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X-ray powder diffraction data for norethisterone enanthate, C27H38O3

Published online by Cambridge University Press:  12 January 2021

Jingwen Fan ,
Zhicheng Zha ,
Qing Wang Open the ORCID record for Qing Wang [Opens in a new window]  and
Shoujun Zheng
Jingwen Fan
Affiliation:
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
Zhicheng Zha
Affiliation:
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
Qing Wang*
Affiliation:
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
Shoujun Zheng
Affiliation:
Medical College of Panzhihua University, Panzhihua 617000, China
*
a)Author to whom correspondence should be addressed. Electronic mail: qingwang@yzu.edu.cn

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for norethisterone enanthate, C27H38O3, are reported [a = 6.191(4) Å, b = 12.711(3) Å, c = 31.396(2) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 2471.16 Å3, Z = 4, ρcal = 1.104 g cm−3, and space group P212121]. All measured lines were indexed and are consistent with the P212121 space group. No detectable impurities were observed.

Keywords

norethisterone enanthatesteroidX-ray powder diffraction

Information

Type
Data Report
Information
Powder Diffraction , Volume 36 , Issue 1 , March 2021 , pp. 65 - 67
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Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

I. INTRODUCTION

Norethisterone enanthate (Figure 1), a fatty acid ester of norethisterone, is a widely used long-acting intramuscular depot contraceptive drug (Ravinder et al., Reference Ravinder, Shatrugna, Nair and Sivakumar1997). It can prevent conception by inhibiting ovulation. This drug also can result in high suppression of spermatogenesis, which could be attributed to its constant suppression of gonadotropins on testis (Behre et al., Reference Behre, Zitzmann, Anderson, Handelsman, Lestari, McLachlan, Meriggiola, Misro, Noe, Frederick, Festin, Habib, Vogelsong, Callahan, Linton and Colvard2016).

Figure 1.

Molecular diagram of norethisterone enanthate.

In order to better understand the difference between norethisterone enanthate and norethindrone acetate in their binding ability to human serum albumin, we analyzed the single-crystal structure of norethisterone enanthate (Wang et al., Reference Wang, Ma, He, Li and Li2015b). The single crystallographic data at 110 K of norethisterone enanthate [a = 6.09236(14) Å, b = 12.7347(3) Å, c = 30.1234(8) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 2337.10(10) Å3, Z = 4, ρ cal = 1.167 g cm−3, and space group P212121] had been deposited with the Cambridge Crystallographic Data Center (CCDC) with a supplementary publication number of CCDC-1030994 (Wang et al., Reference Wang, Ma, He, Li and Li2015a). To date, the detailed X-ray powder diffraction (PXRD) data for norethisterone enanthate have not been reported.

II. EXPERIMENTAL

A. Sample preparation

The sample was purchased from J&K Scientific (Beijing, People's Republic of China). The melting point and measured density of norethisterone enanthate are 69–70 °C and 1.083 g cm−3, respectively. The crystallization of norethisterone enanthate at room temperature was successful using a mixture of 75% ethanol in water as a solvent. The crystals have a prismatic and transparent crystal structure. Then, the crystals were dried, smashed, screened through 75 μm mesh size, and pressed flat to a zero background plate.

B. Diffraction data collection and reduction

PXRD was performed at 298 K using an X'Pert PRO diffractometer (PANalytical Co., Ltd., the Netherlands) with a PIXcel 1D detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected over the angular range from 4° to 50° 2θ with a step size of 0.01313° 2θ and a counting time of 30 ms step−1. Some peaks in the diffraction pattern display asymmetry may be due to stacking faults (Langford and Louër, Reference Langford and Louër1991).

The software package Material Studio 8.0 (Accelrys Co., Ltd., CA, USA) was used to process the data in the Analytical & Testing Center (Sichuan University, Chengdu, China). The PXRD pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component. The Peaks tab was used to automatically search for peaks in the diffraction pattern. Automatic indexing results were obtained by X-cell method (Neumann, Reference Neumann2003). The indexing results were then refined using Pawley (R wp = 9.34%) (Pawley, Reference Pawley1981), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental PXRD pattern. All measured lines in the raw data were indexed. The method of determination of intensity was peak height above background.

III. RESULTS

Pawley refinement results confirmed that norethisterone enanthate is orthorhombic with space group P212121 and unit-cell parameters: a = 6.191(4) Å, b = 12.711(3) Å, c = 31.396(2) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 2471.16 Å3, Z = 4, ρ cal = 1.104 g cm−3, and space group P212121. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, Δ2θ are listed in Table I.

Table I.

Indexed X-ray powder diffraction data for norethisterone enanthate

The d-values were calculated using CuKα 1 radiation (λ = 1.5405981 Å).

Due to the powder diffraction data being collected at 298 K and the single-crystal diffraction data being measured at 110 K, the cell parameters, volume, and calculated density exhibit slight differences. The deviation in results observed for the two methods were between 0.10% and 5.74%. Based on the single-crystal diffraction data, the simulated pattern of norethisterone enanthate was generated by using Mercury. The comparison of the experimental PXRD pattern with the simulated pattern is shown in Figure 2. The shifts in peak positions for the calculated pattern were due to differences in the temperature of measurement.

Figure 2.

X-ray powder diffraction pattern of norethisterone enanthate using CuKα radiation at 298 K (black line) and the simulated pattern of the crystal structure at 110 K (red line).

IV. DEPOSITED DATA

The C27H38O3_diffraction_pattern.raw data file has been deposited with ICDD. You may request this data from ICDD at info@icdd.com.

Acknowledgement

This work was supported by the Scientific Research Staring Foundation of Yangzhou University and Panzhihua University.

References

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Figure 0

Figure 1. Molecular diagram of norethisterone enanthate.

Figure 1

Table I. Indexed X-ray powder diffraction data for norethisterone enanthate

Figure 2

Figure 2. X-ray powder diffraction pattern of norethisterone enanthate using CuKα radiation at 298 K (black line) and the simulated pattern of the crystal structure at 110 K (red line).