(−)-Crebanine

Tanwawan Duangthongyou; Arthit Makarasen; Supanna Techasakul; Nitirat Chimnoi; Sutatip Siripaisarnpipat

doi:10.1107/S1600536811001231

. 2011 Jan 15;67(Pt 2):o402. doi: 10.1107/S1600536811001231

(−)-Crebanine

Tanwawan Duangthongyou ^a, Arthit Makarasen ^b, Supanna Techasakul ^a, Nitirat Chimnoi ^b, Sutatip Siripaisarnpipat ^a,^*

PMCID: PMC3051729 PMID: 21523075

Abstract

The asymmetric unit of the title compound [systematic name: 9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline], C₂₀H₂₁NO₄, contains two independent molecules with very similar bond lengths and angles. The crystal packing exhibits voids of 131 Å³.

Related literature

For related structures, see: Israilov et al. (1980 ▶); Blanchfield et al. (2003 ▶). For the chemistry, pharmacology and traditional uses of the title compound, see; Montririttigri et al. (2008 ▶) and Semwal et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₂₁NO₄
M _r = 339.38
Orthorhombic,
a = 4.4029 (3) Å
b = 20.5847 (15) Å
c = 39.612 (3) Å
V = 3590.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.22 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
31211 measured reflections
5054 independent reflections
3592 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.105
wR(F ²) = 0.249
S = 1.2
5054 reflections
453 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ▶; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 ▶.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001231/hg2768sup1.cif

e-67-0o402-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001231/hg2768Isup2.hkl

e-67-0o402-Isup2.hkl^{(242.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Dr Narongsuk Chaichit, Department of Physics, Faculty of Science, Thammasart University, for the data collection and the Department of Chemistry, Faculty of Science, Kasetsart University, for financial support.

supplementary crystallographic information

Comment

Crebanine is an aporphine alkaloid (Israilov et al., 1980; Blanchfield et al., 2003). It was isolated from the crude hexane extract of the dried tuber of Stephania venosa, which is native to Thailand and commonly used for treatment of variety of aliments under the local name "sabulead" (Montririttigri et al., 2008; Semwal et al.,2010). S. venosa tuber and leaves were collected from Prachuabkirikhan province in the southern part of Thailand.

The asymmetric unit of the title compound [systematic name: 9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline], C₂₀H₂₁NO₄, contains two independent molecules. There is very little difference between the bond lengths and angles of these molecules. The molecules are nearly planar (r.m.s deviation = 0.2894Å and 0.2413 Å). The molecule consists of four fused-rings (A, B, C and D). The six membered-rings B and C are both in distorted half-chair conformations. The porous crystal packing exhibits voids of 131 Å³. The structure is devoid of any classical hydrogen bonds.

Experimental

Crebanine was isolated from the crude hexane extract of the dried tuber of Stephania venosa. After purification by classical liquid chromatography on silica gel and recrystallization from hexane-dichloromethane, crebanine was obtained as colorless needles, m.p. 115–116.5°C.