Crystal structure of 3-{5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-1H-pyrazol-1-yl}indolin-2-one ethanol monosolvate

The title compound crystallizes as a 1:1 ethanol solvate, with the pyrazole ring almost normal to both of the indol-2-one ring and indole rings. In the crystal, molecules are linked by pairs of N—H⋯O and O—H⋯O hydrogen bonds, forming an inversion molecule–solvate dimer with an (12) ring motif.


Chemical context
Heterocyclic compounds containing the pyrazolone nucleus, indole, and its derivatives play an important role in biological activities. The synthesis and biological activity of some new indole derivatives containing a pyrazole moiety have been reported (Raju et al., 2013). Pyrazole and its analogues have been found to exhibit industrial and biologically active applications (el-Kashef et al., 2000;Taha et al., 2001;Brzozowski & Są czewski,, 2002). Consequently, synthesis of indole derivatives has been a major topic in organic and medicinal chemistry over the past few decades. Nitrogen-containing heterocycles are universal systems in nature and are consequently considered as privileged structures in drug discovery (Raju et al., 2013). A literature survey shows that some pyrazoles plays an essential role in biologically active compounds and also in medicinal chemistry (Penning et al., 2006), exhibiting phenomena such as antibacterial (Pevarello et al., 2006), antifungal, antiviral (Meghashyam et al., 2011), anti-oxidant (Singarave & Sarkkarai, 2011), anti-inflammatory (Mana et al., 2010), and anticancer (Pathak et al., 2010) effects etc. Certain indole derivatives have also been reported to exhibit widespectrum activities such as antiparkinsonian and anticonvulsant effects (Siddiqui et al., 2008;Archana et al., 2002). In addition, pyrazoles have played a crucial role in the development of theory in heterocyclic chemistry, and are also used extensively as useful synthons in organic synthesis. Isatin, an endogenous indole and its derivatives have been shown to exhibit a wide range of biological activities (Daisley & Shah, ISSN 2056-9890 1984Pandeya et al., 1999). In addition, the biological significance of fluvastatin, an indole derivative, is well established (Repič et al., 2001). As part of our studies in this area, we now present a pyrazole as a central unit linked with 3-[3-(4fluorophenyl)-1-isopropylindolin-2-yl]acrylaldehyde and 3-hydrazonoindolin-2-one, synthesized according to a procedure reported in the literature (Elkanzi, 2013).

Figure 2
The crystal packing of the title compound viewed along the b axis. The N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. The ethanol molecule is disordered over two positions with refined site occupancies of 0.560 (14): 0.440 (14). The disorder components were restrained to have similar geometry. The N-bound H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically (C-H = 0.93-0.98 Å ) and refined using a riding model with U iso (H) = 1.5U eq (Cmethyl) and 1.2U eq (C) for other H atoms.   program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

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.

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