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X-ray powder diffraction data for drospirenone, C24H30O3

Published online by Cambridge University Press:  03 November 2015

Qing Wang ,
Qiao Mei Sun ,
Shan Shan Li ,
Liu Qi Guo  and
Hui Li
Qing Wang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qiao Mei Sun
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Shan Shan Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Liu Qi Guo
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 drospirenone, C24H30O3, are reported [a = 12.897(1) Å, b = 12.618(1) Å, c = 12.252(1) Å, α = β = γ = 90°, unit-cell volume V = 1994.13 Å3, Z = 4, ρ cal = 1.229 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

X-ray powder diffractiondrospirenone

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 31 , Issue 1 , March 2016 , pp. 63 - 65
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Copyright
Copyright © International Centre for Diffraction Data 2015 

I. INTRODUCTION

The title compound drospirenone (Figure 1), systematic name 6,7,15,16-dimethylen-3-oxo-17-pregn-4-ene-2,17-carbo-lactone, is a novel progestogen with anti-mineralocorticoid and anti-androgenic characteristics (Muhn et al., Reference Muhn, Fuhrmann, Fritzemeier, Krattenmacher and Schillinger1995; Cagnacci et al., Reference Cagnacci, Piacenti, Zanin, Xholli and Tirelli2014). Drospirenone can counteract the estrogen-induced stimulation of the reninangiotensin–aldosterone system and blocks testosterone from binding to androgen receptors (Krattenmacher, Reference Krattenmacher2000). Hence, it has the potential to reduce body weight, blood pressure, and low-density lipoprotein levels and to enhance high-density lipoprotein levels.

Figure 1.

Structural formula of drospirenone.

The single crystallographic data of drospirenone [a = 12.236(2) Å, b = 12.592(2) Å, c = 12.879(2) Å, α = β = γ = 90°, unit-cell volume V = 1984.25 Å3, Z = 4, ρ cal = 1.227 g cm−3, and space group P212121] was obtained by Parisi et al. (Reference Parisi, Freire, Rusjan, Moreno, Bonadeo and Vega2013). To date, the detailed X-ray powder diffraction (XRD) data for drospirenone have not been reported.

II. EXPERIMENTAL

A. Sample preparation

The title compound was purchased from Zhejiang Xianju Pharmaceutical Co., Ltd., China (high-performance liquid chromatography, HPLC ≥ 98%) and characterized by ultraviolet and Fourier transform infrared spectrometer. The melting point and measured density of drospirenone are 200–201 °C and 1.236 g cm−3, respectively. Crystallization of drospirenone at room temperature was successful using ethyl acetate as solvent. Then, part of crystals was dried and ground into powder.

B. Diffraction data collection and reduction

XRD measurement was performed at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with a PIXcel one-dimensional detector and CuKα radiation (generator setting: 40 kV and 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 30 ms step−1.

The software package Material Studio 4.2 (Accelrys Co., Ltd., USA) was used to process the data in the State Key Laboratory of Polymer Materials Engineering (Sichuan University, China). The XRD pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component (Li et al., Reference Li, Wu, Pan, Cheng and Li2014). Automatic indexing results were obtained by the X-Cell method (Neumann, Reference Neumann2003; Wu et al., Reference Wu, Tang, Li, Zhang and Li2014). The indexing results were then refined using Pawley, which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental powder XRD pattern (Wang et al., Reference Wang, Zhang, Wu, Pan, Su and Li2013).

C. Single-crystal XRD

XRD data for drospirenone were collected on an Xcalibur, Eos diffractometer. The crystal was kept at 293.15 K during data collection. The structure was solved with olex2 (Dolomanov et al., Reference Dolomanov, Bourhis, Gildea, Howard and Puschmann2009), a structure solution program using charge flipping and refined with the ShelXL (Sheldrick, Reference Sheldrick2008) refinement package using least-squares minimization.

III. RESULTS

Pawley refinement results confirmed that drospirenone is orthorhombic with space group P212121 and unit-cell parameters: a = 12.897(1) Å, b = 12.618(1) Å, c = 12.252(1) Å, α = β = γ = 90°, unit-cell volume V = 1994.13 Å3, Z = 4, and ρ cal = 1.229 g cm−3. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, and Δ2θ are listed in Table I.

TABLE I.

Indexed XRD data for drospirenone, C24H30O3. The d-values were calculated using CuKα 1 radiation (λ = 1.540 56 Å).

The single crystallographic data of drospirenone [a = 12.2379(5) Å, b = 12.6069(8) Å, c = 12.8921(8) Å, α = β = γ = 90°, unit-cell volume V = 1989.01(19) Å3, Z = 4, and ρ cal = 1.224 g cm−3] and the experimental data are listed in Table SI.

The comparison of XRD pattern with the simulated patterns of single-crystal structure and Parisi's is shown in Figure 2. Results showed that both single-crystal and powder diffraction methods can get similar structure data.

Figure 2.

XRD pattern of drospirenone using CuKα radiation (black line) and the simulated pattern of single-crystal structure (red line) and Parisi's (blue line).

SUPPLEMENTARY MATERIALS AND METHODS

The supplementary material for this article can be found at http://dx.doi.org/10.1017/S0885715615000822

References

Cagnacci, A., Piacenti, I., Zanin, R., Xholli, A., and Tirelli, A. (2014). “Influence of an oral contraceptive containing drospirenone on insulin sensitivity of healthy women,” Eur. J. Obstet. Gynecol. Reprod. Biol. 178, 48–50.Google Scholar
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Krattenmacher, R. (2000). “Drospirenone: pharmacology and pharmacokinetics of a unique progestogen,” Contraception 62, 29–38.CrossRefGoogle ScholarPubMed
Li, S. S., Wu, X. Q., Pan, Q. Q., Cheng, Q., and Li, H. (2014). “Comparison of the accuracy of powder and single crystal X-ray diffraction techniques in determining organic crystal structure,” Chin. Sci. Bull. 59, 497–501.Google Scholar
Muhn, P., Fuhrmann, U., Fritzemeier, K. H., Krattenmacher, R., and Schillinger, E. (1995). “Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity,” Ann. NY. Acad. Sci. 761, 311–335.CrossRefGoogle ScholarPubMed
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Wu, X. Q., Tang, P. X., Li, S. S., Zhang, L. L., and Li, H. (2014). “X-ray powder diffraction data for meloxicam, C14H13N3O4S2 ,” Powder Diffr. 29, 196–198.Google Scholar
Figure 0

Figure 1. Structural formula of drospirenone.

Figure 1

TABLE I. Indexed XRD data for drospirenone, C24H30O3. The d-values were calculated using CuKα1 radiation (λ = 1.540 56 Å).

Figure 2

Figure 2. XRD pattern of drospirenone using CuKα radiation (black line) and the simulated pattern of single-crystal structure (red line) and Parisi's (blue line).

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