N-[(2-Chloro-3-quinolyl)methyl]-4-fluoroaniline

In the title compound, C16H12ClFN2, the dihedral angle between the quinoline ring system and the flourophenyl ring is 86.70 (4)°. In the crystal, molecules are linked into chains along the a axis by N—H⋯N hydrogen bonds. In addition, C—H⋯π interactions involving the two benzene rings are observed.

In the title compound, C 16 H 12 ClFN 2 , the dihedral angle between the quinoline ring system and the flourophenyl ring is 86.70 (4) . In the crystal, molecules are linked into chains along the a axis by N-HÁ Á ÁN hydrogen bonds. In addition, C-HÁ Á Á interactions involving the two benzene rings are observed.
In the title molecule ( Fig. 1), the 2-chloroquinoline ring system and 4-fluoroaniline ring are bonded to a methane carbon, C10. The dihedral angle between the mean planes of the planar chloroquinoline ring system (dihedral angle between rings = 0.92 (5)°) and the flourophenyl ring is 86.70 (4)°. Bond distances (Allen et al., 1987) and angles are in normal ranges.
The molecules are linked into chains along the a axis by N-H···N hydrogen bonds (Fig. 2). In addition, C-H···π interactions involving the two benzene rings (Table 1) influence crystal packing in the unit cell.

Experimental
In a mixture of 3-(chloromethyl)-2-chloroquinoline (0.003 mol) and substituted phenyl amine (0.003 mol) in 20 ml of absolute ethanol, 1 ml of triethylamine (TEA) was added and refluxed for 12-15 hrs (Fig. 3). After completion of the reaction, content of the flask was reduced to half and left overnight. The crystalline mass obtained was filtered off, washed with water, dried and re-crystallized from ethanol to give N-[(2-chloroquinolin-3-yl)methyl]-4-fluoroaniline. X-ray quality crystals were obtained by slow evaporation of a methanol solution (m.p. 413-415 K).

Refinement
All of the H atoms were placed in their calculated positions and then refined using the riding model with atom-H lengths of 0.93 Å (CH), 0.97 Å (CH 2 ) or 0.86 Å (NH). Isotropic displacement parameters for these atoms were set to 1.2 times U eq of the parent atom. Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme and 50% probability displacement ellipsoids.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.