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X-ray powder diffraction data for bisacodyl, C22H19NO4

Published online by Cambridge University Press:  10 June 2014

Shan Shan Li ,
Xiao Qing Wu ,
Qing Wang ,
Pei Xiao Tang  and
Hui Li
Shan Shan Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xiao Qing Wu
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qing Wang
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

In this paper, X-ray powder diffraction data, unit-cell parameters, and space group for bisacodyl, C22H19NO4, are reported [a = 9.081(3) Å, b = 10.631(5) Å, c = 11.549(6) Å, α = 111.492(4)°, β = 108.082(3)°, γ = 101.501(3)°, unit-cell volume V = 922.368 Å3, Z = 2, and space group P-1]. All measured lines were indexed, and no detectable impurity was observed.

Keywords

X-ray powder diffractionbisacodyl

Information

Type
New Diffraction Data
Information
Powder Diffraction , Volume 29 , Issue 3 , September 2014 , pp. 295 - 297
Copyright
Copyright © International Centre for Diffraction Data 2014 

I. INTRODUCTION

Bisacodyl (Figure 1), systematic name 4,4′-(2-pyridylmethylene) bisphenol diacetate, is a poorly absorbed diphenylmethane which acts locally on the colon as a peristaltic stimulant (Adams et al., Reference Adams, Meagher, Lubowski and King1994). Bisacodyl can affect the prostaglandin, kinase, and ATP from the colon, and restrain the absorption of water. As a mild laxative, bisacodyl has been commonly studied in gastroenterology for bowel preparation (Clark et al., Reference Clark, Godfrey, Choudhary, Ashraf, Matteson and Bechtold2013).

Figure 1.

Structural formula of bisacodyl.

At present, the crystal structure of bisacodyl by single-crystal diffraction or powder diffraction has not been reported. Although there was already a reference pattern for bisacodyl in the ICDD Powder Diffraction File (00-043-1744), there were no precise unit-cell data, only d-spacings and intensities were reported.

II. EXPERIMENTAL

A. Sample preparation

The title compound was purchased from Heowns Biochem Technologies LLC., China, with 98% purity and characterized by UV and FTIR. It was recrystallized in acetone, dried for 6 h at 40 °C, then ground into powder, and sieved through a 200-mesh screen.

B. Diffraction data collection and reduction

X-ray powder diffraction measurement was performed at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with a PIXcel 1D detector and CuKα 1 radiation (λ = 1.54056 Å, 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 0.01313° 2θ and a counting time of 30 s step−1. The experimental X-ray powder diffraction pattern is depicted in Figure 2.

Figure 2.

X-ray powder diffraction pattern of the bisacodyl, using CuKα 1 radiation (λ = 1.54056 Å).

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 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 the X-Cell method (Neumann, Reference Neumann2003) and the indexing results were refined using Pawley refinement (R wp = 6.73%). Direct-space approach based on Monte Carlo algorithm in Powder Solve package (Engel et al., Reference Engel, Wilke, König, Harris and Leusen1999) was used for structure solution. It allowed for the optimized bisacodyl molecule searching conformation, position, and orientation in the refined cell to maximize the agreement between the calculated and the measured diffraction data. In the Rietveld refinement (Young, Reference Young1993; Li et al., Reference Li, Wu, Pan, Cheng and Li2014), a pseudo-Voigt (Sánchez-Bajo et al., Reference Sánchez-Bajo and Cumbrera1997) peak-shape function was employed, and variables such as cell parameters, atomic coordinates, thermal vibration, and preferred orientation were adjusted by least-squares methods to obtain the final crystal structure. After Rietveld refinement, the R wp was 9.11%. The crystal structure results of bisacodyl from single-crystal X-ray diffraction were also obtained, but not been reported in this paper. Results showed that both single-crystal and powder diffraction methods can get similar structure data.

III. RESULTS

Pawley refinement results confirmed that bisacodyl is triclinic with space group P-1 and unit-cell parameters: a = 9.081(3) Å, b = 10.631(5) Å, c = 11.549(6) Å, α = 111.492(4)°, β = 108.082(3)°, γ = 101.501(3)°, unit-cell volume V = 922.368 Å3, and Z = 2. 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 X-ray powder diffraction data of bisacodyl, C22H19NO4. Only the peaks with I rel of 1 or greater are reported [a = 9.081(3) Å, b = 10.631(5) Å, c = 11.549(6) Å, α = 111.492(4)°, β = 108.082(3)°, γ = 101.501(3)°, unit-cell volume V = 922.368 Å3, Z = 2, and space group P-1]. All measured lines were indexed and are consistent with the P-1 space group. The d-values were calculated using CuK α 1 radiation (λ = 1.54056 Å).

ACKNOWLEDGEMENT

The authors would like to thank the State Key Laboratory of Polymer Materials Engineering in Sichuan university for the software providing.

SUPPLEMENTARY MATERIALS AND METHODS

The supplementary material referred to in this article can be found at http://www.journals.cambridge.org/pdj

References

Adams, W. J., Meagher, A. P., Lubowski, D. Z., and King, D. W. (1994). “Bisacodyl reduces the volume of polyethylene glycol solution required for bowel preparation,” Dis. Colon Rectum 37, 229–234.Google Scholar
Clark, R. E., Godfrey, J. D., Choudhary, A., Ashraf, I., Matteson, M. L., and Bechtold, M. L. (2013). “Low-volume polyethylene glycol and bisacodyl for bowel preparation prior to colonoscopy: a meta-analysis,” Ann. Gastroenterol. 26, 319–324.Google Scholar
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
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.CrossRefGoogle Scholar
Neumann, M. A. (2003). “ X-Cell: a novel indexing algorithm for routine tasks and difficult cases,” J. Appl. Crystallogr. 36, 356–365.Google Scholar
Sánchez-Bajo, F., and Cumbrera, F. L. (1997). “The use of the Pseudo-Voigt function in the variance method of X-ray line-broadening analysis,” J. Appl. Crystallogr. 30, 427–430.Google Scholar
Young, R. A. (1993). The Rietveld Method, IUCr Monographies of Crystallography (Wiley, Oxford).Google Scholar
Figure 0

Figure 1. Structural formula of bisacodyl.

Figure 1

Figure 2. X-ray powder diffraction pattern of the bisacodyl, using CuKα1 radiation (λ = 1.54056 Å).

Figure 2

Table I. Indexed X-ray powder diffraction data of bisacodyl, C22H19NO4. Only the peaks with Irel of 1 or greater are reported [a = 9.081(3) Å, b = 10.631(5) Å, c = 11.549(6) Å, α = 111.492(4)°, β = 108.082(3)°, γ = 101.501(3)°, unit-cell volume V = 922.368 Å3, Z = 2, and space group P-1]. All measured lines were indexed and are consistent with the P-1 space group. The d-values were calculated using CuK α1 radiation (λ = 1.54056 Å).

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