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Crystal Structure Determination of New Antimitotic Agent Bis(p-fluorobenzyl)trisulfide

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Abstract

The purpose of this research was to investigate the physical characteristics and crystalline structure of bis(p-fluorobenzyl)trisulfide, a new anti-tumor agent. Methods used included X-ray single crystal diffraction, X-ray powder diffraction (XRPD), Fourier-transform infrared (FT-IR) spectroscopy, differential scanning calorimetric (DSC) and thermogravimetric (TG) analyses. The findings obtained with X-ray single crystal diffraction showed that a monoclinic unit cell was a = 12.266(1) Å, b = 4.7757(4) Å, c = 25.510(1) Å, β = 104.25(1)°; cell volume = 1,448.4(2) Å3, Z = 4, and space group C2/c. The XRPD studies of the four crystalline samples, obtained by recrystallization from four different solvents, indicated that they had the same diffraction patterns. The diffraction pattern stimulated from the crystal structure data is in excellent agreement with the experimental results. In addition, the identical FT-IR spectra of the four crystalline samples revealed absorption bands corresponding to S–S and C–S stretching as well as the characteristic aromatic substitution. Five percent weight loss at 163.3 °C was observed when TG was used to study the decomposition process in the temperature range of 20–200 °C. DSC also allowed for the determination of onset temperatures at 60.4(1)–60.7(3) °C and peak temperatures at 62.1(3)–62.4(3) °C for the four crystalline samples studied. The results verified that the single crystal structure shared the same crystal form with the four crystalline samples investigated.

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Authors and Affiliations

  1. ACEA Biosciences, Inc., 6779 Mesa Ridge Road, Suite 100, San Diego, CA, 92121, USA

    Haoyun An, Xiaopeng Mo, Wanhong Xu, Xiaobo Wang & Xiao Xu

  2. Analytical and Measurement Center of Zhejiang University, 38 Zheda Road, Hangzhou, 310027, China

    Xiurong Hu, Jianming Gu, Linshen Chen & Weiming Xu

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  1. Haoyun An
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Correspondence to Haoyun An.

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An, H., Hu, X., Gu, J. et al. Crystal Structure Determination of New Antimitotic Agent Bis(p-fluorobenzyl)trisulfide. AAPS PharmSciTech 9, 551–556 (2008). https://doi.org/10.1208/s12249-008-9081-5

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  • DOI: https://doi.org/10.1208/s12249-008-9081-5

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