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—H⋯O hydrogen bonds, forming A–A and B–B inversion dimers with R 2 2(8) ring motifs. The dimers are stabilized by C—H⋯O hydrogen bonds and linked via C—H⋯F and C—H⋯N hydrogen bonds into a three-dimensional network. Several C—H⋯π interactions are also present.

In the asymmetric unit of the title compound, C 27 H 27 FN 2 OÁ-0.25CHCl 3 , 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-HÁ Á ÁO hydrogen bonds, forming A-A and B-B inversion dimers with R 2 2 (8) ring motifs. The dimers are stabilized by C-HÁ Á ÁO hydrogen bonds and linked via C-HÁ Á ÁF and C-HÁ Á ÁN hydrogen bonds into a threedimensional network. Several C-HÁ Á Á interactions are also present.

Synthesis and crystallization
The synthesis of the title compound has been previously described (Ullah, 2012;Eastwood, 2000). Rod-like colourless crystals of the title compound were obtained by slow evaporation of a solution in chloroform.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. The NH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.95, 1.00 and 0.99 Å for CH(aromatic), methine, and methylene H atoms, respectives, with U iso (H) = 1.2U eq (C).

Comment
In ongoing efforts to develop new antipsychotics, we have synthesized a series of compounds which are structural analogs of adoprazine and bifeprunox and have disclosed their dual D2 and 5-HT 1A receptor binding affinities and structure-activity relationship (Ullah, 2013;Ullah & Al-Shaheri, 2012). Herein, we describe the crystal structure of one such molecule, a piperidine quinoline derivative.  (Table 1 and Fig. 2), with R 2 2 (8) ring motifs (Bernstein et al., 1995). The dimers, are stabilized by C-H···O hydrogen bonds, and linked via C-H···F and C-H···N hydrogen bonds forming a three-dimensional network (Fig. 2).
The network is further stabilized by a number of C-H···π interactions (Table 1)   A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).