Received 24 April 2009
In the title compound, C23H30N2O4·C2H6O, the indole derivative has four fused rings, forming an indolo[2-3a]quinolizine system, in which one six-membered ring is directly connected to the indole unit and has a distorted chair conformation. The fourth ring is also a six-membered ring, depicting a regular chair conformation. In the crystal, the molecules are linked by N-HO and O-HN interactions, forming a C(7) chain.
For previous crystallographic analysis of mitragynine salts (hydrobromide and hydroiodide), see: Zacharias et al. (1965). For the method of extraction, see: Ponglux et al. (1994). For synthetic studies, see: Ma et al. (2009). For medicinal properties, see: Boyer et al. (2008); Weibrecht et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 and ORTEP-3 (Farrugia, 1997).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2206 ).
This work was supported by the NIH-NCRR (grant No. 5P20RR021919). The authors also thank the Center for Disease Control and Prevention, USA, for providing financial assistance (CDC cooperative agreements 1UO1 CI000211-03 and 1UO1 CI000362-01). This investigation was conducted in a facility constructed with support from Research Facilities Improvement Program grant No. C06Rr-14503-01 from the National Center for Research Resources, National Institutes of Health.
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