8-{1-[(4′-Fluoro-[1,1′-biphenyl]-4-yl)methyl]piperidin-4-yl}-3, 4-dihydroquinolin-2(1H)-one chloroform 0.25-solvate

In the asymmetric unit of the title compound, C27H27FN2O-0.25CHCl3, there are two independent molecules (A and B) together with a partially disordered chloroform molecule situated about an inversion center. The conformation of the two molecules is very similar. The bridging piperidine rings each have a chair conformation while the piperidin-2-one rings of the quinoline moiety have screw-boat conformations. The benzene rings of the biphenyl moiety are inclined to one another by 26.37(4) and 23.75(15)° in molecules A and B, respectively. The mean plane of the central piperidine ring [r.m.s. deviation = 0.241(2)Å in both molecules A and B] is inclined to the benzene ring of the quinoline moiety by 80.06(4) in A and 83.75(15)° in B, while it is inclined to the adjacent benzene ring of the biphenyl group by 73.623(15) in A and 75.65(14)° in B. In the crystal, individual molecules are linked by pairs of N - HO hydrogen bonds, forming A-A and B-B inversion dimers with R 2²(8) ring motifs. The dimers are stabilized by C - HO hydrogen bonds and linked via C - HF and C - HN hydrogen bonds into a three-dimensional network. Several C - Hπ interactions are also present.