Crystal structure of methyl 1-methyl-3,5-diphenyl-7-tosyl-3,6,7,11b-tetrahydropyrazolo[4′,3′:5,6]pyrano[3,4-c]quinoline-5a(5H)-carboxylate

In the title compound, C35H31N3O5S, the piperidine ring adopts an envelope conformation, with the methine C atom as the flap, and the pyran ring adopts a sofa conformation. The mean planes of these two rings are almost normal to one another, making a dihedral angle of 85.96 (5)°. The two phenyl rings, one attached to the pyrazole ring and the other to the pyran ring, are inclined to one another by 65.41 (11)°. They are inclined to the mean planes of the rings to which they are attached by 12.59 (11) and 70.09 (9)°, respectively. There is an intramolecular C—H⋯π interaction involving the tosylate methyl group and the phenyl ring attached to the pyrazole ring. In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons parallel to (10-2). The ribbons are linked by slipped parallel π–π interactions involving inversion-related pyrazole rings [inter-centroid distance = 3.672 (2) Å], forming slabs parallel to (001). A preliminary report of this structure has been published [Bakthadoss et al. (2014 ▶). Eur. J. Org. Chem. pp. 1505–1513].

In the title compound, C 35 H 31 N 3 O 5 S, the piperidine ring adopts an envelope conformation, with the methine C atom as the flap, and the pyran ring adopts a sofa conformation. The mean planes of these two rings are almost normal to one another, making a dihedral angle of 85.96 (5) . The two phenyl rings, one attached to the pyrazole ring and the other to the pyran ring, are inclined to one another by 65.41 (11) . They are inclined to the mean planes of the rings to which they are attached by 12.59 (11) and 70.09 (9) , respectively. There is an intramolecular C-HÁ Á Á interaction involving the tosylate methyl group and the phenyl ring attached to the pyrazole ring. In the crystal, molecules are linked by C-HÁ Á Á interactions, forming ribbons parallel to (102). The ribbons are linked by slipped parallelinteractions involving inversion-related pyrazole rings [inter-centroid distance = 3.672 (2) Å ], forming slabs parallel to (001). A preliminary report of this structure has been published [Bakthadoss et al. (2014). Eur. J. Org. Chem. pp. 1505-1513.
Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5015).

S1. Comment
Sulfonamides are widely used as antimicrobial (Genç et al., 2008;Özbek et al., 2007), antifungal (Briganti et al., 1997), anti-inflammatory (Borne et al., 1974) and antiviral agents as well as HIV protease inhibitors (De Clercq et al., 2001). In view of their importance, a series of such compounds were synthesized and the crystal structure of the title compound was briefly reported (Bakthadoss et al., 2014). Herein we report on the full details of the crystal structure of the title compound.
In the crystal, molecules are linked by C-H···π interactions (Table 1)

S2. Experimental
g, 1 mmol) and 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one (0.174 g, 1 mmol) was placed in a round bottom flask and heated at 453 K for 1 h. After completion of the reaction, as indicated by TLC, the crude product was washed with 5 ml of an ethylacetate/hexane mixture (ratio 1:49) which successfully provided the pure title product as a colourless solid in 96% yield (0.58 g). Diffraction quality crystals were obtained by slow evaporation from an ethyl acetate solution.
supporting information

S3. Refinement
Atoms H10, H19 were located in a difference Fourier map and freely refined. The other C-bound H atoms were positioned geometrically and treated as riding atoms, with C-H = 0.93-0.97 Å and with U iso (H) = 1.5U eq (C) for methyl H atoms and = 1.2U eq (C) for other H atoms.

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level (H atoms have been omitted for clarity).

Figure 2
A partial view along the b axis of the crystal packing of the title compound, showing the π-π interaction (red circles represent the centroids of the pyrazole rings; H atoms have been omitted for clarity).

Figure 3
A view along the c axis of the crystal packing of the title compound, showing the C-H···π interactions as dashed lines (H atoms as silver balls; see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity). where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.29 e Å −3 Δρ min = −0.46 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0095 (12) 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.