[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

The title compound, C19H16FNO, crystallizes with two independent molecules in the asymmetric unit. In the two molecules, the dihedral angles between the benzene and quinoline rings are 72.6 (5) and 76.2 (5)°, between the cyclopropane and quinoline rings they are 65.2 (5) and 66.0 (5)°, and between the benzene and cyclopropane rings they are 25.9 (5) and 33.9 (5)°. There are intermolecular O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, as well as intramolecular C—H⋯O hydrogen bonds, which may be effective in stabilizing the crystal structure.


Comment
Derivatives of quinoline are important chemical materials. We report here the crystal structure of the title compound which has been prepared in our laboratory.
The title compound crystallizes with two independent but closely similar molecules per asymmetric unit ( Fig. 1 and   Fig. 2). In the two molecules, the dihedral angles between benzene and quinoline rings are 72.6 (5) and 76.2 (5)°, between cyclopropane and quinoline rings are 65.2 (5) and 66.0 (5)° and between benzene and cyclopropane rings are 25.9 (5) and 33.9 (5)°. The molecular packing (Fig. 3) is stabilized by intermolecular O-H···O, O-H···N and C-H···O hydrogen bonds (Table 1). In addition, intramolecular C-H···O hydrogen bonds are also present in the crystal structure.
The crystal structure of a closely related compound has been reported (Prasath et al., 2010).

Experimental
A dry, 250-ml three-neck flask was charged with 100 ml of THF, 3.27 g (57.47 mmol) of KBH 4 , and 5.46 g (57.47 mmol) of MgCl 2 . The reaction mixture was heated under reflux for 2 h, then 10.0 g (57.47 mmol) of methyl 2-cyclopropyl-4-(4fluorophenyl)quinoline-3-carboxylate was added dropwise over 5 min and refluxed for an additional 40 min. After cooling, methanol (15 ml) was carefully added dropwise to quench the reaction and the white inorganic solid was filtered and washed with 80 ml of THF/MeOH (10:1). The combined filtrate was concentrated to dryness, MeOH (40 ml) was added to the residue and concentrated to dryness again. The resulting residue was dissolved in 300 ml of ethyl acetate and washed with brine, dried over MgSO 4 and concentrated to dryness to provide 7.58 g (yield 90.3%) of the title compound as colourless crystals.

Refinement
All H atoms bonded to the C atoms were placed geometrically at the distances of 0.93 or 0.97 Å, and included in the refinement in riding motion approximation with U iso (H) = 1.2U eq (C/O) of the carrier atom. Fig. 1. The presentation of a molecule of (I), showing the atom-numbering scheme; displacement ellipsoids have been plotted at the 50% probability level.