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Volume 65 
Part 6 
Pages o1441-o1442  
June 2009  

Received 24 April 2009
Accepted 8 May 2009
Online 29 May 2009


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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.089
Data-to-parameter ratio = 14.1
Details

(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate

Paulo Carvalho,a Edward B. Furr IIIa and Christopher McCurdyb*

aDepartment of Medicinal Chemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA, and bDepartment of Medicinal Chemistry and Department of Pharmacology, University of Mississippi, 417 Faser Hall, University, MS 38677, USA
Correspondence e-mail: cmccurdy@olemiss.edu

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-H...O and O-H...N interactions, forming a C(7) chain.

Related literature

For previous crystallographic analysis of mitragynine salts (hydrobromide and hydroiodide), see: Zacharias et al. (1965[Zacharias, D. E., Rosenstein, R. D. & Jeffrey, G. A. (1965). Acta Cryst. 18, 1039-1043.]). For the method of extraction, see: Ponglux et al. (1994[Ponglux, D., Wongseripipatana, S., Takayama, H., Kikuchi, M., Kurihara, M., Kitajima, M., Aimi, N. & Sakai, S. (1994). Planta Med. 60, 580-581.]). For synthetic studies, see: Ma et al. (2009[Ma, J., Yin, W., Zhou, H., Liao, X. & Cook, J. M. (2009). J. Org. Chem. 74, 264-273.]). For medicinal properties, see: Boyer et al. (2008[Boyer, E. W., Babu, K. M., Adkins, J. E., McCurdy, C. R. & Halpern, J. H. (2008). Addiction, 103, 1048-1050.]); Weibrecht et al. (2008[Weibrecht, K. W., Courtney, J. M., Halpern, J., McCurdy, C. & Boyer, E. W. (2008). Clin. Toxicol. 46, 395-399.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C23H30N2O4·C2H6O

  • Mr = 444.56

  • Orthorhombic, P 21 21 21

  • a = 7.60450 (10) Å

  • b = 11.7534 (2) Å

  • c = 26.5735 (4) Å

  • V = 2375.11 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.70 mm-1

  • T = 100 K

  • 0.12 × 0.09 × 0.06 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: none

  • 34365 measured reflections

  • 4158 independent reflections

  • 3649 reflections with I > 2[sigma](I)

  • Rint = 0.083
Refinement

  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.089

  • S = 1.05

  • 4158 reflections

  • 295 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1758 Friedel pairs

  • Flack parameter: 0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5...N2 0.82 2.07 2.876 (2) 169
N1-H1...O5i 0.86 2.01 2.866 (2) 170
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2206 ).

Acknowledgements

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.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort]
Boyer, E. W., Babu, K. M., Adkins, J. E., McCurdy, C. R. & Halpern, J. H. (2008). Addiction, 103, 1048-1050.  [CrossRef] [PubMed]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [ChemPort] [details]
Ma, J., Yin, W., Zhou, H., Liao, X. & Cook, J. M. (2009). J. Org. Chem. 74, 264-273.  [CrossRef] [PubMed] [ChemPort]
Ponglux, D., Wongseripipatana, S., Takayama, H., Kikuchi, M., Kurihara, M., Kitajima, M., Aimi, N. & Sakai, S. (1994). Planta Med. 60, 580-581.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Weibrecht, K. W., Courtney, J. M., Halpern, J., McCurdy, C. & Boyer, E. W. (2008). Clin. Toxicol. 46, 395-399.
Zacharias, D. E., Rosenstein, R. D. & Jeffrey, G. A. (1965). Acta Cryst. 18, 1039-1043.  [CrossRef] [ChemPort] [details]

Acta Cryst (2009). E65, o1441-o1442   [ doi:10.1107/S1600536809017309 ]

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