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Volume 69 
Part 9 
Pages o1389-o1390  
September 2013  

Received 1 July 2013
Accepted 29 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.114
Data-to-parameter ratio = 13.4
Details
Open access

Tetrahydroalstonine

aLaboratoire de Pharmacognosie, UMR CNRS 8638, Faculté des Sciences Pharmaceutiques et Biologiques de Paris Descartes, 4, avenue de l'Observatoire, 75270 Paris Cedex 06, France, and bLaboratoire de Cristallographie et RMN biologiques, UMR CNRS 8015, Faculté des Sciences Pharmaceutiques et Biologiques de Paris Descartes, 4, avenue de l'Observatoire, 75270 Paris Cedex 06, France
Correspondence e-mail: francois-hugues.poree@parisdescartes.fr

In the title compound, C21H24N2O3 [systematic name: methyl (20[alpha])-16,17-didehydro-19[alpha]-methyl-18-oxayohimban-16-carboxylate], the molecule adopts an L-type conformation. The crystal packing is governed by one N-H...[pi] and one C-H...[pi] interactions. The crystal cohesion is ensured by intermolecular van der Waals contacts [shortest O...O contact = 3.199 (2) Å].

Related literature

For the extraction of tetrahydroalstonine (THA) from natural sources, see: Zenk & Juenger (2007[Zenk, M. H. & Juenger, M. (2007). Phytochemistry, 68, 2757-2772.]); Mandal et al. (1983[Mandal, S., Srivastava, V. K. & Maheshwari, M. L. (1983). Indian J. Pharm. Sci. pp. 23-26.]); Langlois et al. (1979[Langlois, N., Diatta, L. & Andriamialisoa, R. Z. (1979). Phytochemistry, 18, 467-471.]). For stereochemistry studies, see: Wenkert et al. (1961[Wenkert, E., Wickberg, B. & Leicht, C. L. (1961). J. Am. Chem. Soc. 83, 5037-5038.]); Wenkert & Roychaudhuri (1957[Wenkert, E. & Roychaudhuri, D. K. (1957). J. Am. Chem. Soc. 79, 1519-1520.]); Shamma & Richey (1963[Shamma, M. & Richey, J. M. (1963). J. Am. Chem. Soc. 85, 2507-2512.]); Lounasmaa & Kan (1980[Lounasmaa, M. & Kan, S.-K. (1980). Tetrahedron, 36, 1607-1611.]); Höfle et al. (1980[Höfle, G., Heinstein, P., Stöckigt, J. & Zenk, M. H. (1980). Planta Med. 40, 120-126.]). For the semisynthesis, see: Poirot (2007[Poirot, R. (2007). PhD thesis, p. 129. Institut National Polytechnique de Toulouse, France.]); Beziat & Hatinguais (1977[Beziat, D. & Hatinguais, P. (1977). Patent FR2397415.]); Zsadon et al. (1979[Zsadon, B., Barta, M., Dezseri, E. & Dancsi, L. (1979). Patent FR7929088.]); Guéritte et al. (1983[Guéritte, F., Langlois, N. & Pétiard, V. (1983). J. Nat. Prod. 46, 144-148.]); Hemscheidt & Zenk (1985[Hemscheidt, T. & Zenk, M. H. (1985). Plant Cell Rep. 4, 216-219.]) and for synthetic studies, see: Gutzwiller et al. (1971[Gutzwiller, J., Pizzolato, G. & Uskolovic, M. (1971). J. Am. Chem. Soc. 93, 5907-5908.]); Wenkert et al. (1976[Wenkert, E., Chang, C.-J., Chawla, H. P. S., Cochran, D. W., Hagaman, E. W., King, J. C. & Orito, K. (1976). J. Am. Chem. Soc. 98, 3645-3655.]); Zou et al. (2010[Zou, H.-B., Zhu, H.-J., Zhang, L., Yang, L.-Q., Yu, Y.-P. & Stöckigt, J. (2010). Chem. Asian J. 5, 2400-2404.]). For the biological activity of TMA, see Zou et al. (2010[Zou, H.-B., Zhu, H.-J., Zhang, L., Yang, L.-Q., Yu, Y.-P. & Stöckigt, J. (2010). Chem. Asian J. 5, 2400-2404.]); Sharma et al. (1988[Sharma, P., Shirataki, Y. & Cordell, G. A. (1988). Phytochemistry, 27, 3649-3652.]). For a related structure, see: Laus & Wurst (2008[Laus, G. & Wurst, K. (2008). Helv. Chim. Acta, 91, 831-837.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24N2O3

  • Mr = 352.42

  • Orthorhombic, P 21 21 21

  • a = 6.719 (1) Å

  • b = 8.169 (2) Å

  • c = 34.120 (5) Å

  • V = 1872.8 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.50 × 0.30 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (COLLECT; Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]) Tmin = 0.982, Tmax = 0.992

  • 3300 measured reflections

  • 3300 independent reflections

  • 2537 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.114

  • S = 1.01

  • 3300 reflections

  • 247 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

  • Absolute structure parameter: -0.3 (17)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8-C13 and C2/C7/C8/C13/N1 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...Cg1i 0.86 2.85 3.550 (2) 139
C6-H6A...Cg2ii 0.97 2.8 3.429 (3) 121
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2388 ).


Acknowledgements

The authors thank Université Paris Descartes and the CNRS for financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Beziat, D. & Hatinguais, P. (1977). Patent FR2397415.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guéritte, F., Langlois, N. & Pétiard, V. (1983). J. Nat. Prod. 46, 144-148.
Gutzwiller, J., Pizzolato, G. & Uskolovic, M. (1971). J. Am. Chem. Soc. 93, 5907-5908.  [CrossRef] [ChemPort] [ISI]
Hemscheidt, T. & Zenk, M. H. (1985). Plant Cell Rep. 4, 216-219.  [CrossRef] [ChemPort]
Höfle, G., Heinstein, P., Stöckigt, J. & Zenk, M. H. (1980). Planta Med. 40, 120-126.
Langlois, N., Diatta, L. & Andriamialisoa, R. Z. (1979). Phytochemistry, 18, 467-471.  [CrossRef] [ChemPort] [ISI]
Laus, G. & Wurst, K. (2008). Helv. Chim. Acta, 91, 831-837.  [CSD] [CrossRef] [ChemPort]
Lounasmaa, M. & Kan, S.-K. (1980). Tetrahedron, 36, 1607-1611.  [CrossRef] [ChemPort] [ISI]
Mandal, S., Srivastava, V. K. & Maheshwari, M. L. (1983). Indian J. Pharm. Sci. pp. 23-26.
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Poirot, R. (2007). PhD thesis, p. 129. Institut National Polytechnique de Toulouse, France.
Shamma, M. & Richey, J. M. (1963). J. Am. Chem. Soc. 85, 2507-2512.  [CrossRef] [ChemPort] [ISI]
Sharma, P., Shirataki, Y. & Cordell, G. A. (1988). Phytochemistry, 27, 3649-3652.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wenkert, E., Chang, C.-J., Chawla, H. P. S., Cochran, D. W., Hagaman, E. W., King, J. C. & Orito, K. (1976). J. Am. Chem. Soc. 98, 3645-3655.  [CrossRef] [ChemPort] [ISI]
Wenkert, E. & Roychaudhuri, D. K. (1957). J. Am. Chem. Soc. 79, 1519-1520.  [CrossRef] [ChemPort] [ISI]
Wenkert, E., Wickberg, B. & Leicht, C. L. (1961). J. Am. Chem. Soc. 83, 5037-5038.  [CrossRef] [ChemPort] [ISI]
Zenk, M. H. & Juenger, M. (2007). Phytochemistry, 68, 2757-2772.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zou, H.-B., Zhu, H.-J., Zhang, L., Yang, L.-Q., Yu, Y.-P. & Stöckigt, J. (2010). Chem. Asian J. 5, 2400-2404.  [CrossRef] [ChemPort] [PubMed]
Zsadon, B., Barta, M., Dezseri, E. & Dancsi, L. (1979). Patent FR7929088.


Acta Cryst (2013). E69, o1389-o1390   [ doi:10.1107/S1600536813021168 ]

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