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Volume 69 
Part 6 
Page o833  
June 2013  

Received 11 January 2013
Accepted 28 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.089
Data-to-parameter ratio = 16.1
Details
Open access

15-Methoxy-14,15-dihydroandranginine

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
Correspondence e-mail: great7701@126.com, hhp760222@126.com

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-H...O hydrogen bonds connect the molecules into centrosymmetric dimers.

Related literature

Indole alkaloid derivatives obtained from Melodinus yunnanensis have been investigated due to their antimalarial and anticancer properties, see: Kanfan et al. (1974[Kanfan, C., Massiot, G., Ahond, A., Das, B. C., Husson, H. P. & Potier, P. (1974). J. Chem. Soc. Chem Commun. pp. 164-165.]). For the structures of related compounds, see: Danieli et al. (1977a[Danieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519-6523.]) and for applications of similar compounds see: Danieli et al. (1977a[Danieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519-6523.],b[Danieli, B., Lesma, G., Luzzani, M., Passarella, D. & Silvani, A. (1977b). Tetrahedron, 34, 11291-11296.])

[Scheme 1]

Experimental

Crystal data
  • C22H26N2O3

  • Mr = 366.45

  • Triclinic, [P \overline 1]

  • a = 6.914 (3) Å

  • b = 11.232 (4) Å

  • c = 11.806 (4) Å

  • [alpha] = 91.079 (6)°

  • [beta] = 100.737 (5)°

  • [gamma] = 96.317 (6)°

  • V = 894.5 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 153 K

  • 0.43 × 0.23 × 0.13 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 8672 measured reflections

  • 4028 independent reflections

  • 2868 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.089

  • S = 1.00

  • 4028 reflections

  • 250 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O3i 0.859 (17) 2.187 (16) 2.9759 (18) 152.6 (15)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2092 ).


Acknowledgements

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).

References

Danieli, B., Lesma, G., Luzzani, M., Passarella, D. & Silvani, A. (1977b). Tetrahedron, 34, 11291-11296.
Danieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519-6523.
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.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o833  [ doi:10.1107/S1600536813011604 ]

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