N-Methyl­isosalsoline from Hammada scoparia

Jarraya, R.M.; Bouaziz, A.; Hamdi, B.; Salah, A.; Damak, M.

doi:10.1107/S160053680802477X

Volume 64
Part 9
Page o1714
September 2008

Received 28 July 2008
Accepted 1 August 2008
Online 6 August 2008

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.001 Å
R = 0.033
wR = 0.089
Data-to-parameter ratio = 23.0
Details

N-Methylisosalsoline from Hammada scoparia

Raoudha Mezghani Jarraya,^a Amira Bouaziz,^a Besma Hamdi,^b Abdelhamid Ben Salah ^b and Mohamed Damak ^a ^*

^aLaboratoire de Chimie des Substances Naturelles, Faculté des Sciences de Sfax, BP 1171, 3000 Sfax, Tunisia, and ^bLaboratoire des Sciences de Materiaux et d'Environnement, Faculté des Sciences de Sfax, BP 1171, 3000 Sfax, Tunisia
Correspondence e-mail: mohamed.damak@fss.rnu.tn

The title compound (systematic name: 1,2-dimethyl-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol), C₁₂H₁₇NO₂, is a major alkaloid isolated from Hammada scoparia leaves. It belongs to the isoquinoline family and it was characterized by NMR spectroscopy and X-ray crystallographic techniques. The absolute configuration could not be reliably determined. An intermolecular O-HN hydrogen bond is present in the crystal structure.

Related literature

For related literature on Hammada scoparia and isoquinoline alkaloids, see: Baker (1996); Benkrief et al. (1990); Carling & Sandberg (1970); El-Shazly & Wink (2003); El-Shazly et al. (2005); Iwasa et al. (2001); Jarraya & Damak (2001); Vetulani et al. (2001, 2003).

Experimental

Crystal data

C₁₂H₁₇NO₂
M_r = 207.27
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5942 (6) Å
b = 10.8082 (8) Å
c = 13.2716 (10) Å
V = 1089.33 (14) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 200 (2) K
0.48 × 0.37 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (Becker & Coppens, 1974) T_min = 0.961, T_max = 0.988
23859 measured reflections
3132 independent reflections
2870 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.089
S = 1.06
3132 reflections
136 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N1ⁱ	0.84	1.90	2.6970 (10)	159
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2131 ).

Acknowledgements

The authors gratefully acknowledge Professor Jean-Claude Daran (Directeur de Recherche, Laboratoire de Chimie de Coordination, CNRS-Toulouse) for helpful comments regarding this paper.

References

Baker, B. J. (1996). -Carboline and isoquinoline alkaloids from marine organisms. In: Alkaloids: Chemical and Biological Perspectives, edited by W. S. Pelletier, vol. 10, pp. 357-407. New York: Pergamon.
Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.
Benkrief, R., Brum-Bousquet, M., Tillequin, F. & Koch, M. (1990). Ann. Pharm. Fr. 48, 219-224.
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Carling, C. & Sandberg, F. (1970). Acta Pharm. Suec. 7, 285-288.
El-Shazly, A. M., Dora, G. & Wink, M. (2005). Pharmazie, 60, 949-952.
El-Shazly, A. & Wink, M. (2003). Z. Naturforch. Teil C, 58, 477-480.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Iwasa, K., Moriyasu, M., Tachibana, Y., Kim, H. S., Wataya, Y., Wiegrebe, V., Bastow, K. F., Cosentino, L. M., Kozuka, M. & Lee, K. H. (2001). Bioorg. Med. Chem. 9, 2871-2884.
Jarraya, R. & Damak, M. (2001). J. Soc. Chim. Tunis. 4, 941-948.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vetulani, J., Antkiewicz-Michaluk, L., Nalepa, I. & Sansone, M. (2003). Neurotox. Res. 5, 147-155.
Vetulani, J., Nalepa, I., Antkiewicz-Michaluk, L. & Sansone, M. (2001). J. Neurol. Transm. 108, 513-526.

organic compounds