9-[3-(Dimethylamino)propyl]-2-trifluoromethyl-9H-thioxanthen-9-ol

In the title compound, C19H20F3NOS, the dihedral angle between the mean planes of the two benzene rings attached to the thioxanthene ring is 41.8 (7)°; the latter has a slightly distorted boat conformation. The F atoms are disordered over three sets of sites [occupancy ratio = 0.564 (10):0.287 (10):0.148 (5)] and the methyl groups are disordered over two sets of sites [occupancy ratio = 0.72 (4):0.28 (4)]. The crystal packing is stabilized by O—H⋯N and C—H⋯S hydrogen bonds and weak C—H⋯Cg interactions.

In the title compound, C 19 H 20 F 3 NOS, the dihedral angle between the mean planes of the two benzene rings attached to the thioxanthene ring is 41.8 (7) ; the latter has a slightly distorted boat conformation. The F atoms are disordered over three sets of sites [occupancy ratio = 0.564 (10)

Experimental
The title compound was obtained as a gift sample from R. L. Fine Chem. Ltd., Bangalore, India. The compound was recrystallized from dichloromethane (M.pt.: 389-391 K).

Refinement
The fluorine atoms on C14 are disordered over three positions [occupancy ratio 0.564 (10); 0.287 (10); 0.148 (5)] and the methyl groups on N1 are disordered over two positions [occupancy ratio 0.72 (4); 0.28 (4)]. The O-H hydrogen atom was located by Fourier analysis and refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with atom-H lengths of 0.95 Å (CH), 0.99 Å (CH 2 ) or 0.98 Å (CH 3 ). Isotropic displacement parameters for these atoms were set to 1.18-1.20 (CH) or 1.20 (CH 2 ) times U eq of the parent atom.

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 > σ(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.