AtalaphyllineThis paper is dedicated to the late His Royal Highness Prince Mahidol of Songkla for his contributions to the development of medical education in Thailand.

Chantrapromma, S.; Boonnak, N.; Razak, I.A.; Fun, H.-K.

doi:10.1107/S1600536809051885

Volume 66
Part 1
Pages o81-o82
January 2010

Received 19 November 2009
Accepted 2 December 2009
Online 9 December 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.118
Data-to-parameter ratio = 12.2
Details

Atalaphylline¹

Suchada Chantrapromma,^a ^*⁺ Nawong Boonnak,^a Ibrahim Abdul Razak ^b and Hoong-Kun Fun ^b ⁺⁺

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

The title acridone alkaloid [systematic name: 1,3,5-trihydroxy-2,4-bis(3-methylbut-2-enyl)acridin-9(10H)-one], C₂₃H₂₅NO₄, known as atalaphylline, was isolated from Atalantia monophylla Corrêa, a mangrove plant. The molecule contains three fused planar rings with an r.m.s. deviation of 0.026 (2) Å. Both 3-methylbut-2-enyl substituents are in a (-)anticlinal conformation. An intramolecular N-HO hydrogen bond generates an S(5) ring motif, while an intramolecular O-HO hydrogen bond generates an S(6) ring motif. In the crystal structure, the molecules are linked into screw chains along [010] by intermolecular O-HO hydrogen bonds. These chains are stacked along the a axis by [pi] - [pi] interactions with centroid-centroid distances of 3.6695 (13) and 3.6696 (13) Å.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For details of acridone alkaloids and their biological activity, see: Basu & Basa (1972); Itoigawa et al. (2003); Kawaii et al. (1999a,b). For a related structure, see: Chukaew et al. (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental

Crystal data

C₂₃H₂₅NO₄
M_r = 379.44
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0650 (1) Å
b = 15.0131 (4) Å
c = 24.5813 (5) Å
V = 1869.20 (7) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.40 × 0.21 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.964, T_max = 0.996
17852 measured reflections
3142 independent reflections
2525 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.118
S = 1.03
3142 reflections
257 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1O2	0.82	1.82	2.554 (2)	149
O3-H1O3O2ⁱ	0.82	1.93	2.752 (2)	175
N1-H1N1O3	0.86	2.34	2.692 (3)	105
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2692 ).

Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. NB thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. Mr Arnon Chukaew is acknowledged for supplying the authentic sample of atalaphylline. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Basu, D. & Basa, S. C. (1972). J. Org. Chem. 37, 3035-3036.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chukaew, A., Fun, H.-K., Chantrapromma, S. & Ponglimanont, C. (2007). Acta Cryst. E63, o3723-o3724.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Itoigawa, M., Ito, C., Wu, T. S., Enjo, F., Tokuda, H., Nishino, H. & Furakawa, H. (2003). Cancer Lett. 193, 133-138.
Kawaii, S., Tomono, Y., Katase, E., Ogawa, K., Yano, M., Takemura, Y., Ju-ichi, M. & Furakawa, H. (1999b). Leuk. Res. 23, 263-269.
Kawaii, S., Tomono, Y., Katase, E., Ogawa, K., Yano, M., Takemura, Y., Ju-ichi, M., Ito, C. & Furakawa, H. (1999a). J. Nat. Prod. 62, 587-589.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

Atalaphylline1