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Powder X-ray diffraction of 1-(4-Nitrophenyl)-2-piperidinone, C11H12N2O3

Published online by Cambridge University Press:  13 August 2015

Qing Wang ,
Xin Nuo Xiong ,
Jia Wei He ,
Pei Xiao Tang  and
Hui Li
Qing Wang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xin Nuo Xiong
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Jia Wei He
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Pei Xiao Tang
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 for 1-(4-Nitrophenyl)-2-piperidinone, C11H12N2O3, are reported [a = 9.514(3) Å, b = 12.308(6) Å, c = 9.175(1) Å, α = 90°, β = 91.811(2)°, γ = 90°, V = 1073.94 Å3, Z = 4, ρ cal = 1.362 g cm−3 and space group P21/n]. All measured lines were indexed and are consistent with the P21/n space group. No detectable impurities were observed.

Keywords

1-(4-Nitrophenyl)-2-piperidinoneX-ray powder diffractioncrystal structureapixaban

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Rapid Communication
Information
Powder Diffraction , Volume 30 , Issue 4 , December 2015 , pp. 366
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Copyright
Copyright © International Centre for Diffraction Data 2015 

1-(4-Nitrophenyl)-2-piperidinone is an intermediate in the synthesis of the anticoagulant, Apixaban (Jiang and Ji, Reference Jiang and Ji2013; Zikria and Ansell, Reference Zikria and Ansell2009). Commercial 1-(4-Nitrophenyl)-2-piperidinone was purchased from Haoyuan Chemexpress Co., Ltd., (Shanghai, China), recrystallized in methanol and dried. The sample was then ground into powder (HPLC >98%, ρ = 1.327 g cm−3, T melt = 95–96 °C) and mounted on a flat zero background plate. X-ray powder diffraction measurement was performed at room temperature 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 0.013 13°2θ and a counting time of 30 ms step−1. 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, China). The X-ray powder diffraction pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component. Automatic indexing results were obtained by DICVOL91 method (Boultif and Louër, Reference Boultif and Louër1991). The following figures of merit were achieved: F 20 = 36.2 (0.0094, 59) (Smith and Snyder, Reference Smith and Snyder1979) and M 20 = 18.8 (de Wolff, Reference de Wolff1968). The preliminary cell from indexing was refined using the Pawley method (Pawley, Reference Pawley1981). The indexing results were then refined with the type of Pawley. Pawley refinement results confirmed that the sample crystallizes in the monoclinic space group P21/n (14), with a = 9.514(3) Å, b = 12.308(6) Å, c = 9.175(1) Å, α = 90°, β = 91.811(2)°, γ = 90°, V = 1073.94 Å3, Z = 4, and ρ cal = 1.362 g cm−3. The crystal structure result [a = 9.163 19(19) Å, b = 12.2880(4) Å, c = 9.506 85(18) Å, α = 90°, β = 91.843(2)°, γ = 90°, V = 1069.89(4) Å3, Z = 4, and ρ cal = 1.367 g cm−3] from single-crystal X-ray diffraction was also obtained. Results showed that both single-crystal and powder diffraction methods can get similar structure data. Figure 1 shows the Powder X-ray diffraction pattern of the compound.

Figure 1.

Powder X-ray diffraction pattern of 1-(4-Nitrophenyl)-2-piperidinone.

ACKNOWLEDGEMENTS

This work was supported by the Applied Basic Research Project of Sichuan Province (Grant no. 2014JY0042), the Testing Platform Construction of Technology Achievement Transform of Sichuan Province (Grant no. 13CGPT0049), and the National Development and Reform Commission and Education of China (Grant no. 2014BW011).

SUPPLEMENTARY MATERIALS

For supplementary material for this article, please visit http://dx.doi.org/10.1017/S0885715615000639

References

Boultif, A. and Louër, D. (1991). “Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method,” J. Appl. Crystallogr. 24, 987–993.CrossRefGoogle Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.CrossRefGoogle Scholar
Jiang, J. and Ji, Y. (2013). “Alternate synthesis of apixaban (BMS-562247), an inhibitor of blood coagulation factor Xa,” Synth. Commun. 43(1), 72–79.Google Scholar
Pawley, G. S. (1981). “Unit-cell refinement from powder diffraction scans,” J. Appl. Crystallogr. 14(6), 357–361.CrossRefGoogle Scholar
Smith, G. S. and Snyder, R. L. (1979). “FN: a criterion for rating powder diffraction patterns and evaluating the reliability of powder indexing,” J. Appl. Crystallogr. 12, 60–65.CrossRefGoogle Scholar
Zikria, J. and Ansell, J. (2009). “Oral anticoagulation with factor Xa and thrombin inhibitors: is there an alternative to warfarin?,” Discov. Med. 8(43), 196–203.Google Scholar
Figure 0

Figure 1. Powder X-ray diffraction pattern of 1-(4-Nitrophenyl)-2-piperidinone.

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