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
. 2022 Sep 27;7(Pt 9):x220932.
doi: 10.1107/S2414314622009324. eCollection 2022 Sep.

(E)-1-(2-Hy-droxy-4,6-di-meth-oxy-phen-yl)-3-(naph-thalen-1-yl)prop-2-en-1-one

Affiliations

(E)-1-(2-Hy-droxy-4,6-di-meth-oxy-phen-yl)-3-(naph-thalen-1-yl)prop-2-en-1-one

Dongsoo Koh. IUCrdata. .

Abstract

In the title compound, C21H18O4, the relative conformation of the C=C and C=O double bonds in the central enone group is s-cisoid; there is a trans configuration about the C=C bond. The dihedral angle formed by the naphthalene ring system and the benzene ring is 16.80 (2)°. The meth-oxy groups at the ortho and para positions of the benzene ring are tilted to the ring by 169.8 (1) and 174.5 (1)°, respectively. The hy-droxy group in the benzene ring participates in an intra-molecular O-H⋯O hydrogen bond. In the crystal, C-H⋯O inter-actions link mol-ecules into linear chains along the a-axis direction.

Keywords: C—H⋯O inter­actions; O—H⋯O hydrogen bond; chalcone; crystal structure.

PubMed Disclaimer

Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound, showing the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. The dashed bond represents the intra­molecular O—H⋯O hydrogen bond.
Figure 2
Figure 2
Part of the crystal structure of the title compound with weak inter­molecular C—H⋯O inter­actions shown as green dashed lines.

References

    1. Adams, D. J., Dai, M., Pellegrino, G., Wagner, B. K., Stern, A. M., Shamji, A. F. & Schreiber, S. L. (2012). Proc. Natl Acad. Sci. USA, 109, 15115–15120. - PMC - PubMed
    1. Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
    1. Elkanzi, N. A. A., Hrichi, H., Alolayan, R. A., Derafa, W., Zahou, F. M. & Bakr, R. B. (2022). ACS Omega, 7, 27769–27786. - PMC - PubMed
    1. Hostetler, G. L., Ralston, R. A. & Schwartz, S. J. (2017). Adv. Nutr. 8, 423–435. - PMC - PubMed
    1. Kumari, S., Badana, A. K. & Malla, R. (2018). Biomark. 13, 1177271918755391. - PMC - PubMed

LinkOut - more resources