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. 2023 Oct 19;79(Pt 11):1044-1048.
doi: 10.1107/S2056989023009003. eCollection 2023 Nov 1.

Crystal structure and supra-molecular features of a bis-urea-functionalized pillar[5]arene

Mickey Vinodh  1 , Fatemeh H Alipour  1 , Talal F Al-Azemi  1
Affiliations

Crystal structure and supra-molecular features of a bis-urea-functionalized pillar[5]arene

Mickey Vinodh et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The crystal structure of a bis-urea derivative based on A1/A2-functionalized pillar[5]arene (DUP) that encapsulates dimethyl formamide (DMF) inside the macrocyclic cavity is reported. The crystal structure of DUP·DMF, C63H70N4O12·C3H7NO, reveals that out of two urea functionalized spacers, one arm is oriented above the macrocyclic cavity with strong hydrogen-bonding inter-actions between the urea H atoms and DMF guest, whereas, the other arm is positioned away from the macrocycle, leading to inter-molecular hydrogen-bonding inter-actions between the urea H atoms of two adjacent pillar[5]arene macrocycles, resulting in the formation of a supra-molecular dimer.

Keywords: crystal structure; dimer; pillararene; receptor; urea substitution.

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Figures

Figure 1
Figure 1
Crystal structure of DUB·DMF with displacement ellipsoids at the 30% probability Hydrogen atoms are omitted for clarity.
Figure 2
Figure 2
Inter­molecular inter­actions between the pillar[5]arene host and the DMF guest; π2, and π5 are the centroids of the phenyl rings C8–C13 and C29–C34, respectively. Hydrogen atoms except those on urea moieties and the DMF mol­ecule are omitted for clarity.
Figure 3
Figure 3
Dimer formation of the DUB·DMF system in the crystal through urea spacers. Symmetry code: (i) 1 − x, 1 − y, 1 − z; π1 and π7 are the centroids of the C1–C6 and C50A–C55A phenyl rings, respectively. Non-inter­acting hydrogen atoms on the pillar[5]arenes are omitted for clarity.
Figure 4
Figure 4
Packing pattern of DUB mol­ecules in the crystal. Hydrogen atoms except those on the urea moieties are omitted for clarity.
See this image and copyright information in PMC

References

    1. Al-Azemi, T. F., Vinodh, M., Alipour, F. H. & Mohamod, A. A. (2019). RSC Adv. 9, 13814–13819. - PMC - PubMed
    1. Bi, J., Zeng, X., Tian, D. & Li, H. (2016). Org. Lett. 18, 1092–1095. - PubMed
    1. Cheng, M., Wang, Q., Cao, Y., Pan, Y., Yang, Z., Jiang, J. & Wang, L. (2016). Tetrahedron Lett. 57, 4133–4137.
    1. Deng, H., Shu, X., Hu, X., Li, J., Jia, X. & Li, C. (2012). Tetrahedron Lett. 53, 4609–4612.
    1. Duan, Q., Xia, W., Hu, X., Ni, M., Jiang, J., Lin, C., Pan, Y. & Wang, L. (2012). Chem. Commun. 48, 8532–8534. - PubMed

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