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

In the title compound, C10H13NO2S, the heterocyclic ring adopts a half-chair conformation and the bond-angle sum at the N atom is 347.9°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(8) loops.

In due course of our study, we have synthised a series of 1,2,3,4-tetrahydroquinoline with derivatives of suloponyl chlorides they exhibit a few pharmacological activities (our unpublished data).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 compared with crystal structure of 1tosyl-1,2,3,4-tetrahydroquinoline(II) (Jeyaseelan et al., 2014) .

S2. Structural commentary
The molecular structure of the title compound(I) is shown in Fig. 1. In both the compounds (I) and (II), the C1/C6-C9/N1 rings are in a half-chair conformation, with the methylene C9 atom as the flap, but the bond-angle sum at the N atom in the compound (I) and (II) are 347.9° and 350.2°, respectively.

S5. Synthesis and crystallization
To a stirred solution of 1,2,3,4-tetrahydroquinoline (10 mmol) in 30 ml dry methylene dichloride, triethylamine (15 mmol) was added at 0 -5°C. To this reaction mixture methanesulfonyl chloride (12 mmol) in 10 ml dry dichloromethane was added drop wise. After 2h of stirring at 15 -20°C, the reaction mixture was washed with 5% Na 2 CO 3 and brine. The 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 from a slovent mixture of ethyl acetate and hexane(1:2) to yield colourless prisms of (I).

S6. Refinement details
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 = 0.93-0.99 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).

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.