Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid

The title compound, C(20)H(36)O(2)·CH(3)OH [systematic name: (3S)-4-[(S)-3-hy­droxy-3-methyl­pent-4-en-1-yl]-3,4a,8,8-tetra­methyl­deca­hydro­naphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z′ = 2. The sclareol mol­ecule comprises two trans-fused cyclo­hexane rings, each having an equatorially oriented hydroxyl group, and a 3-methyl­pent-1-en-3-ol side chain. In the crystal, O(s)—H⋯O(s), O(s)—H⋯O(m), O(m)—H⋯O(s) and O(m)—H⋯O(m) (s = sclareol, m = methanol) hydrogen bonds connect neighboring mol­ecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC(50) = 66.4 ± 1.0 µM ml(−1)) against standard miltefosine (IC(50) = 25.8 ± 0.2 µM ml(−1)).