6′-(1,3-Diphenyl-1H-pyrazol-4-yl)-7′-(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5′,6′,7′,7a’-tetrahydro-1′H-spiro[indoline-3,5′-pyrrolo[1,2-c][1,3]thiazole]-7′-carbonitrile

In the title compound, C41H32N6O2S, the pyrrolothiazole ring system is folded about the bridging N—C bond. The thiazolidine and pyrrolidine rings adopt envelope (with the fused C atom as the flap) and twisted conformations, respectively. The two phenyl rings attached to the pyrazole ring are twisted from the plane of the latter by 6.8 (1) and 52.8 (1)°. The allyl group is disordered over two conformations in a 0.805 (6):0.195 (6) ratio. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.


Related literature
For the biological activity of spiroheterocycles, see: Kilonda et al. (1995); Ferguson et al. (2005). For related structures, see: Jagadeesan et al. (2012a,b). For ring conformations, see: Cremer & Pople (1975 Table 1 Hydrogen-bond geometry (Å , ). drug candidates owing to their ability to act as selective glycosidase inhibitors, which are used in the treatment of diabetes, cancer, malaria and viral infections, including AIDS (Kilonda et al., 1995). Herewith we present the title compound (I), obtained in our group and containing glycospiroheterocycles.

Refinement
Amino H atom was located on difference map and isotropically refined. C-bound H atoms were positioned geometrically, with C-H = 0.93 -0.98 Å, and allowed to ride on their parent atoms, with U iso (H) = 1.2-1.5 U eq (C). The positions of methyl hydrogens were optimized rotationally.

Figure 1
The molecular structure of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids. For the disordered allyl group, only major part is shown.

6′-(1,3-Diphenyl-1H-pyrazol-4-yl)-7′-(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5′,6′,7′,7a′tetrahydro-1′H-spiro[indoline-3,5′-pyrrolo[1,2-c][1,3]thiazole]-7′-carbonitrile
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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ.