![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
research communications
![Open Access](/logos/open.png)
Synthesis and E)-1-[3,5-bis(benzyloxy)phenyl]-3-(4-ethoxyphenyl)prop-2-en-1-one
of (2aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, bDepartment of Chemistry, Sri Chandrasekharendra Saraswathi Viswa Mahavidyalaya, (Deeded to be University), Kanchipuram 631 561, India, cPG & Research Department of Physics, Government Arts College, Melur 625 106, India, and dNanosciences/Nanotechnology Laboratories, University of South Africa (UNISA), Pretoria, South Africa
*Correspondence e-mail: profmani.au@gmail.com
In the title compound, C31H28O4, the phenyl rings of the chalcone unit subtend a dihedral angle of 26.43 (10)°. The phenyl rings of the pendant benzyloxy groups are orientated at 75.57 (13) and 75.70 (10)° with respect to their attached ring. In the crystal, weak C—H⋯O and C—H⋯π interactions link the molecules. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, which showed a breakdown into H⋯H (49.8%), H⋯C/C⋯H (33.8%) and H⋯O/O⋯H (13.6%) interactions with other types making negligible contributions.
CCDC reference: 2182630
1. Chemical context
α,β-unsaturated carbonyl (enone) bridge connecting two aromatic rings. The chalcone scaffold exhibits anti-cancer efficacy on various human cancer cells (Zhuang et al., 2017; Liu et al., 2022
). DrugBank lists three chalcone-based drugs namely hesperidin methylchalcone (DrugBank: DB15943), dihydroxymethoxychalcone (DB14122) and 3-(4-hydroxyphenyl)prop-2-en-1-one (DB07500). In general, the anticancer efficacy of is enhanced by attaching different substitutents at ring A of the chalcone, which is attached to the C=O group (Mai et al., 2014
). As part of our studies in this area, we have prepared and undertaken a single-crystal X-ray diffraction study of the title compound, C31H28O4, (I)
, and the results are presented here.
2. Structural commentary
The molecular structure of (I) is illustrated in Fig. 1
. The C12–C17 and C19–C24 phenyl rings of the chalcone unit subtend a dihedral angle of 26.43 (10)°: the most significant twist occurs about the C11—C12 bond, as indicated by the C10—C11—C12—C13 torsion angle of −13.0 (3)°. The dihedral angles between the C19–C24 and C26–C31 pendant phenyl rings and their attached C12–C17 ring are 75.57 (13) and 75.70 (10)°, respectively. The C3—O1—C2—C1, C14—O4—C25—C26 and C16—O3—C18—C19 torsion angles of 177.2 (3), 176.21 (18) and 179.5 (2)°, respectively, indicate an anti conformation in each case.
![]() | Figure 1 The molecular structure of (I) ![]() |
3. Supramolecular features
In the crystal of (I), the molecules associate via weak C—H⋯O interactions (Table 1
), forming C(15) chains propagating along [101] (Fig. 2
). In addition, inversion-related molecules are linked by pairwise weak C—H⋯π interactions (Fig. 3
).
|
![]() | Figure 2 Detail of the packing of (I) ![]() |
![]() | Figure 3 Detail of the packing of (I) ![]() |
4. Hirshfeld surface analysis
To further characterize the intermolecular interactions in (I), a Hirshfeld surface analysis was performed using Crystal Explorer 21 (Spackman et al., 2021
) and the associated two dimensional fingerprint plots were generated. The HS mapped over dnorm in the range −0.09 to +1.53 a.u. is illustrated in Fig. 4
, using colours to indicate contacts that are shorter (red areas), equal to (white areas), or longer than (blue areas) the sum of the van der Waals radii (Ashfaq et al., 2021
).
![]() | Figure 4 A view of the Hirshfeld surface mapped over dnorm for (I) ![]() |
The overall two-dimensional fingerprint plot, Fig. 5a, and those delineated into H⋯H interactions (49.8%), H⋯C/C⋯H (33.8%), H⋯O/O⋯H (13.6%), C⋯C (1.8%) and O⋯C/C⋯O (1%) interactions are illustrated in Fig. 5
b–f, respectively, together with their relative contributions to the HS. The most important interaction is H⋯H, which is reflected in Fig. 5
b as widely scattered points of high density due to the large hydrogen content of the molecule with the tip at de = di = 1.10 Å. As a result of the presence of C—H⋯O interactions, the H⋯O/O⋯H contacts contribute 13.6% to the overall crystal packing, as reflected in Fig. 5
d with the tips at de + di = 2.50 Å.
![]() | Figure 5 Two-dimensional fingerprint plots for (I) ![]() |
5. Synthesis and crystallization
Equimolar concentrations of 3,5-dibenzyloxyacetophenone and 4-ethoxybenzaldehyde were dissolved in ethanol in separate reaction flasks and then mixed. Drop by drop, utilizing a magnetic stirring device, 2 ml of 10% sodium hydroxide in water were introduced at room temperature. The course of the process was tracked using
After the process was complete, the resulting product was placed on crushed ice. The finished product was vacuum-filtered, dried, and then recrystallized from ethanol solution to yield colourless blocks of the title compound.IR (cm−1): 3032 aromatic C—H stretch, 2934 and 2875 aliphatic C—H stretch, 1651 C=O stretch, 1568 aromatic ring C=C stretch (see table in the supporting information).
6. Refinement
Crystal data, data collection and structure . H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å, with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.
|
Supporting information
CCDC reference: 2182630
https://doi.org/10.1107/S2056989024007552/hb8103sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024007552/hb8103Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989024007552/hb8103Isup3.cml
Footnotes
‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.
References
Ashfaq, M., Tahir, M. N., Muhammad, S., Munawar, K. S., Ali, A., Bogdanov, G. & Alarfaji, S. S. (2021). ACS Omega, 6, 31211–31225. Web of Science CSD CrossRef CAS PubMed Google Scholar
Bruker (2017). APEX2, and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Liu, W., He, M., Li, Y., Peng, Z. & Wang, G. (2022). J. Enzyme Inhib. Med. Chem. 37, 9–38. Web of Science CrossRef PubMed Google Scholar
Mai, C. W., Yaeghoobi, M., Abd-Rahman, N., Kang, Y. B. & Pichika, M. R. (2014). Eur. J. Med. Chem. 77, 378–387. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
![Open Access](/logos/open.png)