. 58, 1–5.Google Scholar
Young, R. A. (1993). The Rietveld Method, IUCr Monographies of Crystallography (Wiley, Oxford).CrossRefGoogle Scholar
Figure 0

Figure 1. Structural formula of norandrostenedione.

Figure 1

Figure 2. X-ray powder diffraction pattern of norandrostenedione, using CuKα1 radiation (λ = 1.540 56 Å).

Figure 2

Table I. Indexed X-ray powder diffraction data of norandrostenedione, C18H24O2. Only the peaks with Irel of 1 or greater are presented reported [a = 26.3955(15) Å, b = 8.0476(4) Å, c = 7.3002(3) Å, α = β = γ = 90°, unit-cell volume V = 1550.71 Å3, Z = 4, and space group P212121]. All measured lines were indexed and are consistent with the P212121 space group. The d-values were calculated using CuKα1 radiation (λ = 1.540 56 Å).