5-(4-Chlorophenyl)-1-methyl-3-phenyl-3,6,8,9-tetrahydropyrazolo[3,4-b]thiopyrano[4,3-d]pyridine

The title compound, C22H18ClN3S, was synthesized by the reaction of 4-chlorobenzaldehyde, tetrahydrothiopyran-4-one and 3-methyl-1-phenyl-1H-pyrazol-5-amine in acetic acid without a catalyst. The pyridine and pyrazole rings are almost coplanar, the dihedral angle between their mean planes being 2.50 (1)°. The thiopyran ring exhibits an envelope conformation. The crystal packing is stabilized by intermolecular C—H⋯Cl hydrogen bonds and by C—H⋯π and π–π interactions [centroid–centroid distances of 3.825 (2) Å between pyridine rings and 3.557 (2) Å between pyrazole and pyridine rings.

Please define Cg1 is the centroid of the C17-C22 ring.

Comment
The pyrazolo[3,4-b]pyridine system as a key heterocycle represents the core skeleton of a pharmaceutically important class of heterocyclic compounds that possess a broad range of biological activities (Beutner et al., 2009), such as anxiolytic activity (Meiners et al., 1982), and can be used in the inhibition of xanthine oxidases (Lynck et al., 1988), cholesterol formation and in the treatment of Alzheimer's disease, gastrointestinal diseases, anorexia nervosa, drug and alcohol withdrawal symptoms, drug addiction and infertility. They have also been reported as potent and selective inhibitors of A1 adenosine receptors (Manetti et al., 2005), phosphodiesterase 4 (PDE4) inhibitors in immune and inflammatory cells (Hamblin et al. 2008), glycogen synthase kinase-3 (GSK-3) inhibitors (Witherington et al., 2003) and kinase inhibitors of p38 as anti-inflammatory drugs (Revesz et al., 2006). Because of the biological activities they exhibit, these compounds have distinguished themselves as heterocycles of profound chemical and biological significance.
Thus, the preparation of these molecules has attracted considerable attention (Lee et al., 2009) In this paper we report the crystal structure of the title compound, C 22 H 18 ClN 3 S, which was synthesized by the reaction of 4-chlorobenzaldehyde, tetrahydrothiopyran-4-one, and 3-methyl-1-phenyl-1H-pyrazol-5-amine in acetic acid without catalyst.
Even shorter interactions exist between the pyrazole and pyridine rings with corresponding distances of 3.557 (2) and 3.516 (1) Å, respectively.

Refinement
All H atoms were positioned geometrically and treated as riding, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C) for aromatic H atoms, with C-H = 0.97 Å and U iso (H) = 1.2U eq (C) for methylene H atoms, and with C-H = 0.96 Å and U iso (H) = 1.5U eq (C) for methyl H atoms.