Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Jul 31;76(Pt 8):1403-1406.
doi: 10.1107/S2056989020010336. eCollection 2020 Aug 1.

Crystal structure of 1-ferrocenyl-2-(4-nitro-phen-yl)ethyne

Sara M Delgado Rivera  1 , Jean C González Espiet  2 , Jesús M Dones  1 , Sebastián A Henríquez López  1 , Ana R Guadalupe  1 , Dalice M Piñero Cruz  2 , Ingrid Montes González  1
Affiliations

Crystal structure of 1-ferrocenyl-2-(4-nitro-phen-yl)ethyne

Sara M Delgado Rivera et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The title ferrocene derivative, [Fe(C5H5)2(C8NO2)], including an alkyne bonded to a para-nitro-phenyl substituent, which was synthesized from a copper-free Sonogashira cross-coupling reaction between ethynylferrocene and 4-bromo-1-nitro-benzene, crystallizes in the P21/n space group. In the ferrocene unit, the penta-dienyl (Cps) rings are in an eclipsed conformation. The angle of rotation between the substituted cyclo-penta-dienyl ring and the p-nitro-phenyl group is 6.19 (10)°, yielding a quasi-linear extension of the ferrocenyl substitution. Important inter-molecular inter-actions arise from π-π stacking between the Cp rings and the p-nitro-phenyl, from corners of the Cp rings that are perpendicularly aligned, and between the O atoms from the nitro substituent and carbons at the corners of the Cp rings, propagating along all three crystallographic axes.

Keywords: 4-nitro­phenyl­ethyne; Sonogashira coupling; crystal structure; ferrocene; green chemistry.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Mol­ecular structure of the title compound, including atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
Crystal packing of the title compound along the a axis with short-contact inter­actions shown as dashed lines.
Figure 3
Figure 3
A view of the Hirshfeld surface of the title compound mapped over d norm with the four main inter­molecular contacts in the crystal lattice.
Figure 4
Figure 4
Full (a) and individual (b)–(j) two-dimensional fingerprint plots showing the nine inter­molecular contacts present in the crystal structure.
See this image and copyright information in PMC

References

    1. Bobula, T., Hudlický, J., Novák, P., Gyepes, R., Císařová, I., Štěpnička, P. & Kotora, M. (2008). Eur. J. Inorg. Chem. pp. 3911–3920.
    1. Coutouli-Argyropoulou, E., Tsitabani, M., Petrantonakis, G., Terzis, A. & Raptopoulou, C. (2003). Org. Biomol. Chem. 1, 1382–1388. - PubMed
    1. Dai, J.-J., Fang, C., Xiao, B., Yi, J., Xu, J., Liu, Z.-J., Lu, X., Liu, L. & Fu, Y. (2013). J. Am. Chem. Soc. 135, 8436–8439. - PubMed
    1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
    1. Fu, N., Zhang, Y., Yang, D., Chen, B. & Wu, X. (2008). Catal. Commun. 9, 976–979.

LinkOut - more resources