Synthesis and Crystal Structure of 3-((m-Tolylamino)-methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione

Wu-Lan Zeng; Hui-Lian Liu

doi:10.14233/ajchem.2014.16510

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Issue Published : July 5, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Crystal Structure of 3-((m-Tolylamino)-methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione

https://doi.org/10.14233/ajchem.2014.16510

Wu-Lan Zeng

Microscale Science Institute, Department of Chemistry, Chemical Engineering and Environmental Engineering, Weifang University, Weifang 261061, P.R. China

Hui-Lian Liu

Microscale Science Institute, College of Bioengineering, Weifang University, Weifang 261061, Shandong Province, P.R. China

Corresponding Author(s) : Wu-Lan Zeng

wulanzeng@163.com

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14
Article Published : July 6, 2014

Abstract

A new N,O-containing spiro compound 3-((m-tolylamino)methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione was synthesized and its crystal structure was determined by X-ray crystallographic techniques. The compound crystallizes in triclinic, space group P-1 with a = 7.0264 (14) Å, b = 7.8523 (16) Å, c = 14.102 (3) Å, a = 94.75 (3)º, b = 98.14 (3)º, g = 96.29 (3)º, C₁₇H₁₉NO₄, Mr = 301.33, V = 761.7 (3) Å³, Z = 2, Dc = 1.314 g/cm³, F (000) = 320, μ(MoKa) = 0.094 mm^-1, the final R = 0.0496 and wR = 0.3294. The 1,3-dioxane ring is in a distorted envelope conformation while cyclohexane ring assumes a highly symmetric chair conformation. There exist some intra- and intermolecular hydrogen bonds, C-H···p supramolecular interactions and p···p stacking interactions in the title compound. All above hydrogen bonds and intermolecular interactions play a significant role in stabilizing the crystal structures.

Keywords

Synthesis Crystal structure 1,5-Dioxaspiro[5.5]undecane-2,4-dione Spiro compounds

Zeng, W.-L., & Liu, H.-L. (2014). Synthesis and Crystal Structure of 3-((m-Tolylamino)-methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione. Asian Journal of Chemistry, 26(14), 4356–4358. https://doi.org/10.14233/ajchem.2014.16510

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References

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H. Kikuchi, Y. Miyagawa, Y. Sahashi, S. Inatomi, A. Haganuma, N. Nakahata and Y. Oshima, J. Org. Chem., 69, 352 (2004); doi:10.1021/jo035137x.

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P. Kongsaeree, S. Prabpai, N. Sriubolmas, C. Vongvein and S. Wiyakrutta, J. Nat. Prod., 66, 709 (2003); doi:10.1021/np0205598.

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Siemens, Area Detector Control and Integration Software, USA (1996).

D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975); doi:10.1021/ja00839a011.

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Synthesis and Crystal Structure of 3-((m-Tolylamino)-methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione

Corresponding Author(s) : Wu-Lan Zeng

Abstract

Keywords

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