Propan-2-yl r-4-(4-fluorophenyl)-3-hydroxy-c-6-methyl-2-phenyl-4,5-dihydro-2H-indazole-t-5-carboxylate

In the title compound, C24H23FN2O3, the cyclohexene ring adopts a screw-boat conformation. The fluorobenzene ring attached to the cyclohexene ring and the phenyl ring attached to the indazole moiety are inclined to one another by 57.77 (13)°. In the crystal, molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds, forming chains with C(5) and C(10) graph-set motifs. There are also C—H⋯π interactions present. The isopropoxycarbonyl group undergoes considerable thermal motion.

In the title compound, C 24 H 23 FN 2 O 3 , the cyclohexene ring adopts a screw-boat conformation. The fluorobenzene ring attached to the cyclohexene ring and the phenyl ring attached to the indazole moiety are inclined to one another by 57.77 (13) . In the crystal, molecules are linked by O-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, forming chains with C(5) and C(10) graph-set motifs. There are also C-HÁ Á Á interactions present. The isopropoxycarbonyl group undergoes considerable thermal motion.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2500).

Comment
Indazole derivatives possess a wide spectrum of pharmacological activities, such as analgestic, anti-inflammatory, antidepressant, anti-hypertensive, anti-viral and anti-cancer (Jain et al., 1987;Palazzo et al., 1966;Popat et al., 2003;Beylin et al., 1991;George et al., 1998;Roman, 1990). In the view of these important attributes, the title compound was synthesized and its crystal structure is described herein.
The precipitated solid was filtered off by suction (yield 70%, M.p. 493 K) and recrystallized from ethanol giving blocklike colourless crystals.

Refinement
The isopropycarboxylate group undergoes considerable thermal motion. Atom O52 was refined as disordered over two positions (O52/O52′) and had a final refined occupancy ratio of 0.724 (15):0.276 (15). The C-bound H-atoms were included in calculated positions and treated as riding atoms: O-H = 0.82 Å, C-H = 0.93, 0.98 and 0.96 Å for CH(aromatic), CH and CH 3 H-atoms, respectively, with U iso (H) = k × U eq (parent C-atom), where k = 1.5 for OH and CH 3 H-atoms and = 1.2 for other H-atoms. Reflection 1 0 0 was partially obscured by the beam stop and was omitted.

Computing details
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999) Table 1 for details). 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.

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