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X-ray powder diffraction data for norethindrone

Published online by Cambridge University Press:  10 October 2013

Pei Xiao Tang ,
Xiao Qing Wu ,
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
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

Experimental X-ray powder diffraction data, unit-cell parameters, and space group for norethindrone, C20H26O2, are reported [a = 20.7484(12) Å, b = 12.1678(9) Å, c = 6.5561(2) Å, α = β = γ = 90°, unit-cell volume V = 1655.17(16) 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 diffractionnorethindrone

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 29 , Issue 1 , March 2014 , pp. 46 - 47
Copyright
Copyright © International Centre for Diffraction Data 2013 

I. INTRODUCTION

The title compound norethindrone (Figure 1), systematic name 17-alpha-ethynyl-17-beta-hydroxyoestr-4-en-3-one, an anabolic steroid drug used as short-acting oral contraceptives, post coital contraceptives, treatment of dysfunctional uterine bleeding and infertility, is a chemical synthetic drug. As time flies, there have turned up a number of different methods of birth control, but oral contraceptives still accounts for about 14% of those modern means (The United Nations Population Division, 2001). In the process of obtaining norethindrone from intermediates like norandrostenedione, the reactant makes the synthesized compounds impurity and residues in norethindrone tablets (Walker et al., Reference Walker, Cowan, James, Lau and Kicman2009). So it is very important to detect and control the percentage of norethindrone as well as make certain of its powder diffraction data.

Figure 1.

Structural formula of norethindrone.

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

At present, the single-crystal structure of norethindrone can be seen from a search in the Cambridge Structural Database (CSD). But the powder diffraction data has not been published.

II. EXPERIMENTAL

A) Sample preparation

The title compound was obtained from Hubei Sanjing Bio-Tech Co., Ltd. It was re-crystallized in 95% ethanol, then, dried and grinded into powder. The structure of norethindrone was characterized by IR, UV, high-performance liquid chromatography (HPLC) and P4 single x-ray diffractometer.

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 6.0 (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 X-ray diffraction (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 X-Cell method then the indexing result was refined with the type of Pawley (Pan et al., Reference Pan, Guo, Duan, Cheng and Li2012). After Pawley refinement of the unit cell, the final R wp of the structure was converged at 8.30%.

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 2. Indexing results show that norethindrone is orthorhombic with space group P212121 and unit-cell parameters: a = 20.7484(12) Å, b = 12.1678(9) Å, c = 6.5561(2) Å, α = β = γ = 90°, unit-cell volume V = 1655.17(16) Å3, Z = 4, space group P212121 (Table I). After Pawley refinement, the unit-cell parameters of norethindrone were solved. The results were compared with single-crystal data [a = 20.7713(12) Å, b = 12.1600(9) Å, c = 6.5448(2) Å, α = β = γ = 90°, unit-cell volume V = 1653.06(16) Å3, Z = 4, space group P212121] which were collected on an Oxford Diffraction Xcalibur Nova system with MoKα radiation (λ = 0.710 73 Å) at room temperature and the 2θ from 6.528 to 52.696°, the deviations of the two methods were between 0.064 to 0.128%. 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 the norethindrone, using CuKα 1 radiation (λ = 1.540 56 Å).

Table I.

Indexed X-ray powder diffraction data of norethindrone, C20H26O2. Only the peaks with I rel of 1 or greater are presented reported [a = 20.7484(12) Å, b = 12.1678(9) Å, c = 6.5561(2) Å, α = β = γ = 90°, unit-cell volume V = 1655.17(16) 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 CuK α 1 radiation (λ = 1.540 56 Å).

References

Harris, K. D. M. (2012). “Powder diffraction crystallography of molecular solids,” 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. (China). 57(30), 3867–3871.Google Scholar
Tang, P. X., Wu, X. Q., Pan, Q. Q., Zhang, L. L., Cheng, Q., and Li, H. (2013). “X-ray powder diffraction data for norandrostenedione,” Powder Diffr. (USA). (doi:10.1017/S088571561300047X).Google Scholar
The United Nations Population Division, (2001). World Contraceptive Use.Google Scholar
Walker, C. J., Cowan, D. A., James, V. H., Lau, J. C., and Kicman, A. T. (2009). “Doping in sport-2. Quantification of the impurity 19-norandrostenedione in pharmaceutical preparations of norethisterone”, Steroids 74(3), 335–340.Google Scholar
Wu, X. Q., Tang, P. X., Pan, Q. Q., Cheng, Q., and Li, H. (2013). “Crystal structure determination of three polycyclic compounds and comparative Rietveld refinement between MS and GSAS programs,” Chin. Sci. Bull 58, 2430–2434.Google Scholar
Figure 0

Figure 1. Structural formula of norethindrone.

Figure 1

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

Figure 2

Table I. Indexed X-ray powder diffraction data of norethindrone, C20H26O2. Only the peaks with Irel of 1 or greater are presented reported [a = 20.7484(12) Å, b = 12.1678(9) Å, c = 6.5561(2) Å, α = β = γ = 90°, unit-cell volume V = 1655.17(16) 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 CuK α1 radiation (λ = 1.540 56 Å).