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In the title compound [systematic name: (7-methyl-4,6,6a,7,8,9-hexa­hydro­indolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate], C16H18N2O·H2O, the non-aromatic ring (ring C of the ergoline skeleton) directly fused to the aromatic rings is nearly planar, with a maximum deviation of 0.659 (3) Å, and shows an envelope conformation. In the crystal, hydrogen bonds between the lysergol and water mol­ecules contribute to the formation of layers parallel to (10\overline{2}).

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The title compound {systematic name: (6aR,9S)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hy­droxy-2-methyl-3,6-dioxoocta­hydro-8H-oxazolo[3,2-a]pyrrolo­[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexa­hydro­indolo[4,3-fg]quinoline-9-carboxamide}, C33H35N5O5, was formed by an epimerization reaction of ergotamine. The non-aromatic ring (ring C of the ergoline skeleton) directly fused to the aromatic rings is nearly planar [maximum deviation = 0.317 (4) Å] and shows an envelope conformation, whereas ring D, involved in an intra­molecular N—H...N hydrogen bond exhibits a slightly distorted chair conformation. The structure displays chains running approximately parallel to the diagonal of bc plane that are formed through N—H...O hydrogen bonds.

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The title compound, also known as cis-zearalenone (cis-ZEN), C18H22O5, has already been reported elsewhere [Griffin et al. (1981). ACA Ser. 29, 35], but no atomic coordinates are publicly available. The mol­ecule is of inter­est with respect to its toxicity. In the crystal, intra­molecular O—H...O hydrogen bonds stabilize the mol­ecular conformation, while inter­molecular O—H...O hydrogen bonds link the mol­ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

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In the crystal structure of the title compound, C8H10BrN2O+·Br, inter­molecular N—H...Br hydrogen bonds link the mol­ecules into infinite chains along [001]. The inclined angle between the pyridine ring plane and the plane defined by the acid amide group is 63.97 (4)°.
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