X-ray and computational investigations of ethanoanthracenes: 9,10-dihydro-9,10-ethanoanthracene-12-carboxylic acid and 9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylethanamine

Abstract

Two ethanoanthracenes 3 and 5 have been synthesized, crystalized and computationally investigated. The ethanoanthracene 3 and 5 were crystallized in a monoclinic system; P2₁/c, a = 6.1899 (2) Å, b = 35.4668 (11) Å, c = 11.7945 (3) Å, β = 103.071 (1)°, V 2522.23 (13) ų, Z = 8 and ethanoanthracene 5 was crystallized in a monoclinic system; P2₁/c, a = 11.0125 (3) Å, b = 32.1735 (7) Å, c = 11.1222 (3) Å, β = 114.026 (1)°, V = 3599.29 (16) ų, Z = 4. The Hirshfeld analysis was employed to identify the intermolecular interactions of ethanoanthracenes 3 and 5 crystals. The molecular packing of ethanoanthracene 3 depends on H…H (57.1-59.1%), H…C (19.2-22.7%) and O…H (15.6–15.8%) contacts in addition to minor contributions from the C…O (1.1–2.5%) and C…C (2.1–4.7%) contacts, while the H…H (59.6–57.1%), H…C (21.2–22.7%) and Cl…H (15.6–17.1%) are the most important contacts in ethanoanthracene 5 molecular packing. The calculated dipole moments values for ethanoanthracene 3 (1.1452 Debye) are lower than ethanoanthracene 5 (8.8291 Debye). In addition, the atomic charge distribution, molecular electrostatic potential map and reactivity descriptors of the ethanoanthracenes 3 and 5 were reported.

Keywords:

• DFT
• ethanoanthracenes
• Hirshfeld analysis
• HOMO
• LUMO
• X-ray

Acknowledgements

The authors would like to extend their sincere appreciation to Taif University Researchers Supporting Project number (TURSP- 2020/136), Taif University, Taif, Saudi Arabia.

Additional information

Funding

The authors would like to extend their sincere appreciation to Taif University Researchers Supporting Project number (TURSP- 2020/136), Taif University, Taif, Saudi Arabia.