Received 11 January 2013
aSchool of Pharmacy, Anhui University of Traditional Chinese Medicine, Hefei 230038, People's Republic of China, and bState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China
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The title polycyclic alkaloid, C22H26N2O3, an indole derivative obtained from Melodinus yunnanensis, comprises three chiral C atoms and crystallizes as a racemate. Its seven-membered heterocyclic ring has a twisted conformation, with the N atom within the plane of the indole moiety and with two adjacent C atoms deviating in opposite directions from its plane by 0.756 (3) (methylene C) and -0.802 (3) Å (methine C). In the crystal, pairs of N-HO hydrogen bonds connect the molecules into centrosymmetric dimers.
Indole alkaloid derivatives obtained from Melodinus yunnanensis have been investigated due to their antimalarial and anticancer properties, see: Kanfan et al. (1974). For the structures of related compounds, see: Danieli et al. (1977a) and for applications of similar compounds see: Danieli et al. (1977a,b)
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2092 ).
This work was supported financially by the National Natural Science Foundation of China (2107298, 81001592) and the Natural Science Foundation of th Education Committee of Anhui Province (KJ2010A210).
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Kanfan, C., Massiot, G., Ahond, A., Das, B. C., Husson, H. P. & Potier, P. (1974). J. Chem. Soc. Chem Commun. pp. 164-165.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.