rac-1-[6-Hydroxy-4-(4-methoxyphenyl)-3,6-dimethyl-4,5,6,7-tetrahydro-2H-indazol-5-yl]ethanone

The title compound, C18H22N2O3, represents a (4S,5R,6S)-stereoisomer, crystallizing as a racemate in a centrosymmetric space group. The six-membered aliphatic ring adopts a half-chair conformation, with the hydroxy- and acetyl-substituted C atoms deviating by 0.458 (2) and −0.366 (2) Å, respectively, from the plane defined by other four ring atoms. The pyrazole ring is essentially planar [r.m.s deviation = 0.004 (2) Å]. In the crystal, the molecules are linked into chains along the b axis by N—H⋯N hydrogen bonds. The chains are linked by O—H⋯N hydrogen bonds into layers parallel to the bc plane.

[1]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[2]  D. Cremer,et al.  General definition of ring puckering coordinates , 1975 .

[3]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.