Crystal structure of 1-tosyl-1,2,3,4-tetrahydroquinoline

In the title compound, C16H17NO2S, the heterocyclic ring adopts a half-chair conformation and the bond-angle sum at the N atom is 350.2°. The dihedral angle between the planes of the aromatic rings is 47.74 (10)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds to generate [010] chains.


Related literature
Hydrogen-bond geometry (Å , ).  et al., 2007). In the course of our study, we noticed that 1,2,3,4-tetrahydroquinoline derivatives exhibit a few pharmacological activities (our unpublished data). As a part of our study we have undertaken crystal structure determination of the title compound and the results are presented here.

S2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. In the title molecule, the planes of the C1-C6 and C10-C15 benzene rings form a dihedral angle of 47.74 (9)°. The C1/C6-C9/N1 ring is in a half-chair conformation, with the methylene C9 atom as the flap. The molecular structure is stabilized by intramolecular C9-H9A···O1 and C2-H2···O2 hydrogen bonds (Fig. 2).

S5. Synthesis and crystallization
To a stirred solution of 1,2,3,4-tetrahydroquinoline (10 mmol) in 30 mL dry dichloroethane, triethylamine (15 mmol) was added at 0 -5°C. To this reaction mixture 4-methylbenzene-1-sulfonylchloride (12 mmol) was added drop wise. After 2h of stirring at room temperature, the reaction mixture was washed with 5% Na 2 CO 3 and brine. Organic phase was dried over Na 2 SO 4 and then it was concentrated on vacuum to yield titled compound as colourless solid. The crude product was recrystallized in the mixture of ethyl acetate and hexane(1:1) to get colourless prisms.

S6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were positioned with idealized geometry using a riding model with C-H = 0.95-0.99 Å. All H-atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom). The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 R-factors(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.