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X-ray powder diffraction data for olmesartan medoxomil, C29H30N6O6

Published online by Cambridge University Press:  17 February 2016

Xiaochun Chen ,
Peixiao Tang ,
Shanshan Li ,
Kailin Xu  and
Hui Li
Xiaochun Chen
Affiliation:
Research Center of Analytical Instrumentation, Key laboratory of Bio-resource and Eco-environment, Ministry of Education, College of Life Science, Sichuan University, Chengdu 610064, China
Peixiao Tang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu, Sichuan 610065, China
Shanshan Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu, Sichuan 610065, China
Kailin Xu
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu, Sichuan 610065, China
Hui Li*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu, Sichuan 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 olmesartan medoxomil, C29H30N6O6, are reported [a = 12.3969(7) Å, b = 21.2667(3) Å, c = 10.9603(5) Å, α = γ = 90°, β = 101.38(9)°, unit-cell volume V = 2832.72 Å3, Z = 4 and space group P21/c ]. All measured lines were indexed and are consistent with the P21/c space group. No detectable impurities were observed.

Keywords

X-ray powder diffractionolmesartan medoxomil

Information

Type
Data Reports
Information
Powder Diffraction , Volume 31 , Issue 1 , March 2016 , pp. 73 - 76
Copyright
Copyright © International Centre for Diffraction Data 2016 

I. INTRODUCTION

Olmesartan medoxomil (OLM, Figure 1) [systematic name (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)-methyl-4-(2-hydroxypropan-2-yl)-2-propyl-1-(-[2-(2H-1,2,3,4-tetrazol-5-yl)-phenyl]phenylmethyl)-1H-imidazole-5-carboxylate] is an ester prodrug of olmesartan, which shows excellent pharmacological actions and good tolerance in clinical trials performed on hypertensive patients (Makoto et al., Reference Makoto, Toshio, Masahiro, Norio, Masaaki, Hiroaki and Hiroyuki1995; Smith et al., Reference Smith, Dubiel and Jones2005).

Figure 1.

Structural formula of OLM.

The unit-cell parameters determined by single-crystal methods were reported by Hiroaki et al. (Reference Hiroaki, Yoshiya, Takuro, Yasuo, Koichi, Yoshiko, Toshio, Makoto, Masahiro, Shuichi, Youji and Hiroyuki1996) and Richard et al. (Reference Richard, Eric, Thomas, Alaloor, Hemmige and Thomas2013). The average values of cell parameters are a = 12.358(8), b = 21.232(9), c = 10.909(7) Å, α = γ = 90°, β = 101.05(5)°, unit-cell volume V = 2809.48 Å3, Z = 4, and space group P21/c. Until now, the detailed X-ray powder diffraction data have not been reported.

II. EXPERIMENTAL

A. Sample preparation

OLM (99.2% purity) was obtained from Wuhan Biocar Biology Technology Co., Ltd. The single crystal of OLM was obtained in acetone–water solution (V/V = 2:1) at room temperature. The crystal was then grinded into powder (T melt = 173 °C) and sieved through a 200-mesh screen. The experimental density of the title compound is 1.338 g cm−3 at 25 °C. The elemental analysis showed that the content of C, N, and H was 15.06, 62.36, and 5.04%, respectively.

B. Diffraction data collection and reduction

An X'Pert PRO diffractometer (PANalytical Co., Ltd., The Netherlands) equipped with a PIXcel one-dimensional (1D) detector and CuKα 1 radiation (generator setting: 40 kV and 40 mA) was used to obtain the X-ray powder diffraction data. The diffractometer was operated in the angular range from 4° to 50°, 2θ with a step size of 0.013 13°2θ, and a counting time of 30 ms step−1. All data were collected at relative humidity of 60% and temperature of 25 °C.

Data evaluation was carried out using the software package Material Studio 4.2 (Accelrys Co., Ltd., USA). The diffractogram was indexed by discover tools (Xu et al., Reference Xu, Liang, Wu, Zhang, Tang and Li2014; Zhang et al., Reference Zhang, Pan, Xiao, Wu, Wang and Li2014) and refined according to the Pawley methods (Engel et al., Reference Engel, Wilke, König, Harris and Leusen1999). After refinement, the final R wp was converged at 5.59%.

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 2. Indexing results confirmed that OLM is monoclinic with space group P21/c and unit-cell parameters: a = 12.3969(7), b = 21.2667(3) Å, c = 10.9603(5) Å, α = γ = 90°, β = 101.38(9)°, unit-cell volume V = 2832.72 Å3, and Z = 4 (Table I). Using Pawley refinement, the powder pattern of OLM was successfully indexed. These results are in good agreement with those single-crystal data of OLM.

Figure 2.

X-ray powder diffraction pattern of the OLM recrystallized in acetone–water solution, using CuKα 1 radiation (λ = 1.540 56 Å).

Table I.

Indexed X-ray powder diffraction data of OLM, C29H30N6O6. Only the peaks with I obs of 1 or greater are reported [a = 12.3969(7), b = 21.2667(3), c = 10.9603(5) Å, α = γ = 90°, β = 101.38(9)°, unit-cell volume V = 2832.72 Å3, Z = 4, and space group P21/c]. All measured lines were indexed and are consistent with the P21/c space group. The d-values were calculated using CuKα 1 radiation (λ = 1.5406 Å).

SUPPLEMENTARY MATERIAL

To view supplementary material for this article, please visit http://dx.doi.org/10.1017/S0885715615000925

References

Engel, 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. Crystallogr. 32, 1169–1179.CrossRefGoogle Scholar
Hiroaki, Y., Yoshiya, A., Takuro, K., Yasuo, S., Koichi, F., Yoshiko, K., Toshio, S., Makoto, M., Masahiro, I., Shuichi, M., Youji, F., and Hiroyuki, K. (1996). “Nonpeptide angiotensin II receptor antagonists: synthesis, biological activities, and structure-activity relationships of imidazole-5-carboxylic acids bearing alkyl, alkenyl, and hydroxyalkyl substituents at the 4-position and their related compounds,” J. Med. Chem. 39, 323–338.Google Scholar
Makoto, M., Toshio, S., Masahiro, I., Norio, F., Masaaki, M., Hiroaki, Y., and Hiroyuki, K. (1995). “Pharmacology of CS-866, a novel nonpeptide angiotensin II receptor antagonist,” Eur. J. Pharmacol. 285, 181–188.Google Scholar
Richard, B., Eric, H., Thomas, G., Alaloor, S. D., Hemmige, S. Y., and Thomas, S. (2013). “Redetermination of the structure of olmesartan medoxomil, (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)-methyl-4-(2-hydroxypropan-2-yl)-2-propyl-1-(-[2-(2H-1,2,3,4-tetrazol-5-yl)-phenyl]phenylmethyl)-1H-imidazole-5-carboxylate, C29H30N6O6 ,” Z. Kristallogr. NCS 228, 141–143.Google Scholar
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Xu, K. L., Liang, B., Wu, X. Q., Zhang, L. L., Tang, P. X., and Li, H. (2014). “X-ray powder diffraction data for levetiracetam,” Powder Diffr. 29, 51–52.CrossRefGoogle Scholar
Zhang, L. L., Pan, Q. Q., Xiao, D., Wu, X. Q., Wang, Q., and Li, H. (2013). “X-ray powder diffraction data for deoxyschisandrin,” Powder Diffr. 28, 231–233.CrossRefGoogle Scholar
Figure 0

Figure 1. Structural formula of OLM.

Figure 1

Figure 2. X-ray powder diffraction pattern of the OLM recrystallized in acetone–water solution, using CuKα1 radiation (λ = 1.540 56 Å).

Figure 2

Table I. Indexed X-ray powder diffraction data of OLM, C29H30N6O6. Only the peaks with Iobs of 1 or greater are reported [a = 12.3969(7), b = 21.2667(3), c = 10.9603(5) Å, α = γ = 90°, β = 101.38(9)°, unit-cell volume V = 2832.72 Å3, Z = 4, and space group P21/c]. All measured lines were indexed and are consistent with the P21/c space group. The d-values were calculated using CuKα1 radiation (λ = 1.5406 Å).

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