Received 24 November 2010
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Chemistry, Faculty of Science, Silpakorn University, Rajamanka Nai Road, Muang Nakhon Pathom 73000, Thailand, and cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: email@example.com
The title schulzeine derivative, C22H24N2O4, crystallizes with two crystallographically independent molecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetrahydroisoquinoline and -lactam moieties. In both molecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation. The two methoxy groups are slightly twisted from the attached benzene ring [C-O-C-C torsion angles = -21.3 (2) and -20.5 (2)° in molecule A, and -6.3 (2) and -16.2 (2)° in molecule B] and the benzamide moiety is in a (-)-synclinal conformation with respect to the lactam ring. In the crystal, molecules are linked into V-shaped dimers by intermolecular N-HO hydrogen bonds and weak C-HO interactions. These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked in an antiparallel manner. C-H interactions are also observed.
For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For background to schulzeines, see, for example: Kuntiyong et al. (2006); Melo et al. (2006); Takada et al. (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
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: RZ2531 ).
PK thanks the Thailand Research Fund (TRF) for financial support. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.
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.
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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Kuntiyong, P., Akkarasmiyo, S. & Eksinitkun, G. (2006). Chem. Lett. 35, 1008-1009.
Melo, E. B., Gomes, A. S. & Carvalho, I. (2006). Tetrahedron, 62, 10277-10302.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Takada, K., Uehara, T., Nakao, Y., Matsunaga, S., van Soest, R. W. M. & Fusetani, N. (2004). J. Am. Chem. Soc. 126, 187-193.