Synthesis, crystal structure and Hirshfeld surfaces of 1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl) prop‑2-en-1-one

Abstract

Abstract A new chalcone, 1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop‑2-en-1-one (3), was synthesized, characterized by spectroscopy (IR, 1H, 13C NMR, LC-MS) and single crystal X-ray diffraction method. The compound crystallizes in the monoclinic crystal system (space group C2/c) with unit cell dimensions a = 34.940(6) A, b = 5.4090(9) A, c = 16.668(3) A, β = 108.400(8)°, Z = 8, and V = 2989.1(9) A3. The dihedral angle between the terminal phenyl ring is 16.39 (10)o and intramolecular hydrogen bond of the type C-H…O is observed. The intermolecular hydrogen bonds (O-H…O and C-H…O) and short contacts of the type C-H…π were involved in the crystal structure stabilization. The O-H…O and C-H…O intermolecular hydrogen bond generates R22(18) and R22(14) ring motifs, respectively. The intercontacts in the crystal packing were analyzed using Hirshfeld surfaces method using 2D fingerprint plots and electrostatic potential surfaces. The major intercontact contributing to the Hirshfeld surfaces are found to be from H…H and C…H. In addition, the thermal analysis shows two-step degradation of the 3.