Desoxyhemigossypol 6-methyl ether

The title sesquiterpene [systematic name: 6-methoxy-10-methyl-7-(propan-2-yl)-2-oxatricyclo[6.3.1.0^4,12]dodeca-1(11),4,6,8(12),9-pentaen-5-ol], C₁₆H₁₈O₃, was isolated from pathogen-infected stele tissue of Gossypium barbadense. There are two mol­ecules in the asymmetric unit and the dihedral angle between their naphtho­furan systems is 86.48 (2)°. In the crystal, O—H...O hydrogen bonds between the hy­droxy groups and etheric O atoms link the mol­ecules into centrosymmetric tetra­mers. These tetra­mers are assembled into (010) layers via stacking inter­actions between the naphtho­furan systems [inter­planar distance 3.473 (3) Å] and short C—H...O contacts.

Lacinilene C 7-methyl ether

The title compound, C₁₆H₂₀O₃ [systematic name: 1-hy­droxy-7-meth­oxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2(1H)-one], is a sesquiterpene isolated from foliar tissues of the cotton plant and is of inter­est with respect to its anti­bacterial properties. Its phenyl ring is ideally planar, and the maximum of deviation in the second ring is 0.386 (3) Å. The hy­droxy group and the methyl group are oriented in an equatorial fashion and axial, respectively, to the second ring. In the crystal, inversion dimers are formed through pairs of O—H...O hydrogen bonds. Weak C—H...O hydrogen bonds link the dimers into columns along the c axis. These columns form a crystal structure with a crystal packing factor of 0.66.

2,2′-Bis{8-[(benzyl­amino)­methyl­idene]-1,6-dihy­droxy-5-isopropyl-3-methyl­naphthalen-7(8H)-one}

The asymmetric unit of the title compound, C₄₄H₄₄N₂O₆, contains two independent mol­ecules with similar conformations. The di­hydro­naphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two di­hydro­naphthalene ring systems is 83.37 (4)° in one mol­ecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hy­droxy and imino groups via intra­molecular O—H...O and N—H...O hydrogen bonds. In the crystal, mol­ecules are linked through O—H...O hydrogen bonds into layers parallel to (001), and adjacent layers are further stacked by π–π inter­actions between di­hydro­naphthalene and phenyl rings into a three-dimensional supra­molecular architecture. In the crystal, one of the isopropyl groups is disordered over two positions with an occupancy ratio of 0.684 (8):0.316 (8).