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X-ray powder diffraction data for ertapenem side chain, C20H19N3O7S

Published online by Cambridge University Press:  18 May 2017

Xiang Lin ,
Wei Ling Zhuo ,
Qiao Hong Du ,
Xi Lin Peng  and
Hui Li
Xiang Lin
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Wei Ling Zhuo
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qiao Hong Du
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xi Lin Peng
Affiliation:
Sinopharm Chuankang Pharmaceutical Co., Ltd., Chengdu 611731, 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 ertapenem side chain, C20H19N3O7S, are reported [a = 4.907(6) Å, b = 18.686(3) Å, c = 22.071(1) Å, α = γ = 90°, β = 90.759(5)°, unit-cell volume V = 2023.82 Å3, Z = 4, ρ cal = 1.462 g cm−3, and space group P21/c]. All measured lines were indexed and are consistent with the P21/c space group. No detectable impurity was observed.

Keywords

X-ray powder diffractionertapenem side chainintermediate

Information

Type
Data Reports
Information
Powder Diffraction , Volume 32 , Issue 3 , September 2017 , pp. 203 - 205
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Copyright
Copyright © International Centre for Diffraction Data 2017 

I. INTRODUCTION

Ertapenem is an important first-line carbapenem antibiotic. It provides a new, potent, and convenient choice in the treatment of mixed aerobic/anaerobic polymicrobial infections (Shah and Isaacs, Reference Shah and Isaacs2003). Ertapenem side chain (Figure 1) is the key intermedium for synthesis of ertapenem, and is also the important raw material for a new ertapenem intermediate by reacting with carbapenem derivative (Sheng, Reference Sheng2014).

Figure 1.

Structural formula of ertapenem side chain.

Presently, the detailed X-ray powder diffraction (XRD) data for ertapenem side chain have not been reported.

II. EXPERIMENTAL

A. Sample preparation

Ertapenem side chain (High Performance Liquid Chromatography [HPLC] ≥ 98%), was obtained from Shandong Xiya chemical industry Co., Ltd., Shandong, China. The melting point and measured density of ertapenem side chain are 258–259 °C and 1.449 g cm−3, respectively. The Fourier transform-infrared (FT-IR) spectrum of ertapenem side chain was presented in Supplementary Figure SI.

B. Diffraction data collection and reduction

The diffraction pattern for ertapenem side chain was collected at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., The 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 4° to 50°2θ with a step size of 0.01313°2θ and a counting time of 50 ms per step (Figure 2).

Figure 2.

XRD pattern of ertapenem side chain using CuKα radiation.

Data evaluation was performed using the software package Material Studio 8.0 (Accelrys Co., Ltd., San Diego, California, USA) in the Analytical & Testing Center (Sichuan University, Chengdu, China). The XRD pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα2 component. Automatic indexing results were obtained by X-Cell method (Neumann, Reference Neumann2003). The indexing results were then refined using Pawley (Pawley, Reference Pawley1981), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental XRD pattern.

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 2. Indexing results show that ertapenem side chain is monoclinic with the space group P21/c and unit-cell parameters: a = 4.907(6) Å, b = 18.686(3) Å, c = 22.071(0) Å, α = γ = 90°, β = 90.759(5)°, unit-cell volume V = 2023.82 Å3, Z = 4 and ρ cal = 1.462 g cm−3. 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 XRD data for ertapenem side chain. The d-values were calculated using CuKα 1 radiation (λ = 1.54056 Å).

SUPPLEMENTARY MATERIAL

The supplementary material for this article can be found at https://doi.org/10.1017/S0885715617000513.

ACKNOWLEDGEMENTS

This work was supported by the Large-scale Science Instrument Shareable Platform Construction of Sichuan Province (Grant No. 2015JCPT0005-15010102).

References

Neumann, M. A. (2003). “X-cell: a novel indexing algorithm for routine tasks and difficult cases,” J. Appl. Crystallogr. 36, 356–365.CrossRefGoogle Scholar
Pawley, G. S. (1981). “Unit-cell refinement from powder diffraction scans,” J. Appl. Crystallogr. 14(6), 357–361.CrossRefGoogle Scholar
Shah, P. M. and Isaacs, R. D. (2003). “Ertapenem, the first of a new group of carbapenems,” J. Antimicrob. Chemother. 52(4), 538–542.CrossRefGoogle ScholarPubMed
Sheng, L. (2014). “New ertapenem intermediate, prepared by subjecting carbapenem derivative and ertapenem side chain to condensation reaction to obtain mixture, reacting with acid, and adding to water,” CN patent 103772389-A; 103772389–B.Google Scholar
Figure 0

Figure 1. Structural formula of ertapenem side chain.

Figure 1

Figure 2. XRD pattern of ertapenem side chain using CuKα radiation.

Figure 2

Table I. Indexed XRD data for ertapenem side chain. The d-values were calculated using CuKα1 radiation (λ = 1.54056 Å).

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