Crystal structure and Hirshfeld surface analysis of (2E)-3-(4-chloro-3-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

• Main Authors: Sevim Türktekin Çelikesir, S. N. Sheshadri, Mehmet Akkurt, C. S. Chidan Kumar, M. K. Veeraiah
• Format: Article
• Language: English
• Published: International Union of Crystallography 2019-07-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; E configuration; 4-chloro-3-fluorophenyl ring; 3,4-dimethoxyphenyl ring; disorder; Hirshfeld surface analysis
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989019007783

The molecular structure of the title compound, C17H14ClFO3, consists of a 4-chloro-3-fluorophenyl ring and a 3,4-dimethoxyphenyl ring linked via a prop-2-en-1-one spacer. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The F and H atoms at the meta positions of the 4-chloro-3-fluorophenyl ring are disordered over two orientations, with an occupancy ratio of 0.785 (3):0.215 (3). In the crystal, molecules are linked via pairs of C—H...O interactions with an R22(14) ring motif, forming inversion dimers. The dimers are linked into a tape structure running along [10\overline{1}] by a C—H...π interaction. The intermolecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H...H (25.0%), followed by C...H/H...C (20.6%), O...H/H...O (15.6%), Cl...H/H...Cl (10.7%), F...H/H...F (10.4%), F...C/C...F (7.2%) and C...C (3.0%).